Leo Explores Life

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April 29, 2013

How to Live an Interesting Life, Part 2

In the first post of this series, I discussed the value of being willing to do things by yourself. In this post, I’m going to talk about being open to unexpected opportunities.

Say “yes” to as many opportunities as possible.

Most people have plans and goals and bucket lists. Sometimes, however, you have the opportunity to try something unexpected. This could be a chance to go to a new restaurant, pick up a new hobby, or enter into a new line of work. It’s tempting to stay in your comfort zone, but trying new things can make your life immensely more rich and interesting. Not everything you try will be a great experience, but some things will be, and it’s not unusual for some small event to cause a chain reaction that changes your entire life for the better.

How do you decide whether to say “yes”?

My personal philosophy is that, assuming you have enough free time, it makes sense to say “yes” to almost anything that doesn’t have a high associated cost. For example, if someone asks you if you want to try rock climbing or windsurfing or a Fijian restaurant, it’s almost always worth it to go. If you don’t like the experience, you might have lost $25 and a couple of hours of time, which is only mildly unpleasant. On the other hand, you might find a new life-long passion or meet your future best friend or at least have a great story to tell. Either way, you tried something interesting and expanded your horizons. Maybe you didn’t enjoy rock climbing because you got tired quickly, so you decide to start working on your endurance. Or maybe you didn’t like anything at the Fijian restaurant except for the kava drink, and you decide to buy that on Amazon. Or maybe you really got nothing out of experience — sometimes that’s okay, too.

More “costly” opportunities should considered more carefully. If you’re a lawyer and one of your friends tells you they think you’d make a great chef, you can’t just drop everything and apply to Le Cordon Bleu. If you get a chance to go Masa in NYC, you should first figure out if you actually have $500 and if you like sushi that much. When you have the chance to do something interesting but risky, it’s wise to remove some of that risk with smaller experiments. This might mean trying to exactly replicate a recipe from a high-end cookbook, or going to a $15pp and a $40pp Japanese restaurant and seeing if you actually appreciate the difference between a good sushi meal and a great one. If your initial experiments are promising, you can follow-up with bigger experiments, or take the plunge.

For illustrative purposes, here are few things I’ve tried in the past year just because the opportunities presented themselves:

  • Rock climbing. This was an awesome experience and now I find myself climbing for 10+ hours per week.
  • Yoga. This was interesting, but not interesting enough for me to make time for it on a regular basis.
  • Archery. Same as yoga.
  • Visiting a ghost town. This was much more creepy than cool.
  • Fine dining. One of my friends had never tried molecular gastronomy, so we went to a restaurant with 2 Michelin Stars. It didn’t live up to its reputation (or its price!), but it was still fun and I’m glad I got to introduce my friend to something new.
  • Angel Investing/Business Advising. I tried this on a whim when some friends were launching a startup investment fund, and I ended up find the process to fun and educational that I’m now focusing my professional efforts on this rather than on software engineering.
  • Reading books people have recommended. Some of the books were enjoyable (West with the Night), others were educational (King Leopold’s Ghost, Common Sense), and one was somewhat life-changing (Give and Take). A few of the recs were duds, but a few hours of time is such a small price to pay for understanding your friends better.
April 24, 2013

Near-term Goals

I turn 32 today, and that seems like a great opportunity to think about what I’d like to do over the next year or two. In past years, I’ve set arbitrary goals like “run a 6-minute mile” or “get a 20% return on my investments”. Recently, however, I’ve come to appreciate that goals are better when they focus on things that can be controlled. I can hope for a 20% return or a faster mile-time, but what if the stock market tanks this year, or if a 6-minute mile is impossible with my height and build? With this in mind, I’m going to list some goals that I believe are within my control:


  1. Go rock climbing or bouldering 100 times. If I could climb a 5.12a before my next birthday, I would be ecstatic.
  2. Keep my weight under 200 lbs.
  3. Spend 13 hours of cumulative practice on each of: handstands, triple-unders, back squats, and deadlifts. This is about 15 minutes per exercise per week. I’d love to get to a 30-second handstand hold, 50 consecutive triple-unders, a 325lb back squat, and a 425lb deadlift.


  1. Get a job. A job could be programming or angel investing or running my own company, but I’d like to start getting paid again. This “no salary” thing can only go so far.
  2. Make something useful. I’ve been doing investing for the last few months, and that’s a lot of fun, but I miss building things, too. I’d like to release a useful product, even if it’s just a small side project.


