<aside> đź’ˇ For my previous letters, please see here (If they show up as "Untitled", that means they're private for now):


To Shareowners:

This letter is overdue. A few reasons for the delay:


All of that said, the past quarter has been a roller-coaster of work, play, emotions, and self-knowledge. Let's dive into it.

10 Pearls of Wisdom

<aside> đź’ˇ In this section, I capture the ten key insights I've picked up over the past four months.


  1. Problems are opportunities:

    I've learned that all problems are fundamentally opportunities. You may choose to work on problem $Z$, but the situation may throw at you $A^2$. Do you then tackle $A^2$ or do you only want to tackle $Z$? The past four months have taught me it's much better to tackle whatever's in front of you, head on. Regardless, even if you choose to do $Z$, you will never be able to enforce it. There will always be something that you hadn't anticipated.

  2. FingerspitzengefĂĽhl:

    The world is changing, constantly. So, specific and concrete guidelines are useless, because the "roads" themselves are changing. Instead of guidelines, optimize for the finger-tip feeling or fingerspitzengefĂĽhl. Think of this complicated word as a synonym for your 'gut instinct.' As long as you're headed in the right direction, you're in the clear. As I reflect on the past four months, even though I've gone many different routes, I've felt that I'm somewhat headed in the right direction. (This is important to feel.)

  3. No Big Deal:

    Most things you do, unless you're Musk or Jobs, will be 'no big deal'. Which is why nobody really cares. If you're doing dishes or preparing for an investor pitch, your problems are your problems. Sure, if you end up making something useful, others will use your product or service, but do they still care about you? Probably not. I've learned that nobody has the bandwidth or time to understand and/or solve your problems. Sure, friends and/or family can give you emotional support, but everyone has their own stuff to deal with as well.

    <aside> đź’ˇ Note: It's not a bug that "everything is NBD"; it's a feature.


  4. Everybody is figuring it out:

    In Tim Urban's words:

    Stupid is when you don’t know that much about anything and you feel like everyone else does. The good news is, everyone else doesn’t. At all. The world is full of exciting, complex things that almost no one understands. Once you realize this, all the stuff you don’t know isn’t upsetting, it’s exciting.

    On average, everybody is figuring it out, nobody really knows everything, everybody is mediocre in their own ways. (Except, of course, if you're like Musk, Jobs, Gates, or the Collisons.)

    I've sat in on high-powered meetings, and have basically realized that, for 47.9% of the things, if I know 1% about X, chances are others would know maybe 20-30% of X... (Not an incredibly BIG difference as I imagined.) The point being, as long as you follow your curiosity, accept that you don't know EVERYTHING, and are willing to accept that you're a beginner in most things, you'll "succeed" at what you do.

  5. I contain Multitudes, and so do you:

    Because everybody is figuring it out, the most definitive resolutions change first. This insight is loosely related to the classic "Strong Convictions Loosely Held" idea. The main point is that, everybody will change their mind about some pivotal thing, at some point. This is normal. Expect this. In fact, it's impractical to be an "idealist" (like 'Howard Roark from Fountainhead' in the real world), and much more practical to be, well, a "realist" (much like a hybrid of 'Howard Roark and Peter Keating from Fountainhead').

  6. Optics Matter:

    From CS Lewis's commencement speech:

    Boris now clearly understood—what he had already guessed—that side by side with the system of discipline and subordination which were laid down in the Army Regulations, there existed a different and more real system—the system which compelled a tightly laced general with a purple face to wait respectfully for his turn while a mere captain like Prince Andrey chatted with a mere second lieutenant like Boris. Boris decided at once that he would be guided not by the official system but by this other unwritten system.

    While law and statutes might give guidance that $X>Y$, the reality is more psychologically-driven. It doesn't matter what the law says "in reality". Functionally, things might be the complete opposite of $X>Y$. This is especially true in cases of power imbalance, executive presence, communication, IMPACT of your points, persuasion power, and so on.

    Due to the Flynn effect, chances are that everybody is as, if not more, intelligent as you. (After all, there is a normal distribution of people I can attest to.) In this case, because intelligence is not a differentiating factor, optics inevitably end up as the things that end up mattering. Things like, how you communicate, your executive presence, your attire, and everything BUT merit, begin to matter. It's not that these things should or should not matter... It's just that, in the absence of a completely meritocratic system of power where the best idea wins, this is the next best alternative.

    The book is important, but the cover of the book is what makes the book important.

