Alvin Li — A Small World

Over the past few years, I've spent a lot of time thinking about how to create sustainable happiness, make better decisions, optimize my time, build deeper relationships, grow as a person, notice when something is making life subtly worse, and move toward the things that make it better.

The pieces here will be quick, imperfect notes on how I approach life across every dimension: career, friendships, dating, health, hobbies, self improvement, goal setting, decision making, and broader optimizations. A lot of them will come from places where I feel like the conventional approach is wrong, incomplete, or at least worth questioning.

These snippets aren't meant to be perfectly polished, but I do want them to feel authentic. Some will be short. Some will be messy. Some I may change my mind about later.

A lot of these thoughts usually stay in my head, or come out in conversations with friends. Enough people have told me I should share them somewhere that I've decided to commit an hour each week to writing them up as short notes.

If something here resonates with you, reach out! I'd genuinely be happy to chat.

Thought 01

Initiate More

Initiating is the most underrated thing you can do to improve your life.

It will enable you to get ahead of people who are smarter than you, work harder than you, are more talented or more resilient, simply because you're willing to go after things and they aren't. This applies to your career, social life, dating, everything.

Most people, myself included for a long time, just don't do enough of it. And the cost is bigger than it looks, because if you never initiate, you are letting other people choose your opportunity set for you.

The reason this matters is that the opportunities that come to you by default are often not the best opportunities available to you.

There’s certainly cases where amazing people, jobs, friendships, and opportunities will find you naturally without you having to initiate. But in general, there is a lot of adverse selection to passivity. The best outcomes are usually not sitting around looking for you specifically. The people you most want to date likely have many other options. The best companies that you want to work for have many other options. The people you most want to add to your social circle have many other options. If you only choose from whoever happens to come to you first, you are usually choosing from a narrower and less exciting pool than the one you could have reached for yourself.

Dating is the easiest place to see this. As a deliberately oversimplified thought experiment, imagine there were some 1-to-10 measure of overall romantic desirability, where the number captures some messy combination of looks, maturity, ambition, emotional availability, communication, values, chemistry, and countless other factors. Obviously this is not how real attraction works. People cannot be reduced to numbers, attraction is subjective, and two people can be perfect for each other regardless of where anyone else would rank them. But as a simplified model, it makes the underlying point easier to see.

Imagine you’re a 7 (just for the purpose of this example). If you never initiate, most of the people initiating with you may be somewhere in the 1-to-7 range, because people generally tend to pursue only the people they see as at their level or above it. Your best case is that another 7 initiates with you, and the two of you hit it off.

But if you do initiate, you are mostly reaching toward people you are genuinely excited about: the 8s, 9s, and 10s in your world, however you personally define that. Many of them will say no. Some will not be interested. Some moments will be awkward. But at the very least, you are repeatedly putting yourself in front of the people you actually want.

And if you keep doing that, eventually someone will say yes. In the worst case, that someone is an 8 on your scale, which is already above your best case scenario if you never initiated. Over enough attempts, you give yourself access to higher outcomes that would almost never have come to you if you never initiated with anyone.

The same thing applies to your career. The recruiters who reach out are not necessarily coming from the companies you most want to work for. Often, they are from companies at or below your current opportunity set, because the best companies are not always going to randomly find you, recognize your potential, and pull you in.

If you want to work at Anthropic, Jane Street, Blackstone, SpaceX, or whatever your version of that is, waiting around is probably a bad strategy. Apply for the role. Set up a call with the hiring manager. Ask people in your circle for warm intros. Maybe nothing comes of it. Maybe you get ignored or rejected. But if you never try, the opportunity would never exist in the first place. And if it fails, you are usually just back where you already were: without that job, without that connection, without that door opening. The difference is that by initiating, you at least created a chance where there was previously nothing.

It applies to friendships too. Waiting for people to invite you to things, introduce you to others, or make plans with you may feel easier. But if you never reach out to the people you admire, never ask the interesting person to coffee, never host the dinner, never invite someone into your life, your social world becomes shaped mostly by whoever happens to choose you first.

This is the hidden cost of being too passive or scared to initiate: you cap your upside. You let your best-case scenario be determined by whatever happens to come to you, instead of actively reaching for the things you actually want.

Initiating is not about being pushy or desperate. It's about creating paths that would not have existed otherwise, and refusing to let blind luck be the main force deciding your life.

Not every lion that chased a deer caught it, but every lion that caught a deer chased it.

Thought 02

Take Asymmetric Bets

One of the quickest ways to change your life is to repeatedly seek out asymmetric bets, which are decisions where the upside vastly outweighs the downside. These opportunities are everywhere, but we routinely pass them up because a small, immediate downside is easy to feel, while a massive, distant upside feels entirely abstract.

Let’s go through some examples.

Maybe you’re deciding whether to even try to apply for a job you feel underqualified for, something that feels like a reach. Most people focus on the possibility of rejection. They imagine the awkward interview, the disappointment of not getting an offer, the sting to their confidence if things don’t work out. But if you step back, the actual downside is surprisingly small. You spend a few hours preparing, you have a few conversations, and if it doesn’t work out, you’re right back where you started. But if it works, the payoff can be enormous. Maybe you dramatically increase your income. Maybe you meet people who change the trajectory of your career. Maybe the role opens doors that compound for years afterward.