  1. Write at least 60 meaningful blog posts. This one does not count.
  2. Be a dramatically more helpful, positive influence on everyone around me, whether they’re family, friends, colleagues, or strangers. I know goals are supposed to be quantifiable, but I don’t know how to quantify this. I’ll just have to settle for the “I’ll know it when I see it” test. In my opinion, the word “dramatically” makes this very easy to judge.

The last goal, the goal of helping people around me as much as possible, is the most important one. If I achieve that and nothing else, it will be a great year.

My main driving force right now is that I want to produce more than I consume. I want to write things that people will read instead of only reading things that other people wrote. I want to help others build great companies instead of just buying great companies’ products. I want to give more to the people around me than they give to me. If I could do this a little better each year, I will be very happy with the life that I end up living.

Wish me luck! Or better self-discipline, I suppose.

April 20, 2013

How to Live an Interesting Life, Part 1

Earlier this year, I wrote an answer on Quora that became relatively popular. Here’s what I wrote, in its entirety:

Question: How can you live an interesting life?


Three tips that I’ve found helpful for leading a more interesting life:

  1. Be willing to do things by yourself. A lot of people want to take art classes or try new restaurants or travel to exotic countries, but few people consider doing these things without companions. If you’re not willing to do stuff by yourself, you end up missing out on a lot of interesting opportunities because there’s no one around to join you.
  2. Say “yes” to as many opportunities as possible. If someone asks you if you’d like to go to a new restaurant or volunteer for a charity or do a weekend road trip together, say “yes”. The more things you try, the more interesting your life will be.
  3. Stop caring about what is normal or expected. Sometimes the only thing stopping you from doing something cool is that you’re afraid of looking stupid or weird. The problem is that many things seemed stupid or weird until they didn’t: traveling for a year after college, dropping out of school to start a tech company, joining an online dating site, etc. It’s hard to veer off the beaten path and have an exceptional life if you’re always looking of social acceptance.

When creating this answer, I deliberately tried to be succinct in contrast to the other (very good) submissions. I think it might be interesting to elaborate on each of the three points, and I’m going to do that over a series of three posts.

Be willing to do things by yourself.

I’ve noticed that most people don’t like to do try things by themselves. For many people, their potential activity lists look something like this:

Things I would do with friends:

  • Travel to a country I’ve never been to.
  • Go on a weekend road trip.
  • Eat at that new Somali restaurant in San Jose.
  • See that new indie flick that features Ryan Gosling covered up in tattoos and acting like a disturbed James Dean.
  • Sign up for next month’s archery/meringue/scuba/cooking/yoga/trapeze/pottery/____ class

Things I would do by myself:

  • Read.
  • Watch TV.
  • Try to find a friend who is reading or watching TV so that maybe we can do something fun together.

The problem with this approach is that other people are busy. Or they’re available, but at different times than you are. Or they have different budgets. Or they want to try salsa dancing while you really want to try yoga. Or they want to go on a trip with a group of 7-8 people while you want to go in a group of 2-3. There are so many ways in which waiting for someone to join you can fail, and all of those go away if you are willing to try stuff by yourself.

Maybe you’re not willing to go to Syria without a big group of friends (and an armed escort) — and that’s totally understandable — but how about doing a solo weekend trip to Yosemite, or driving out to Monterey to rent a kayak and hang out with sea otters for a day? Perhaps you don’t want to take a partner dance class unless you have a friend to go with, but there are lots of activities that are mostly solitary, like archery or pottery or people-watching. Give one of those a try — by yourself — and you’ll be surprised at how pleasant they can be.

I do have a confession: this advice is more effective for someone like me (a strong introvert) than for someone who craves being around other people 24-7. That’s okay. There’s a balance between doing interesting things and doing things with friends and being happy, and the most important part is to understand that every choice you make or don’t make has its trade-offs. If you’re happy hanging out with friends, even if that means you don’t get to enjoy some of the experiences that interest you, then fine. Just be aware that that’s the decision your making, whether implicitly or explicitly.

If you’re waiting for other people, then you’ll mostly be waiting; if you’re willing to do things alone, then you’ll mostly be doing. The choice is yours.

April 17, 2013

No Pain, No Gain

I’ve been doing CrossFit for many years, and I’ve racked up lots of little injuries during that time. I’ve scraped up my ankles, knees, shins, elbows, and forearms against everything from barbells to climbing ropes to gymnastics rings. I’ve ripped up blisters on the pull-up bar, given myself welts with the jump rope, and bruised my collarbone with a heavy barbell. I’ve even dropped a 150+ pound weight on my head (which is not as bad as it sounds). And all of these things are just the tip of the iceberg.

Some of my friends wonder how any of this can be appealing. To tell the truth, it isn’t. Injuries are never fun, but dealing with discomfort is necessary for getting better at things.

