38 Lessons over 38 Years

No sudden wisdom has dawned on me. No life-altering epiphanies. Birthdays come and birthdays go. This will be just another day and the start of another year. But looking back is important. Weighing my current beliefs and recording them seemed important (especially given how this year has shaped up for the world). At 76, I want to be able to look back and shake/ nod my head when I read this. 

So here goes:

Work and People 

  1. Vectors are important: one needs magnitude and direction. Speed is immaterial. Velocity is everything.

  2. Expertise is real. Listen to experts. But beware of experts who don’t understand or acknowledge their own ignorance. 

  3. As a generalist, go really broad. To make a living: build a couple of areas of depth. 

  4. No life decision made at 18 is binding. I will completely change my careers at least 5 more times. 

  5. You become the average of the 5 people you surround yourself with. Work with good and exceptional people. Avoid assholes. 

  6. “Strong opinions held loosely” is supercritical in any collaborative environment. Beware of people who hold weak opinions strongly. They are toxic. Not having an opinion is a virtue. It allows you to listen. 

  7. Passive-aggressive people are toxic. Don’t be like them. Value people who can disagree openly, build consensus and then commit to a course of action. 

  8. Don’t be aggressive towards others. Use your aggression to cut through situations and problems like a tempered steel blade. 

  9. Avoid people with a zero-sum mentality. Life is not zero-sum. 

  10. Hire people who can teach you at least one skill you are poor at. As a matter of principle: hire people who are as smart/ competent or smarter than you. 

  11. Carve out time every day to think. Carve out large chunks of time to do deep uninterrupted work. 

Building Things

  1. Ideas alone are meaningless. Execution is important. Don’t be the person who only comes up with ideas. Be known for execution. 

  2. Have a workman-like approach to building and creating things. Discipline and time spent help better your craft. Be a craftsman, not an artist. 

  3. Voltaire was right. Perfect is the enemy of good.

  4. A creator can choose to not take a political stand. Don’t hold it against them. 

  5. Good people sometimes make terrible things. Terrible people make phenomenal things every now and then. Don’t let the creator’s character come in the way of you experiencing what they have created. 


  1. Parenting is the hardest thing I have ever done. Everything else pales in comparison. 

  2. I was right at 22. Becoming a parent does not make you an expert on children (it barely makes you an expert on your own kid). Teaching kids well and writing for kids well has nothing to do with being a parent. Don’t let them tell you otherwise.

Personal Philosophy

  1. Holding opposing points of view in your head all the time can get exhausting. It leads to diminishing returns even at an intellectual level. Choose a side. Feel free to change sides if you turn out to be wrong. Admit openly and often when you are wrong. 

  2. Learn to fold your cards - in poker and in life. Live to fight another day.

  3. Praising/ complimenting people is hard. We don’t do it enough.  

  4. Being older is better than being younger. More or less.

  5. Correlation does not equal causality. P-hacking has ruined science. 

  6. We will soon live inside games. 

  7. Magic happens at the intersection of things. Massive value is generated by those who can adapt to intersections. 

  8. Practice enlightened self-interest. Help others whenever possible. It all comes back with huge dividends. 

  9. Poets and scientists are two faces of the same coin - they are both trying to understand the universe with the tools at their disposal. 

  10. Travel a lot when you are younger. Travel when you have young kids (it is super painful but worth it). Travel alone. Travel with strangers. Travel with a loved one. Travel with friends. But travel. 


  1. Becoming aware of your ignorance is a powerful growth tool. This is your personal roadmap. 

  2. Meditation is life-saving. Start meditating early in life. Meditate regularly. Also: my dad is always right.  

  3. The learning loop can only be completed when you try and teach others. Teaching is the single greatest learning hack. 

  4. Every creator should learn the fundamentals of business and should understand how distribution works. 

  5. Learning new languages becomes more difficult as you get older. Learn as many languages as possible when you are young. 

  6. Learn to change a baby’s diaper with one hand. 

  7. Workout at least three times a week. 

  8. There will never be enough hours in the day to read every book and watch every TV show. Abandon early. Reread and rewatch favourites. You will learn something new about yourself each time. 

  9. Finding a solution is easy if you spend enough time in the problem space and keep reframing the problem until the solution is obvious. 

  10. Good frameworks are like good scientific theories: they stand the test of time. However - coming up with new frameworks is as important to the intellectual pursuit as building new theories is to the advancement of science.