Scattered thoughts and changes on turning 30
What has changed
I kind of automatically stopped playing computer games
My mom used to be really worried that I would just become some sort of wastrel, and yeah, I did waste a lot of time playing video games: a fuckton during high school and NS, but during/after uni, it just naturally stopped without me having to put in any sort of Herculean effort to change this "bad habit".
Why? I think video games are a hyperstimulus for progress and a social life, and counterintuitively, hyperstimuli are understimulating.
re: social life, when I was young and life was boring and I had no money and we couldn't meet IRL because we had a curfew and what would we do anyway, then video games are a great way to spend time. But as I got older, life just sort of opened up, and you could just hang out with people IRL and do lots of fun things together. At some point, cooking dinner together, or just chatting and walking down the river, became a lot more compelling than playing video games.
I still play from time to time, but much less frequently, and I don't have the desire to engage in any of those time suck multiplayer games anymore. And when I do, I really do enjoy it fully; there's no undercurrent of guilt there that I used to have, lying in bed thinking "Fuck I wasted my whole day". Which brings me to the following:
I'm kinder to myself now
I used to beat myself up a lot for not measuring up to perfection. if you look at my old diary entries, it's always like, urgh I'm so lazy, why do I keep procrastinating, why do I keep playing video games etc. I was obsessed with productivity, fitness, progressing in life etc.
I don't know what changed, again, maybe just age, but that sort of thinking seems to have reduced by itself. Now I think more of, "I'm doing my best and it will be fine". I don't obsess so much about
I am still a type A personality, and I don't think that will ever go away completely, but I don't beat myself up if i have a bad day or week.
What I've learned
Most decisions don't matter that much
The decisions younger folks face FEEL extremely high stakes (because we haven't had that much practice making many of them) but honestly often tend not to be in reality. For example, looking back, it's so ridiculous that I spent two weeks in J1 agonising over whether to take Physics or Biology H2: spoiler alert, i don't think it would have mattered at all.
i think with age you just mellow and chill, and having lived through more things, and having made more decisions and seen the results of said decisions, you understand that "this too shall pass" — most things are not as bad as you think, most decisions not as critical.
One big decision I think ended up being important was which university to go to. I agonised over whether to go to Oxford vs NTU, it really went to the wire there, and while it's impossible to know the counterfactual, I really, really enjoyed my time at Oxford (far more than most — I was very lucky — see joy)
But the truly important things you can't really control anyway: who your professors are, who your friends end up being (they put us together by last name when I matriculated; that's how Lieu, Maatta, Mahmud and Ortiz became good friends. If I were a Tan instead my friends would probably be completely different.)
Sadly, I don't think this is something that can be speedrun or something that can change just reading advice. There are decisions that keep me up at night today as CEO which I'm sure in a decade, will seem equally as ridiculous as which H2 subject to take... This reminds me of the Kierkegaard quote: life must be lived forward but can only be understood backward.
Not blundering and not giving up is 90% of success
I think people think of success as having this stroke of genius or wonderful insight that then propels you to success. And there might be a bit of that, but the vast majority of the time it's just plodding along, executing the strategy step by step, and not giving up, or blowing up.
Taleb writes in Fooled by Randomness that it's impossible to distinguish luck from skill in the short term. you can't tell if a trader really has a good strategy or they've just been lucky with a bad one. Worse yet, because the actually good traders will manage their risk well, they usually don't put out the spectacular numbers that the cowboys do.. until the risk catches up and the wunderkind are caught with their pants down. I've seen a similar dynamic play out in my field as well: projects and founders that have what seem like an unassailable lead, they look unstoppable, ... and then the fall comes because they took big risks, made bad deals, or just burned out and went crazy on Twitter.
As I write in Advice for finalists, the body affects the mind, and:
when your judgement is affected, the first thing to go is the ability to judge that your judgement is affected. Learn to listen to your body, because it really, really affects the mind.
to underline that, making sure you're in a good mental and physical state is important to reduce the chance of you blundering.
Sometimes people look way more impressive than they actually are
Some people feel the need to project success more than others, maybe due to their personality or how they were brought up. The people who look super successful and are "out there" may not actually be, especially the public founders, influencers etc. whose brand and commercial success depends on projecting said image of success. On the other hand I know many people who are quietly very successful and feel no compulsion whatsoever to tell the world about it, in fact, they prefer to downplay their success, and therefore you won't have heard of them.
The same holds with external shows of confidence, competence, belief etc: the people with the most epistemic humility are the ones most unlikely to be externally confident themselves, which is often read as weakness or incompetence.
VCs are masters of projecting competence and conviction, and I don't blame them, they kind of have to. I remember one time I was asking a VC investor over a beer about some very bullish thesis he had posted on Twitter. He looked at me very seriously and said, "I don't fucking know what's going to happen dude, we don't fucking know anything, we are just very good at pretending that we do."