Regardless of your proficiency level at a skill, whether you’re an absolute newbie, a battle-hardened veteran, or a world-class expert, the only way to get even better is to do things outside of your comfort zone. You try something that’s just beyond your current abilities, you succeed (or almost succeed), and your proficiency improves in the process. If you keep practicing things that are too easy, your skill level will plateau; if you try things that are too far out of your league, you’ll get discouraged and won’t progress. The trick is to find things just outside of your comfort zone and focus on them relentlessly.

Basically, it’s like this:

Different activities come with different types of discomfort. If you’re doing something physical, like CrossFit or rock climbing, you’ll get sore and occasionally injure yourself. If you’re working on public speaking or on getting more dates, then you’ll experience anxiety and rejection. If you’re trying to become a Nobel Prize-winning physicist, you’ll face burn-out from thinking about the same problems for months or years at a time. In most worthwhile endeavors, discomforts are simply tollbooths on the highway of progress: you pay your dues and continue going forward.

This is all well and good, but how do you deal with the pain? How do you come up with the initiative to risk injury or rejection or burn-out? That’s a hard question to answer, but one thing that has worked well for me is to frame discomfort as a normal cost of doing business rather than as a special event.

When you go out to a restaurant, you have to pay for your meal. Having to pay is unpleasant because it would be much nicer to eat for free, but all of us accept that this is not how the world works, that giving up some cash is one of the costs of going out to eat, and that a good meal is worth much more than its price. If we huffed and puffed each time we had to pay for a meal, we would never enjoy ourselves; treating paying as a predictable burden helps us enjoy our dining experiences.

Improving yourself is similar to eating out: you pay with discomfort instead of money, and the value of what you get is much greater than what you paid. If you treat a certain level of discomfort as normal, you’ll be able to endure it much better than if you treat it like a special thing that deserves sympathy or self-pity. I imagine this is what sleeping must be like before and after having kids. Before having kids, you might be sensitive to a bird chirping outside. Once you have kids, you have experience a period of sleep-deprivation, and then you readjust to the new status quo and are able to survive on whatever sleep you get — and you no longer notice the bird as long as your kid is sleeping soundly. How you react to the bird is all about framing.

So if you feel like your progress in something has stalled, think about what you can do that’s just outside of your comfort zone, and then do it. You might feel uncomfortable, but it won’t be that bad, and you’ll get used to the discomfort quickly. I can almost guarantee that after a try or two, you’ll start making progress again. You might experience a little pain, but you’ll also experience a lot of gain.

April 16, 2013

No Fear

A few months ago, I read a profound quote by David Foster Wallace: “You’ll worry less about what people think about you when you realize how seldom they do.”

At first glance, I found this quote upsetting. Being surrounded by people who are completely self-absorbed is not my idea of nirvana. However, after continuing to think about Wallace’s words, I decided that his observation is more empowering than depressing. We avoid so many things due to fear of failure and fear of embarrassment, but those fears are unfounded because hardly anyone is paying attention to what we do.

Furthermore, even when you do fail or embarrass yourself, the ego blow is transient. Most things that seem important now won’t matter in five or ten years. For example, here is an assortment of things I was ashamed or self-conscious of during my teenage years and my early 20s:

    • I was courted by a prestigious university, bragged to all of my friends that I was a shoo-in, half-assed the application, and then promptly got rejected for not taking the process seriously.
    • I didn’t have a girlfriend until a few years later than many of my friends.
    • In track, I was one of the slowest runners. I ran slower than some people walked.
    • During the basketball unit in P.E., grades were based on a free-throw test. I made one out of ten shots, and the coach thought I could do better so he told me to try again. I scored zero points in the next twenty attempts.
    • During the football unit in P.E., the first game that I played ended with me scoring a touchdown against my own team.
    • I got a 1 on one AP exam and a 2 on another one.
    • I almost failed my senior year English class.
    • I probably missed out on being one of the first few hundred employees at Google.

I could continue, but instead I’ll tell you a secret: even though I was embarrassed or regretful about each of these when they happened, now that ten years have passed, I could not care any less. All of these things started out as scarlet letters but eventually became anecdotes and funny stories. I’m confident that most people reading this have had a similar experiences: things that felt like a big deal a few years ago are no longer a big deal.

The challenge is to project this line of thinking to the present. That is, five years from now, no one — not even you — will look down on things that happen today. So whatever it is that entices you and scares you at the same time, whether it’s requesting a raise, signing up for a marathon, attempting a hard climb at the climbing gym, writing a book, or asking someone out, you should go for it. Studies show that we regret things we didn’t do more than things we did do, and the best vaccine against future regret is to be fearless in the present.