10 Things I Wish I Knew as a Lost College Student

Part 1: Getting lost and finding yourself

I’ve been getting a lot of questions from aspiring college students - and maybe unsurprisingly, Asian parents aspiring for their kids - around the age-old question of career and life path. So I’m going to take a quick detour from my normally scheduled programming around tech and games, and take you back ten years to when I was a lost college student arriving on campus. I’ll reflect on what I wish I knew—or wish I’d done—back then.

From the outside my path might look quite straightforward: Columbia → McKinsey → Riot → a16z. But underneath the linear trajectory are a lot of zig zags and false starts: getting rejected hundreds of times, pivoting from bio to consulting to games to tech, moving cross-country to LA with no friends, and dealing with some serious contractions in both the games and crypto markets. My thread here chronicles some of this journey:

It all started with a cold email

The things I cared most about in college were career, dating, and friends, and I doubt that’s changed over the last decade. So while I’ll focus mostly on the career piece in this essay, I’ll interlace some frameworks on the latter two that are arguably even more important long term.

College students, this is for you. Parents, this is for you. Everyone else, feel free to swipe left on this essay, I won’t be offended.

1. Status is a tool, not a trophy

College is full of social status games. What fraternity / sorority you belong to, what party you’re going to, what company you’re interning at, and what grade you got. It can be easy to get caught up in these games, and they can be very useful at giving you external motivations for achievement. However, you must remember that direction matters more than speed.

You can run really quickly at a goal that is a mimetic desire, socially constructed. Think about it. Do you really want to be a banker/consultant because you deeply enjoy the job, or because it pays well, is prestigious, and there are a lot of other smart people you respect at those networking events? Do you want to join the social group because you inherently click with the people, or because that social club/group is the top business/social/whatever club?

This isn’t to say that grades / jobs / social groups are not important, they most certainly are. But I wish I had spent more time asking myself why I wanted what I wanted, and recognizing that getting a prestigious internship is not an end in and of itself. I pivoted several times already, from finance to research to consulting to games and now to tech. It’s ok to pivot, and it’s ok to go in the wrong direction for a while. But remember, if you’re too caught up in the race itself, you won’t re-evaluate whether you’re in the right race altogether.

So, Robin, how the hell do I pick a race? Well, first you need to run into the woods, embrace exploration over choosing a pre-defined path too quickly.

2. Lost is a feature, not a bug

To understand yourself, you must fail and get lost. Up until now, getting into a good college has probably been the one career goal that’s been assigned to you. You probably haven’t failed that much, and you probably haven’t been very lost at all. Now the paths get broader and you will have to make tangible decisions that affect your future self with limited data on whether you’re optimizing correctly.

That’s why you need to get lost. People will sell you optionality because it’s a very attractive alternative and certainty compared to not knowing what you want to do. Just take this next step, and postpone the decision. Well, it turns out that at some point you need to decide what you want your life to look like, and you might as well figure this out earlier rather than later.

My process has always been as follows: get lost, try things, develop a hypothesis, go deeper, and re-evaluate whether I need to get lost again or double down. This applies not just to jobs, but also to friends and to significant others too. I completely changed friend groups after freshman year. I went through multiple breakups in college too. I got rejected from hundreds of jobs and internships. It is inevitable that you’ll feel lost, but it’s just part of the process. College is a unique time when you have the safety net to try and to fail. A bad grade now won’t matter as much as later on if you made a strategic mistake for a company that lost them millions of dollars, you might get fired, but you have a family, kids, and mortgage to support.

Think about it this way, the true expectations and responsibilities on your shoulders right now are relatively low. You’re not (yet) responsible for hundreds of people, budgets in the hundreds of millions, or landmark shows/games/scripts/books/etc.

The only thing that will be hurt by failure is your ego.

If you make an app and no one uses it, so what? You’ve learned that product-market fit is hard. If you start a TikTok / YouTube and no one views it, that also means no one has seen you fail, only yourself. You need to remember that everyone starts as a novice, and really internalize that it’s only by trying will you get better and succeed. When you were a kid, did you worry about being bad at basketball / soccer / dance / swimming? No, you just did it. So especially now, you shouldn’t mind being bad at writing/coding/selling/building/drawing when you start. Develop shamelessness. Everyone has imposter syndrome.

Once you’ve found a thing you like, I generally find a stack ranking exercise useful to figure out whether to double down. Here are the parameters that matter to me when evaluating a job choice:

• Industry: Do I like the overall mission of the company? Do I believe that this market will do well?

• Function: Do I like my day to day role and activities?

• Compensation: Am I compensated fairly for my work? Does my pay scale well into the future?

• Hours: How much do I care about work-life balance?

• Location: Does my proximity to friends / family matter? How do I like the overall city structure and people?

• Risk: How much inherent risk am I taking with this job? What’s the worst downside scenario?

• Culture: How do I like the people I work with? Do I learn a lot from them and do they inspire me to be better?

You should figure out what matters the most to you. For me, I care a lot about the people I work with and the content of what I do, and less about the pay / hours / location. But for some people that’s really important! Once you have your stack rank, you should be able to find ikigai—your vocation, the thing only you’re uniquely suited to pursue. For instance, gaming and investing works for me well because I grew up in and around finance, and I’ve put tens of thousands of hours into games cumulatively. I have an inherent edge on anyone else who hasn’t put in the hours and isn’t as interested in the subject matter.

