Since then, life has been a whirlwind. I launched my own strategic advisory practice, client work has picked up, and I’ve been able to create more time and space for my personal life and pursuits. Things are good and I literally have no complaints—I look at my life today and cannot imagine how I managed to get here given some of the events of the last few years.

But here we are. As I’ve been reflecting and working on new pieces of writing, I hope to share more in the coming weeks and months. In the meantime, do enjoy this and let me know what you think; I had initially intended to do a piece looking at the state of media in Singapore and how I see it evolving in the coming years, but as I wrote it, the process took me back to a lot of the early idealism that got me wanting to write about Singapore in the first place.

So I went with that, and on balance I think it was the right thing to do. As with all storytelling, the truth is much more complex than narratives like this can truly capture. But that’s for us to unpack some other time.

Lastly, I started a Telegram group. Many of you have been following my writing since 2021 and I’ve always wanted to build a community around this newsletter. I’m not 100% sure where this will lead, but please join if you’re keen to be part of the journey. Right now I’m mostly sharing about my writing process and we chit chat a little now and then about different things. Hope to see you there!

Take care in the meantime 👋🏻

A love letter to the RICE audience and to Singapore

For the last 2 months, I’ve had countless conversations with friends, family, and professional acquaintances about RICE Media’s acquisition. In some cases, people were curious about how exactly this happened. What were the events that led up to something that caught so many by surprise?

Mostly, they’ve wanted to know: how does it feel to let go of your baby?

I suppose it’s a fair question. I started RICE back in 2016 with my co-founder Mark, wrote almost all of RICE’s early pieces (including the first one that went viral), grew the team, left, returned, and finally left again in March this year—this time, for good.

But how do you compress a 10-year journey into a single conversation?

In 2016, the year we started RICE, I was fresh out of university, armed with nothing more than my bachelor’s degree in English literature. I was also slightly burnt out, having spent the previous 4 years mostly skipping classes to work as a barista, tuition teacher, and freelance writer.

I want to say that RICE started simply because I looked at my reality and then at the reality the mainstream media sought to shape and sanitise about life in Singapore, and I saw a gap. And I sought to fill that gap.

This did happen. But it was also not that simple.

Few of us start companies or go into entrepreneurship because we think it will make us rich. For both Mark and I, we couldn’t help ourselves. We had always been outsiders; in each of our own ways we had never fit into any script about what a Singaporean should do or who they should be.

So we started a digital magazine. And as RICE’s first writer, I wrote from a deep yearning—for stories that I knew existed but were not immediately accessible. Stories about people living at the margins, people trying fiercely to carve out lives they could own and be proud of, stories that captured concepts and philosophies (both personal and academic) about how life could be ... more. More fulfilling. More equitable. More fun. More compassionate. More alive.

Surely, I thought, there must be beauty in this country.

This quickly became our cultural signature. Remember, this was 2016. There were maybe a handful of niche publications floating around occasionally covering the kinds of topics we did. But it was RICE that normalised the coverage of of “taboo” topics like race, gender, LGBTQ issues, religion, and socio-economic inequality, amongst others. We paid serious attention to sub-cultures and underground communities, and we took risks with investigative reporting and political commentary.

We did it this way because we believed these were stories worth telling. That yes, there was beauty to be found, if only we cared enough to look.

Over the years, many people have called RICE controversial. It is a characterisation I have never understood. After all, it was not as though we covered stories that were untrue. RICE has always simply endeavoured, in my view, to reflect what already exists in Singapore.

Looking back at 25-year-old me, I know that RICE was my attempt to give voice to many of my frustrations about how my life felt. I was nursing a gnawing sense of displacement and disconnection; an angst at how being Singaporean felt like it meant being cynical and transactional, like everything could be reduced to a policy trade-off.

This was not who I wanted to be, and as both a writer and entrepreneur, I brought to our work a vision for what we believed could be different. We brought a hunger and passion that I now look back on and sometimes wonder: how did I even keep going like that? We serviced the work with our own peculiar concoction of innocence, inexperience, and mental health challenges that helped us pull the business through some tough moments, but also came at great personal cost.

And it has been 10 years. In the same month that I decided to exit RICE Media, I turned 35. In Singaporean terms, this means I am now legally able to purchase an HDB flat as a single person.

In adult terms, it also means that life looks very different now. I am a different person now.

For both Mark and myself, what began as a dream to tell stories had also slowly become a constraint—for both our personal identities and the kind of lives we wanted to build. Sometimes, wisdom is knowing when to let go.

I would be lying if I said there aren’t days when I wish it was still 2016. The temptation is to think: it was so much better then. People still wanted to read, they cared about long form writing, we didn’t live in a world optimised for algorithms and doom-scrolling.

But this is what I’ve realised. I’ve realised that it will always be 2016.

By this I mean that there is no expiry date on dreaming. Things are always changing and there will always be something worth fighting for.

In September last year, I ran a series of focus groups interviewing RICE readers. I wanted to understand the texture of their everyday lives: what were their aspirations, what was going well, where were they feeling challenged, what continued to give them hope?

These data points, I hoped, would inform how RICE could continue to evolve and stay relevant.

What struck me about these conversations was that yes, on the surface, many of the concerns were material in nature—cost of living, job prospects, lack of third spaces, having little to no energy, and so on. But really, they were about the texture of living in Singapore; that sense of connection to place, society, community, heritage that give a life purpose.

One participant, when sharing about purchasing their HDB flat, said, “The day I got my keys, I felt relief and panic at the same time. Like I just signed away my next 25 years.”

Another said, “We’ve grown up so efficiently we don’t know how to need people.”

But in those same conversations, people also said things like, “I left tech. I don’t make sales now. I just make,” or, “Creativity is freedom, I’m now learning it’s about being brave enough to say what I think.”

People talked about the micro, often invisible ways in which they were slowly, mindfully, courageously constructing lives that they felt in control of—lives they did not need to explain to anyone else or to compare to anyone else’s.

It was a reminder that where there is despair, there is also hope. The yearning never goes away, and neither does our pursuit to meet and soothe that yearning.

Last year, as RICE doubled down on community building and in-person events, I met and spoke with so many of you who I’ve now come to recognise as the quintessential RICE reader: Singaporeans who are in touch with how challenging things are, but who have not lost hope. Who continue not just to yearn, but also to act. Who understand that change doesn’t need to be big to be radical, that it happens also through small, consistent, everyday transformations.

It has been said to death that Singaporean society is deeply nostalgic. Because of the pace of transformation this country has experienced, we have lost so much, from physical infrastructure and cultural ecosystems to values and ways of being. We are a culture that is always grieving, and these days it can seem like we are not just grieving what has been lost, but also what we know we will eventually lose.

While I do agree that as a culture we are deeply nostalgic, my suspicion is that it is not the past we are yearning for.

Rather, it is for a future in which we can see ourselves. It is for a story in which we are the ones deciding what happens in our lives, where there is space to exhale and consider what we really want, instead of feeling as though we are at the mercy of global events, national policies, or even some abstract, deeply ingrained belief that it is better to play it safe.

As Singaporeans, so much of our yearning is about our search for connection, rootedness, belonging. It’s about a want for simpler things that finds itself running headlong into how we actually organise our lives through credential-chasing, property accumulation, or even busyness masquerading as social currency (and so it goes).

I am not an academic. But to me, this is what this nostalgia, this grief, is really pointing to. It is what many of us continue to search for.

In the past 2 months, what I’ve missed most about RICE is the view this platform has given me into the lives of Singaporeans who are giving themselves the permission to be different: to want different things, to have different standards for living a good life, being a good parent, being an active citizen; to fight, resolutely, incrementally, for crafting a life lived with intention.

It was also a reminder that these stories existed even before RICE started telling them. And they will continue to exist regardless.

In the earlier years of RICE, there would be days when in between chasing deadlines, closing clients, agonising over public comments about our work, and managing HR issues, I would wonder what this was all for.

Perhaps, I would think, I would one day wake up to a world where the work was finally ‘done’, and we were finally ‘there’—where the angry teenager in me could look at Singapore and think, this is finally the world I want to live in, where I finally feel like I belong. Maybe that day was just around the corner.

Since then, I’ve learnt two things:

One, there are many ways to get where you want to go. For me, RICE was one way to do it. And at some point, the joy of pursuing stories became operational overload from trying to make a business work.

Two, that it is in fact not even about ‘getting there’. That it’s not about finding the answers to the questions I have—like, “What does it truly mean to have a Singaporean identity I can connect with and be proud of?”—but about continuing to ask such questions.

One of the unassailable national narratives that we have become so familiar with is that Singapore and Singaporeans have to stay competitive. What tends to get left out of the conversation is: what are we competing for?

As I move on from RICE, my hope is a simple one. My hope is that we, in our own individual Singaporean ways, will compete for a life that is ours. A life in which we feel safe, empowered, connected, dignified, creative, expansive, restful, content. Not a life lived by proxy, where we want the things that seem to make other people happy, or that appear to promise a “good” life.

For the last 10 years, RICE has been a mirror to Singapore. It has reflected the reality that Singaporeans are so much more than what we give ourselves credit for. It is my hope that this that will continue, and that these stories will continue to be told.

With that, I wish nothing but the best to the new team. I’m super excited to see what Ilyas, the current editor, will bring to RICE’s vision, and I’ve had great conversations with the leadership at Hustle SG. Right now, I don’t think there is a better team suited to taking RICE into its next chapter.

May we never stop yearning.

Something I might have written about before but that has been coming up a lot for me in the last few weeks is this idea that we need to earn the right to live the life we think we deserve.

When we have done a lot of work on ourselves, we can wake up one day to realise that life is pretty good. Maybe you are sitting in traffic waiting for the bus to move when it occurs to you: the right opportunities are showing up in your life, you are surrounded by people you love and who love you back, and you are not really lacking in anything. You have a job you love, a home to return to, money for food, and friends to call.

What more could you want?

But if you are not careful, you can end up taking it all for granted. What once felt like peace begins to feel like boredom. What was once shiny and exciting begins to lose a little bit of its novelty. Maybe you got exactly what you wanted, and it's no longer so clear what the 'next thing' you should be striving for is.

We talk a lot about this in sobriety circles—that the lie many of us can tell ourselves is that we are finally done healing, and we can start drinking/using again. But it is precisely when you start getting complacent that relapse happens. It is not just the bad days we need to be wary of, it is also the good days.

I think this applies to most things. You just got promoted at work, that doesn't mean you won't be laid off. Your relationship is going well, that doesn't mean it can't come to an abrupt end.

This is not to say that all paths lead to loss or suffering, but to recognise that having is not the same as keeping. It is not the same as nurturing, building, and deepening.

Earlier this week, when I woke up on Monday to go to my first meeting with a client, I found myself feeling surprisingly heavy. I was a little bit tired, and in some ways still recovering from a string of activities that took place over the Christmas and New Year's break.

But if I'm being honest, I was really just feeling sleepy and lazy, and knew that if I asked to postpone this meeting, the other person would have readily agreed without making a big deal out of it.

In other words, I just didn't feel like getting out of bed, and in that moment it was easy to slip into a narrative that I had a lot going on, and that I needed a break. Because this is also somewhat true.

I currently lead community and partnerships work at a media company while continuing to juggle some co-founder responsibilities. I've taken on a fractional role at an investment platform that I'm really excited about, and I'm still running my coaching practice.

On the side, I mentor several individuals and am involved in a number of community initiatives, and I'm also working towards completing my professional certification in the Enneagram this year.

All this is on top of trying to be more intentional about staying in touch with people I care about, while also leaning into what I joked with some friends would be my 'year of dating aggressively' (lol).

So while I'm incredibly grateful for how my life looks like these days and feel very focused and excited for the year ahead, I'm also aware that all of this is ... a lot.

No one has forced me to do any of this, and at one point this was exactly what I wanted. Yet there I was, feeling like a victim in the life I had created for myself.

And so as I plodded through this week, I've found it necessary to remind myself what all of this is really for.

On one hand, I have been getting a clearer sense of where my life is headed. I previously shared about how at some point I see myself exploring opportunities outside of Singapore and maybe even starting a family, and more importantly wanting to be able to do all of this on my own terms. I want to live a full life while having the freedom and flexibility to do it my way.

On the other hand, I know that I'm not yet in that season. A big part of why I'm doing so much is because I'm still waiting to see what connects and emerges. I am very much still building the resources and leverage that would hopefully allow me to make the choices that are right for myself.

This means that I often find myself wrestling with this tension where I feel like things are great, but they're not moving fast enough. Sometimes I can feel like I really like where I am in the present moment, but at the back of my mind there is a voice whispering observations about how this is also kinda not quite where I eventually want to be.

I often joke that I make life incredibly difficult for myself, and these days I do genuinely say this in good humour. But there was a time when I often wondered why I couldn't just be happier with less—doing less, having less, being less.

A lot of this stemmed from wanting to fit in and to appear less different than others. Yet I've also learnt that if you try to suppress and minimise what is authentic and good about yourself, that part of you doesn't disappear. It simply finds another way out, and it can surface in ways that are not so pleasant.

Looking back on my mid-20s, I now recognise how so much of this manifested less as a genuine desire to be ambitious, and more as need to be seen as ambitious. And so I was always busy, always taking things on, always finding ways to make others reliant on me. It came from a place of needing to prove myself.

And the truth is that this phase of my life did not happen that long ago. As much as I now find it much more effortless to be ambitious about things that matter to me and that I enjoy (in and of themselves), this part of my personal history continues to cast its shadow over a lot of what I do. It is a shadow that shrinks a little bit more with each passing day, but nonetheless it is there.

Perhaps this is what I mean when I talk about that tension—to see that yes I may have once lived in ways that I now feel sad about, but also I have changed and am still changing and am moving in what I hope is a different and better direction.

To hold this tension is to hold both realities as true, and to not lean too much in either direction to be paralysed by guilt and victimhood or towards arrogance and the belief that I am done working on my baggage and am no longer capable of fucking up.

It is such a cliché to say that while it is important to work hard—at work, at our hobbies, at the things we care about, and at becoming better people—we musn't forget to have fun along the way. But I'm also realising that growing up is recognising that while we don't know everything, we also already know everything that we need to know. Clichés are just a cynic's characterisation of timeless and essential wisdom.

So here’s what I do know.

One day, my life in its current season will end, and I will step into something new. I hope it will be wonderful and that it will be exactly what I've been working so hard for. But it also means that I will look back on what once was, and I will miss it.

This is simply the natural cycle of things. I am not dreading it, I am just mindful that it will eventually come to pass.

Inspired by a friend who shared that she no longer sets annual goals, but instead chooses two words that will define her year, I decided that mine would be 'discipline' and 'pleasure'.

I am still figuring out exactly what this means for me, but I find myself saying more things like,

"I've already done a lot this week, it's time to stop."

"I'm comfortable with the journey I'm on, I don't need to fix everything today."

"I really want that to work out, but it's also totally okay if it doesn't."

And eventually, what got me out of bed on Monday morning was just remembering that if I want to do all the fun things that I'm excited about, I need to earn the right to do so.

Sometimes, this means accepting that I first need to have the boring meeting.

As always, if you want to support introspective long-form writing like mine, do consider upgrading your subscription.

I am in Istanbul, sitting outdoors at a restaurant when a stray kitten crawls into my lap. It takes me a second to realise it is not here for me.

It is here for my food, which it ploughs into with the kind of pure and savage hunger only animals are capable of. By the time I notice and lift it off my plate, its face is covered in sauce and it has kebab hanging off its teeth. It looks like I've peeled a small lion off a fresh and steaming carcass.

