My Life Advice for My Past Selves (at 25)

  • How you choose to arrange the content of your life – i.e.: who you associate with and what you do with your spare time – is less important to how you are perceived by others than how confident you are in these choices. Personal coherence and integrity is more important than interpersonal commonality.
  • Defining yourself by uncommon virtues is the best way to cultivate a healthy distance from the judgments of others.
  • Making a fool of yourself to impress others is a race to the bottom that you cannot win.
  • Don’t be so quick to label an act of someone else as a betrayal.
  • When a new theory contradicts common sense, try to test it in an environment as isolated as possible.
  • 95% of skill acquisition is entelchy: the art and strategy of turning theory into practice.
  • Wage war against disrespect. I am referring here to cases where another person’s actions are either intrinsically harmful to you or they are the kinds of actions that, if sanctioned by you, would set a negative precedent for others. Life in a world where others never respect your personal boundaries would be hardly worth living.
  • Just like a good social game will always trump a good strategic game on Survivor and Big Brother, a contrived gameplan for new social situations is vastly inferior to being genuinely interested in other people. Be Dan Gheesling or Derrick Levasseur, not Russell Hantz.
  • Without some long-term vision of the action you will be taking, or an overwhelming desire for something, what you are experiencing is not life.
  • You can’t be half a gangster. If a goal is important enough to you, you should have the capability of putting yourself on Death Ground in order to achieve it.
  • Successful enterprises and ventures are almost always predicated on an edge. Markets breed competition, and thus, necessitate that you are better than your competition on some dimension. The more important the dimension(s), the better situated you are. If you do not have an edge in any important dimension, quit and do something else. Or rebuild.
  • Your life story is supremely interesting…to yourself. But for the love of God, do not make it the sole topic of conversation when you are on a date.
  • Confidence – qua attractive attribute – is an emotion, not an abstract belief-state. It is a kind of natural stubbornness that is needed in order to crystallize rational thoughts into deeply-held convictions.
  • A philosophy that tells you that it is more selfish for somebody else to have your money is a confused philosophy.
  • The desire to be a different kind of person – to have a different essence, so to speak – is misguided. There is no special substratum of character; what appears to be so can always be broken down to habitual behaviours and attitudes. Adopt new behaviours and attitudes, become a new person.
  • Conceptually, truth is not merely that which works. But once you have a plan or a goal, you are only pursuing truth for its utility.
  • First, learn to transcend the negative feelings associated with losing or failing, like the Stoics were able to. But once you have this mastered, the next step is to reacquire the orgiastic thrill of victory and the gut-wrenching agony of defeat – insofar as these are conducive to a goal that you are seeking. And both matter equally.