Similarly, how people present externally has little bearing with their internal conviction and I find it is difficult to ascertain who "got that dawg in them". The people who sound extremely outwardly confident may not be the ones with the intestinal fortitude to push through and succeed down the line. I've seen so many founders come and go, they look so impressive, making all these posts about how motivated and awesome they feel, (which makes me feel bad because how come I don't feel like that?), how they're shipping really fast and hitting all these amazing milestones, and they have everything all figured out etc.,... and then two weeks later they post that they're shutting down the company.
The corollary of this is not to compare to others, "this guy is so successful, I should be at his level". you never really know what people are really facing behind the scenes.
Women will naturally like you
this one is a big change
You should not always "maximise optionality": committing opens up options too.
The advice to young people is often "maximise optionality"; I actually think this is retarded advice, sorry; or rather, it's not bad advice per se, but it's misused to gaslight young people to take up soul-sucking jobs at McKinsey or Bain and co.
There are certain things you can only do if you commit and compound. Committing to one thing itself opens up options otherwise unavailable. Two examples:
In 2022, fresh off having raised money for my startup, and coming off a Covid-19 rebound, started living the life of a "digital nomad". In the space of five months I was in Darmstadt, Geneva, Glasgow, Reykjavik, Brussels, Croatia, London, then Oxford. That was really nice, and I recommend everyone do it! Being a digital nomad means you meet a lot of other interesting young people, and that's lots of fun,. But I realised there were things I was giving up, too. Because I was hopping around so much, I couldn't form deep and meaningful long-term friendships. I was missing out on building my relationships back home.
If you look at all the startup literature out there, the YC stuff, they all primarily focus on the early stage finding PMF part. And the kind of implicit assumption is, by elision, that once you find PMF, the rest is like easy. And to be clear, finding PMF is the hardest and most critical part: without a product people will pay for, you have nothing. But I've realised now, with the benefit of already having found PMF, that there are yet more challenges to overcome. The challenges are different and more interesting and I enjoy my job now more (five years in) than when I started. If you do a startup for two years and exit and restart, you never get the chance to face and tackle these types of "scaling" or "post-PMF" problems. So that is an example of something that only happens when you commit and compound for a long time.
Speaking of compounding:
We really underestimate the power of consistent compounding
I am naturally pretty ADHD and I have "phases" of getting super obsessed with something, then losing interest and flitting away. i think there are advantages to this (your hyperfocus lets you learn something extremely quickly) but overall I think this ends up being a disadvantage.
Most things in life, fitness, relationships, language learning, skill acquisition, all of these benefit from putting in the work consistently every day, as opposed to intensely for a short period and inconsistently or not at all thereafter. We overestimate what we can do in a month and underestimate what can be done in a year.
Think about what success looks like and whether or not you want it
Here's something that's happened quite a few times: a bright young founder asks me whether they should start a startup that does XYZ, where XYZ is the hot new thing (at time of writing, AI, prediction markets). And I tell them:
Things always take longer than they should; so before you start something, try to visualise what success looks like, and make sure you want it! If you succeed, you'll be stuck doing that thing for a long time, so make sure that that's something you actually want to be doing. The worst thing is to wake up and be trapped doing something you hate, even (especially) if it's going well.
You might be stuck in a good business doing bad and that will come at the price of your soul.
What has not changed
Wanting to build things that matter
Sometime in 2019 I started saying that I wanted to do "difficult, interesting, and impactful work". Reason being, if it's not interesting, I can't bring myself to do it. If it's not impactful, what's the point of doing it. And if it's not difficult, let someone else do it.
With age, I have changed my view: not that I don't think "difficult, impactful and interesting" is correct, but rather, I think the most important thing, bar none, is focus on "impactful".
Why is that? Because I realise that everything in this world is more difficult that it seems. The skill ceiling is very high. And if it's difficult and impactful, then it will naturally become very interesting to you. You will go into a flow state
What makes work impactful for me, is to work on something I know is positive-sum, building on solid foundations, unharried, sustainable growth over the months and years. See the above: think about what success looks like and whether or not you want it.
What does it mean to blunder? It doesn't just mean doing something wrong. The process of life is making decisions with incomplete information, and just because a decision ended up to be the wrong one doesn't mean you made a mistake. The process of finding product market fit for a startup is often very much just trying, failing, trying again: none of this I consider a blunder. A blunder in chess is something like hanging a piece: this is something that a simple rule like "before making a move, check if any of your pieces are currently hanging" can fix. In real life it's not quite so straightforward to know, so I think of a blunder as a "big mistake that could reasonably be avoided with the information you had at the time and the right thought patterns/process".