I feed it what I can—bits of tuna salad and grilled meat—and with each bite it begins to calm down. It shivers less and the growling in its tiny body subsides. When it's done eating, it folds itself into my lap and goes to sleep. Somewhere in my chest, a candle flickers to life.

The thing is, I did not come to Istanbul for the cats. But in this moment it feels like I was meant to be here for the cats.

Perhaps there is a lesson here, in how cats are not trying to be anything other than what they are. My reward is that I too get to be myself—a living, breathing heat source with food and a warm jacket; a human being scratching the head of a small animal, in awe of how much joy it is possible to feel in something so unremarkable.

Or maybe it is also not so unremarkable after all, that sometimes we get to hold and be close to things that are warm and alive, things that in their own innocent way have chosen us, and in return we decide that we will allow ourselves to be chosen.

Heading into the end of 2024, I've been feeling like I spent very little of this year writing about what I actually needed to write about. I published pieces of writing I'm proud of, but for the most part, I wrote around the things I really wanted to say.

I don't think it's because I lacked the words. Instead, I've been nursing a quiet, delusional hope that if I didn't confront these things in the light of day, maybe I could still believe that they didn't happen.

Perhaps this is one of those afflictions of being a writer. We want to keep so much to ourselves, to keep living our favourite stories on the inside, yet there is a part of us that knows this cannot be. Life, real life, is lived on the outside, in the choices we make, the conversations we have, the things we do, and the people we become.

So this is what has taken me over a year to say.

18 months ago, I ended 3 relationships. I quit full-time work, closed the chapter on the first true love story of my life, and decided I was done drinking alcohol.

If we are lucky, relationships are invitations to become more of who we already are. But sometimes, when we are troubled, ignorant, and searching for the feeling of home, we concern ourselves instead with making relationships work, with making them last. We play roles and characters, fabrications that help us preserve some external facade of what we think we want, but in fact are disconnecting us from what we really need.

Then one day we wake up and realise what we have lost. We did not do it intentionally, and we did not do it all at once. One could even say we had a lot of fun along the way.

But the truth is: we are right back where we started, and we did not find what we were looking for. Can we say that we really did not know what was happening? That we were genuinely blind to what is now so plain?

There is a saying that alcoholics tend to become emotionally arrested at the level of maturity when they became serious problem drinkers. In Blackout, Sarah Hepola writes that quitting drinking was the first true act of her adulthood.

All these things have been true for me.

I started drinking professionally when I was 21, and never really took a day off. Since stopping, all I've been doing is processing the grief of everything that's happened in the last 12 years—decisions I both made and didn't make, seeing with so much clarity how I fell short of the person I wanted to be.

With that has come a lot of the things I've been running away from: anger, sadness, guilt, regret. Heavy heavy shit that for a long time was much easier not to look too closely at.

I am writing about this now because it was one thing to own up to all of this. Moving forward in the aftermath has not been so easy.

In the TV series Shrinking, there is an episode in the most recent season where Gaby's sister Courtney, who is a recovering addict, laments that she made a few years' worth of mistakes and now feels like she's being made to pay for them with the rest of her life.

"It's like nothing I do will ever be enough!" Courtney says, which Gaby finds extremely challenging to accept because of all that she endured when Courtney was deep in the throes of active, full-blown addiction.

But Gaby also knows that her sister is right. Courtney has suffered the consequences, she has been punished many times over, and she has made more than her fair share of amends.

When I was reflecting on the things I want to bring into 2025, this was one thought that surfaced: Things will hurt both more and less than I expect. Feel what needs to be felt, but don’t punish yourself for what has already finished.

I was quite proud of how I managed to sum this up so nicely for myself, because I am SO BAD AT THIS. Sometimes I can avoid feeling difficult things, only to be eventually confronted by them in ways I can no longer escape. In processing all the guilt and sadness that comes with this, I can keep finding ways to inflict suffering on myself, to cut myself off from love, and to tell myself that it still needs to hurt more, as though I will finally get to a point where the pain rips a hole in space and time, and I can step back into the past and fix it.

Yet it doesn't work this way. And now, more than a year later, wisdom has become possible.

What is wisdom? Wisdom, I'm guessing, is realising that the goal is not to keep punishing myself.

Instead, it is to do better.

This is one of those counter-intuitive paradoxes of life. When we think we are undeserving of things like love and forgiveness, we end up behaving in ways that seek to earn, win, or even subdue these things, or we can deny ourselves the experiences that would bring these things into our lives. In doing so, we end up hurting both ourselves and the ones closest to us.

But if we can embody a whole-hearted acceptance of our wretchedness and our innocent fallibility, then we can start acting clearly. We can be measured, healthy, and safe.

Over the last couple of months, I've heard myself say this several times: "I just want to finally start living my life." I've said it to friends, to my Enneagram teachers, and many times out loud to myself.

This newsletter has evolved a lot since I started publishing in 2021. I think of it as having gone through seasons, much like how musicians will release new albums and you can see how their music mirrors the life transitions they've been navigating.

Sometimes people tell me that my writing can be heavy and somewhat depressing, and I take this feedback seriously because at the heart of it, I have always been interested in revealing the truth of what life is really about. And life is very much about the hard moments.

At the same time, I can see where these people are coming from. It is in this vein that I recall something I once read:

What’s surprising to me—this is something that comes from society—is that we think of younger people as wild and free and open and interesting. Many times, it is exactly the opposite. Younger people can be heavy, taking everything so seriously. While sometimes older people are freer. They definitely have more of a sense of humor and lightness about things.

Elinor Carucci, This is (Almost) 53: Fine Art Photographer Elinor Carucci Responds to The Oldster Magazine Questionnaire

This is not to say that I intend to pivot into writing only happy things, but that I too am trying to find that balance where we can look squarely in the face of life's anguish and still discover in it the gifts of freedom, joy, and becoming.

I often say that this newsletter is probably the purest and most authentic expression of who I am. When I am writing this I am not trying to impress anyone, to seek any kind of validation, or to optimise for certain material outcomes.

But I am also reminded that this newsletter is really just a window into what my life is like on the inside. Looking at my life as a whole, there are spaces where I am creative, disciplined, and visionary, and there are places where I am soft, stable, and yielding. I can be funny, assertive, and spontaneous, but I can also be dumb, distracted, self-righteous, reclusive, and melancholic.

As much as there are things I continue to struggle with, I no longer see life as a pointless, unjust, and endlessly gruelling expedition. Perhaps this doesn't show up as much in my writing, and I do want to find new ways to do more of that. I want my writing to ignite things in people.

And so as I continue publishing this newsletter, I think I'm aspiring to a little more honesty, a little more courage, and a little more defiance. I want to lean more into my experiences to see them for what they have been—mistakes, lessons, triumphs—and still be able to speak to the steadfast pursuit of a life worth fighting for.

To me this means writing less abstractly and more concretely on the questions of love, friendship, addiction, healing, meaningful work, and the journey towards being more alive in our existence.

It also means preserving a lot of the raw, emotional texture that I think makes my writing what it is.

On that note, I wanted to say thank you to everyone who has continued to read what I write; for those who haven't stopped paying for your subscriptions despite my inconsistency, and for those who tell me how much my work means to you. There are no words for how grateful I am and how much I appreciate the safety I've found in having my inner life witnessed by both strangers and loved ones.

Here's wishing everyone a very happy new year—may you too be held and treasured in all your beautiful human-ness.

See you at the next one 👋🏻

As always, if you want to support introspective long-form writing like mine, do consider upgrading your subscription.

There are very few places in the world where a sentiment like this just makes sense. One of those places is Jakarta.

It goes without saying that Jakarta is nothing like Singapore. In Jakarta, self-appointed traffic wardens plant themselves at congested intersections, performing a kind of waltz as they weave in and out of the chaos, halting, directing, and guiding the flow of vehicles. As cars pass them by, windows lower and drivers hand them cash, and this is how they make their living.

Some will say, thank god Singapore is more orderly and predictable.

My thoughts are that, in Singapore, when things don't work, we as individuals are rarely the first ones to try and fix anything. There is always an expectation that someone else does it first.

What do we gain from the cities we choose to live in? What do we lose in the process, that we may not even be aware of?

A few days before I arrive in Indonesia, I am running a workshop for just over 20 people. It feels like it has quite gone well, but I am too tired to fully appreciate any of it.

It begins at 7 in the evening, and while we end at 9, many stay behind to chat and hang out. This part is nice and I remember most of it. At 10 PM I start gently telling everyone we need to close up, and I pack up as quickly as I can. I'm grateful that with whatever energy I have remaining, I get to catch up with a friend as we share a cab back to our corner of the island.

I've started realising that sometimes, even when I'm exhausted, I can still, through sheer focus and willpower, summon the energy that I need to function. But the trade-off is that this kind of energy makes me feel frantic. It's sort of like getting a speed boost in Mario Kart—you go faster, but you have less control.

In this case, I can fend off the fatigue, but I am also more impatient and less present. I have more opinions, and I can forget to slow down and listen. It's been a while since I've seen this friend, so I remind myself that it is enough to just have a conversation, even if it's about nothing in particular.

How would I rather others perceive me? As someone who is sleepy and kind, or as someone who is energetic but unforgiving? This is what I think about an hour later when I'm packing—something which I have left to the last minute.

As a result, I lack the presence of mind to be strategic or meticulous. I overpack, and end up bringing stuff I don't need.

5 hours later, in a car on the way to the airport, it occurs to me how lucky I am that I get to say I overpacked. To say that I have stuff I don't need.

In other words, I already have enough. My job is to pay attention.

During the previous night's conversation, my friend comments that I am leading the jet-set life. My instinct is to laugh it off, to downplay and dismiss it. But I stop, and then a moment later, say, "This is the life I wanted, and it's slowly coming together."

These days, I feel like I am finally learning that there is no 'arriving', at least not in the way I often expect. It is more important instead to try and notice the little surprises along the way—like, for instance, the fact that things are going well.

I am now in Bandung, walking through the hills and forest surrounding Kampung Cireundeu. Because this area is considered sacred ground by the local villagers, shoes are not allowed. And so I am walking barefoot.

It's amazing how quickly you can go from fear to acceptance when you simply surrender to what is happening. Later, our host comments that I look so comfortable, it's as though I've been doing this for years.

In a way, it feels like I have. Somewhere in my body, I am recalling a sensation. It feels new, yet also like it has been there since forever. It feels like a vastness and also a kind of lightness.

With each step, I scan for both danger and support. There is no room for anything else in my mind, and I have no choice but to trust that wherever I choose to step, it will be okay.

On certain stretches of the path, there are small rocks, broken branches, and dried grass that is both scratchy and slippery. As we head into the late morning, the ground begins to warm. At certain points, it's not possible at all to stop moving. Stop, and your feet will be scorched.

This is not, by any means, a relaxing stroll. We start going downhill, and some steps I take actually hurt. Yet it does not help to be too careful. If you are too careful and do not commit to gripping the earth with your feet, that is how you lose your balance.

I don't know if this is a strange thing to say, but I have not always been aware of having a body. When I'm walking barefoot on the earth, conscious of every step that I'm taking, I begin to remember.

Joseph Campbell, the author who wrote The Hero With A Thousand Faces, said that we are not seeking the meaning of life. Instead, what we're really seeking is the experience of being alive.

I feel like maybe I'm starting to understand what this means. Only on two other occasions have I felt this way: the time I went surfing, and whenever I worked as a barista, had great colleagues on shift, and everyone knew exactly what to do without a single word needing to be exchanged.

It is the sensation of being fully present, and of being carried by something invisible. I am moving my feet against the earth, but the earth is also moving me.

As always, if you want to support introspective long-form writing like mine, do consider upgrading your subscription.

To talk about friendship and relationships in general is to try and make sense of the difference between allowing, accepting, and witnessing.

Parenting, as most of us likely know it (including our parents themselves), is a lot of allowing and accepting. Allowing always contains some degree of reluctance, and it begins when parents realise how little control they really have over what their children do or who they become. If we are lucky, this matures into acceptance—"Fine, this is who you are, and I accept that."

Acceptance approximates love because it implies an embracing of wholeness. For instance, you are rarely just accepting someone else's behaviour, you often have to concurrently accept your own part in it, that this person behaved in a way that you did not want them to.

Romantic love is a lot of early witnessing that gradually settles into an ongoing negotiation between accepting and allowing. We go from, "Wow you are amazing, I want to be around you all the time," to the back and forth between "I don't know why you're like this but I accept it because I love you," and "I would rather you not do that but we love each other/are married so fine, I'll allow it."

This is the arc of love that we don't talk about as much. I had a separate reflection on this recently: in love we seek safety and security, and in finding it we can begin to settle into a kind of self-forgetting, where there's no longer an urgency to strive, grow, impress, and in each other's eyes we become a little less radiant.

I'm not saying this happens all the time, but I do see it a lot, and I hear it a lot in the stories others share with me in confidence.

Romantic partnership, on the other hand, is mostly accepting and witnessing. To use some of today's popular parlance—if romantic love is the pursuit and/or failure of attachment, then partnership is what I like to think of as a more spiritual assignment.

Love is, by its very nature, self-referencing. Partnership, on the other hand, is other-referencing. And I don't just mean this in the sense of 'other people', but also that it looks outwards; beyond.

It aspires towards a future ideal, and is devoted to transformation as an enduring constant, recognising that our lives will change and we will likely become very different people, but it is better when we do it together. It is concerned only with the journey, and not necessarily with arriving.

Friendship, true friendship, in my opinion, is the purest form of this. It is pure witnessing—what the poet and activist Andrea Gibson describes as constantly seeing the people you know as mysteries, which to me means never assuming you know everything about them, being committed to the ever-ongoing process of their gradual unfolding, and therefore greeting every interaction with forgiveness and curiosity.

Witnessing then, must be a kind of letting go. It is saying, "I never expected anything of you to begin with. Wow, I never knew that about you. That is so interesting. Tell me more. Do you want to get coffee?"

It is saying and doing that over and over again until one of us dies.

Witnessing reminds me that so much of our lives can be lived in a state of tension. Where everything we do carries with it an unconscious fixation on optimal outcomes—is it going to be this or that? Will it work or not? Am I going to fail or succeed?

This is why parental and romantic relationships often feel so high stakes. There is always an underlying fear—if I do this/ask for this, will I be validated or rejected? Will I still be loved or will my significance in this person's life begin to diminish?

In friendship we hope we never have to ask or even contemplate these questions. We are safe in the knowledge that we can show up imperfectly.

So I am adrift in the ocean, and eventually I realise that to ask this question—what is friendship for?—is to assume that all things in life can be quantified in some way. As though all things can be isolated, assigned a value, and then judged on its merit of whether it is worth fighting for.

After all, if something cannot be quantified, why pursue it?

Yet I think this is precisely the point. It is not wrong for me to say that if I'm alone, I do not need to coordinate plans, and I do not need to account for the needs of others. This is good, and there are days when I will both want and need to live like this.

But friendship reminds me that I do not always need a good reason.

I just know that there are people with whom, like when I'm out at sea, I feel peaceful, honest, and connected; I feel fully human and alive. Is that not enough?

And the truth is, like my friends always say, "When we have more people, we can order more food."

Announcements

Coincidentally, my friend Ee Chien and I are running a paid event at the end of December, loosely themed around the topic of building and sustaining friendships in adulthood. This run is specifically catered to guys, so if you or someone you know might be interested, please don’t hesitate to drop me a note and I’ll reserve you a spot. We are finalising details and will be doing a public launch very soon.

That’s all for now. A very warm hello and welcome to all of you who subscribed in the last week or so. I love hearing from my readers, so if you feel like it, hit reply and share with me your thoughts on my writing!