3. Know your game

As you explore the college sandbox, you need to figure out what the rules of the game are, and what strategies you can employ to win (if you want to win, which I hope you do).

For instance, if you’re an aspiring doctor, the game is grades. How do you min / max your amount of knowledge and studying to pass with flying colors. For a PhD, the game is research. Who are the best professors doing interesting research in the field you like, and how can you work for them and build a relationship with them. For investing, the game is preparation and practice. What theses on the market do you have, how have you generated alpha, and have you mastered all the basics of finance and business.

Some games are way more multi-dimensional. Dating is one of them. Startups are another. For dating of course looks and status play a role, but a lot of it comes down to timing, luck, and vibes too. There’s no cheat code for dating—just trial, error, and serendipity. Same with startups. You know you’ll need an excellent team, the ability to code a great product, and an interesting idea, but after that the environment is too multi-faceted and non-deterministic for you to have any one dominant strategy. You could be making an AI app that OpenAI then comes out with a feature for, or have a co-founder dispute on vision, or run up against the age old question of retention.

Either way, you should seek to understand the system you’re playing in, and what is under your control and what is not. Very practically, that means reading everything there is on the internet about your industry. Leverage the power of AI search and reasoning tools to your advantage. Cold email (or, even better, warm email!) as many industry professionals that you respect as you can, and then email more. Be prepared for those conversations to make them high throughput. Do the job, before you even have the job. Build, trade, code, create.

Every game has a different win condition. I used the McKinsey brand to cold email all the games investors in the industry. And I sent them startups I found interesting to provide value. I worked at Riot to build my network and credibility, and broke into investing when the timing was right. Now, my game is finding the most talented founders out there. That’s why I write, scrape Twitter & LinkedIn, host events, and grow my network with high quality people. Once you know yourself, you can know the game and how to win.

4. The summit worth climbing has no trail

After inevitably getting yourself lost, I encourage you to choose the riskier path. My one regret with college is not being more risk-on: with investments, relationships, and careers. You probably got here because you were risk averse. You got good grades, studied well, showed leadership, and did good extra curricular activities. Now it’s time to embrace risk.

I talked about how college is a safety net, but it’s also one great learning experience. And you learn faster by taking risks and making decisions. From the small minute things like whether to take a hard class or join a particular club, to the larger ones like what to invest in and what career to pick, I’d encourage you to choose the harder path each time. It is often not as treacherous as it seems and will be much more rewarding.

“Ships are safe in harbor, but that’s not what ships are for.”

Think about it this way. Dropout startup founders are, at the beginning, fundamentally unqualified to lead a large company. They haven’t risen through the ranks and learned fundamental management skills. However, because they were the ones that created something from nothing, because they are the owners of their capital, they are able to gain a position that will enable much faster learning than any other regular job out of college.

Or you can think about it purely financially too. This is probably one of the lowest points in terms of your overall net worth, and so you will overvalue a hundred dollars now versus later. Remember that your income and net worth will grow exponentially in the coming ten years if you do well.

Say your net worth is $100 today. Maybe you take $20 to invest in the stock market. But the net present value of your net worth is actually $1000, based on future earnings in the near term. By that logic you should actually be investing way more into the market. Take more risk, find the asymmetric bet of the next generation, and go all in. Do not lose all your chips, but seek the areas where you have asymmetric upside. Of course, this only applies if you are not financially burdened by debt or family responsibilities, in which case those will take priority.

5. Your time is fucking valuable

A very common college mindset is to undervalue your time. You’ll go to an event you don’t care about for boba, scroll TikTok mindlessly, or just procrastinate by doing a whole lot of nothing. Don’t think this way. A good principle from Naval Ravikant (founder of Angel List) is to put a dollar value on your time (like $200) that seems way too high, and then double it. Now you have a litmus test for how to make the most of your time.

College students are becoming content creators, doing fundamental research, creating startups, building open-source projects, and making hundreds of thousands of dollars from investing. You should build, you should network, you should learn. Make the most of your time and value it appropriately. Success may look easy from the outside, but the messy middle is a lot of repetitive tasks and discipline and failure.

If I were to think about how I spent my time in college, I would prioritize fitness, friends, projects, work and relationships, the classic things. Cut the extrinsic stuff that gives you low value: going out too often, clubs you don’t care about, classes that aren’t important, manual labor that trades your time for a low wage. Make a list of things you want to get done each week, each day, and get them done. Keep yourself accountable with a task list. It’s important to build internal accountability now; you need to discipline yourself to have intrinsic motivation.

By the way, this might seem at odds with the second principle around getting lost. It isn’t. Getting lost means that you were playing the game and trying and it didn’t work out. You got lost because you were at least venturing somewhere. But you should never stay still.

Conclusion

College is your sandbox—experiment boldly, fail fast, and remember: the path to meaning is rarely a straight line. In Part 2, I’ll focus more on the personal side of college, the importance of hard work, cultivating real relationships, and finding the tribe you belong to.

Thanks as always for reading :)