Observations on People, the World, and Everything Else
A collection of things that are true to me.
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Friends,
There is a certain category of article that I find difficult to name, but which I always enjoy reading. We might call it a collection of musings, a set of opinions, a list of miscellaneous observations. Alex Guzey calls his version “Lifehacks,” Laura Deming refers to hers as “mental models,” and Nat Friedman prefaces his as “some things I believe.”
Each offers a numbered list of thoughts. Some are simple, others deceptively profound. Part of what is enjoyable about these lists is that the things I find simple, you are likely to find profound, and vice versa. Equally, those that I enthusiastically endorse, you may consider absurd.
Whatever one’s take on the individual insights, as a whole, they represent efficient distillations of someone’s mind. Read them and you feel as if you know the person a little better; as if you have gotten a tour of their inner landscape. More importantly, you start to see your own mind reflected.
Today, I’m sharing my version. It is a collection of observations that are true to me. I would be surprised if, in ten years’ time, I don’t disagree with myself, but for the moment, it is an authentic distillation of my mind. My hope is that it sparks some interesting reflections for you and perhaps introduces some new lenses through which you view your work, goals, and interactions.
If you have one truly good idea in your life, that is more than enough.
To improve your mind, read fiction. We spend the vast majority of our professional lives in pure knowledge-gathering mode; there are different, deeper truths hidden in stories.
“Never quit” is terrible advice. Try lots of things, quit lots of things. Your time is not infinite. Sometimes you have to give up an old dream for a better one to emerge.
It’s more impactful to know your most talented contemporaries than your heroes. Meeting a hero is unlikely to change the course of your life. But if you meet the most talented minds of your generation early, you can spend the next fifty years collaborating with them as they scale.
Status transactions are happening everywhere, all the time. If you’re not attuned to this, you will miss half of what’s happening in a given conversation.
Learning how to ask good questions is a legitimate discipline worth studying. We underestimate how much insight, connection, and alpha are unlocked by the right series of words. Exponents of this art form change the texture of a conversation at any moment.
Resist other people’s attempts to categorize you. They are missing too much context to do so well.
If you want to really remember a book, buy the physical version and read with a pen in your hand.
It is possible to reinvent yourself at any moment. Cultivate a loose attachment to your view of yourself.
Debate is one of the least effective ways of making up your mind on a topic. It is only worthwhile as a theatrical enterprise. (Written debate is better.)
“Where is it written…” Assume that most conventions are arbitrary and illegitimate. Rules are more malleable than we believe.
Imagine “pulling forward” skills from your future self into the present. If you wish you were a better public speaker, imagine the future version of yourself giving that ability to the present version of yourself.
Genius is narrower than we tend to believe. It extrapolates poorly outside a given field, era, or context. A genius pontificating on something outside of their discipline is probably less reliable than a regular person.
Even the best of minds suddenly burn out. (See: Newton, Grothendieck, Fischer.) Before you persuade yourself that there must be some hidden brilliance in a genius’s proclamations, consider this.
Learn keyboard shortcuts; use snippets.
Listening to the audiobook is fine for entertainment, not for retention.
The current founder trend of prioritizing attention above all else misunderstands greatness. No legendary company won through stunts. At some point, you actually have to build something valuable.
It should concern you if you have never failed at something. You should fail badly, relatively often. Otherwise, you are playing it too safe.
The pressure to be “well-informed” has made us more ignorant. Unless you work in one of a small number of professions, there is no value in reading the day’s news. It stales quickly, tends toward the histrionic, and underweights relevant historical context. Much better to scan the headlines every couple of weeks and pick a relevant topic to learn about from higher-quality sources.
We overvalue the freshness of information. Read old books. There is usually a reason they survived.
Amor fati.
The finest practitioners of a given discipline are often the worst at articulating their craft. Too much of their skill comes from inherent qualities, or abilities illegible even to themselves. Better to watch these people rather than ask them to explain.
Most modern writing advice is copywriting advice. Be careful.
Striving for legibility is overrated. It is much better to adopt a degree of inscrutability. What you lose in definition, you gain in freedom and flexibility.
If someone tells you to pick between two trade-offs (e.g., speed vs. cost), default to rejecting the premise. Sometimes you really do have to make a choice, but you can find a way to have both more frequently than you expect.
You can neutralize most conversational risks by calling them out. (E.g. “I’m being quite direct here…”; “I recognize this is very persistent of me…”)
There is huge alpha in carefully reviewing the source material. (See: Eli Dourado.)
Question the assumptions and run the numbers yourself. Everyone assumed it was economically infeasible for a private company to build rockets until Elon opened his spreadsheet.
Test out vastly disparate career paths as early as you can. Most people test within an extremely narrow band (e.g., going from banking to consulting to big tech).
If you want to become the best at something, you have to devise a kind of differential training. You cannot achieve something new by adhering to the same path as those before you.
Great things happen at the collision between fields.
The collective opinion on who the “best” is in a given industry is usually spotty or simply wrong. Proximity is often required to assess quality, and the most skilled practitioners may not advertise their approach.
Love is easy. The difference between bad relationships and meeting your spouse is not a matter of degree, but category. Compatibility is unignorable and effortless.
Earning your first $1 on the internet can change your life.
“Art is never finished, only abandoned.”
If you have not changed your mind about something important in the past ten years, you should be concerned.
You cannot have an interesting conversation without an element of risk. One person, or both, must subtly push the boundaries.
Every once in a while, you’re reminded that people perceive the world so differently from you that they may as well be on another planet. This is happening all the time, whether you notice it or not.
Allow yourself to be the dumbest person in the room. You will ask better questions and go to better rooms.
“A Prince who is not himself wise cannot be well advised.”
You become solely responsible for your education once you leave school. You must learn to become your own teacher; most do not.
To make an impact on the world, you must pay a debt to modernity. It is romantic to imagine succeeding just as your heroes once did, but they lived in a different time, in different circumstances. A concession to the present day is necessary.
The same skills that made you a good student may make you a bad employee.
“How you do anything is how you do everything” is a perfect encapsulation of what is not true. Brilliance is context-dependent. Energy is context-dependent. Insight is context-dependent. (See: Jobs’ pathetic job application.)
Set yourself a curriculum. What books do you want to read this year? How can you organize them? What gap in your knowledge still bothers you? These questions are your responsibility to answer.
At some point, you must internalize the fact that people will dislike you through no fault of your own, and that it is not your job to change their minds.
“Real artists ship.”
The first time you think you’ve missed the wave, there are probably still a couple of decades left. (See: the internet, crypto, AI.)
Sleeping on an important decision really does help.
Billions of dollars have been invested in making social media platforms addictive. Relying on willpower alone is a lot to ask. Invest in content blockers as you rewire yourself. Cold Turkey is a good one.
Learn to respect the process of the unconscious mind, especially in creative matters. Sometimes, you cannot chase the answer; you must wait for it to come to you.
You become the stories you tell yourself about yourself.
Respect your process. If you do your best work at 4 AM with a bowl of candied ginger, do that. Give yourself the latitude to be a difficult artist when necessary.
Simply decide that you are willing to go first. That could be raising your hand to volunteer for something, taking the first leap off the high dive, or responding to a question that leaves an awkward silence. You reduce social anxiety and increase your agency by just defaulting to taking responsibility.