See you at the next one 👋🏻

As always, if you want to support thoughtful, meandering, long-form writing like mine, you can also consider upgrading your subscription.

For a while now I've had an idea for a short story. Here are the broad plot points that describe what hopefully happens:

• A character in the story mysteriously disappears, leaving behind a note telling everyone they've ever known to not come looking for them

• All of this person's closed loved ones refuse to accept this reality. How could someone like that do something like this? This character was loved and respected, a pillar of their community, someone who seemed to have all their shit together. No one understands, and they all feel that they must understand

• As they begin seeking answers, an AI startup launches a product that promises to "explain life's greatest mysteries with AI". Basically: feed it enough information from enough different perspectives, and it will stitch everything together, analyse it, and distill the truth about what really happened

• They agree to try this service, and after some bickering over how to split the $15/month subscription fee, they individually take turns to visit the startup's offices, meeting with a robot/computer screen thing to dictate their respective theories and frustrations. Everyone gets their chance to tell their side of the story and to ask the questions they want answers to.

• This AI startup promises a 7-day turnaround, but on the 7th day, it announces that it has run out of funding. All customer data disappears, offices are shuttered, the startup’s founder vanishes, and chaos ensues.

• For this character's closed loved ones, this is yet again another unacceptable reality. And so they each individually embark on their own journeys—perhaps one attempts to hunt down the AI startup's founder, another takes to social media to lament what happened, another starts blaming everyone else, and so on.

As of this moment, I haven’t quite decided how this short story ends.

There are a few ideas that I'm playing with, but on the whole this concept still feels a little trite, like it's better off existing as a fun thought in my head than an actual, published piece of prose.

I am not a religious person, but I love this thing that was allegedly said by the road manager of the rock band AC/DC: "God is the name of the blanket we throw over mystery to give it shape."

When I first heard this quote, it reminded me of the TV series Dark Matter, where a physicist discovers a way for humans to access and navigate countless parallel realities where they can locate versions of themselves who have lived out different lives. To do this, one enters a box and injects themselves with a serum, which then transforms the box into an endless hallway with doors that open to said parallel realities.

The physicist explains this phenomenon by describing how the human brain has not sufficiently evolved to visualise four-dimensional space. And so the 'hallway' is simply what we project in order for our minds to make sense of it.

All this to say that when I was recently home on a Saturday afternoon, drinking coffee and contemplating a nap, a thought suddenly came to me that I was wasting my life.

One moment I was perfectly peaceful, looking out the window and staring at trees, and the next, I found myself wondering: Should I be doing something more significant with my time? Should I be having more fun? Spinning up a new project?

Should I be doing something?

At first this surfaced as a kind of muted restlessness. A prickle of nervous energy dancing across my skin. Then it began to swell. It began to grow feet and arms and tentacles; eventually the feet began to stretch, planting themselves in the floor of my gut as the tentacles slowly wound their way up my spine and around the base of my neck.

And it occurred to me that I did not like this. Which was new.

Because more often than not I would have gotten up, abandoned my coffee, and started busying myself with something. I wouldn’t have stopped to notice.

As I slowly shifted my attention back into where I actually was, I realised: Everything is fine, nothing is actually happening. I am just a human being lounging in a chair. Everything is fine.

In fact, it’s kind of amazing.

These days, I am learning again to be fascinated by my own mind.

This is as opposed to feeling trapped by it, feeling like I need to fully comprehend it, or that I need to tame and apprehend it and coerce it into behaving exactly as I want it to.

If I had to describe my relationship with my mind, 'fascination' is not the kind of language I would typically use. Instead, my mind typically feels like something that needs to be appeased, comforted, and negotiated with. These are all things that feel heavy, demanding, unreasonable.

Fascination, on the other hand, has a different texture. It has a lightness to it, and it encourages me to step back. To observe and describe, rather than analyse and judge. It reminds me of how art historian Jennifer Roberts requires her students to spend a "painfully long time" looking at a single painting.

She describes her own experience doing this, referring to the painting Boy With a Squirrel by artist John Singleton Copley:

It took me nine minutes to notice that the shape of the boy’s ear precisely echoes that of the ruff along the squirrel’s belly—and that Copley was making some kind of connection between the animal and the human body and the sensory capacities of each. It was 21 minutes before I registered the fact that the fingers holding the chain exactly span the diameter of the water glass beneath them. It took a good 45 minutes before I realized that the seemingly random folds and wrinkles in the background curtain are actually perfect copies of the shapes of the boy’s ear and eye, as if Copley had imagined those sensory organs distributing or imprinting themselves on the surface behind him.

This is what fascination feels like to me. With fascination there is more humour and forgiveness, and yet it is not the kind of relationship I've always had with my own mind.

And as I'm learning to work with this, this is where I seem to find myself landing. It might sound somewhat stupid, but I'm just going to say it:

Sometimes, we need to allow mysteries to simply be mysteries. When we expect a mystery to be anything other than mysterious, we are trying to exert control over something that, by its very nature, cannot be anything else.

Here are a few things I've been doing to nurture and re-learn what it means to be fascinated by my own mind. The goal, and the very specific thing I'm working on, is to allow myself to see things as they are, and not feel the need to explain and make sense of every life event.

1. Slow down, do fewer things, allow more space for boredom.

2. Create space to hear myself. When commuting, I try to refrain from listening to music or podcasts. I've started to notice that by always wanting to drown out the outside world, I end up drowning my inside world as well. So I think of this as a way to allow myself to wander inwardly and to simply observe what's happening there.

3. Check in with myself when I'm doing things. Do I like this? How do I feel about this? It's less about landing on an answer, and more about getting in the habit of stopping to ask.

4. Intervene less. Say fewer things in work meetings, offer fewer solutions, and discern more when my contributions are actually needed, and when I can simply let things be.

And of course, I am also taking more naps.

Announcements

1. Last week I mentioned that I’m running a retreat in November with some friends. Early bird pricing ends in 3 days, so if this is something you might be interested in, do consider signing up!

2. I’ve also launched sign-ups for the journalling workshop I’m running under RICE Media’s community events programming. I’m quite excited about this because it’s really more than just a standalone workshop—it’s part of what we’re also trying to do to grow the brand in new and meaningful ways, and to deepen the impact we can have on our community. You can sign up here.

That’s all for now. For those who subscribed to this newsletter in the past week, it’s so wonderful to have you here. Feel free to hit reply and share your thoughts on my writing!

See you at the next one 👋🏻

As always, if you want to explore working with me 1:1, you can book a time to chat with me here. And to support creative, meandering, long-form writing like mine, you can also consider upgrading your subscription.

Many years ago, in what now feels like a past life, I met a girl. We spent nearly all our time together, holding hands and having long conversations. One day, she said, "If you were to ask me to be in a relationship with you, I would say yes."

I thought that this was incredibly romantic, and believed the sentiment alone to be enough. I cradled it in my mind, observing and fiddling with it as one might a pen or a toy with restless fingers. Unbeknownst to me, a gradual unwinding had commenced in the background.

We started spending less time together. Being the teenagers that we were, we never talked about it. Eventually we drifted apart, and for months after I couldn't stop wondering what had gone wrong.

Looking back now, it's obvious what happened. And it's also very clear to me that this was not a story about love or teenage romance. Instead, this was a story about how, if we don't make our own choices in life, life will make them for us.

I am thinking about how we did not grieve such events back then—we simply accepted and internalised. As an adult, I now understand that in the absence of truth and information, we all create stories, beliefs, and hypotheses about how the world works.

The formula is simple: reality = confusion + time.

I think that our lives have a way of knowing when we are choosing to live with one foot in safety and the other in limbo, and we will be reminded of this until we are ready to start doing differently.

In Emily P. Freeman's new book, she coins the term 'liminal hallways'—non-spaces that we languish in because of choices that we are not making, where we experience the events of our lives not with consciousness or with resolve, but with a kind of helplessness. And because of this, we are neither 'here' nor 'there'. Instead, we are stuck, and we somehow believe this to be destiny.

A couple of months back, I found myself in a space where despite seeing that there were many things happening in my life, I felt tired and lost.

I was having lots of fun dabbling in projects, yet I couldn't shake this concurrent feeling like I was out at sea; on one hand it felt pleasant and free, on the other I also felt directionless. Each day I would go to meetings or do little things here and there, always planning or exploring and not really doing or accomplishing much, and the whole time I would be aware of a fist tightening in the pit of my stomach, reminding me that this was somehow not it.

My life was telling me that I was stuck. I was bobbing along, and occasionally a wave would nudge me this way or that. But I was not taking control of where I wanted to go. It's funny reading what I wrote 2 months ago and realising that what felt like clarity then looks like chaos today. So much gets left out of the story when we are trying to make sense of things.

Then I woke up one morning, and from what remained of a dream, an image surfaced in my mind. I saw a camper van on a road trip across rural Japan. Partner, kids, 2 dogs.

On hindsight, I can rationalise how this happened. There had been a recent conversation with a friend, and just that night before I had read an article that made me realise the goal of my life is to find the right projects to build and nurture, whether it is family, my social circle, or the good I want to create in the world.

None of this made the image any less visceral. I lay in bed that morning smelling grass and rain and hand-ground coffee beans, daydreaming about endless driving.

Never mind that all of this was purely imaginary. It occurred to me that when I was younger I spent so much time looking for significance and an abstract inner knowing that I was living a life that mattered. As a result, I never quite knew what I was looking for.

This image, on the other hand, was real enough. And the only question I asked as I climbed out of bed that day was, "What do I need to do to make this happen?"

The thing about commitment is that it has to be specific.

You cannot simply commit to a direction, in the sense that you cannot commit to 'figuring out your life' or 'seeing what happens'. Instead, you have to commit to actions, responsibilities, defined areas of work, and it is in the process of pursuing these things and holding yourself accountable that you will figure out your life.

I recently shared a professional update on what this currently looks like for me, and I am very much still in the process of living out this path and refining it even as I am navigating it. But what was genuinely surprising was that as I committed in such a public way to what is now a much clearer vision of what I want my life to look like, I felt, for the first time, that I was finally taking myself seriously.

It's not that I've previously lacked seriousness. Rather, it's that I've become aware that for much of my life I have simply stumbled into things. Whether they were jobs, relationships, or life circumstances, many were decisions I had wandered into because they happened to be there and felt like the safest or easiest paths to take.

Some of these turned out to be wonderful, beautiful experiences. But just because they were good and important did not mean that I had always consciously chosen them.

I think that commitment is scary because we don't just commit to actions. We commit also to consequences, because by choosing a path to take we choose also the paths to sever ourselves from.

In a sense, life must narrow and shrink before it can expand. In order to enter a room, we must necessarily leave another and close the door behind us.

The thing is, we have to leave. Often, we don't do this; we just remain long enough to watch the room crumble around us, wondering what went wrong.

And this is what I realised: Sometimes I will refuse to make a decision despite having a hope or an expectation of a certain outcome. Yet when things don't go according to plan, I end up feeling wronged, like it was somehow unfair.

I realised that in order to be at peace with the outcome, regardless of whether it is the outcome I'm hoping for, I have to make a choice. It is in choosing and committing that we stand up for ourselves and the life we want to have. Ultimately, this is what matters.

When we resist choosing something, it is usually because we have a belief about how reality must work.

Often, it is a narrative about how we are not worthy of it, that we are ‘not ready’ or ‘not good enough’. Sometimes, it can be because we fear getting and then losing it, but this also comes back to the belief that if we lose this good thing then it would prove that we did not deserve it in the first place.

I've seen this many times in both myself and some of the individuals I work with.

A person will literally earn the job/opportunity/recognition they deserve, but because they believe they have somehow not ‘earned’ it, they continue to behave in ways that are constrained and timid.

I remember once saying to someone, "But it has already been given to you and you are already doing it. Everyday you go to work in this job that you always thought you deserved, yet you still behave as though you need permission to do what you think is right."

But what if we are already in possession of the lives we are meant to be living? And there is no longer a question about whether we are deserving?

What is the hard work we would now need to put in to live up to this responsibility? How would we make ourselves proud?

I saw the image of road trip and the camper van and the 2 dogs, and I asked myself these questions. As I began piecing together the answers, I saw a path emerge and I knew that I could not keep exploring and waiting. Instead, I had to commit—both to what would remain and what could not.

A note

A big thank you to all of you lovely people who subscribe to this newsletter. I took a bit of a break because I was figuring some stuff out—some of which I tried to capture in this week's issue.

I am truly grateful that none of you cancelled your paid subscriptions during this time, and in fact I've welcomed many new readers over the last 2 months. Hopefully, as things begin to connect and get clearer for me, I'll be back to publishing regularly again.

For now, some quick additional things:

• I will be running a couple of upcoming events.

  • The first is a retreat in November that I’ve organised with some friends. Our focus is to help tired individuals move out of their thinking and feeling patterns, and get back in touch with their physical bodies. You can find out more about this here.

  • The second is a journalling workshop in around mid-October. Details are being finalised, but if you would be keen to attend something like this, drop me a note and I will personally drop you the sign-up link when we launch!

• As I continue to pursue my professional certification in the Enneagram, I am looking to work with a small number of individuals on a 1-1 basis. If you are interested in exploring this with me or just curious about what it might entail, let me know.

That’s all for now, I’ll see you at the next one 👋🏻

But I’ve found myself really thinking only about one thing. It’s nothing particularly weighty or complex, but it was significant in that I did not know this was something it was possible to experience until I experienced myself experiencing it.

As I've written about before, the last year of my life has been all about navigating big changes. Along the way, there have been moments when I've found find myself subconsciously seeking anchor, even when there was nothing to anchor myself to.

By this, I mean that I was looking for signs that would tell me I was on the right track, that I could finally exhale and feel secure and know that I had arrived, and that from here on out, things would only get better and less uncertain.

This realisation that I was anchor seeking would surface typically when I was dealing with something frustrating or disappointing. I would catch myself feeling uncharacteristically upset about something that hadn't seemed like such a big deal, only to realise later that, oh, I was really hoping that thing would work out a certain way, because I believed it would lead to other things which would then give me the feedback I needed to know I’m finally doing well.

Sometimes these were potential collaborators or clients I was looking forward to working with, sometimes they were opportunities be a part of certain projects. As each one failed to materialise, I would find myself losing a little more hope.

Yet over the last few months, as things have shifted in form and potential, it started getting so much easier to let things flow in and out of my life.

As I'm writing this, I am actively working on 9 different projects (or work streams, as they like to call it in the Singapore government). I am busier than ever, but I am also enjoying myself tremendously and working with people that I really like being around.

One other thing which has really surprised me is that I no longer want to do things alone. Many of these projects didn't start as things I wanted to do—they started because people came to me with ideas, I saw what these ideas could become, and they resonated with what I thought was possible.

This has, in fact, always been a pattern in my life, and it is one that I am now consciously leaning into. It was very much the case with Rice Media; it was not originally my plan to start it, but it wouldn't be what it is today if not for the vision and the creative energy I brought to it.

Now, I no longer put so much pressure on myself to be original and to be constantly coming up with new ideas for projects. I just focus on what I'm already doing, and I try to be around people that I like and who help me understand what my experiences are worth.

But I realised I was only able to get to this point because I allowed things to flow out of my life. Whether they were potential projects or partners, it has gotten so much easier to know when something is no longer worth striving for. And as things leave, there is again space for others to enter.

A friend who is now turning into a business partner recently said to me, "We don't need to rush or have big dreams, we just need to know what we're going to do next."

