I turned 30 earlier this year. Naturally, I now know things that I wish I had known earlier in my life. Here are ten things I've learned in my twenties, from both my success and failures -- but mostly failures.

  1. The Geographic Location of Your College Matters

    This matters for two reasons: work and friends. All things being equal, you are much more likely to end up working for a company in the area than elsewhere (there are many forces that contribute to this, from the on campus recruiting to the perceived coolness of the surrounding industries that are ingrained in you over the years). Because of this, your friends are likely to stay in the general area of the school (e.g. East Coast vs West Coast). This means that even if you defy the odds and start working elsewhere, you will lose many of the good friends you made in college.

    I personally experienced this going to an East Coast, Wall Street feeder school and going back to Silicon Valley. Yet another factor to consider when considering the impossible question of which school to attend.

    Bonus tip: On campus recruiting is 10x easier than off campus recruiting after graduating. Take advantage of it! (I never did it and paid the price for it, as the financial crisis hit)

  2. Under Load on Courses during Your First Semester of College

    The first 6 or so weeks of college are when everyone is looking to meet new people and make friends. After this period, people become comfortable with spending increasing amounts of time with whatever cohort they have discovered for themselves. It's also the time where you can try out a bunch of different student clubs and see what works for you. And for many (including myself), you can use the extra time to adjust to a new city and a new stage in your lives where you will need to make decisions and set schedules by yourself.

    I overloaded on courses my first semester and paid the price both physically and mentally. I hardly slept or ate, losing 15 pounds over the first 6 weeks of college. I felt completely burnt out, and was not performing well academically. My schedule was a mess and I was living hour to hour, let alone day by day. This remains one of the three darkest times of my life.

  3. Take Difficult Courses Your First Year

    It will be torture, but you will make lifelong friends there who will there, suffering alongside you. There is a reason why Vietnam vets remain lifelong comrades. That "we're in it together" environment fosters lifelong bonds.

    For me, this was Physics 105, the Physics major track Mechanics course. Problem sessions would run weekly on Thursdays from 8pm to indefinite in the Physics building in the corner of campus. We would be there until 2am, give up for the night, go play Mario Kart 64 at one of our rooms until 4am, split up, meet up again at 11am the next day, keep working until 4:50pm, and make a mad dash to the Physics building to make it in time for the 5pm deadline. It was hellish and made me give up any hope of majoring in Physics after that course. But the guys who struggled alongside me and the brilliant ones who would lend us a hand at tackling the problems became my best friends in college and thereafter.

  4. Be a Host

    Feel like you're losing touch with friends because you're too busy? Having trouble meeting new friends? Got some money but no time? Host events!

    Board game night, video game night, poker night, chess night, movie night, Super Bowl parties, GoT viewings, you name it. Buy some beer, chips, grapes, order pizza, and encourage but don't require guests to bring something as well, from extra chess boards to deviled eggs (I have a friend who keeps bringing deviled eggs to chess night because he wants to eat them himself). You don't need to drive anywhere, friends will slowly bring their friends from other social circles, and you'll all have a great time.

  5. Investment or Hobby?

    With each purchase, know whether you're doing it as an investment or as a hobby. This applies from everything from a car, an education, to a home.

    If your car purchase is a hobby, you only have to think about how much you enjoy the car. If you need it as an investment so that it will enable you to reap financial windfalls from it (you need to get to work), then its utility and ROI should be your concern.

    If your education is a hobby and your are doing it for the love of the subject and do not need to make a living, then you can choose to study an esoteric humanities discipline and get away with it. If you need to support yourself after college, then you need to consider the return on your tuition you will gain from your studies.

    If your finances are such that your home purchase needs to increase in equity value, then you must consider your alternatives and evaluate whether purchasing a home has the best probability weighted expected return on your capital. If your home falling 20% in value makes no difference whatsoever to you, then you can buy whatever your heart pleases even if the property is very illiquid or macroeconomically likely to fall in value (e.g. Japanese real estate).

