on choosing well
文章目录
Life is a choosing problem. Your quality of life depends directly on the choices you make. The person you marry. The rooms you choose to put yourself in. The job you decide to take, or the decision to not work a regular job at all.
A lot of universal advice in the tech world for making it big is to either join a rocketship company early or start your own. Or be a really savvy investor in one of said companies.
I think the problem is that pattern matching is really hard. Person A and Person B work at two different companies. Let’s say both come in with the same knowledge and pedigree, work the same intensity of hours, but Person A ends up with a better outcome. Usually this comes down to choosing the right company to work for. But most people are NOT good at choosing. That’s why investors’ entire careers are hinged around the ability to choose well - namely, which startup is n of 1 and return the rest of their fund.
Choosing well comes down to a few things: (1): Luck: Sometimes being in the right room, at the same time (2): Alpha: Knowing something before it becomes obvious to everyone else (3): Judgement: Either influenced by past experiences, advice from trusted networks, or the values/POV you have on the world.
Disclaimer - I’m writing this blog post as someone who has NOT experienced outlier returns on any of my choices. But I’m writing this because I spend a lot of time thinking about this and analyzing different people’s journeys. I do think I’ve chosen well in love and friendships though :).
luck
Sometimes, people are just very darn lucky. Maybe you find yourself in the right room at the right time. You strike up a conversation with someone in line for the bathroom, and they become one of your most trusted friends. You take a job that said friend recommends you for and that company IPOs. Some people are also just born lucky (aka nepo).
You can’t exactly replicate or manufacture luck. But you CAN increase your surface area for it. I keep coming back to “A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox” because it’s incredibly true. Posting my thoughts online has made me much more visible: it’s led to people DM-ing me who’ve become my close friends and founders who I’ve now invested in, or put me back on the radar of existing friends who reach out to catch up.
Posting online also leads to more people who can root for you. One tangible example of this working out for me was when I really wanted to intern at Replit. I made a website that looked like the product, listed all the reasons I wanted to work there, and posted it publicly. Originally, I planned to email the website to the hiring manager, but decided to tweet it online and tag the CEO. It went viral; the recruiter said “it lit up their Slack like a Christmas tree”. Thousands of internet strangers were rooting for me to get the job. There was no way I could fail, and at the same time, dozens of other startups offered to interview me if it didn’t work out because they admired my grit and tenacity.
Being genuinely kind also increases your surface area for lucky encounters. Smiling and making conversation with your local barista might lead them to offer you an assortment of pastries before they close shop for the day. Do good for other people and trust that someone else will pay it forward and help you.
Putting yourself out there and applying for jobs you may be unqualified for increases your probability of getting said dream job more than not applying at all. Cold emailing people and reaching out to older mentors you really admire bring people into your life you might not have a close relationship with otherwise. A phrase that’s been ingrained in my head from a good mentor is “don’t ask, don’t get”. For cold emails, keep it short and professional, include a specific ask at the very beginning, and share your interests/background to make it compelling for them to meet with you. Do your homework on the person you’re meeting with. Remember you want people to root for you!
Many ex-co-workers I'm close with now are people I only got closer to after they left the company I worked at. Which is super ironic! Part of me never thought to reach out while we overlapped because I thought they were too senior and busy to talk to me, but it turns out we have much more in common than I ever could have imagined. And now I’m actually at one of their homes writing this very blog post on a Sunday morning.
DM people you find interesting. Ask them to get coffee, go on a walk, or grab dinner. Or hosting something semi-frequently makes this much lower stakes - you can invite someone you’ve met recently or want to get to know better to one of your gatherings to bring them into your world. Lean on your friends! Life is better when more of your friends know each other. When you do good by your people, they’ll vouch for you. Warm intros go a long way, and soon you’ll realize that everyone is just a few degrees away from each other, and you can get in touch with anyone you want if you really try.
alpha
The next piece is alpha: knowing something before it becomes obvious to everyone else, and acting on it.
This is how people end up at outlier companies before anyone else knows it. Not because they were necessarily smarter or worked harder, but because they had access to early information.