This was so powerful because it helped me to see that at this point in my career, I have done and failed enough to know that I can trust myself to generally make the right decisions. I know when something is worth committing to, I aim to do things to a high standard without cutting corners, and I understand that it's really about being someone of purpose and creating things that have genuine value to others.

When this is my foundation, perhaps there is no need to lose so much sleep over long term strategies and competitive advantages and total addressable markets. I can just focus on the principles that will always matter, and keep taking the next right step.

Sometimes, I still don't know what the right step is. But it has gotten much clearer to me when I'm about to take the wrong one, and it's hard to describe, but it surfaces as a kind of sticky, sludgy inner sensation, like I'm slightly disgusted with myself, or that I finally see how I'm about to sacrifice some degree of self-respect by convincing myself I still want something that very clearly is not right for me.

This is not really a new experience. What is new is that I am actually paying attention and allowing myself to feel it when it happens. In the past I would try to think my way out of it by inventing arguments and strategies and stories in which I saw myself persisting and emerging victorious.

I don't have the energy for such nonsense anymore.

I don’t because I now know that the heart of it, really, is that I don't want to be wrong. I don't want to make bets on people and opportunities and realise only much later how completely off the mark I was.

And so the final thing that has really helped is asking myself if I chose wrongly, or if I simply had incomplete information. Sometimes I do make bad decisions; I get distracted by short term incentives or the promise of prestige, and I push harder than is needed to try and bring a project to life.

But sometimes, I simply made the best decision I could with the information I had at the time. Recognising this has made it so much easier to then let things go, to acknowledge that I didn't make a mistake—I was simply learning. And this helps me release the need to prove to myself that I was right, because I was never wrong in the first place.

So as some things have closed and others have opened up, I find myself measuring success by a new metric. Previously, I used to think: I need to know what the goal is, I need to know exactly what the next few steps in the plan are. Now, I think: can I see myself doing this for a long time to come? If yes, keep going.

When I orient towards this, I bump into more people who value what I do, there are more projects that I’m excited about and willing to embrace discomfort for, and the money takes care of itself.

This is good enough for now. Let’s see where we are again when Q3 rolls around.

PS. A very warm hello and welcome to everyone who’s newly subscribed to this newsletter. If you would like to know more about me and my story, this is a good place to start.

And while I know that it sounds like I’m quite busy, I am actually still looking to take on 2 additional coaching clients in the coming months. If you’d like to work with me, please don’t hesitate to get in touch.

Take care for now, and I’ll see you at the next one 👋🏻

So this week’s newsletter comes to you in three separate but connected threads. I quite enjoyed writing it this way, and may do it more often.

1

If someone were to ask, "How do you do things?", my answer would be, "By myself."

I imagine other people might say things like, "To the best of my ability," or, "With enthusiasm."

Perhaps a smart-ass might say, "Reluctantly."

I was recently labouring through a pile of ironing when realised that I—by default—am always imagining myself as a singular entity. This is despite the fact that I have always wished I was closer to others, whether it's friends, family, or the people I work with. This is despite my deep belief that connection and community are core to living a meaningful life.

I started thinking about this because someone recently asked me if I would be keen to work on something together. As the question surfaced, I felt a fear rising from my gut and constricting in my throat.

I was curious about this, because there was literally a person in front of me, saying, "Would you like to do this with me?"

And all I could think of was, "Shit, what if I'm not able to make this succeed?"

As though this was something I had been asked to do on my own.

2

There is a specific childhood memory that returns to me from time to time. Whether or not this actually happened, I cannot say. But the details are always the same.

I am in kindergarten, and I am sitting at the back of the class. In my mind, I am just minding my own business. Existing. Out of nowhere, the teacher calls on me to do something for my classmates—they need help arranging some chairs in the right order; try as they might, they just can't seem to do it correctly.

Suddenly, I'm annoyed. I'm annoyed because, in this memory, arranging the chairs in the right order is something I've showed my classmates over and over again. In dramatic, child-like fashion, I roll my eyes, get up, arrange the chairs for them, and mumble under my breath, "... So irritating."

Again, I'm not entirely sure that this really happened. But many moments in my life have felt this way: that others just don't get how the chairs are supposed to be arranged, and I'm annoyed that I always have to be the one to fix it.

Nothing about this narrative is true of course. It is just what I internalised and accepted for as long as I can remember.

As I've become more aware of this, I've begun to notice how this has shaped the ways in which I resist help and invitations. People will ask me what I need or how they can support me, and I'll say, "I'll let you know," and never get back to them.

I used to think that this was about self-reliance, and that it was because I believed I had to do everything myself. Only much later did I realise this was about trust; that I have a hard time trusting others to do things the way I want them to be done. I simply don't want to risk having others fall short of my expectations.

On the flip side, when I do decide to trust others, I expect them to be perfect—to know what I'm thinking and to see the world exactly as I do. Which is silly, because we will all disappoint each other eventually, and the point is not to be perfect. The point is to keep building, repairing, negotiating.

Relationships, I'm learning, are not about arriving at a thing and realising that you are happy. We like to talk about 'finding love', but when I think of how relationships are fundamentally about a kind of striving towards, and about having the courage to keep going, then I wonder if perhaps love is not something to be found. Instead, love is what finds us along the way.

Maybe this is something my childhood self did not understand—it was never about getting it right or fixing anything. It was just about helping.

As an adult, I now also understand that it is not always other people who are the problem. Sometimes and often, the problem is me. The good news is that I can't change other people, but I can change myself.

3

Two individuals and their stories have been on my mind for the past week. In the first, they went through a divorce and lost not just their spouse but also their entire social circle. In the second, they lost their job and not just their income, but also their entire sense of identity and life's purpose.

Because of the work that I do, it can be easy to think that what these people need is help. They need coaching, individualised support, reflection, and to take powerful action to create change and rebuild their lives. The more I think about this, the more it doesn't seem quite right.

Of course we are each responsible for our own lives, but there is also something happening on a societal level that is leading to a kind of deep disconnection many people seem to be facing.

Recently, I had flashback to what life was like when I still worked in tech: every day was a confusion of Slack messages and back-to-back meetings, with the actual work squeezed into the gaps between. I had to execute things at an operational level, but also plan strategy, gather data, break things down to first-principles, all while trying to practise empathy and active listening when engaging with others.

So much of modern work looks like that these days, and we are constantly distracted, over-stimulated, and rushing from one thing to the next. It's no wonder people just want to order in, doom-scroll, and zone out to Netflix at the end of a long day. All while feeling we should be doing more to pursue personal growth.

It made me think about whether we need more discipline and motivation, or whether what we really need is a new vision for modern life. Where it's not just about scale and quantity and more more more, but also about going deep and slowing/scaling down.

What might that look like?

Or to ask the question differently: do we need more therapy, or do we need more hobbies (and the time to do them, and people to do them with)?

4

Not a thread but a quote. I just finished Gabrielle Zevin's The Storied Life of A. J. Fikry and loved it. I have not felt this way about a book for a long time; when I finished it, it felt as though something inside me shifted, realigned, clicked back into place.

The last time I felt this way, it was right after surfing and indomie, and I was wrapped in a towel on the beach in Bali. I had been freezing the whole time I was in the sea, and was finally warm again after some food and laughter. There was a moment amidst all the activity—I felt the wind on my face, the toasty prickliness on my skin as the salt water evaporated—when I exhaled and it was suddenly clear to me what mattered.

I'm a little peeved that this novel didn't get quite as much attention as Tomorrow, and Tomorrow, and Tomorrow, but perhaps this also makes the book a little more special to me.

Anyhow, this seems like a good place to end on:

"It is the secret fear that we are unlovable that isolates us, but it is only because we are isolated that we think we are unlovable ... Someday, you do not know when, you will be driving down a road. And someday, you do not know when, he, or indeed she, will be there. You will be loved because for the first time in your life, you will truly not be alone. You will have chosen to not be alone."

— The Storied Life of A. J. Fikry, Gabrielle Zevin

I’ll see you at the next one 👋🏻

I have always had a disproportionate affection for airports. Specifically, it is the airport routine of any travel itinerary that I find myself looking forward to almost more than anything else.

I know I have to check in online, and that I have to be there 2.5 hours before my flight leaves. I know exactly where to print my boarding pass, and how to find my way to the departure terminal. Everything works as it should.

Of course, this isn't entirely true. Familiarity with these procedures doesn't mean that things can't go wrong.

For many years, the airport checking in process was a huge source of anxiety. Because the input fields when you purchase your ticket online are often formatted for Western names, there would inevitably be a technical discrepancy with my official identification (where my Chinese name precedes my English one). That my name contains a comma only further complicated things, and on more than one occasion I've actually had to fork out money to rectify this.

Yet when I think of airports, I recall only the predictability and the slow, languid coffee that I usually have time for while waiting to board. This is despite multiple experiences of airports so crowded that being 3 hours early did not prevent me from barely making it to my boarding gate on time.

When I was recently in Tokyo, I woke up one morning to the jarring squawk of the Earthquake Early Warning blaring from my phone. Upon googling what one should do in such situations, and reading the advice to seek shelter and keep my head covered, I thought this sounded like a perfectly good reason to go back to sleep.

And so I pulled the sheets over my head, and promptly did just that. It was 6:30 in the morning after all.

Later on, however, I couldn't help thinking—what if things had turned out differently?

Advancements in technology and building construction mean that we are safer than ever during events like this. In fact, you should want to be in a taller building rather than a shorter one during an earthquake.

But does this mean that there is no danger? Or is life simply more manageable when we believe that we are not perpetually at risk of death or permanent disability due to bad luck and happenstance?

Just this year on January 1st, the earthquake that struck Japan's Noto Peninsula left 260 casualties. There are still people missing; over 3300 residents remain evacuated, and the region is still recovering from the structural damages sustained.

These things can and do happen. Maybe they don't happen to all of us all of the time, but they do happen.

Every once in a while, when I'm working with a coaching client, they'll start noticing that even though their lives are improving, they still find themselves wrestling with difficult emotions or unhealthy thinking patterns.

Sometimes, they'll ask: "When does it stop?"

This question can surface in various forms, but it is always kinda sorta about the same thing.

• How can I get rid of my desire?

• How do I never feel fear/anger/sadness/envy ever again?

• When will I stop needing validation from others?

In other words, what do I need to do so I never ever have to suffer again?

I never have the right answer, because in every case what they are hoping I will say is that these are the exact steps you need to follow. Do this and that and this, and it will stop.

"Honestly, I too wish that life worked like this," I usually say, and we have a good laugh about it.

We laugh because it is so human to want life to be like this, but deep down we also understand that the goal of working on our shit is not so we will never feel pain or suffering ever again.

The reality is also that the older we get, the heavier life becomes. There is more joy, but also more loss. More to look forward to, but also more that we are no longer in control of.

We cannot run away from the fact that we are all seeking security—for some of us this looks like meeting our material needs, for others it could be about surrounding ourselves with people we love (and who love us back), or about achieving things that tell us we are worth something in this world.

Yet my own life has also taught me that even though there are many things I can do to shape and influence my environment, I cannot fundamentally control what happens.

So what then, is the goal? What can we hope to seek security in?

Tara Brach, in her book Radical Acceptance, talks about the concept of meeting our experiences with ‘unconditional friendliness’. She says:

Instead of turning our jealous thoughts or angry feelings into the enemy, we pay attention in a way that enables us to recognize and touch any experience with care. Nothing is wrong—whatever is happening is just “real life.”

This made me think about how our need to control the content of our outer lives often reflects our need to control something within ourselves.

So perhaps instead of seeking security in building fences, avoiding risk, playing small, or conversely, in seeking status or accumulating excess, we should aim to seek it in ourselves: in having confidence that no matter what happens, we'll figure it out; in learning how to ask for help and rely on others; in accepting that life is hard but realising that we are capable.

I don't think we will ever stop doing what we need to do to survive and to trudge on in the face of life's shocks and disappointments. But I do think we owe it to ourselves to see our lives as they are and to be honest about what is happening.

I may not have died in an earthquake, but for a few days after, I kept feeling pulled to questions about how I've been using my time. Have I been restricting or expanding my life? What more do I want to lean fearlessly into?

I am reminded of a scene from the movie Annie Hall, where the young protagonist Alvy is sitting in a doctor's office.

Next to him, his mother laments, "All of a sudden he's depressed! He can't do anything!"

When the doctor asks why, Alvy answers, "The universe is expanding. If the universe is expanding, one day it will break apart and that will be the end of everything."

"What is that your business???" his mother retorts. To the doctor, she exclaims, "He's stopped doing his homework!"

In response, Alvy mutters, "What's the point?"

It's hilarious to watch, and also very poignant because I think there is a little bit of all of us in this child wrestling with overwhelming questions about the nature of life and the universe. But this scene also unearths a particular truth, which is that the stories we choose to tell ourselves are often what shape the texture and trajectory of our lives.

Later in the same scene, Alvy's mother says, "You are here in Brooklyn! Brooklyn is not expanding!"

"It won't be expanding for billions of years! Why don't we try to enjoy ourselves while we're here, huh? Huh?" the doctor adds.

The adults are condescending and dismissive, but they're not wrong.

If we choose to tell stories about tragedy and hopelessness, then it becomes easy to be cynical, to believe that we have little agency over the events of our lives.

If we choose to tell stories about hope and tenacity, then it becomes easier to see life as a constant unfolding of possibility and opportunity.

"Life shrinks or expands in proportion to one's courage," as Anais Nin writes in her journals.

As always, if you are keen to work with me, don’t hesitate to get in touch.

For 5 days this week, I logged on to Zoom each night from 11 PM to 6 AM for a series of live webinars that are part of the Enneagram professional certification programme I’m pursuing.

I initially had this grand plan to acclimatise to Pacific Time, which is where the instructors are based. I told myself I would start a day early, going to bed in the afternoon, waking up at 10 PM, and establishing that as the 'start' of my day. My body clock would then adjust accordingly—or so I assumed.

Unsurprisingly, I wasn't sleepy at all when that first afternoon came around. I ended up squeezing in a nap from around 7 to 10 PM, and then suffered through day 1 of the course before crawling into bed at 6 AM. After waking up a few hours later, I groggily muddled through the day, and found myself crashing in the early afternoon.

I realised very quickly that I thought all this out quite poorly. By day 2, I was floating outside of my body, experiencing a strangely comforting weightlessness.

As I've written about before, I am typically hopeless at listening to what my body needs. But this time, I figured I would just go with the flow. I would sleep when I needed to, work where I could, and prioritise being fully present for those 7 hours each day.

I ended up getting a nice routine going: from days 3-5, I slept from 6 AM-12 PM, took a nap in the late afternoon, went for a run at 9 PM, then logged into Zoom at 11 PM.

Before I knew it, I was transitioning back into GMT +8, which also explains why this week's newsletter is in point form—I am still very sleepy and it was much easier to write this way.

So some quick thoughts from 5 days of learning to work with the Enneagram:

• Spending this much time with 30 people from 11 countries reminded me that we are all more alike than we realise. I think that we are the most human when we are telling our stories, and it is such a surreal experience listening to people who look nothing like you describing experiences that make you feel like surely they must have lived a version of your existence. When I was younger, this would have made me feel less special. These days, it gives me hope that I might yet live a decent life.

• Many of us find ourselves attracted to personality typing systems because it is a way to know who we are. But this shouldn't become a quest to justify oneself—the goal is not to say, "This is who I am, therefore I am like this." Instead, the goal is to use these systems first as a way to see the box that we're in, then as a map to find the way out. It's about bringing awareness to all our automatic/mechanical reactions, and seeking to identifying less with them in order to live more freely.

