2025 Advice to my old selves (and future yous)

I turned a birthday recently and it was so busy (DataCouncil + sg flight) that i never really got the chance to sit and reflect. a lot of things are going well, lots more could be better. I’m the only person responsible for preserving the good and fixing the bad. I’m now back on a plane again and on the right mood/medication to write with honesty, sternness and lowered barriers.

I think a useful device is writing “letters to self” - thinking about myself in a specific situation at specfic ages, and sending along messages that would undo my biggest mistakes or be the right interventions for me-at-that-time to have dramatic changes in trajectory. of course if i actually did those things i’d be a different person today, but still its a fun what-if and perhaps immediately useful to somebody of that age, which is what makes it worth publishing rather than keeping to self.

what got particularly challenging is the letters to your YOUNGEST self and those to your OLDEST self. Idk if i did a good job or not and would welcome prompts and critiques to evoke better responses out of me.

35 years old

• Invest in professional/personal coaches and therapy. And a personal/virtual assistant. Max out your phone, computer, tablet. Stop being cheap on essentials. it costs ~2-3k a month and that currently costs you a lot more than that in missed opportunity
• Journaling. medically assisted if possible.
• Stop dating trash women out of desperation/laziness/learned helplessness. Write a dateme doc, be intentional and go after the good ones. They’re still out there and they’re also pissed at the apps.
  • actually have good platonic female friends that you love
• you actually aged pretty well. Bryan Johnson Blueprint worked, and hanging out with Gen Z has given you a youthful energy/optimism that others your age wish they had. keep it up (you didn’t…).
• Do everything with business partners but don’t thoughtlessly give away control. have the defining conversation up front.
• stop traveling, start being Very Good At Online. Very Very Good. This means:
  • newsletter: research and opine, don’t summarize
  • genuinely neutral socials: engage, have fun, summarize
  • youtube: teach, demo, review
  • do whatever it takes on a weekly basis to ensure you have at least one Big Hit a year (see separate post on How To Thoughtlead). You currently hit at about a 4% and you’re considered one of the industry best, but you can do a lot better if you tried and you’re just excusing yourself from trying so that you can’t fail. no prizes for that. there is no world in which not being good online doesn’t help you do anything you need to do.

30 years old

• You’re done learning how status quo works. More accurately, you’re out of time and will have to learn what’s left on the job. Go build.
  • Basically everything fucked up in the world is real, you’re not just dumb or don’t understand, the ungroomed universe tends towards fuckedness. You have too many possible Missions.
  • Basically everything good in the world is made by people like you who decided to one day do something about it instead of wait.
  • talk to everyone you met along the way to get your best ride or die group.
  • the group tries and abandons Missions quickly and cheaply until you find The Mission. Build, don’t buy along the way.
  • group comes before mission usually, then let Market pull you.
  • serve the Mission and you’ll be happy and rich and be the change you want to see in the world.
  • lack Mission and be depressed like the rest of them.
• Men were not made to Climb like Apes. They can level the Jungle, dissect it, transform it, take Paradise and put up the Parking Lot. You can do so much better than Just Climb.
• Really take 1-6 months off and go on a vision quest, do things you’ve never done before and prove to yourself that you still got it.
• If you misstepped the last 5-10 years, it’s fine. You’re still young. You’re still talented. You are Not Old. You can basically completely reinvent yourself for your 30s with no baggage to your 20s.
  • This is of course a last resort - the first one is to have the picture perfect career, house, 2.5kids. But you don’t. Ok, but fix now.
• Genuine, well researched and considered, cold email to one top person a week for a year. Make ambitious but reasonable asks. They WANT to work with you — if you can follow through. Demonstrate that you do and they will be beating down your door.
• Pick a big Megatrend and be wholly invested in it, go whole hog put everything on the line. Given you’re not an idiot, you basically cannot go wrong on a 5-10 year horizon - your hit rate will be about 75%, not 5%. Act like it, aka have the Courage of your Convictions.
  • Even IF you are wrong (GraphQL) people respect your commitment and that will bail you out - its the lack of having conviction or having tried to do hard things that i can’t do anything about.
• The formula of {OLD NEED THAT PEOPLE ALWAYS HAD} + {NEW TECH/NEW MEDIUM/NEW GENERATION} is the sweet spot.
• Dominate valuable superlatives. not “Best” - but “Fastest”, “Cheapest”, “Biggest”, “Funniest”, “Most Well Produced”. know what you deliver and get very very good at delivering it for people, they will pay you rather than compete with you.
• Peak metabolism is done. kill the alcohol, cardio and lift 4x/week, dress well. aggressively chase pretty privilege rather than secretly despise it. Most don’t even try, and the ones that do try very hard to look like they aren’t trying. Try. Please try. You can’t think/write/bullshit your way out of science/animal brain.
  • go 75% salads. can’t overdo it given where you’re starting.
• Actively take strong positions on important things and try to be either wrong quickly or very very very correct. It is more valuable to be contrarian ultrabullish on a consensus thing than to be inconsequentially contrarian. and always better bullish than a critic.
• Figure out if you have any of the big 3: Sleep Apnea, ADHD, High blood pressure/cholesterol.
  • learn how to fix all of them now, don’t haha and wait 10 years for your partner to kick you in the head
• Diving > Skiing
• Make a list of everything you want to do by 40 and really work backwards and whittle it down to timelines or it will fly by.
• Have High Integrity. You’re not in your 20s anymore. Hold weight to carry weight.