Dating works the same way. Maybe there’s someone you’re interested in, and you’re deciding whether or not to pursue them. Worst case, you get rejected, feel a little embarrassment, and your ego gets bruised. It might feel bad for a day or two. The upside, on the other hand, is measured in years or decades. This person could become your partner, your spouse, and the person you build a life with.

The same pattern shows up in smaller ways too.

Maybe you’re hesitating on whether to go to a house party where you barely know anyone. Worst case, you have a few awkward conversations and leave early. The upside is meeting a new friend, a romantic interest, or someone who introduces you to an entirely new social circle.

Maybe you’re deciding whether to build a personal brand on social media. Worst case, nobody cares, a few people judge you, or you feel embarrassed for putting something into the world. The upside is that one of your posts might blow up. You may start attracting opportunities, people, and conversations that would never have happened otherwise.

People often treat these potential small failures like it’s catastrophic, and they treat life-changing upside like it’s too abstract to matter. But if you actually ask, “What happens if this goes badly?” the answer is usually incredibly underwhelming. You feel awkward. You lose a few hours. Something doesn’t work. A post flops. A party is uncomfortable. Someone isn’t interested. Then life continues. That is the whole trade: a small, survivable downside in exchange for a nonzero chance at a much better life.

I’ve been thinking about this a lot recently and have been trying to make asymmetric bets in my own life, both big and small ones.

Leaving a high-paying quant trading job to found my own startup is one example. The downside is real, but it’s also manageable. If things don’t work out, I can easily pivot into building another startup or pave a new path elsewhere. I’ll be okay.

The upside, though, is extraordinary, both from a financial and fulfillment standpoint. I get to spend my days building something I genuinely care about. I can create something that has meaningful positive impact on people’s lives around the world, work on problems I find interesting, curate a tight knit team of ambitious people who all want to swing big in life, and chase a vision that feels far larger and more exciting than what I left behind.

I’ve also been making a conscious effort to reach out to more people. Sometimes that means introducing myself to someone who seems interesting. Sometimes it means sending a message I could easily talk myself out of sending. Sometimes it means asking a friend for an intro to someone who might be helpful, inspiring, or fun.

Most of these messages will not change my life. Some have gone nowhere. Some will be ignored. Some will lead to one polite conversation and nothing else. But occasionally it leads to a new friendship, a new perspective, a valuable piece of advice, or an opportunity that would have never existed otherwise.

I’ve been experimenting with smaller bets too.

Earlier this week, I signed up for a mobility class at my gym. I had low expectations going in, and somehow it still severely underperformed them. But that’s almost beside the point. All I lost was a single wasted hour. The potential upside was that I might have learned something that could improve my physical health for decades, reduce chronic pain, or prevent some future life-altering injury. That is a bet worth taking.

Most of these bets won’t work. That’s fine. The goal is not to be right every time. The goal is to keep taking asymmetric bets where being wrong is survivable, and being right is transformative. Over time, a few of them will work. And those few wins are often enough to completely change the trajectory of your life.

Thought 03

The Local Maximum Trap

At first glance, most people would assume that the worst situations in life to end up in are local or global minima. The logic seems obvious. If you're at the bottom, things are bad. If you're at the absolute bottom, things are really bad.

But in many areas of life, I think a far worse place to find yourself is a local maximum. A local maximum is a point that is better than everything immediately around it, but below the highest point that you can reach.

Local and global minima provide clarity. When you're at a low point, you know something needs to change. You're unhappy, frustrated, or dissatisfied. The pain creates urgency.

Local maxima are dangerously seductive. When you're in a medium high point, things are good enough. Your job pays well enough. Your relationship is stable enough. Your social circle is enjoyable enough. Your city is comfortable enough. Nothing is actively wrong, but nothing is pulling you toward something substantially better either. Everything around you is worse, so every direction out feels like a mistake. You look left and right and see only downgrades, so you stay.

And because moving away from a local maximum often requires accepting a temporary decline, most people stay put. This shows up everywhere. Someone stays in a career they no longer find meaningful, but the compensation is good and the work is comfortable. Leaving would mean uncertainty, rebuilding credibility, and potentially making less money for a period of time. Someone remains in a relationship that is perfectly fine but lacks the deeper connection they are actually looking for. The relationship isn't bad enough to leave, but it may never become what they truly want. Someone lives in a city they have outgrown because their routine works. Their friends are there. Their favorite coffee shop is there. Their life functions smoothly.

The challenge is that many of the best opportunities in life require us to suffer through an initial decline in life quality and stability. To get from one peak to a higher one, you often have to descend first, and you have to descend without certainty on whether a higher peak exists. You might have to leave the stable job before finding the opportunity that excites you. You might have to leave the familiar city before discovering the community you actually want. You might have to leave a relationship with someone you love and endure the loneliness that follows before finding someone who is more compatible with you. You might have to walk away from something good before discovering something great.

This is why some of the largest life changes happen when people are forced out of local maxima rather than choosing to leave them. A company lays them off. A relationship ends. A lease expires. A plan falls apart. At the time, these events often feel disastrous. In reality, they often remove the comfort that was inhibiting them from growing and evolving.

Of course, not every local maximum should be abandoned. There is a real cost to constantly chasing the next thing. The difficult question is whether the comfort you're experiencing is a reward you've earned or a trap you've settled into.

The people who consistently reach higher peaks aren’t necessarily better at predicting the future. They’re just more willing to leave local maxima, absorb short-term pain and instability, and chase the possibility of something substantially better.

It’s certainly not easy to do. I’m still trying to figure this out myself.