• Through this, we can begin to see how our personalities developed to help us stay safe from experiences that confused us, left us feeling helpless, or that deprived us of love and connection. It's almost as though we are all walking around in adult body mecha suits that serve as armour to defend against never having to ever feel these things again; our weapons are the things we avoid, the habits we lean on, or the false selves that we temporarily inhabit to get our needs met.

• We are also different in ways that never cease to surprise me. Take the example of people who exhibit perfectionist tendencies. While all of them might look like a perfectionist, Person A may actually be striving to do things perfectly, while Person B wants to be perfect, and Person C wants to look perfect to others, and Person D fears that doing anything less than perfectly will make them feel incompetent. Actions that look indistinguishable from the outside can be motivated by entirely different things.

• Which made me realise that while it is fun and intellectually invigorating to understand human nature through so many new dimensions, this has also been about cultivating compassion and appreciation for the human experience. My new mantra when it comes to people who annoy me is, "I don't like what this person is doing, but they probably have a really good reason for it. I wonder how they were hurt when they were growing up."

• For me this is powerful because I am also learning that we don't see people as they are. We see them as we are. We are always telling stories about what is going on with others or why something happened because we believe, perhaps unconsciously, that these stories are preferable to reality. In this sense, the 9 types of the Enneagram really describe the 9 universal ways in which we have all learnt to stay safe in the world.

• I used to think that growth, accomplishment, and meaning could be found in seeing what others had, and then doing what I had to do to gain those same things. But the more I do this work, the more I realise that it's about coming back to yourself. I find myself asking questions like, "Who was I before I was afraid? Who was I when I never used to second guess anything I wanted to do?"

If you are interested in learning more about your Enneagram type, there are free tests you can take, but I highly recommend this paid one from the academy I'm studying with. I think it's more accurate, and it also comes with a report that describes possible growth paths.

Drop me an email if you're keen to give this a shot, and I will send you a code for 20% off. (This is not a sales pitch btw! I have genuinely found this extremely useful)

Some other things

A few of my friends are doing very cool things, so I wanted to just give them a quick shout out here.

1. A workshop on 'Navigating Your 30s', run by Nat and Chris at Our Curiosity Collective. I attended and really enjoyed their previous one, which focused on identifying your personal values. Sign up here.

2. A community for LGBTQ+ entrepreneurs called Huddle, started recently by my friend Glenn. While it's intended to help people network with one another, he's also focusing on delivering very actionable takeaways that will help participants to build more successful businesses. It's free to attend, and you can register here; you can also join their Telegram group, and feel free to share this with anyone you know who might be interested!

3. "Finding your own unconditioned path and figuring out what matters to you"—if these are words that resonate with you, Lin is putting together a self-paced workshop and a 9-week coaching programme specifically dedicated to this. Just drop her an email if you want to find out more and/or get early access.

As always, I’m continuing to share interesting things that I’m reading in the subscriber chat, so do check that out.

Otherwise, I’ll see you at the next one 👋🏻

When a reporter asked band member Don Henley if they would ever perform together again, he famously replied, "When hell freezes over."

This line would go on to become the name of the live album they recorded when, 14 long years after vowing never to do so, the band reunited.

I'm reminded of this story every time Don Henley's The Heart of the Matter pops up on my Spotify. It's usually the studio version, but I still find myself transported back to the first time I saw this played live on Hell Freezes Over. Ever since learning of the story behind this album, it's been impossible not to feel like it just hits a little bit differently, especially when he sings with his unmistakable rasp, "I think it's about ... forgiveness."

After all, while the song alludes to lost love and moving on, it is also about this. It is about forgiveness—of the other, and also of yourself.

The Eagles are not singular in choosing to do what at one point seemed insane and laughable. Other bands that have reunited after very publicly and dramatically falling out include Pink Floyd, Fleetwood Mac, Led Zeppelin, Van Halen ... and the list goes on.

Outside the world of rock and roll, we hear about this all the time in professional sports. Chalk it up to the promise of money, redemption, or just general restlessness, but it's no longer surprising when a famous athlete decides to come out of retirement.

Likewise for us, we return to jobs, hobbies, places, people. Perhaps at one point we said never again. But time passes, and maybe we learn or we forget, and choices that once seemed so unimaginable become a little less so.

And yet I still wonder: is it really okay to return to something that you once swore you were done with?

2 weeks ago, I decided to return in a part-time, consulting capacity to the company that I co-founded and ran from 2016 to 2021. I won't go into what this entails, but I wanted to unpack some of the things that were wrapped up in me making this decision.

This company was a big part of my life for a long time, and as such I had somewhat complicated feelings about the idea of working there again. By no means am I back in the job I used to do, but I'm very much aware of the baggage I still carry.

For instance, I didn’t always manage people well, and there are organisational decisions that I still think about and wish I had made differently. I also worked in an extremely unsustainable way, which these days can still make me slightly risk-averse and unwilling to commit to projects out of fear of taking on too much.

So in the month or so before I made this decision, I wrestled with a few things.

One, I kept thinking about how, for at least the last 3 years, this was a chapter of my life that I was convinced was finally closed. I told myself I was done and I was never going back.

Back in 2021, a big part of my decision to leave was that I wanted something new; to do new things and to grow in a new environment. On hindsight, perhaps I was also looking for a second chance to "do it right this time", rather than having to face, on a daily basis, all the things I knew I could still do differently and yet somehow did not have the energy or motivation for.

Sometimes, it is just so much easier to end a chapter than to try and finish the story. And as I thought about going back, I wondered if I was starting a new chapter or if I was still trying to finish the story.

Two, I kept questioning: if I'm choosing to go back, does it mean that I'm giving up on my current path and returning to an old one? Am I regressing? Is this a flight to safety?

Many good and difficult things happened during those years, and I think I've always believed that for them to have significance, they have to be memorialised—like a kind of museum exhibit to be visited but not relived.

There are many ways to talk about decisions like this. I could be neutral and simply say, "I changed my mind." Or I could call it a 'pivot', and make it feel somewhat more empowering. Or someone less compassionate might say that I 'backpedaled' on the decision that I made all those years ago.

And yet these too are just words and stories.

Eventually, this is where I landed:

I think that it is okay to return to things. Sometimes we need distance and time to clarify what we have always known to be true. Sometimes things can leave our lives, but then we change, or the thing changes, and what wasn't previously possible now is.

But while it is okay to return to something, it is also imperative that you return with a pure heart and clear intentions.

I often say that there are no good reasons to have kids, only bad ones. I think this holds true for decisions in general. Sometimes there are no good reasons to do something, but there are very obviously bad ones. Whether it is jobs, relationships, personal pursuits, etc, if we choose to pick them up again, it does help to know why.

In this case, I knew what a bad reason to return to my company would look like. It would look like treating this as an opportunity to rewrite my legacy, to clear my conscience, or because things weren't going well in other areas of my career, and I just needed something to do.

(For the record, I don’t think I made this choice for any of these reasons.)

One way to figure out who you are is to look at who you've always been. You can ask yourself: what are the patterns that have always ruled my life? And then you can say, that is who I am.

Another way to figure out who you are, which I know is the path some prefer, is to ask: who do I want to be? And then endeavour to become that version of yourself.

I'm undecided about where I stand on this second approach, but what I've found myself leaning more and more towards is simply deciding who I don't want to be. While I don't always know if I'm doing things for the right reasons, I usually know when I'm doing them for the wrong ones.

Over the last 2 weeks, as I returned to my old office and sat amongst new colleagues, I became acutely aware of how much I am no longer that person from 2020/2021. In fact, I’m not even the same person I was 12 months ago.

It made me realise that at no point in our lives do we become the person we are going to be forever.

Of course there is always the possibility that in some way, the old versions of ourselves may continue to weigh us down. But now I'm seeing that this is a choice, and not an inescapable reality.

And so these days, a lot of my choices revolve around asking, "What would me 3-5 years ago do in this situation?" And then I literally go and do the opposite of that. So far, I'm getting the sense that it might be possible to live a pretty decent life this way: by not worrying so much about what to do, and simply being clear about what not to do.

This is where I’m also learning what forgiveness really is—a practice; a constant acting on the certainty that I can continue doing differently, and that there is no need to fear returning.

PS. A big thank you to everyone who wrote in to volunteer for my experiment with coaching individuals on building a writing practice. I was hoping to work with just 3 people, but 9 of you responded, and I eventually decided I could take on 6. I am holding my remaining capacity for paid coaching work, so if you're interested to work with me in this capacity, you can reach me here.

I am also immensely grateful to those of you who signed up for paid subscriptions after my last newsletter. I was truly not expecting that to happen, and each of you really made my week.

That’s all for now, I’ll see all of you at the next one 👋🏻

It was one of those weeks where every time I sat down to try and write something, I would feel an overwhelming inertia, almost like the blood in my body had turned into concrete.

The way I write this newsletter is that I'm usually compiling snippets of ideas—bits that come to mind or experiences I find myself reflecting on—and after every newsletter gets published, I go back to this list and see what resonates. Sometimes, something completely new comes up, and I go with that instead.

None of that worked this week. Staring at my list, I felt bored and disconnected. I previously said that writing this newsletter is my way of working on myself, but what no one tells you is that working on yourself is exhausting. I get why people don't do it; I frequently still have days when I genuinely believe life would be so much easier if I just went back to being cynical and self-destructive.

But a major growth area that I've been working on has been to have more discipline, whether this is in sticking to routines or simply following through on what I've committed to doing.

So I thought I would force myself to do this anyway. I tried to take the advice I often give other writers: just write what's in front of you. Write what you can see, what you can hear, and what you can touch. Close the gap between your thoughts and your words. There is no one to impress, no goal to reach, no story to tell, and no truth to deliver. Just look, and describe.

What is that Rumi quote that gets thrown around a lot? Walk, and the path will appear.

Do that. Show up and hit publish, even if it is to say that I have nothing to say.

I've never had the best relationship with discipline. I have a theory about why, and it's that specific things came effortlessly to me when I was much younger. Academically, I wasn't the best at at math and the sciences, but I always did well in the arts, and particularly in subjects like Literature and General Paper. So while I wasn't necessarily smarter than other kids, I did always in some way feel like I was 'better' than them.

I was arrogant and complacent, and took for granted that I just needed to show up, be myself, and everything would work out. The shadow side of this was that I was often passive or indecisive. I would think that I didn't care, or that I was too good for something, when in reality I was just afraid of not getting the things I wanted to pursue.

As an adult, I now see how I developed these attitudes as defence mechanisms against specific events. But I'm also still dealing with the reverberations.

Sometimes, for instance, I will notice things in my life that I know I should take more seriously and put more effort into. Yet I would inadvertently begin to distance myself from any kind of action or resolution.

At the heart of it, I think, is my need to believe that it is enough to just be who I am in my most natural and unfiltered state.

But what I'm learning about discipline is that being yourself does not = doing nothing. Being yourself means being honest about what matters to you, and actively shaping your life so you can have those things.

Earlier this week, I got my 10th paid subscription to this newsletter. It's a milestone insofar as a single digit became a double digit, but I share this because switching on paid subscriptions was one of the few things in recent months that I was really, genuinely, terrified of doing. But I did it anyway.

I did it because I needed to understand what it means to balance both ends, to inherently believe in what I do, but also look externally to the world to give it a chance to tell me what my work is worth.

And so my thinking was: if I switch on paid subscriptions and people do pay for this newsletter, I will know that my work matters; if I switch it on and no one subscribes, I will survive it, because this is not what I need to know that my work matters. Both realities can coexist.

10 paid subscriptions is not a lot. For me, it amounts to an additional $800 in income this year.

But this week, seeing a new paid subscription was a reminder that this is what discipline has been about for me.

As I've continued on this path of being self-employed, I've tried things and seen results that I'm happy with. At the same time, I've started to feel like I should be experimenting more and getting clearer about how I want to shape and grow what I'm doing.

It's not so much that I'm feeling impatient and left behind, or that I don't trust the process. It's more that I don't think I'm giving the process enough material to work with.

I recently finished Travelers to Unimaginable Lands, a book about how dementia affects the lives of those who suffer from it, and those who care for them in turn.

I've since found myself coming back over and over again to this particular bit:

When communicating, we partially redress whatever chaos, unpredictability, and unruliness exist around us. All conversation is, in a sense, hopeful. By conversing, we create and acknowledge the possibility that clarity, meaning, and connection exist even when there appears to be only strangeness and futility.

In a similar way, the solution to feeling like I really didn't want to write this week was simply to write.

By doing and daring, we hope that life unfolds itself and that things happen. And I try to think of discipline and writing and life in the same way—that I have no right to expect any of this to be easy, but if I start, if I do something, I can perhaps make all of this a little less strange and a little less futile.

Email me!

What does it really mean to be alive?

Sometimes, when I think it's no longer possible to be surprised by the human experience or by anything in this world, something comes along that knocks me off my feet.

Earlier this week, my brother told me about this excel sheet that he shares with his girlfriend. On it, they log every game they've ever played together—whether it's a board game, console game, etc. They've logged thousands of sessions so far, and the goal, he tells me, is that when they die, the person who has won more games gets to laugh at the other.

That is what he says, but of course it is also about so much more than that.

Maybe this sounds perfectly mundane to you. Maybe this is something unremarkable that couples do when they've been together for a while and need to keep things interesting.

But it was a profound moment for me, and I was quietly overwhelmed by the thought of everything invisible and unexplainable that must have collided to become this very specific expression of love. How this combination of absurdity and playfulness may perhaps be possible only in their story, and not in anyone else's.

I have similar feelings about bluetooth technology. There are still days when I will plug my wireless earphones in—these frail pieces of plastic and aluminium, and it still blows my mind that music, MUSIC, is playing over high frequency radio waves.

I know there is science behind this. But to me, this is a supernatural phenomenon.

All this to say that I was recently listening to a podcast episode with John Fiorentino, a product inventor and entrepreneur who has bootstrapped four products to hundreds of millions of dollars. When asked about what exactly it is that he competes on, that has allowed him to find such success, he answers: “I deeply believe that magic is real.”

He goes on to say:

"You can't plan for it. The things that shape the world are these anomaly things, these events that no one ever could ever see coming. And they happen and then the entire world is different.

You can't plan for these things. And you sort of have to get to that magic by throwing out every rule and exposing yourself to this. The only rule is that there are no rules.

... Anyone who's made anything that has truly resonated with another human being, I think when I try to explain this to them, they really, really understand it because they've been there. And that's unbelievably scary because your brain immediately wants to have these rules that lead you to a specific outcome.

When you start to build something in that way, it feels really good and it makes you feel calm and secure. But I can almost guarantee that if you can quantify your plan with a certain number and a certain step, there will be no magic that emerges from that."

I was in the middle of a run when I heard this, and it made me stop.

I stopped because it made me think about how little I understand about what it really means to be alive; to exist as a human being in this world.

That we walk around in bodies made of flesh—bodies that bleed and leak and poop and fall asleep. That you can meet someone one day and just like that, they become your center of gravity. That you can eventually come to find them boring, or maybe you lose them and it literally feels like you are dying.

That something a stranger carelessly said to us 20 years ago can still be haunting us, and will likely continue to do so for another 20 years. That for some of us, joy is jumping out of airplanes, while for some of us it is taking a nap on a patch of grass.

That we can be completely ignorant of why something works until it does, and yet we are still expected to trust the process, trust the timing, and trust that hopefully, in spite of there being no guarantees, it will work.

Over the last month or so, 2 things happened.

One, I found myself wrestling with a decision. The details are not important, but it was essentially about whether or not I should accept an opportunity to do something I've already done before.

I ran it by a couple of friends, most of whom asked me incredulously, "Why do you want to go and do that again?" One friend was particularly unforgiving in their delivery, which made me hate them for a second. But it was also what I needed to hear.

