All In

I turn 29 in a couple of months. T-W-E-N-T-Y-N-I-NE. This is doubly a shock because in my head I feel forever young, partly as a function of always having been the youngest person in every single circle I have run in, from friends to career to everything else really. I started blogging when I was 15 — nearly 15 years ago! — at a time when Tripod.com was a hosting provider, content management systems transmitted your passwords in plain text, and leaving a message on a ShoutBox was a valid way of engaging on the Internet.

That young life and everything that encompassed feels as faraway as the era in which I packed 30 Compact Discs to school in a metallic CD holder, and my music skipped — as I skipped — on the way to school through the deserted carpark of my housing estate at six in the morning, every morning. My peers are entrepreneurs and CEOs (being a high-flying lot), my friends are married and/or engaged, my contemporaries have published books, plural, and I show up in magazines occasionally as the Older Role Model For Younger Women. Wow, that’s old.

All of that just means it’s great fun. It’s more fun when you’re of age. At least that’s how it’s been for me. When it seemed dire — sometime around the final year of university, panicking, wondering: what do I do with my life? — when it seemed as though all that life had in store was some dead end office job and an indeterminate life (growing up gay in 1990s Singapore: hard), it’s been hard to really envision the sort of life I wanted to carve out for myself. For the most part it was even difficult to articulate what that life would be. At almost-29, having seen a bit of the world, having that much more clarity, I have to say Fuck Yeah, It’s Great. Anything is better than the black holes and the black spots that so terrify you when the alternatives aren’t immediately obvious.

A hundred and seven weeks ago I left this city (KL) in a mad haste. I didn’t know how to ship a puppy three hundred and seventy kilometres back to the city I was born and bred in. I didn’t know how to step away from that comfortable but middling life I had built for myself over a couple of years. I didn’t know how it was going to be. I’d set up a company at the tender age of twenty three, in an industry I knew nothing about. I learned more in those years than in all my years of education put together; I grew to love the hustle. That hustle was addictive, but I didn’t know measure, and I didn’t know the upper limits of my ambition and my ability. I got very, very ill. In a way, I had to lose it all in order to be a better person along the way.

I’ve now carved out a life for myself in the city I grew up in. The city I rebelled against and hated with every inch of my being (it was a much different place, then). It has been surprisingly good for me. Chalk it down to the stability of ‘home’ and a rock-solid support network I’m lucky to have back here; to the incredible opportunities I get from being here; there’s hardly a week which passes without the ability to reinvent myself in any of three or more amazing ways.

A decade ago I was a wimpy teenager with nothing but a half-baked sense of the general direction I wanted to move towards. The hardest part, it felt at the time, was to learn how to leapfrog the various handicaps I felt I had then: the curse of being female, gay, and opinionated. These days all of those things feel like strengths.

In the decade since, I’ve relentlessly pursued every single one of my goals in life and in love. It hasn’t been an easy journey, but at least I can say this: I failed, I stumbled, I felt I could not recover from some of those setbacks; I bounced back, even if it took a very long time in some of them. I’ve managed to create a life for myself across continents which appears charmed and easy and privileged and opportunistic to some, but which I’ve worked really hard for.

A few months ago while having a bit of an existential crisis, I’d written in my (paper) journal: I’m ambitious and a perfectionist in my career, so why not in happiness? That’s what drives me at the end of it all: the seemingly elusive happiness, defined by you and you alone. It was clear I could never be happy pushing paper behind a desk, so I ran from it. It was evident I could pretend to be happy in the sort of middling arrangement in which I had all of the trappings of comfort but none of the excitement of an inspirational love, so I had to learn to be happy on my own before I could hazard such risks again. I’ve spent the past hundred and seven weeks figuring stuff out, which is perhaps as self-indulgent as it comes, but I learned I just wasn’t ready. You grow up a ton when you have bills and thousands of dollars in taxes to pay for your youthful mistakes.

This is what I do differently now:

  1. Write clear, concise emails. I wish I knew it earlier, but learning to ask for things clearly and briefly is a life skill.
  2. Talk about money without feeling weird. I don’t know about you, but I used to find it difficult to talk about money. Expected compensation, ballpark estimates, money you will render for a good or a service — maybe girls aren’t really brought up to be OK asking for what you think you’re worth? I don’t know. But ever since learning to do this, things get done faster, and more importantly expectations are met — or not — in a more efficient manner.
  3. Say no. I believe it’s a trait of many a person’s younger life that saying no is just the most difficult thing you can do, next to talking about money, often together. A month ago I was at the cusp of a huge career development: I had three major opportunities, each better than the other. At the end of it I realized (a) you already know what the best option is, if you trust your gut (b) but that takes time and experience to learn to trust. I said no to the first two opportunities, and I’m happier for it.
  4. Having to prove yourself is bullshit. There’s a difference between establishing credibility and having to again and again prove your worth — and that’s true in business and in love. With age I’ve also become more comfortable with the big idea of Who I Am and What I Stand for, and it’s (related to the previous point) been easier to move towards what you really want as a result. For example, social media contests for popularity in order to “Win Something” — that’s all bullshit. You have better ways to expend your time and energy.
  5. Pay It Forward. Your mileage may vary, but I truly believe that paying it forward is one of the best things you can do. I run an NGO, organize community events for causes I Give A Shit About, and mentor some younger gay and trans kids because… why wouldn’t you? It’s so much more fulfilling that way. You get back in spades what you give, and not solely in the monetary sense.
  6. Give A Shit, Or Don’t. This part was hard to figure out. I’ve had some arguments and lost some friends over this. My version of it: in general, I try to be a nice person, and perhaps succeed at it. But I feel I’ve come to that point in my life where I’m aware of the limitations — of myself, more than anything else. And when I don’t feel like it, or when someone or something has a negative impact on my happiness or that of a loved one’s, not giving a shit is the only way I know how to deal with it these days. Anything else — the awkward pretense? the song and dance of adolescent and young adult social niceties? Fuck that. My only rule is if a person or organization or thing has a nett positive effect on the things I care most about — that’s great. Life’s way too short for people who tire you out and worse still, people who subtract from the world.
  7. Sleep More. I’m late to the party, but I’m a new convert to the Sleep Is Really Important school of thought. It’s related to aging, but damn, it’s magic. Not sleeping, however, is toxic. No matter for what ends.
  8. Do What You Love. I’m not a fan of this pithy statement. It’s almost too slick. But there’s some truth to it. What I prefer, though, is a combination of that with “Change What You Don’t”. I love a lot of things — aviation, gin, India, travel, and so much more — but I’m not about to run out and eke out a living out of every single one of them. What helps me keep balance (and sanity) is the other part. What bothers me so much that I cannot sit idly by? For now, it’s girls’ education in India. Xenophobia in Singapore. In a couple of years it might be religious fundamentalism in Singapore. Or something else which will surprise me.
  9. Learn Something New. It wasn’t always so, but of late I’ve had a strict personal rule. That I should learn something I don’t know anything about, whenever it feels like I’m stagnating. Last year, it was diving. And swimming. This month, it’s classical guitar and gardening.
  10. Know Thyself. Then Adjust Accordingly. As I previously mentioned, I set up my own company at age twenty three knowing fuck-all about tech and business. I now know how important it is to have strict accounting and paper-filing standards. When I was ill in KL it felt like the sort of health-related traffic red light which made me stop to take stock of my life, health and my abilities. I have always known I’m not temperamentally suited to conventional employment, yet I did not feel ready enough — financially or mentally, since I was for a long time at that point in my life where I could not even remember passwords or how to populate spreadsheets, so I could not.

Lastly, this: Jump On The Train When It Pulls Into The Station. In my industry there are various ways to convey this. One of it is, when the rocketship arrives, get on and don’t ask which seat you’re on. The other one is, do you want to spend the rest of your life selling sugared water? In that respect, I’ve just had my metaphorical train pull up into the station. So I’m going all in.

In a month and a bit, I get to pick up where I left off and call this past 107 weeks officially over. It wasn’t possible without a lot of hustling, but here I finally am. I’m starting a new company which combines the two things I Give A Shit most about, tech and female empowerment in Asia. I have a great team, enlightened investors, and nothing to prove this time but to see how far technology can improve lives (tech solutionism? perhaps.) in that part of the world I care the most about. We get started — first in Jakarta, then in Yangon, which also brings me back to how everything comes full circles and all the dots connect if you let it, that I spent the better part of my youth ‘aimlessly’ wandering around these parts finding things to do. When things happen, you grab them by the bloody balls.

None of this would have been possible if it wasn’t for the incredible people in my life, especially my family, my peers and the amazing woman I now call my girlfriend. They keep me grounded, in all of the best ways. My dad, because he’s never once flinched at being the rock of my life; my circle of best friends, because they never let me get too arrogant or too hurt, all at once; my girlfriend, because she keeps me grounded in some very real ways, sometimes literally — we are planting microgreens and crops this week. Mostly, because I have a home to come back to, in the literal and the figurative sense.

I’m excited to embark on the next phase of my life with the sum of every single goddamn part, and so much more.