A List of Really Obvious Things

6 min read

Perhaps the least obvious thing is that the most obvious things are not obvious. Common sense is uncommon. Simple things are hard.

Since I discussed this with my friend, Jake, I started writing down obvious things as Ray has written about in Principles. I want to share that with you.

At this moment, I believe these to be timeless. But I often look back at things I wrote even six months ago and wonder what I was thinking. I may not agree with these in the future, but this will serve as a snapshot of what I believe as of August 27, 2023.

Many of these are inspired by things I read and jotted down as I read them without the source. So if it sounds like something from X person, it probably is, and full credit should go to them. Any errors are mine and mine alone.

Obvious Things

  • Being absolutely right and being spectacularly wrong feel exactly the same.
  • Meaning is being connected to something that lives on after you're gone. Build one to throw away. Build some to keep forever.
  • It always seems impossible until it is done.
  • If you live your life with a ledger, your bottom line will always sum to rage.
  • Find your tribe by filtering people, not converting them.
  • The secret of any great project is to keep it moving, keep it from losing momentum.
  • Who you work with may matter more than what you work on.
  • The easiest way to lose dangerous amounts of money is with a bad investment. The easiest way to lose dangerous amounts of time is with fake work.
  • "No" is easier than "yes, sometimes."
  • Always check references, especially for the people you are working for.
  • The best way to get better work is to crush the work on your desk.
  • Stereotypes exist for a reason.
  • Writing is not really about writing. It's about thinking. And it's not about a priori thinking. You write, and you think by writing.
  • The best way to find a great partner is to deserve one.
  • Not all moments are created equal. Some hours are more plastic than others.
  • You can't make a good deal with a bad person.  They're always going to win.
  • Curiosity is fragile. It can die. Protect it.
  • Understanding how the world works may be a large component of the meaning of life.
  • There are real differences between people raised with religion and those raised without. Ceteris paribus, for friendship or work, I'd take someone raised with Christian values every time.
  • If you don't feel like you are overcommunicating, you are undercommunicating.
  • Aim to have wisdom, not to be smart.
  • The great myth is that because we are "created equal," we are the same. We are not. Advice that works for others may not work for you. Individual differences matter.
  • The worst thing to do in compounding is to quit. Start small. Experiment and make small mistakes, not big ones. Don’t make big mistakes and don’t lose big money.
  • Toxic people who try to fool you or lie to you or aren’t reliable in meeting their commitments—get them out of of your life, quickly.
  • Do not ignore System 1. If someone or something arouses a sense of disgust within you, don’t go near it.
  • To engineer luck, you have to know 10x more and work 10x harder than to be lucky. But do you want to deserve it and maximize your chances, or depend on a crapshoot?
  • Investing your time is a skill. Investing time is much harder than investing money. If you're an employee, you're an investor. If you're a founder, you're an investor. You must understand the business. Play in the public markets. Pay your tuition. A business must speak to you. What are the variables at play? What is the margin? Competition? Expansion opportunities? Managment skill and return on investment? Cost structure? These must sing to you so you can place a shot.
  • Think by moving. "When in doubt, just try shit." A friend of mine, Stephen, stands by this advice, especially for people in their 20s. If a shark stops moving, it dies.
  • Make yourself into somebody you yourself admire. If you think about the people you admire most and make a list of those traits, you will find those are things you can cultivate in yourself. Clear values. Clear thinking. Calm life. Loving family. Generosity. Authenticity. Curiosity. Openness. A fit body. A complete soul.
  • If you wait to act until it is perfectly safe to do so, you will be too late for the opportunity at hand.
  • A complete shit-show and a product success feel exactly the same way until minutes before it launches.
  • Do the simple things until they don't work anymore. Do things that don't scale. Optimize later. Smart people like optimizing because it's fun. The smartest people do it the dumb way first.
  • Do your best and tell the truth.
  • Practice doesn’t make perfect. Practice makes permanent.
  • You can always tell someone to go to hell tomorrow. But sometimes, they deserve to know right now.
  • If you worry, you don't need to worry. If you don't worry, you need to worry.
  • Never work with someone you don’t trust. Your body will know. Trust your gut.
  • What shapes a person’s character isn’t his internal state, nor the sum total of his past experiences—though something like trauma may be relevant if it is used as something to overcome—character is formed by action only, and only in response to conflict. Literally nothing else matters.
  • The right amount of risk may feel like too much. Some people are built with the right risk compass; most are not. For most, the right risk attitude will always feel like 'too much risk.' But risk taking is a muscle, and you can learn to love it. Start small and work your way up. Talk to strangers. Make friends with them. Then talk to girls you don't know. Then ask them out. Then start a business.
  • The waiter test works. Pay attention to how someone treats other people: do they speak positively or act positively towards them? Do they badmouth them or always portray themselves as the smartest in the room and everyone else is idiots?
  • Show your work. Put stuff out there. The internet is a big place, but also a surprisingly small one. Good stuff gets shared and this is how you create your own luck. I've seen this work again and again for myself and others. But I've also made the mistake of not putting more stuff out there, and often I do under various pseudonyms, and perhaps I make the mistake of not compounding under a single name.
  • Don’t forgo 50x to save 50%. Savings are legible, but potential gains are invisible. It can be tempting to focus on the easily measurable, but not everything important is measurable, and not everything measurable is important. Many options are systematically underpriced.
  • Optimise for freedom. Even when you really like a job, make sure that you extend your runway. Save money. It gives you optionality. You will be able to choose your work and who you work with. My goal is to hit a critical mass where money makes enough money in a diversified portfolio so that I don’t need to work. I, of course, will still work. But it will continue to be from a place of meaning-making.
  • Be interesting.
  • Meditate.
  • Write things down.
  • Be active every day.
  • Body, mind, family, work.
  • Time, relationships, health, wealth, vocation.
  • Read a lot, a lot, a lot.
  • Don’t lose money.
  • Calm is contagious.
  • There is no life-making trade, look for slow and steady compounding.
  • I get energized by reading and researching and thinking and writing about new ideas and talking about them with people.
  • I have to leave the house at least once a day to get the juices flowing and feel complete.
  • Systems over goals.


  • There’s a balance between respect for the market and deferral to it. The market is not always efficient.
  • Rule 1: Don’t lose money. Rule 2: Don’t forget rule 1.
  • Do not sell good businesses when they go above intrinsic value. Keep them and let them compound.
  • Hold cash. Holding liquidity creates opportunities when volatility in markets surface.
  • Risk is the possibility of harm or injury, especially permanent harm.
  • Do not put yourself in a position where, if the market doesn't go with your position, you get taken out of the game with a big permanent loss.
  • One of the hardest things in investments is to not match your cash outflows with your cash inflows. You need to wait for a good pitch. And if it's not there, just let the cash pile up.
  • Find a business that will exist in thirty years and get stronger.
  • This, too, shall pass. It always seems like the worst one when you’re in them. But it does pass.