One way to get alpha is to be in the right rooms where these conversations happen. Schools, programs, events in your local city, the roommates you live with, and the company you work at are all examples of different types of communities. Pedigree can play a small role in getting into more exclusive circles, but you can also create your own.
If your college is known for producing a lot of founders, you hear about companies before they’re companies due to sheer proximity. Or maybe your friend’s hacker house, whose couch you crashed on in the Mission, produced several unicorns. The generational company that’s well known today could’ve been started by your classmate across the hall. Similarly, with certain employers, some places are a founder factory (naturally, other startups!) where you’ll know about the next place before it even has a landing page. Which is why choosing a good college or the right company can give you a bit of a head start on your career, because of the information you’ll have access to as a result of it. (Now I get what my mom was drilling into me!)
But it’s not all reliant on institutional or company affiliation. Pushing for excellence in your craft and being extremely visible about it can go a long way. The internet has made it increasingly possible to create your own pathways into these rooms: sharing what you’re learning as you’re exploring it, publishing that side project, and posting that video. Building strong proof of work will get you on the radar of interesting people. One alum from my school was extremely consistent about posting videos online; over time, that body of work turned into an audience of more than half a million people and put her in the same rooms as the creators she once looked up to. All of this gets you access to information and opportunities.
Where you live plays a role too. Living in the Bay Area, at the epicenter of the major AI labs and the companies building around them, you see more alpha as a byproduct of living here. New stealth companies recruiting at poker nights or one of the next big things releasing in early preview at a demo event. The sheer density of funding, talent, and optimism in San Francisco is as an accelerant for anyone building in tech. Similar arguments apply to other cities: LA for entertainment, NYC for consumer and fintech, and so on. Going to local tech meetups when you're starting out can help you meet more people in the industry and see what's happening in real time. It doesn't mean you need to live in one of these major cities to be successful, but it does put you in closer orbit to more alpha. You can make up some of that distance by getting more plugged in online, seeking out whatever local tech community exists where you are, or starting your own. When I was growing up in high school in the suburbs of Toronto, I used to trek over an hour each way on the weekends to go to coding workshops downtown, to put me in the spaces where people were learning, building, and talking about technology.
VC communities and fellowships are another example. Open AI’s inaugural new grad class was mainly composed of Neo Scholars and finalists. Many of Cursor's early employees also came through Neo; well before many others knew about or got access to these opportunities. Other VC programs work similarly, and being in touch with investors gives you a direct line into their portfolio and a pulse on exciting companies even while they're in stealth.
The alpha you get from VCs is bi-directional. They give you access to their portfolio, early companies, and insights into what they're seeing across the industry. Most of their job is rooted in getting alpha. The benefit to them of building a relationship with you is that they get an early window into whether you or one of your friends are going to start something. It’s why many founder programs are tailored to young builders, and why many VCs have their pulse on early university students. They want to build a rapport with someone before they become someone. Most of the alpha is getting in early, and it's surprising that not many VC's have this as a core strategy.
Which brings up the thing that’s true in the very nature of alpha. It takes having a relationship to be privy to it. You can’t just get access to alpha by asking for it. Which means the reverse is also true: you don’t owe someone alpha just because they had one coffee with you.
Sometimes you get alpha in completely unexpected ways. The best thing to do is pursue what genuinely interests you and bring people along with pure intentions, because you'll somehow end up in a position to get more alpha without ever intending to. The best thing that has come out of design eng club is the permutation of group chats and the peer group inside them. Many of us flagged high-craft design engineering companies to each other as we navigated this new era of design and engineering work, and it turned into a self-reinforcing loop. Rabbitholeathon is similar: some friends and I started it mainly because we wanted to bring together curious, thoughtful people, and it's led me to one of the investments I'm most excited about. I never started either of these things with any intention around alpha, which is exactly why they produced it. Most alpha lives in three-person group chats that spin out of these types of rooms.
Alpha also comes from widening your range. Conversations with people +/- 5-10 years older or younger than you can expose you to perspectives shaped by completely different experiences, technologies, and cultural contexts. Often the younger generation ends up getting the most alpha: I find every new cohort of Waterloo engineering grads more cracked than the last - because of increased access to information and technological progress across generations.
