1. Passivity is Costly

When we make a mistake on a key decision, it’s usually straightforward to reflect on that decision and learn from it. If we answer a multiple-choice test question incorrectly, we can analyze each choice in hindsight and adjust our mental model to improve in the future. The harder mistakes to learn from are those where no explicit decision was made at all. For instance, I went through my entire K-12 education without understanding the significance of olympiads in college admissions. There was never a moment when I explicitly decided whether to compete in one or not. However, my passivity—failing to do more research, talk to more people, and so on—led to my ignorance. In general, it’s better to err on the side of action and initiative. This proactive stance is positive-sum and will open doors you didn’t even know existed.

2. Get Good at Going Deep

It’s tempting to keep up with your peers and mimic everything they do. Just because Sally takes SAT classes after school and Bobby plays the piano before school doesn’t mean you should too. In fact, the most successful people I know are often quite idiosyncratic, resisting the urge to follow trends in favor of deepening their expertise and knowledge in niche topics they are uniquely passionate about.

A corollary to this idea is not to take statements at face value—especially in consequential areas. For example, in the context of investing, it’s common to hear the critique that the stock market is a casino. Don’t accept such ideas without scrutiny. Examine them deeply, do your research, and understand all sides. While the surface-level critique may sometimes be correct, in cases where it’s not, this approach could save you from making poor decisions, like avoiding investing altogether.

3. Success Isn’t Everything, but It’s Also Not Nothing

There seem to be two common failure scenarios among people my age: those who sacrifice almost everything for success and those who have given up on success entirely. The former group often hits a point of realization and regret after a significant event, such as falling ill, losing a family member, or simply burning out. The latter group tends to experience a slower, more insidious pain, often characterized by a sinking feeling as a lack of ambition or initiative leads to dead-end jobs (or no job at all), compounding financial and mental struggles over time.

It’s important to identify the key dimensions that matter most to you and ensure none of them suffer excessively at the expense of another. For me, these dimensions are career, health, and family. Find yours and strive to maintain a healthy balance between them.

4. Counteract Your Predispositions

The biggest blind spots in people are often related to their predispositions. Those who are overly accommodating to others may be taken advantage of, while those who are overly risk-seeking often face unexpected setbacks. For me, I have a natural risk aversion that causes me to resist change out of fear of the unknown. To counteract this predisposition, I look for less consequential decision points and purposely go against my intuition. For example, I might buy a risky stock that seems promising or push all-in at a poker table even when I’m unsure I have the best hand. These small actions, which defy my intuition, help calibrate my decision-making and improve it over the long term.

5. Seek Truth

People won’t always tell you the truth outright. For example, if you’re a manager asking an employee if they enjoy their work and they don’t, some may avoid being honest. Similarly, if you’re openly liberal and speak with a closeted Trump supporter, they might nod along and feign agreement while privately believing you’re misguided.

Becoming skilled at seeking the truth requires introspection. Do you actively seek out multiple viewpoints on a topic, even from people whose perspectives you may strongly disagree with? The more open-minded you are, the more likely others will feel comfortable sharing their perspectives.

A related practice is to steelman your own viewpoint—that is, seek out the strongest arguments against your position. While your closeted Trump supporter may not openly share their opinions, you can still find plenty of well-articulated conservative viewpoints if you make the effort to look for them.

Negativity and pessimism are pernicious because they reinforce bad outcomes. If you get fired at work and become disillusioned with capitalism, you are inevitably going to become even poorer. If you fall into a well and decide there’s no hope and stop treading water, you’ll certainly die.

It’s important to examine the counterfactual in both of these cases. If you don’t give up on capitalism and instead use your setback as a lesson, perhaps you can be even more successful in your next gig because now colleagues will see you as more mature. If you keep treading water with the hope of someone eventually hearing your screams, you might indeed eventually be saved.