Later on, another friend would ask me the question that has continued to stick: "Would that really be enough for you?"

Two, a handful of people informed me that they were leaving their current jobs to either start companies or move on to new opportunities. These all came as huge surprises because, based off our last conversations, they were not due to make these transitions until the end of this year.

"Is that sooner than expected?" I asked all of them. All said yes, and also that they just knew it was the right time. There was no big gesture from the universe, just the unconscious accumulation of thoughts and dreams now surfacing within them as an inner knowing.

So I listened to a podcast, and then these things happened, and I found myself thinking about what it means to be ambitious.

The internet tells me that being ambitious is about having goals, working hard, constantly improving oneself, being resilient, decisive, tenacious, and never settling for anything short of progress. These sound like broadly positive things, but really they are all implicitly oriented towards career success and the accumulation of status symbols.

Instead, I started thinking about magic.

I started wondering when I was last in a place where I had no idea how things worked, and yet I had fun.

Or when I was last in a conversation with someone, and I had no idea what they were going to say next, and yet I didn't want to leave.

Or when I last had no idea where my next month's salary was going to come from, and yet I was completely at peace.

I started wondering when I last felt a genuine, abounding sense of wonder at what's possible in life.

Then I started thinking about how, if the world were to end tomorrow, and I were to find myself standing there, naked and afraid, watching the sun fall out of the sky, what is it I would like to say I was ambitious about?

And I think I would want to say that I was ambitious about:

• Having many perfect days—days when I did something creative, connected with people, did something small that made the world a better place, drank coffee, listened to music, and found that that was enough.

• Loving the people in my life for who they were, and not for who I wanted them to be.

• Laughing a lot, swearing a lot, making many inappropriate jokes in churches and fancy restaurants, and being unafraid of saying the wrong thing.

• Living with less fear and more courage, and never becoming jaded and cynical even when things didn't go my way.

• Forgiving myself for all the mistakes I made and the people I hurt when I didn't know better, and extending this same compassion to others.

• Treating my life and career as one big experiment, learning ways to work and live beyond what I grew up with, and not caring what 'the culture' defined as right or successful.

• Reading many books, taking lots of afternoon naps, being bad at my hobbies, wandering aimlessly in foreign countries, and doing things simply because I wanted to.

I loved that John Fiorentino podcast because he was not just talking about creating million dollar products. He was talking about a way of being in the world, and somehow managed to articulate so precisely the texture of what it means to be human.

It left me thinking about this: What have I not done? What am I hungry for? What still terrifies me? What is it that I know, deep inside, I need to do next?

Some final things:

1. I’m running an experiment to figure out for myself if I want to niche down as a writing coach. As part of this, I’m offering 3x pro bono coaching sessions to 3 individuals. This will be a fun way for me to iterate on my approach, and in return you get some free coaching. The only requirement is that you want to start a writing practice or deepen your existing one; if you’re not sure whether this is for you, let’s chat anyway and see what comes up.
   
   If you’re interested in giving this a shot, you can drop me an email. If you’re wondering why me, you can read more about my background!
   

2. As I mentioned last week (or the week before?), I’ve started sharing links to interesting things in the subscriber chat instead. In case you missed that, you can follow along here or by downloading the Substack app.
   

3. Some of you are new here, so hello and thank you so much for subscribing! If you want to find out a little bit more about the person who writes this strange newsletter, this should help.

Otherwise, that’s all for this week. Stay safe, drink lots of water, and I’ll see you at the next one 👋🏻

It's starting to become a bit of a pattern that I've noticed where I don't know whether something is true until I've said it.

Often, it catches me off-guard. For instance, someone might casually ask a question, and I find myself articulating an idea that had never occurred to me until that very moment. Occasionally, I can somewhat instigate this, usually by bringing stray thoughts to my coach, therapist, or unsuspecting friends.

I have become used to saying, "Hey I have something on my mind. I'm just going to say a few things, then we'll see what connects."

It usually works because things do connect. Alphabets drift together like leaves falling from trees. When they land, they become certainties.

Every time this happens, I am both frustrated and surprised. How is it possible that I can know these things to be true, yet these truths remain hidden from me? I wonder: is my subconscious waging some kind of clandestine war? What else is operating in the shadows?

I am reminded of an incident many years ago. I am face to face with my fellow founder, and he is telling me that I am the problem. There is no one else I know who is capable of delivering such facts with this potent mix of urgency, compassion, and helplessness. So he has my full attention.

To be precise, he is saying, "You are the bottleneck." What he doesn't need to say is, "Please go figure out how to fix this."

He doesn't need to say this because I know he is right. In fact, I had known this for some time, and had thus far been incredibly successful at evading this truth.

When I was finally able to confront this, I began to take, over the course of the following 2 years, the slow, meticulous action of learning how to turn a group of people into an organisation.

What I gained from this experience wasn't so much the knowledge and practice of how to delegate, how to hire your next level of managers, or how to create systems that operate without you. All of this matters, but I was caught most off-guard by the realisation that while I believed I was working that way because of my team, I was really doing it for myself

At the time, I would say yes to everything. I was available to review work at literally any hour, and always insisted on helping where I could.

It was for them, I would tell myself. They need my help.

Really, I was doing it for myself. I was doing it because I liked being good at something, and more importantly I liked feeling useful and needed. Once I was able to see this, I understood that I was not responsible for what other people do; they are.

After this, it became so easy to let go. But it took me years of working this way and being blind to my own motivations to even begin confronting this reality.

The term 'hidden agenda' often implies an agenda that is hidden from others. However, it is also often the case that it is hidden first and foremost from ourselves. I do not believe, for example, that most people who do bad things are inherently evil. It is just that they have found a way to tell themselves a story where, in their world, their behaviour is perfectly reasonable.

These days, I think of this as the shadow at work. And I think I am getting better at seeing how it shows up in my life.

It is more obvious in my experiences of emotions like envy or resentment. Maybe I see someone who has attained a level of success that I do not think they deserve. Perhaps I even have good reasons for this—for example, I have it on good authority that they are just good at selling, even though the quality of their delivery is often poor.

But I find myself thinking, I wish I too had that level of success. Or, I don't think they deserve it.

I now recognise these triggers as opportunities to ask myself questions like, "What is my envy/resentment telling me about my own unfulfilled aspirations? What can I do to make progress towards these things?"

And I know to reorient my effort and attention to my own life, which, unfortunately, is the life I am saddled with.

Then there the moments when my shadow shows up in ways that are mundane, yet no less insidious.

Not too long ago, I was chatting with a friend, and they said to me, "It's like everyone is becoming a coach these days." As someone who has built so much of my identity on being different and doing things my way, my immediate reaction was that I should just stop doing coaching work, and do something else instead.

It was so automatic it took me several minutes to even realise it was happening. Then I remembered that I have clients, I have a business, and this pre-occupation with being unlike anybody else is just a story I'm telling myself.

What has really helped is to hit the emergency stop button that I imagine is buried somewhere in my brain.

Some people have described this as learning to pause, but to me the act of pausing is too gentle and too forgiving. When I first started doing this, what worked for me was not a soft, metaphorical nudge reminding me to chill the fuck out. What I needed was more like a short-circuit—just HOLD THE REACTION, DON'T DO ANYTHING, GIVE IT A FEW MINUTES.

And in that space, I can start breathing and working through the story.

This is not unlike moving through the stages of competence.

Q1: Automatically reacting to things, and believing the problem is always external: events, other people, bad luck.

Q2: Learning to manage my automatic reactions, but still believing the problem is external.

Q3: Beginning to have some awareness that the problem is internal: in my own perceptions, biases, and defence mechanisms.

Q4: In control of my automatic reactions because I am aware of my triggers and how to defuse them.

And as I'm working my way towards becoming consciously competent in managing very specific things, what I'm also learning is that this brings with it its own shadow—which for me is the belief that it is enough to be competent in this, and I no longer need to work on other areas of my life.

Which, of course, is yet another story I'm telling myself.

📢 Quick announcement: Rather than share one big link round-up every newsletter, I realised I much prefer to post them spontaneously in the subscriber chat, which is what I've been doing. Feel free to join me over there by downloading the Substack app, and let me know if it ever gets spammy!

Just over a year ago, I was sitting in a meeting room with 20 others, facilitating a discussion on organisational challenges. As the hour dragged on, I found myself slowly disconnecting from what was happening.

"None of this matters," I kept repeating to myself. "We think it does, and we try to tell ourselves it does, but it really doesn't."

The discussion went decently, but I left it knowing it was time to quit. I wasn't being fair to my team showing up to work like this, and as I would realise later on, this was just one of the many ways in which my life was trying to tell me that I was in the wrong place.

While the work was meaningful and paid well, I had felt stifled for some time. When I started dealing with a number of personal challenges, all the deep restlessness I spent months suppressing finally surfaced in a way that I would not describe as 'gentle'. I lost motivation, stopped caring, and found myself craving a hard reset.

As I served out my notice period, one of the big questions I asked myself was: looking at the life I had, was I proud of what I had accomplished, accumulated, and the person I had become?

Which eventually led me to asking: what do I want my life to look like when I'm 50?

Today, I have a page in Notion titled '2041', where I track everything from my finances and personal priorities to the values that I use to govern my career choices.

To me, this has not simply been an exercise in life or career design. Some of you have heard me say versions of this—that what I'm trying to do is to connect to who I am and what I want in order to feel like I belong in my own life.

It's about moving away from “if I do/get/become x then I will feel x”. Instead, it's about the freedom to be myself and to live on my own terms. This means recognising what I'm good at, going where that value is seen, and cultivating the wisdom to know what's for me and what isn't.

So as we make our way through April, I wanted to do a stocktake of what I’ve done and what's coming up next. While it's mainly a reflection exercise for myself, I thought it might also be useful for anyone who's embarking on their own path, considering it, or just curious what my version of it looks like.

Warning: long post ahead.

purpose & impact

Coming into March this year, a theme began to emerge around how I thought about what I want to do.

Upon graduating from my coaching programme, I reflected on how 'change' was an experience that I never welcomed. I remember feeling at 23 like I had figured out who I was going to be forever, and if it were up to me, I would still be that person.

But life happened, and I saw that I could change, or I could keep repeating time-worn strategies and pretending I wasn't miserable.

Once I very reluctantly embraced this journey, I began to understand this as one of life's essential truths: in this life, shit will happen and we will all encounter suffering, confront the consequences of poor decisions, or wake up to certain realities of how we've been living. In these moments, we can choose to do differently, or we can bury our heads in the sand.

Having made significant changes in my own life, I now want to do work to support others who have chosen the path of transition and transformation.

As I explore opportunities that are aligned with this theme, this is what my day-to-day work currently looks like:

• To start, I write this newsletter. I never expected it, but writing Treading Water has become my spiritual and creative practice, my marketing funnel, and the backbone on which I build my days. It continues to be the single most effective way for me to stay disciplined, attract opportunities, and also work on myself.

• I'm continuing to build my coaching practice and take on paid clients. This is something I'm doing slowly and intentionally as I'm mindful that my ability to support my clients is contingent on my ability to manage my own attention, bandwidth, and emotional presence. I feel very privileged to work with individuals who are serious about living more consciously and deliberately, so this is work that I do not take lightly.

• I've teamed up with a finance publication to write a monthly column on how wider definitions of wealth can help us to live more intentional lives. This will drop sometime this month, and I'm looking forward to sharing it when it's out!

• I've started working on a number of book projects that involve developmental editing and narrative coaching work. I get a lot of personal satisfaction from helping others to bring their creative visions to life, so this is something I was very excited to jump into, and would love to do more of. Back at Rice, I was always proudest of the work that I could support my team to create.

• I've also started mentoring the guys at , who started a publication to help Singaporean youth to explore and capitalise on opportunities in Southeast Asia. A lot is changing in Singapore, and I think there is potential here to confront the very real challenges emerging around talent, labour, and the future of work.

• Lastly, I've previously mentioned wanting to do more work in the men's mental health and well-being space. I've since decided that rather than start something of my own, I would instead get involved in what others are already doing.
  
  The path I'm on means that I do a lot alone—from strategising to lead sourcing to execution. As such, I've been thinking a lot about partnerships and community; how I can collaborate more with others to contribute and build towards shared goals and causes.
  
  So I've signed up to participate in a bunch of these and to meet the guys out there who have already started doing this work. I recently joined a men's group started by Stranger Conversations, and will also be joining Common Ground's Beyond "Man Up": Learning and Being in Community. I'm not sure what all of this will lead to yet, but that's okay for now.

personal growth journey

At a recent networking event, someone asked me, "So what are you working on right now?"

Without thinking, I replied, "Oh, honestly I've just been working on myself."

As the words left my mouth, I realised I hadn't said it to sound smart; I had said it because it was true. I went on to share how, in wanting to build a life that feels intimately 'my own', I did not simply make a list of the things I wanted before proceeding to live my best life. This is a journey that has involved experimenting and iteration, but also frustration and disappointment. I've had to build new habits and do a ton of inner work.

Right now, this takes several forms for me:

• Last month, I graduated from the 6-month coaching programme I embarked on with Collective Change Institute back in October last year. As part of my further studies and training, I decided to pursue a professional certification in the Enneagram, and have enrolled with the Chestnut Paes Enneagram Academy. It's a fairly rigorous programme, and should consume the next 1-2 years of my life.
  
  I might write more about this one day, but discovering the Enneagram and learning that I'm a 4 has been the key to becoming aware of my triggers, making sense of why I am the way I am, and understanding how to grow. This has literally been life-changing.
  
  On one hand, obtaining this certification is about deepening my appreciation of the human condition. On the other, it's also about building my knowledge and capacity to better work with others and on myself.

• In November last year, I also decided to stop drinking alcohol. This is still a complicated subject that I find quite tricky to talk about, but overall this has been a net positive. I lost weight, my sleep improved, I feel more balanced and clear-headed, and I've also saved a ton of money in the process. I've also gained a lot of confidence knowing that I can be completely sober, and still make fun and interesting conversation with strangers at events.

• Lastly, I'm putting a lot more effort into my personal relationships. I only noticed very recently how much of my personal life had been on auto-pilot, and when I was able to be honest with myself, I realised how unhappy I was with the quality of my relationships with friends and family.
  
  As such, I'm trying to lean on the people in my life more, and working on being more intentional about making plans, checking in, and more importantly: opening up so others know what's going on with me. This is still very hard for me, and continues to be a work-in-progress.

what has surprised me the most?

1. How good it feels to know that every single thing that I do every week—from what I work on to who I spend time with—is something that I have consciously chosen.

2. That change is scariest only in the imagination. I have shed so many of the things that used to define me, and am regularly shocked and grateful to see that I have survived.

3. That people will pay me for things. I never thought that anyone would pay me for coaching, or sign up for paid subscriptions to this newsletter.

4. How much work has gone into this journey so far. While I asked myself questions like: "How do I want to feel? What do I want to spend my time on? Who do I want to be around?" I did not find the answers by thinking of them. Instead, I found the answers by taking risks, trying things, dealing with disappointments, and repeat.

5. How much more there still is to be done. Still, I have good and bad days. Still, there are things I don’t know and skill gaps I have to plug. Still, I feel the pull towards old habits and thinking patterns, and on days when I'm grappling with a lot of inertia or insecurity, I have to remind myself that the work, in itself, is the reward.

6. While in many ways I love the life I have, I still question the path that I'm on—whether it will really lead to where I hope it will, and whether it will ever pay enough. This is one of those polarities I'm learning to embrace: that you can see improvement in many things, but still you never really stop worrying; you just get better at dealing with it.