25 years old

• PICK ONE BIG WORLD CITY AND STAY IN IT FOR A LONG TIME. NYC/SF > London >> SG. It’s really really nice to have friend groups >10 years and you’ll never build it unless you start early.
• actually consistently put money in the stock market (value weight) and dont look at the charts. there -is- a plunge protection team.
• pay fair prices for real estate when long term rates are low.
• Learn in Public. write regularly on what you learned and what you think. do your best thinking in public. make resources for yourself that you share. build communities of learning. STOP when you are doing things for clout, or being disingenuous about what interests you. Beware The Metacreator Ceiling AND the Narrative Fallacy.
• Always be building an email list. Lead magnet. 1-4x a month.
• Join a scaleup, not a startup, unless you have truly found The Rocket Ship or The Leader you want to follow. Most scaleups (Series B-D) are at the right balance of responsibility, expected value comp, good/motivated employees and its actually kinda low risk.
• Every time you’ve taken a pay cut it’s led to a lot more money down the line. It won’t always work out of course but the risk is low. esp if you Learn in Public.
• The purpose of a job is not really money. It is not title. It is not prestige or employees managed or whatever. It is 1) the identification of Your Mission and 2) your accumulation of all skills and people potentially relevant to Your Mission. A lucky few have their Mission land on lap through job. If you have to ask, you’re not one of ‘em.
• Find ways to automate/eliminate your work wherever possible. Volunteer to be That Guy for everyone else. Leverage comes from using computers to do everything everywhere. You could equally be saving an hour for yourself and $10m tomorrow for a company, or running 800 databases
• Aggressively listen to what your smartest online peers are doing and saying, no matter how crazy, as long as ambitious for humanity. They will probably be leaders and billionaires in 10 years. you think i’m joking. i am not. Buy options on everything.
• Actively date-to-marry. You won’t figure this out for another 10 years but maybe if you tried harder now you could save yourself a whooooole lot of pain and heartbreak later (keeping divorce possibility in mind). You just need to do this now if you basically ever want to see your grandkids, factoring in your kids having kids older.

20 years old

• learn to have conviction in yourself and your ideas
  • fuck you, REAL conviction. find out what that really means. Men used to have it, everyone is soft now.
  • the biggest trap smart young people can have is collecting optionality like trophies and never converting. addicted to opening doors, not walking through them
  • 80-20 ideas guys by definition don’t know what it takes to do the last 80. pick an 80 that you like and specialize in it.
• and to demand high standards of others.
  • low standards people will infect you with their okayness. you can just not have an okay life. but you need to actively choose it. or else default to okay. its fine! not terrible! just… okay. for life.
  • anti-intellectualism is “cool” in american colleges. both that and overpretentiousness are extremely toxic.
  • be earnest, curious, ambitious. and regularly gather like minds - not for casual social, but to talk ideas.
• really listen to your gut on people. including yourself - if you aren’t a fit, remove yourself from the situation. short term uncomfortable but you basically never ever regret it.
• don’t let Her go because you had “work” or “long distance”.
• spend more time with your little sister. They grow up so fast.
• read Michael Church. the Barbarian stuff happens in a completely different sphere than normal society and you worked hard to get close to it and you should probably actually try to join it rather than shun it, all while keeping your soul.
• things that don’t matter: your degree. your extracurriculars. your GPA. take the hardest classes, not the easiest.
• things that stay with you a surprisingly LONG time, basically the rest of your life in the most unexpected ways you can never imagine: your college friends. your college debt. your college electives. your first job. pay attention, be careful, these are irreversible.
• regardless of your career, learn to code. python, js, and a systems language. postgres, not mongodb. learn about job queues and orchestrators, these are basically what makes money everywhere.

15 years old

• log off. you really are probably spending too much time online/in games, you’ll be much better at doing that later in life, you really, really suck at it right now and you’re not ready so just don’t. like, literally just put it off.
  • unless you’re gonna be global top ranked in a game, in which case you’re really just an updated form of athlete.
• do STEM. the hardest topics of each. break your brain.
• read more of the great fiction, write some of your own. this is your last real chance. especially philosophical fiction. Brave New World, Atlas Shrugged, HPMOR. G.E.B..
• you can just ask your smart friends how they learned to code, you don’t have to assume you aren’t smart enough and waste 15 years before finally caving.
• team sports. not tennis. not choir. lead a group and sweat a lot.
• debaters sound smart but are all deeply depressed/cynical. but pick up on the Really Damn Good ones, you’ll need to channel them.
• guitar now. you could do it later but you’ll never get as many girls.
• apply to stanford and uc berkeley. GET FREE SCHOLARSHIPS. do not take overrated shitty singapore government indentured servitude.
• write letters to your future self. Hi btw, its you in 25 years, it’d be REALLY nice to hear from you but you never wrote.

10 years old

• join a team sport
• do not let a shitty team excuse you from trying to win. most teams suck. you don’t have to just accept this.
• code and make games, don’t just play them. make games for friends.
• animorphs was great. esp the Chronicles-es.
• start journaling. write down everything that gave you joy. you’ll struggle to remember when older and be sad about it.
• piano. not violin. shut up and learn piano.
• do everything scientifically known/legal to maximize height.
• dont be a little shit. your parents sacrificed so much for you.
• please learn to draw. its not just raw talent, it can be learned, in fact it mostly has to be learned, you will see that adults learn do it too but it will be a lot easier for you and surprisingly useful in work and personal life.

50 years old

• I hope you achieved The Mission (and found a new one).
• I hope you have kids. and a loving happy life partner.
• I hope you run for office or strongly back someone who should. Serve.
• I hope you finally learned to sing and play guitar/piano.

80 years old

• I hope you see your grandkids.
• I hope your company is setup to outlive you.
• I hope you gave away most of what you had to people that needed it most.
• I hope you’re working out every day.
• I hope you’re writing the shit out of your life and thoughts because why not.