    Most purchases will fall somewhere between these two extremes, but it's a worthwhile mental exercise for your large purchases.

  6. Watch Some TV

    I urge you to watch some quality TV shows so that you can have it as an conversation topic option when meeting new people. I used to think that talking about TV was uninteresting and frankly beneath me, but I now view it in a different light.

    Conversation topics are just conduits to get a better view of another person's character. Just as we can learn about a person from what part of a Hemingway book resonated and affected them strongly, so can we with TV shows.

    For the last 10 years, I barely watched any TV. Obviously if you don't watch TV shows, you can't have a conversation about TV shows. This can be a problem when you meet people with whom you have little in common with (what do you mean you don't read trashy Sci-Fc novels!?), since TV and sports are usually the two most common and widely accepted fall back options. It's one of the easiest ways to get a conversation going, and you can glean a surprising amount of information about a person from the more meta aspects of any conversation, including TV.

  7. Spend Money on Others

    I recently realized that spending $50 on a random gift for a friend is much more satisfying than buying something for myself. This is anecdotal and I'm not exactly sure how it works, but it seems to be backed by some research as well.

    This also applies to splitting the bill on a meal. If you have a regular group for meals, try taking turns footing the bill rather than splitting it every time. Sure, someone will likely get the short end of the stick, but it'll grow the camaraderie and make it more likely that you'll get together again sooner rather than later.

  8. Overpay When Splitting the Bill

    A couple of bucks here and there is just not worth being labeled a cheapskate to your friends. The appropriate "rounding threshold" will depend on your group. It might be to the nearest 1, 5, or 10 dollars.

  9. Find "Your People"

    "But you find your tribe. Jerry Seinfeld said in an interview last year that his favorite part of the Emmy Awards was when the comedy writers went on stage to collect their prize. “You see these gnome-like cretins, just kind of all misshapen. And I go, ‘This is me. This is who I am. That’s my group.’ ” By your 40s, you don’t want to be with the cool people; you want to be with your people." New York Times

    There was a time in my early to mid 20's where I wanted to be with the "cool people". In High School, scoffed at classmates who played D&D. Looking back, it was a reaction against my own uncoolness and a reflection of my lack of self confidence.

    But I gradually realized that I was just trying to be someone who I wasn't. To the people who mattered to me, it didn't matter where I fell on the objective coolness scale. I felt more alive and invigorated and excited about everything when I re-embraced my deep rooted nerdiness. I felt at home and in my element around my fellow smart, uncool, nerdy folks.

  10. What It Means to "Make the Most Out of Your Mistakes"

    This phrase is such a cliche that I always subconsciously rolled my eyes at it. To be honest, I still roll my eyes at it. Cliches are a problem because their ubiquity prevents us from thinking deeply what the phrase is actually trying to communicate.

    I've made many many decisions that in hindsight can be classified as mistakes. Let's take my own career for example. Going to school in the East Coast was a mistake considering I knew I wanted to be in Silicon Valley high tech. Majoring in EE rather than CS was a mistake. Not committing myself to becoming the best engineer I could be (even if I was never going to be the best) was a mistake. Going to the UK made it even harder to come back. In many ways, my experience in Japan was traumatic, and I made very little money or career progress. I once negotiated way too hard with a semiconductor company and had an offer rescinded. Going to business school was a waste of time and money given who I was and what I wanted to do. My mistakes far outnumbers the optimal decisions I have made.

    Each mistake puts you in a situation that is objectively worse than where you could have been. Some doors that were available to you will now close. But unknowingly, new doors will start to creak open as you move forward in your currently suboptimal path. There will be some cool opportunities that will arise from the things you learn and the people you inadvertently meet. I wouldn't have met my team if I hadn't made all these mistakes in my life. Maybe my optimal path would have put me in a better place (maybe I'd be a Facebook millionaire!), but maybe not. There's no way to know, it's useless worrying about something I no longer have any control over, and I'm quite happy where I am today. That's probably why we say we would do the same things all over again, despite all our mistakes.

Thanks to Kevin Ko for reading drafts of this post.