7. All the good things that have come out of this path have been things I could not have imagined, anticipated, or planned for. I am constantly surprised, and this has taught me a lot about letting go of outcomes, or believing that I can predict the future.

what’s next?

One big priority area is my health. Perhaps I'm dealing with the effects of long Covid (which I caught for the first time last October), but I kept falling sick in February, and recently dealt with a horrible bout of food poisoning when I was in Myanmar. I've also been experiencing a lot of general fatigue, and so while I recently started running regularly, there are weeks when this isn't as consistent as I would like.

So there's definitely more I need to do in terms of eating better and improving my overall immunity.

When I first started this whole life/career redesign thing, I spent a good few months doing a lot of 1-1 networking. While this was a lot of fun, I've decided to slow down to focus on existing projects and to deepen the connections I've already made. Generally, I also feel myself transitioning into a space where I now want to just do and create more.

One of the great joys of the journey I'm on is that I'm working on quite a few different things. While this is extremely fulfilling, it also means that I'm constantly context switching, shifting between deep work, interactions with others, and quick decision making. I'm starting to see the need to create more systems and routines for myself to manage all of this better. This is also where I know I'll come up against my own shortcomings: while I love creating new systems, I really dislike maintaining them. So we'll see how this goes.

I've also been thinking a lot about life beyond Singapore. This was triggered by Tiago Forte's blog post about moving to Mexico, in which I resonated with a lot of his reflections on the importance of not seeing everything through the lens of the country you grew up in.

As I've watched friends like and explore and build lives outside of Singapore, I've been reflecting on how so much of what I define as possible has been limited by the culture of this country. What might become possible if I move elsewhere? What might I learn about other ways to live, to make a living, to find contentment and create purpose?

A few of the hobbies that I picked up last year like drawing and rollerblading have also unfortunately fallen to the wayside as I figured out the 'work' side of things, so I'm trying to carve out a bit more time for them.

And finally, I will soon be launching something new that will hopefully help to evolve this newsletter. I'm currently focusing on the pre-production work, and will share more once it's ready. If we're friends irl, you will definitely be hearing about this from me.

closing thoughts

As we come to the end of this not-really-a-Q1-review, I had a few additional thoughts that I wasn't quite sure where to fit into. I still think they're worth articulating, and hope you'll find them useful too.

• Learning how to change is also a process of learning how to grieve. We must after all let go of the old in order to let in the new. This means taking the time to process, to heal, to honour the past. I only understood this when, through working with one of my coaches, I realised why I was unconsciously holding myself back from stepping into certain opportunities.

• Don't feel like you need to embark on a life/career redesign unless you have a good reason to (good = whatever is good enough for you). So many people have asked me if they should do something similar, to which I always ask, "What are you trying to change?" Often, the response comes back as, "Actually I'm not sure, I'm actually quite happy." There is a lesson here too, which is to want what you have. If your life is good, then just be present and enjoy it!

• If anything I've shared has inspired you to do something different in your life, I'm grateful that I got to play this minor role. At the same time, be careful not to treat my story or anyone else’s as a playbook. Everyone's journey is different, and there is a lot about my life that I do not share in this newsletter. Ultimately, you need to figure out what works best for you.

• While you don't need to reinvent your life, you also have more agency than you think. Speak up at work, start that side project, go for that improv class. What are the small ways in which you can already start to expand your experience of life?

• I'm under no illusion that this is it, and that my life will not continue to change. I might decide one day to return to being a salaried employee, or to start another company. Who knows?

That said, I find myself in a season of my life where I am no longer seeking what is 'big and loud'. I'm not interested in trends, virality, job promotions, or epiphanies. Instead, I'm looking for what is timeless, what remains under-appreciated, and what is quietly profound. I'm seeking opportunities to nurture what's important to me, improve the lives of others, and to pursue the everyday joy of slow and steady progress towards what I hope will eventually be a life well lived.

As always, if any of this has been interesting to you at all and you would like to chat or find ways to work with me, feel free to drop me an email or connect with me.

Did this lead to more questions? Are there things you are curious about and would like me to write more on? Let me know as well.

Take care in the meantime, and I’ll see you at the next one 👋🏻

It is 3:18 AM.

I am due, in 6 hours, for a full-day tour of Mandalay, but I have just sent a text to my driver to cancel it. My phone is inches from my face, and I am curled up in bed in the foetal position.

For the past 24 hours I have been immobilised by what I suspect to be a stomach virus. Between trips to the bathroom, I google my symptoms and other unappetising details, or otherwise wrestle with cramps that feel like a very angry sea urchin blooming from inside my lower abdomen. I keep telling myself that as soon as I can find the right position to contort my body into, I can make it hurt less.

At this precise moment, I am battling a full-blown existential crisis. I am asking myself why I picked this country, these specific dates for travel, as though there was any way I could have known this was going to happen.

"Is the universe sending me a message??" I lament, before launching into a desperate search for flights back to Singapore.

I am not exaggerating when I say that illness reduces me to a shell of myself. I always find it hilarious later on, but in these moments I am predictably self-destructive: I refuse to drink water, I eat badly, I feel sorry for myself, and I take the opportunity to ruminate on all the dumb things I've ever done and all the things that I know I cannot change.

Before making this trip, almost everyone that I told about it looked at me incredulously and said, “Myanmar? Are you sure? Isn’t there a war happening right now?”

And so when I first got here, I couldn't help but feel a sense of suspicion colouring every interaction and experience.

In a country going through a civil crisis, where power outages and road blocks are a common occurrence, people continue to go about their daily lives. Adults hang out in coffee shops, and kids play in the street. It is hot—MUCH hotter than Singapore—but everyone is friendly, and not once did I encounter a tank rolling down a street or even military personnel.

As such, it is not lost on me how ridiculous I'm being.

So this trip didn't go entirely according to plan. Big deal. I'm in a comfortable hotel room with room service, and there is even a swimming pool on the damn roof.

Life could be so much worse. Yet such is the state I am in.

how to dig yourself out of a hole

At one point in this episode, I thought: if only my life was an anime.

I’m thinking specifically about Tokyo Ghoul, and about Kaneki's character who gets tortured to the point of glorious transformation. Not only does he become virtually unstoppable, he even earns himself the #2 spot on Gamerant's 20 Most Iconic Male Characters With White Hair.

Because if this isn’t the prize, then what is the point of suffering?

Alain de Botton once said this thing about how we are not merely seeking to be happy; we are seeking to suffer in ways that feel familiar.

This has always been true for me—I am comfortable with negative experiences, to the point where I unconsciously find ways to perpetuate or even create them. I have had to be very intentional about choosing to be happy and appreciating the good things in my life.

But how exactly does one go about doing this?

To borrow Leonard Cohen's words, digging yourself out of a hole is often about looking for the cracks where the light gets in. Paying attention to the moments that sneak up on you, when you realise you have been chasing the wrong thing, or you have been looking at a problem the wrong way, or you are in a ridiculous argument with someone you love, and choosing to stop, and to turn towards that knowledge.

After all it, is possible to double-down instead; to push that knowledge away and to choose to sink deeper into the hole you are already in. Because stopping and doing differently also means admitting that you were wrong, or that you hurt someone, or that you did something small and stupid.

As I was dealing with this horrible stomach virus, I started to notice the way in which I refused to release myself from the slow drip of false hope.

I kept telling myself that this would be over any minute. Just hang tight, don't do anything, this time will be the last time. Yet every trip to the bathroom brought with it nothing but exhaustion and disappointment.

I wanted so badly to feel fine, I kept looking up my symptoms, thinking that if I could just figure out what was going on, I could make it stop. I kept researching the fastest route back to Singapore, thinking that as long as I could get home I would be okay.

What's funny is, at no point did I actually think to myself that I should try and see a doctor. AlI I needed to do was dial hotel reception for help.

In the midst of all this, there was a moment when I was in the hotel bathroom that I caught a glimpse of my reflection in the shower screen. I looked so miserable, I couldn't help but laugh.

In laughing, I finally saw how I was making myself suffer. I realised that I was in a hole, and that I needed to dig myself out of it.

I needed to let the light in.

So I say to myself, "This is your life now. You can make it worse, or you can try to enjoy it as much as possible."

And at 3:18 AM, I accept that there is no way, in my condition, I am going to somehow still get to play tourist. I cancel all my plans for the next 24 hours, and finally exhale.

I stop searching for flights, and close my web browser.

I ask myself: how will this be funny when I talk about it in a few weeks?

I start drafting what eventually becomes this newsletter.

15 minutes later, I open Netflix, which I proceed to lose myself in for a good 4 hours.

I take a shower. I order room service. I finally manage to fall asleep.

I wake up. I leave my room to sit in the sun for a few minutes.

I text my friends and update my parents on the situation.

I write up up some fun ideas for projects that I know will never make money. I watch more Netflix.

I begin to actually enjoy myself.

PS. I may not have had the most amazing time in Myanmar, but I believe that I just got unlucky. For anyone considering visiting, do it!

Oh, and this was the hotel room in which I suffered for 2 and a half days:

stories, visions, and ideas that moved me this week

I’ve been spending a lot of time reading other newsletters, and so the links this week are all to other Substacks:

• A Word to the Unwise from — A hilarious account of aging ungracefully.

• Sorry I’m Late - I was crying at a comedy show from — On how we try to comfort others when really we are trying to comfort ourselves. Also a good, strong dose of chaotic energy.

• Give your friends a chance to abandon you from — About friendship and inflicting yourself on those you care about.

• The Backpack from — We are all carrying something heavy. Why not set it down, and unpack?

• We Don’t Need ‘Self-Help,’ We Need Support from — For a vision of a better way to live.

• Reading challenging books with kids is fun and probably useful from — This was very pure and made me feel like I was sitting in a pool of warm sunlight.

That’s all for this week. I’ll catch you at the next one 👋🏻

As always, if you enjoy the way I write and think, and are looking for ways to work with me, check this out.

I recently decided to stop engaging the part-time helper that I've been working with for the past 3 years. She had first come into my life via an app, someone selected from a long list of smiling faces and near-identical resumes. I went with her because she was available to start right away.

This decision was one that I had been sitting on for months. When it came time to make the necessary arrangements, I considered just opening the app, hitting a few buttons to cancel all future appointments, and moving on with my life.

Another item checked off my to-do list. One less thing to worry about. No need to make it an emotional thing.

Yet it didn't feel right. And after much agonising, I decided I would be there on her last day to say goodbye and thank you.

Our conversation must have lasted at most a minute. I explained the circumstances as briefly as I could, and told her how grateful I was for everything she had done.

"Yes, it's been 3 years already that I've been working for you," she said, as though she had seen this coming. I heard no surprise in her voice, only a calm sense of knowing and a twinge of optimism as she added, "Hope to see you again."

To which I chuckled awkwardly and responded, "Thank you for all your hard work these few years, not sure if we'll see each other again, but thank you and wishing you all the best."

What does it mean for two people who ostensibly have very little in common, brought together only because one was seeking a cleaning service and the other employment, who now no longer have an agreed-upon exchange of services to keep them in each other's lives, to say, "Hope to see you again?"

Over the last year or so, as I've navigated several life transitions, I've had the unfortunate privilege of also observing my own relationship with change.

It has been said that what holds some people back from pursuing their aspirations is not so much the fear of failure, but the fear of success. In my case, it has always been the fear—and to some extent, belief—that all success is inevitably followed by misfortune. It is why I sometimes hesitate to start things, because I know that it will be good, and then it will be over. It is also why I have trouble allowing things to end, because I am also afraid of watching this fear manifest into reality.

You see how it goes.

So what then does it mean to say that we hope to see one another again?

I think that when we say things like this, it is not so much that we are hoping for the identical events of our past to repeat themselves in the future. Rather, we are hoping for that same essential goodness to return to us—in a form that we do not yet know.

But if we have hope, then we can see things as they are, and sometimes the way things are is that they are no longer meant for us. The job has been done. The relationship has run its course. The thing you love is no longer in production.

Someone once told me that it's about honouring the past in order to move forward into the future. I dismissed this as fluffy and meaningless.

Now I understand this as recognising that nothing that has ended has been lost. Everything that we have ever touched, said, done, felt, witnessed and experienced becomes who we are, and we carry these stories wherever we go.

Letting this person go meant admitting to myself that this phase of my life was really over. It was over, and my life would never look like this again.

But is that really true?

I'm starting to see that hope is foolish but necessary. Because what other choice do we have?

The alternative is to cling and to deny, to believe that we can stop time and keep things the same, even though in the same way that you never step into the same river twice, we are always changing. Every second we exist is a second in which we are becoming someone else.

In Sea of Tranquility, the fictional novelist Olive Llewellyn asks, "What if it is always the end of the world?"

"Because we might reasonably think of the end of the world," she says, "as a never-ending process."

Allowing things to end is allowing things to change, to grow, to surprise, to renew. Even to repair something is to choose to end a state of disrepair.

So we say that yes all of that happened, it was wonderful, and now that is over. Life has changed and we have become different people, and we go on.

THE DEEP END

(This is a new section of the newsletter where I write about something that I'm doing or trying to change in my life)

Earlier this week, I sent out a message using the Substack chat feature about a thing I'm looking to try.

Over the last few years, as I've reflected on my own journey both running a media startup and trying to do life as an Asian dude with lots of feelings and opinions about many things, the issue of male mental health/well-being has become one that’s very close to my heart. Personally, I've always struggled with asking for help and building close relationships, and I know many other guys who feel similarly.

This year, I'm hoping to do more in this space but am not too sure what that's going to look like yet. So as a start, I'm going to experiment with a men's group format, and will see what comes out of that.

The goals of this group will be

1. Community support

2. Personal growth

So come and talk about your problems, and also what you're going to do about them. There is no expectation to 'open up and talk about your feelings' unless you want to. It will be lightly facilitated, but essentially still a space where guys can speak freely and, if they like, ask for support in whatever form they prefer.

I'm planning to keep it small for now, both to ensure the safety of the group and also because it's just easier to organise fewer people. So I'm currently extending the invitation to mainly close friends and readers of this newsletter.

If this is something you or someone you're close to is interested in being a part of, please let me know. You can drop me a note, or if we already know each other in real life, just text me.

More details to follow soon!

Lastly, some fun things

• When writing this week’s newsletter, John Mayer’s In Repair became an incidental reference and inspiration for what I was feeling, which somehow led me to diving into the entire Kings of Leon discography. The Mechanical Bull album in particular was a super fun one.

• Every once in a while I stumble on someone whose writing makes me think, I really hope I get to write like this someday. is one of those people, and I am just so captivated by the texture, wisdom, and cleverness of her work. Check it out here:

• I've been following Phil Plait’s Bad Astronomy newsletter for a while now, mainly because they frequently publish images like this one that have been taken from the James Webb telescope. As Phil describes it: beauty enough to torch a person’s soul.

  

  • On a related note, anyone remember the Scale of the Universe website?

• My friend Lin is designing a small-group workshop targeted at helping young professionals with their personal and professional growth. It will be be actionable and hands-on, and as part of this, she is currently offering a complimentary coaching call for those who answer a quick 2 minute survey.

• Finally, I started playing around with Substack Notes when I was procrastinating on a bunch of things. I’ve been telling myself that at least this is more productive and engaging than scrolling on Threads or Twitter.

And that is all for this week. I’ll catch you at the next one 👋🏻

A big warm hello to everyone who subscribed to Treading Water over the last 2 weeks!

Today’s newsletter took a little longer as I've been busy with a few things. I graduate from my coaching programme in a few weeks, so I've been feverishly catching up on assignments that I’ve been procrastinating on and should have completed months ago. I've also been slowly piecing together ideas for a couple of new projects—both of which I'm excited to share about very soon.