The key word that pessimists cling to is the word “maybe.” Pessimists love to round the probability of “maybe” to zero. What’s the point of finding a new gig if the whole system is broken? What’s the point of treading water if there’s no chance someone will happen to walk by the well I fell into? Indeed, the probability associated with “maybe” is often low, but it’s certainly not zero.

What pessimists often fail to see are the other potential outcomes besides the two most obvious ones. You might drown and someone might find you, but maybe an intermediate state is finding a ledge to grab onto. Or perhaps you have a waterproof iPhone in the backpack you are wearing. All these options ultimately increase the likelihood that you will eventually end up in a positive outcome, but a pessimistic attitude dooms you to failure by blinding you to other possibilities.

How do you know if you are a pessimist? I encourage you to look back at recent messages with friends and family. How many of the messages are of the sort “but X, Y, Z” where X, Y and Z are concerns/fears/worries, and how many are of the sort “yes, and X, Y, Z” where X, Y and Z are new possibilities?

It’s not always easy being optimistic. Especially when negative events are fresh in your memory, the battle is hard. However, I hope this essay opens your mind to the idea of using positivity to win these battles. If you stay resiliently optimistic, you maximize your chances of ultimately ending up in a better place.

This tendency of offloading blame to factors outside my control was convenient for my ego in the short term, but quite pernicious for my long-term interests.

If I didn’t do well in a class, perhaps the teacher was partially to blame, but my tendency to play video games until early morning every day also contributed to my poor grade. Perhaps my manager was incompetent, but I too was at fault for not building a network and finding allies to make it harder for a single person to undermine me in performance reviews.

It’s taken years of self-reflection and deliberate effort to recognize these truths. At the time, my complaints clouded my ability to see my own shortcomings.

What’s most insidious about this tendency is its ability to lull you into complacency and a sense of victimhood. When complaining to friends about work issues, I always presented a skewed perspective, making it unlikely they would see my role in the problems.

The startling fact is that this complaining and blaming others is against my own self-interest! I wasted time and energy stagnating when, in an alternate, more self-aware reality, I could have been working on my weaknesses, becoming smarter and more successful.

So, how do we become more self aware? I’ve found it quite difficult in practice. Of course, a dose of intellectual honesty can get us part of the way there, but what has really helped me personally is actively working to improve at skill-based games like poker and chess.

Both of these games have a notion of level. When you start out in chess, you get assigned a level (called ELO) and get matched with other novices with a similar ELO. When you start playing poker, you typically play at pretty low stakes against mostly other novices that are around the same level as you.

This leveling system is crucial; if you’re not progressing, there’s no one to blame but yourself. There’s no teacher or manager responsible for a stagnant ELO or consistent losses in poker.

As you get better in these games, you are forced to confront your strengths and weaknesses. For example, I have a tendency to fear the worst-case scenario. This tendency initially hurt my poker performance. After being pushed around for hundreds of games, I was forced to introspect and realize my erroneous ways. As I began to stand my ground more, I started to win more hands.

Replacing risk aversion with risk management has also had an effect on my life outside of poker. In the same way I was giving up on many hands due to fear of having worse hands, I was also giving up on many professional opportunities due to the same irrational fear. When I started improving in poker, I also made the decision to take the leap of faith and start a new, risky gig that ultimately made me happier and more fulfilled.

Risk aversion is just one of the many aspects that skill-based games have taught me. Some others include attention to detail, managing emotional state during setbacks, the importance of preparation, and so on. Most importantly, I developed the habit of brutally honest self-reflection whenever things aren’t going well. While I will never be able to identify all my blindspots, I have noticed a significant improvement to accurately assign blame to myself after taking these skill games more seriously.

If you find yourself complaining more often than you’d like, I highly recommend taking a break from complaining and divert that energy into improving at skill-based games instead.

Outputs don’t always need to be numbers. Perhaps it’s the sinking feeling you get when sitting in the first college lecture on computer science and seeing all your classmates immediately understand concepts that you just cannot seem to grasp.