  7. Deliberate Practice should be fluid:

    Given my obsession with productivity and optimizing everything in general, I tend to take the FUN out of most things, put them into a hyperactive process, create a solid framework around it, and automate it. This is good for a LOT of things. In fact, this is precisely what has helped me perform well at work by primarily acting as the 'information powerhouse for senior executives.' That said, the biggest strength can also turn into the biggest weakness.

    When there is too much process, and there is hidden (or subtle) pressure to "follow the process", the juice and fun out of the activity is sucked out. What then remains is a blob of process, meaningless, fruitless, dry.

    Instead, when I focus on the activity at hand, and the process is a byproduct of the activity, I find the activity is much more sustainable, useful, meaningful. For example, take 'journaling'. Throughout the past four months, my focus was to journal, and journal every day. However, I've realized that, if I force myself to journal every day, the day becomes less important and the act of journaling ends up being more important. This is counter-productive.

    This logic also applies to any craft I'm getting better at, any activity, any piece of work, or even any errand. If I am deliberately and consistently doing something, it should feel natural, normal, and effortless. To be more correct, it should feel too easy to be effortless.

  8. The Appreciation of Complexity:

    I've realized that many of my neurons have now forged deeper, more mature connections among themselves, when evaluating any problem. There is this "thing" I call 'organizational maturity,' which I've developed over the past few months, after having learned how "any" problem is not just "any" problem.

    Any problem is only a symptom, an outcome, the tip, of something much deeper, structural, foundational. Even the "simplest" problems seem "simple" because of the inability to appreciate ambiguity that surrounds those problems. Here, giving personal (or work-related) examples would make this point too context-specific and context-dependent, which is why I'm avoiding that. (I dive deeper into the kinds of problems I've helped solve in a more private section, for confidentiality reasons.)

    But the long and short is that I've begun to appreciate complexity, nuance, and multiple perspectives to any problem, which, I find is a timeless skill.

  9. The Value of Entertainment and De-Stressing:

    As much as I like to believe I'm a "hard-worker", I've finally come to terms with the pressing reality, that, entertainment and "time-off" are incredibly important. Growing up, I always thought that entertainment was a luxury, a thing you would do to actively waste time, an indulgence.

    Of late, however, I've learned that entertainment has a great utility value. Entertainment is intrinsically useful or else, without it, mental health will plummet, people will go awry, there will be zero happiness.

    I've learned this particularly after 10pm or toward the end of each month. After 10pm every night, I've found my mind would resist going back to work, partly because it's been tired or stressed, but also partly because it NEEDS to let off steam. Similarly, at the end of each month, I've re-examined whether my Netflix subscription is useful or not — The past four months, I have decided to renew it each time. This tells me something about my behavior, my need-state, and mental health, something I wouldn't have found otherwise.

    Entertainment is important; overdoing it is not.

    Over the past few months, I've watched Sherlock, Better Caul Saul, Snowpiercer, The Matrix series, the movie El Camino, Christopher Nolan's movie clips, Suits S9, space drama For All Mankind, and a hundred other things I've watched and forgotten. In hindsight, I needed to take my mind off work, and these TV shows helped me do just that.

  10. A Lesson In Conviction:

    In this quadrimester, I found that I lacked conviction in many things and ideas. It wasn't that I didn't know what was right or wrong... It was just that I didn't have the courage or conviction to follow through and stick to my beliefs.

    Be it learning about the "Internet" ground-up, or clarifying the Chief of Staff role for myself, or coming up with new ideas for growth in our digital media company, or following through on my strengths, I had an inability to be fully convinced of the thing I was doing.

    I've found that it's incredibly hard to "bet" on something and double down on it. Thoughts like 'Is there a glass ceiling', 'Is it a worthy-enough pursuit', 'Am I the best here' etc are always recurrent. I learned how these thoughts impacted my ability to perform well and how they restricted my abilities to double down. Frankly, from one view, this is good — It forces me to be completely original and really, really be into whatever it is I choose to do; from another view, it's not as good because it prevents me from making any progress.

    That said, I did double down on my work, my relationships, and toward the end, self-awareness and original thinking.

5 Timeless Skills

As the quadrimester winds up, I've learned that specific manifestations of "what" I do are functions of timeless, evergreen skills. Mastering these timeless skills is important. As the world becomes more dynamic, inflection points will become unpredictable. But timeless skills will help tide over the intrinsic uncertainty of every inflection point.