And lastly, I turned 33 (yay?), or as we sometimes say, I made yet another trip around the sun—a phrase I’ve always enjoyed as a reminder that many things in life come in cycles and seasons, and there will always be chances to try again.

I do sometimes get this feeling that time is running out, but I've also been holding close this line that Frank Herbert writes in Dune: "Be prepared to appreciate what you meet."

If anything, isn't this what getting older is all about?

Over the last month or so, I've been thinking a lot about the concept of 'forever lessons'. These are lessons that I suspect I will never finish learning, but the point is in the continuous striving towards, rather than in completion.

A big one right now is the lesson of authenticity and balance. If a friend comes to me with a problem, sometimes I want to show them empathy and compassion, but I also want to grab them by the shoulders to shake them out of their spiralling self-absorption.

Both responses are authentic to who I am, both come from a place of love, and it is likely this friend needs a healthy dose of both. But what does it mean to take a balanced approach when, in the moment, I'm likely to find myself favouring one over the other?

There is, unfortunately, no correct answer. Depending on the context, the tone of the conversation, your relationship with this person, what they had for breakfast, or what personal crisis you're concurrently wrestling with, any number of variables from your delivery to your choice of words to the weather could dramatically alter the course of the conversation.

But while there is no correct answer, you can learn to intuit the right thing to do in the moment. In a podcast I was recently listening to, neuroscientist and psychologist Joel Pearson talks about how it is possible to train your intuition, provided you train it on the right data.

For instance, if you want to get better at arguments, you need to have more arguments and pay better attention to what's happening when you have them. If you want to get better at solving business problems, you need to tackle more business problems and observe the different things that happen when you make different decisions.

Over time, it's not so much that you start to only make good decisions, but that you begin to make fewer bad ones. (there's probably a forever lesson somewhere in here too)

And so here are a few other ‘forever lessons’ that I've been working on:

1. Have urgency but don't rush

As I've gotten older, I've started to observe how knowledge is useful, but it is really experience that teaches us.

I’ve seen this most clearly in how, in both myself and many others I know, we all carry our own versions of 'I got the thing that I thought would fill the emptiness, and it didn't fill the emptiness'.

And the problem wasn't that we set goals or that we were ambitious, but that we were too precise. We wanted what we wanted, and nothing else. What I'm learning is that it is important to be decisive and go after what you want, but at the same time let go of wanting things to work out a certain way.

Some might describe this as not being attached to outcomes. I call this the willingness to let life surprise me, or the willingness to live in a world of 'maybe'.

Maybe this won't work out, but something else will. Maybe I'll lose this, and I'll survive it. Maybe this will go great, but it won't matter as much as I expect it to. Maybe I will get what I want, but it will arrive in some form that I can't even imagine yet.

There is this George Saunders quote which I love, where he says,

So much of this artistic life, I think of it as self-gaming. You’ve got a chance to tell yourself all kinds of stories about what you’re doing. If you tell yourself the right stories, you become more positive and powerful. If you tell yourself the wrong stories, you don’t.

And so I'm slowly learning that choosing what stories to tell is also choosing what stories to let go of.

2. Tell the truth and maintain my privacy

As someone who writes often about my experience of the world, I struggle a lot with navigating that line between what I want to keep to myself and what I'm willing to offer up for public consumption.

On one hand, writing is an anchor in my life. It gives my days structure and makes me more disciplined with how I spend my time. It helps me work through my life experiences, and in turn helps others do the same (or so they've told me). I also just thoroughly enjoy doing it; it is one of the very few activities in which I can access that flow state and be fully present.

At the same time, it is the primary way that most people first encounter me and the work I do. With that, I’ve had experiences where because they’ve read some of my writing, people think that they know me, or they expect me to behave or work in a certain way.

On many occasions, I’ve also wrestled with this feeling of having exposed too much of myself, of wondering if I'm just mining my life for content, and whether what I've written is true, or just a story I'm trying to tell myself.

Here’s how I try to think about it these days:

In work (writing, networking, coaching, etc), I ask, “How can my experiences be of service to others?”

In life and my personal relationships, I ask, “How can I be honest and courageous?”

And so I draw my boundaries accordingly, deciding what to share and what to safe-keep, and I know that these are all versions of me that are authentic.

3. Feel my feelings and identify as more than my feelings

When I was growing up, I remember being so terrified of my emotions that I would literally visualise putting an unpleasant feeling in a box, putting that box on a shelf in a room, and closing the door to that room.

Over the last few years, a lot of the 'working on myself' that I've done has involved learning how to access and work with these emotions. And I've realised that there is a reason why I've never opened these boxes—because feelings suck. They are horrible, thorny things that just slow everything down and make life unnecessarily inconvenient.

What really helped was when I learnt that it is possible to feel your feelings, but not identify with them. Writer Haley Nahman came up with this term called an 'elastic mood', which she describes as being a mood that is so overwhelming you mistake the intensity of it for the longevity of it. For me, this is every single thing that I feel. But it has been helpful for me to remember that I am not just any one feeling.

In moments when I am angry I can also feel compassion. When I grieve I can also be grateful. When I feel regret I can also feel confident that I will never make the same mistake again.

And I think there's a universal lesson here in that we often forget that most things do not exist in isolation. You are not just that one successful thing you did years ago. You are not just the blunder you recently made at work. You are not just the petty argument that you picked with your friend.

These days, I try to remind myself that life is lived in the moments when we remember to see who else we are and how else we can be.

What are your own forever lessons?

THE DEEP END

(This is a new section of the newsletter where I write about something that I'm doing or trying to change in my life)

So here's a crazy story.

Despite how I seem in real life, I am actually extremely introverted. I like the corners of rooms, keeping to myself, and just generally avoiding people. But over the last few months, I've gotten curious about whether this is who I really am or just how I've gotten used to being. As much as I treasure this side of myself, I've also seen the ways in which it has cut me off from connecting with others.

Since then, I've accepted almost every invitation to networking events and house parties. To be clear, this is something I do not do. But I am miraculously still alive and I even made a few friends along the way.

Sometime last week, I happened to be at Humble Origins, a coffee shop that I swing by for beans whenever I'm in the area. The staff are great, and they serve (imo) some of the best coffee in Singapore.

They also source all their green coffee from Myanmar, which made me realise, I should ask them for places to visit in Yangon since I'm headed there soon.

But of course, I had to make this difficult for myself by over-thinking the entire thing, to the point where I had to tell myself to just shut up and ask.

So I did. Amongst suggestions for food and coffee shops, I also got some advice on precautions to take. And then an unexpectedly nice thing happened: the owner who just got back from Yangon remembered that the local SIM card she had gotten still had unused value on it, and insisted I take it.

Which came as such a surprise to me because ... why, I'm just a stranger, are you sure, don't you need it for yourself, okay, okay! If you insist! Thank you for making my life easier.

For anyone who's always wanted to be less introverted, I highly recommend reading Jessica Pan's Sorry I'm Late, I Didn't Want to Come. In it, she quotes behavioural science professor Nicholas Epley, who says, "Nobody waves, but everybody waves back."

This is how I'm trying to think about human interactions these days. If you want to connect, someone has to go first. And often, that person has to be you.

A lot of this is still extremely uncomfortable, and I'm still very bad at it. But it is getting easier to see that sometimes, when I do uncomfortable things, nice things also happen.

Stuff that moved me this week

• I had the chance to check out National Gallery’s Tropical: Stories from Southeast Asia and Latin America which I thought was fantastic. It ends on 24 March, so I really recommend dropping by.

• I finished Expats, another series on Amazon Prime. I really did not expect to like this, but I feel like my soul expanded a little after watching it.

• I also somehow ended up stumbling onto the music of Thai singer-songwriter Stoondio, and this is all I’ve been listening to this week.

That’s all, I’ll catch you at the next one 👋🏻

Quick newsletter announcement

This week onwards, I'm introducing a new section of the newsletter. I write a lot about looking inwards, but often forget that this isn’t the whole point. The point is to do so in order to do what’s actually important: connect outwards.

I want to be explicit about this, and write about things that I'm currently doing, or things that I'm trying to change in my life. The other day, I heard myself saying, "I've spent the past year accumulating all this self-knowledge, it feels like I need to start doing more with it." And so this is a way to keep me accountable to myself.

Hopefully it also inspires you to look at the things in your own life, and to consider what you might want to change, however big or small it is.

For now, I'm calling this section THE DEEP END. I'm still unsure because it feels heavy, and I want something lighter, something that captures the excitement of change and of the possibilities that await us when we pull ourselves out of the dark. But I also wanted a swimming/water related metaphor, and this seems to work for now.

If you have any ideas for what I should call this section, please let me know!

(h/t to for the conversation that inspired this. Here’s us from earlier this week:

Check out Neal’s writing at )

This week's newsletter is kind of a postscript to what I wrote last week.

If you missed last week's newsletter, it was essentially about how most of us don't want to suffer, but inadvertently do so because we pursue our goals the only way we know how—through acting from a place of sacrifice and fear. We can accomplish incredible things, but lose parts of ourselves along the way.

After publishing Stop suffering, start being weird, this is what I was left thinking about: the reason we develop such ways of working and operating in the world is because we all develop attachments to certain identities.

Sometimes that identity is

• I have to do everything for everyone all the time, because I'm the only one who knows how to do it properly

• I'm not the smartest, but I can work longer hours than anyone

• My team is the top priority, so my own views and preferences don't matter

• People inevitably disappoint you, so I'd rather be self-reliant and never depend on anyone else

• No one thinks I can do it, so I'm gonna prove all of them wrong

And identities, at their core, are stories that we tell ourselves about who we are and how we exist in the world.

This made me realise that a big part of my own story has always been that "I'm not like other people." For as long as I've been aware, it has always been the natural, instinctive thing for me to see myself as apart from and different than others.

This same motivation once made me think it was lame to just fly to Vietnam and back for a holiday, and so I flew to Vietnam, and spent 2 months making my way back to Singapore by land. It was what made me decide not to pursue a full-time job when I graduated from university, and to start a media company with guys that I met one time over beers in Jalan Besar.

It was also no coincidence that the underlying ethos of this media brand came to be, "Whatever everyone else is doing, we'll do the opposite."

Conversely, I have also told myself stories like, "I'm not like other people, so ..."

• This piece of advice won't work for me

• I'm not willing to try what someone else has already done before

• I don't need help even if I'm struggling

• This or that doesn't matter to me

• I'm logical and rational, and therefore feelings are inconvenient

• Ordinary experiences are not good enough

Just the other day, I was arranging a coffee chat with someone I really look up to, and was looking for a spot that would be convenient for us to meet at.

After about 5 minutes of frustrated searching, wondering why I couldn't just decide, I caught myself in a thinking loop. I had realised that the best place to meet at was Ya Kun, but I also kept thinking, "I can't meet this person at Ya Kun! It's so basic!" I thought this even though I love Ya Kun and go there all the time.

Even then, I thought it wasn't cool enough. It wasn't special enough for this person that I was really hoping would find me interesting.

But once I caught myself, I realised, why the hell am I doing this when the point is to connect? So I texted this person the location of the Ya Kun, and promptly moved on with my day.

This is a somewhat ridiculous example, but it was a reminder to me that the same impulse that can drive me to do things my way can also cut me off from connecting with others, solving simple problems, and even doing things that I actually really enjoy.

These days, I find myself making more of a conscious effort to embrace ordinary things. I find myself using the word 'nice' a lot, where typically I would always strive for something deeper and more three dimensional.

I am remembering that not everything has to reveal something profound and insightful about life in order to be worth doing.

With that, let's move on to ...

THE DEEP END

So here's something I've been working on.

I recently decided to shift my daily runs to the start of each day. I typically run during lunch or in the late afternoons, and this has worked really well as it allows me to expend a lot of the stale energy that I noticed accumulates in my body throughout the day.

As I've increasingly been taking on more work (and therefore also more meetings), these hours have also gradually filled up.

For a long time, I have always felt like I never have the energy to exercise first thing in the morning. I have no trouble waking up early, but then I want to lounge around, drink coffee, listen to music, stare out the window, read. It's easily the best part of my day.

As you can tell, shifting this habit was hard for this very reason. I had to give something up. Also, rolling out of my warm cosy bed at 6:30 AM in the morning is probably one of the hardest things to do in the world.

But I've been managing to do this somewhat consistently, and this is what has been working for me.

1. Sleeping early. I get into bed by 10 PM, and I read until I feel sleepy (I've been reading S. A. Chakraborty's Daevabad Trilogy, which is fantastic and I highly recommend), after which I just go to sleep.
   
   I've never been the sort to stay up until 2 or 3 AM, but this is still considered early for me. For a long time I resisted this because it felt too disciplined, too responsible. And I thought, this isn't me. I am free and young and I can sleep at any time I want and still have energy for the next day.
   
   This, I've accepted, is no longer true. It was also this acceptance that has made it possible for me to realise how exactly my habits need to change.
   

2. Sleeping earlier has been a game-changer in that when my alarm wakes me up, I have enough presence of mind to tell myself: you get to enjoy the morning breeze and smell trees and touch grass and watch the sun rise.
   
   I am able to remind myself that I'm not really doing this because I need to get my 1 hour of exercise in. I'm doing it because moving my body clears my mind, I get to listen to a podcast, and can keep it fun and easy by running at a slower pace.

There's a very popular life hack that says the easiest way to get up in the morning is to count down from 5: tell yourself, "5, 4, 3, 2, 1," and just get up. This sometimes works for me, but I find myself more willing to do so when I remember that once I get over that initial hump, I actually really love doing this.

And it's been great so far. I'm lucky to be living close to a park connector where there are plenty of trees, and the weather is perfect in the morning. I've also been getting a ton of ideas for things that I want to start working on, so I really hope I'll be able to keep this up.

Stuff that moved me this week

• As I navigate my early 30s, adult friendship is something that I think about a lot: how to make new ones, keep the ones I already have, and connect more deeply with the ones I care about the most as our lives grow in eventfulness and complexity.
  
  Dense Discovery is one of my absolute favourite newsletters, and this recent issue explores some of these very same ideas.
  

• I recently discovered Sublime, a platform for collecting and curating all the internet things that you love and want to eventually come back to. In particular, I love how the community dimension of it allows you to build on each other's libraries and collections. I'm still figuring out how exactly this works, but here's an example.
  

• I first read Lori Gottlieb's Maybe You Should Talk to Someone in 2019, which I loved for being such a beautiful and entertaining read, but also for its emphasis on how, "In therapy, you’ll be asked to be both accountable and vulnerable."
  
  In this interview with Mark Manson, she circles back on this idea, this time contextualising it within a climate where social media has increased access to mental health resources, but also led to crucial misunderstandings of important concepts and ideas.

• This week, I also finished watching the reboot of Mr & Mrs Smith on Amazon Prime. I loved it, that's all I will say. Go and watch it.

• Something useful that I chanced upon: ’s tactical guide on How to Sabbatical—in case you or someone you know is thinking of taking one soon.
  

• And finally, you know how sometimes you come across things on the internet that make you think, "Damn it, I will never be smart and creative enough to create something like that." This particular edition of NY Times Close Read, which explored the woodblock prints (also called 'Ukiyo-e') of Japanese artist Katsushika Hokusai, was exactly that for me.
  
  Combining art criticism with a poetic contemplation of the modern world, this is absolutely worth taking a quiet moment to just experience.

I know that this week's newsletter was a long one. If you enjoy this format or have thoughts on it, please let me know!

Otherwise, catch you at the next one 👋🏻