These outputs could be a result of randomness. Perhaps my most recent unsubscribers were in a bad mood and perhaps you lost out in the computer science aptitude lottery. Of course, these could be true, but an alternate plausible explanation is that I’m not yet a good writer and you don’t yet excel at computer science.

What we don’t see in comparing outputs is the inputs that went into said output. Ultimately, when someone unsubscribes to my blog, they are implicitly signaling that my blog is less good than the other blogs they read. The sad truth is that this very likely might be true! After all, I’ve spent less time writing blog posts than most bloggers have.

What has helped me recently is focusing on the inputs. Instead of looking at open rates, I look at how many posts I’ve written. Instead of looking at the number of subscribers, I try to find bloggers I admire and take time to really dissect what makes their writing great.

This method of focusing on inputs prevents me from getting distracted from my ultimate goal: becoming better at writing. The biggest risk to my goal is not my subscribers going to zero; the biggest risk is giving up on writing altogether.

I started learning a foreign language a year ago. When I began, I had 10 flash cards and could only recall 10% of them in every review session. Today, I have over 700 flash cards and can consistently recall 70+% of them in review sessions. Had I focused on how poor my original 10% number was, I might have given up and never learned the language to the extent I have today.

If you find yourself regularly feeling down about your outputs, I encourage you to start focusing on the inputs instead.

My dad grew up in a relatively lower-class family, doing extremely well, testing into the best high schools and eventually getting a PhD from one of the world’s best universities. At the age of 10, I remember opening his multi-hundred-page dissertation filled with esoteric symbols and words wondering “How am I ever going to top this?”

This expectation I imposed on myself could have been a blessing or a curse. In my case I think it was a blessing. It made me work hard. It made me aim high. When my friends were distracted playing video games freshman year in college, I was thinking about how to land my first internship.

Thankfully, the expectations I put on myself were higher than those my parents had for me. This gave me latitude to adjust and inspect my expectations as I went along. Others aren’t so lucky.

High expectations imposed on you by family members can be an enormous burden. Unlike self-imposed expectations, these expectations are much harder to escape. Unless you want to sever ties, you’ll perpetually be reminded of what’s expected of you. When things aren’t going well, you’ll be perpetually reminded of how much of a failure you are.

I recently shared a video of my apartment with my grandpa. It’s a modest apartment: two bedrooms in a pretty nice city. He responded with photos of my uncle’s apartment, which was triple the size and had a garage, implicitly and explicitly communicating his expectations of me - to top my uncle’s achievements. Of course he did this out of love and good intentions, but as the famous saying goes - the road to hell is paved with good intentions.

What my grandpa doesn’t know is the myriad setbacks and constraints I’m operating under. Whether it’s my RSI (Repetitive Stress Injury), that prevents me from working for long periods of time, or my various vision issues that similarly limit my ability to top my uncle.

Thankfully I feel very little pressure to abide by my grandpa’s expectations. However, this doesn’t seem to be true of everyone. As I age, I continue to see more and more friends and family crushed by the unwavering expectations of them. What should have been a setback becomes a crisis. What should have been a celebrated accomplishment becomes a retrospective on why it didn’t happen sooner.

Of course I’m conveniently not mentioning the happy path. What if you are Magnus Carlsen? He thrived under the heavy expectations placed on him from a very young age. Perhaps without the pressure he wouldn’t have done as well.

I’ve been thinking about this conundrum quite a bit recently, as I’m expecting my first child in a few months. I hope instead of communicating with my daughter via the expectations I have for her, I can have a more meta conversation about expectations and motivations. Why do we do what we do? Should we do things to satisfy the needs and wants of others?

Perhaps this cuts off the possibility of my daughter becoming the next Magnus. But I think that’s ok, especially if it takes away the risk of the many bad outcomes on the other side of the bell curve.