The last way to build alpha is by actually doing the thing. A lot of the examples above are about getting access to alpha by being in the right rooms, but that alpha has to come from somewhere. Working on something for a long period of time gives you earned, specific insight into a space: what’s broken, what people misunderstand, what looks small but is actually important. This is part of why companies acqui-hire. In addition to buying talent, they’re buying the accumulated knowledge, judgement, and execution ability that would be expensive and slow to build themselves. They could try to learn the space from scratch, but by the time they do, being late may cost more than the acquisition itself. To create alpha yourself, you have to be willing to work on things that feel non-obvious or illegible to other people for a while.
judgement
The last piece of this puzzle is judgement: what you actually do with the opportunities luck and alpha put in front of you.
Judgement stems from a few different sources. One is your own lived experiences. If you make a ton of bets and try things early you get more opportunities to learn from your decisions and use them to inform your judgement. You actually learn the most from making not-so-great decisions. At the time, an internship I didn’t enjoy felt like a waste of time. But looking back, taking that role was one of the best career decisions I’ve made. It helped me figure out what kind of work I do enjoy, which I might never have learned. Judgement is built by making choices, observing the consequences, and updating your worldview.
Another source of borrowed judgement is the media we consume and the people we choose to look up to. Our influences shape our point of view, often in ways we don't realize. You can borrow judgement from a mentor, an older sibling, a past co-worker, a fictional character, or listening to someone on a podcast. Despite information being abundant, there are still niche corners of the internet, cultures, and points in history that you might never have encountered otherwise, including things that happened before you were even around.
Olivia Rodrigo is a fun example of this. She was born in 2003, but much of the world she draws from predates her by decades. She surrounds herself with artists from generations before her and pulls from references that aren't necessarily obvious to someone her age. Her recent work launching Daisy Chain Fields, an all-women music festival, was inspired by Lilith Fair, the festival Sarah McLachlan founded in the 90s, long before she was born. That historical range gives her a much bigger palette to draw from. She's not just looking at what artists in her generation are doing and trying to make a slightly better version of it; she's connecting ideas and contexts across generations and turning them into something that feels new. Many of the artists she features on her albums are also significantly older than her, giving her another way to draw on experiences and perspectives outside her own generation. These inputs directly influence the choices she makes in the output she creates as an artist. This example feels only tangentially related to this essay, but I’ve been thinking about this a lot as it’s so timely!
To summarize how to build good judgement: (1) Make more bets! Try a lot of things while the stakes are low. Remember you only need one huge home run to return a fund. Every choice gives you a data point about what you like, don’t like, and how to best spend your time. (2) Improve your inputs. Put yourself in rooms where you're exposed to more people, ideas, and information. Do interesting things that increase opportunities for alpha. Follow people whose work you admire. Read things outside your immediate field. Build relationships with people who see the world differently than you do. (3) Borrow judgement. Find people whose choices you respect and understand how they arrived at them. Talk to mentors, older siblings, friends, former co-workers, or anyone who has already navigated a path you're considering. You don't have to make every mistake yourself to learn from it!
parting words
The combination of luck, alpha, and judgement is what ultimately shapes the quality of choices available to you. Luck can put you in the right room. Alpha is the information you gain from being in said rooms, or trying things yourself. But judgement is what determines whether you actually act on it, and if you act in the right direction. You can be surrounded by resources, have people rooting for you, and even have access to valuable information, but if you don’t know what to do with it, or you’re too afraid to make the bet, it doesn’t compound into anything. The inverse is also true: you can have great judgement, but if you never increase your surface area for luck or put yourself close to interesting information, there may be fewer high-upside choices in front of you to begin with. Success comes from the overlap: being in motion enough for luck to find you, plugged in enough to see alpha early, and clear-headed enough to choose well when it matters.
You might have noticed I didn’t talk about hard work here! I believe working hard does play a big role in unlocking opportunities for you, but I would say luck and alpha are mostly just a by-product of hard-work. There are some things that we of course can’t control, but what we can do is increase our surface area for luck, alpha, and build our muscle for developing good judgement about what to do.
Let me know what you think! Would love to hear what strategies have worked for you on choosing well.
Special thanks to Jac, Mackenzie, Tina, and Sabina for looking at an early draft of this!
