A definitive guide to a life well-lived

As I sat in a cab on Saturday evening being zoomed through some blurry part of Chelsea in the recklessly competent style of the New York cab driver, my friend texted me and asked how I would define a life well-lived. I assumed correctly that she was drunk.

This question brought back memories of a class I took in my senior year at Penn called “Literature of Success,” a popular one among almost-real people getting angstily ready to begin noble consulting and finance professions - both the culmination and beginning point of their lives so far. The class offered a rich reading syllabus with works from Benjamin Franklin (of course), Viktor Frankl, and others which I presently forget, and the goal was to ingest these people’s stories and eventually come to our own answer and plan to achieving success in the real world. And naturally to be graded on the quality of that plan.

I texted her back with a few spontaneous answers from my left thumb and later realized that it would be nice to expand on this list and keep it somewhere.

Here it is. I know that my answers are very influenced by my present conditions and advantages, and that some of these suggestions are more or less within our control. I’m also sure that this list will deserve to be added to and edited over time as more life is lived and more parchment unfolded.

  1. Have a healthy and happy family.

  2. Work every day with people you love and respect, moving toward fulfilling your potential and mission.

  3. Make sure you live the experience of real romantic love and don’t settle until you feel it.

  4. Make sure that your opinions and choices are really yours.

  5. Work to be in great physical shape.

  6. Expand continually out of your current boundaries of comfort and competence.

  7. Do not leave any rock that you find interesting unturned. Similarly, do not let fear stop you from sampling something that you really want to do.

  8. Pay attention to the elephants in the room. When you feel something is wrong, even if only a little, act on it immediately. You are in a position to course correct.

  9. Be aware of your general slope, your dy/dx, and ensure that it’s sloping up and steepening. Keep accelerating.

  10. Don’t spend much time sulking. There is no nobility in suffering for too long… unless it inspires you to compose a nice song or poem.

  11. Reroute and leverage your anger, insecurities and other negative spirals.
    Make sure that they are not the only forces motivating you (otherwise you will implode) but use them as explosive fuel to propel you forward. Anger is like an extremely heavy unwieldy sword that can be very useful.

  12. Prioritize aggressive decisiveness - even if sloppy - over over-analysis.

  13. Realize that even though many people are wrong (except for this author), they have simply been shaped by their life so far and do not explicitly intend to be evil. Several truths can exist at once.

  14. Do not pause your learning, even when you’re in the trenches executing on the current plan or project that has taken over your life.

  15. Do not keep neglecting something you know is fundamentally important to you. Those things are not the same for everyone.

  16. When the time comes, drop everything for the more important person or thing.

  17. Ask yourself what the people you are close to are great at and suffer from. Encourage them to express their greatness more and help them navigate away from their bad habits and pain.

  18. If you have the luxury to, make sure you work on ideas that directly improve life for people. Those that viscerally confront the human condition. There is no such thing as a dearth of ideas. As long as there is suffering, there will be great novels and also problems for you to tackle and solve. If you are in a position to try tackling one of them, it is almost your obligation. Great people will also be attracted to join you because doing something meaningful is one of the most powerful magnets that exists.

  19. Practice random acts of kindness. You will feel good and these will compound. There is an ongoing war in the world between cynicism and naive benevolence. You are contributing to tilting the scale because your behavior is the reality of the person you are interacting with.

  20. Do not pretend to be morally superior (unless you are on Twitter). Your human nature makes you inclined to prioritize yourself. It is hypocritical to deny this, and yet this does not stop you from becoming a kindly-motivated person.

  21. Spend more time with people you love and who have a good influence on you and less time with people you don’t love and who don’t make you someone you are happy being. You already know who falls in which bucket.

  22. Often ask yourself what you will regret not having done at the end of your life and the lives of the people you love… and do those things.

  23. Remember that nothing matters. And that everything matters.

  24. There is no right answer. There is a right answer.

  25. Remember that everyone feels the same spotlight effect you feel. They are more distracted being self-conscious of their own appearance and barely notice you. You are wearing an invisible cloak, so have more fun and don’t worry about how you look on the dance floor.

  26. Realize that most of what you want is within your reach, usually only a few good decisions away.

  27. Prioritize the spontaneous plan over the planned plan. Sunk costs are a real thing.

  28. Speaking of… the thing about cognitive biases is that even very savvy people fall for them. Sunk cost, confirmation bias, loss aversion, endowment effect, anchoring, halo effect, mere exposure effect, bandwagon effect… there are more. Learn about psychology and behavioral economics because you will learn about yourself and discover some of the hidden forces that have been barring you from making the progress you want. Being able to name them is already a big win toward neutralizing them.

  29. While we’re on the topic of savvy people, keep in mind that even the most professionally accomplished among us frequently make terrible decisions in other parts of their lives. Don’t think that someone is necessarily correct across the board because they stand out on one dimension. Similarly, don’t think that just because someone has made a lot of money they are by definition unhappy in the other parts of their lives.

  30. You’re at your worst when you focus on the success of other people and wish it were yours. It’s the biggest and most demoralizing distraction to anyone ambitious. Let them live their lives and focus on your own story.

  31. Never delay telling people you love them. You should take the chances you get and you don’t know what a powerful effect you have on them by telling them that.

  32. Remember that you too are maddening to the people you love, so don’t sabotage your closest relationships over stupid things. You do those things too, or have other charmingly infuriating habits.

  33. Change your mind decisively when you have realized that you are wrong. You are a work in progress and only the truth and resolution matter.

  34. Write the list of things you’ve been wanting to do for a long time, and go down the list doing them now.

  35. No one - not even your spouse or best friend - can or will ever quench your every need and desire. Do not expect that of them and you will put less strain on your relationship.

  36. Enjoy the warm, snug feeling of being dependent on someone but make sure you are autonomous enough to thrive independently and venture out into the snowy woods alone should need be.

  37. Rarely is it worth using your energy to retaliate against someone who has wronged you (unless they are actively still doing so). You will create more value by continuing to create and ignoring them.

  38. The most redoubtable people are not those who get into street fights.

  39. Choose partners who do not have a fixed-pie view of the world. That paradigm is very difficult to unlearn and is unfortunately tainting.

  40. Realize that relationships compound dramatically over time. Be loyal to the people around you and continue to write the story together. You can move so much faster when you have deep-rooted trust.

  41. If you’ve observed yourself mentioning or noticing something more than a couple of times, pay real attention to it. It is likely very important and should be addressed now.

  42. Think of yourself as a professional athlete, aiming for daily excellence. Now balance this image with the realization that it is a handful of key decisions and events every year that will shape your life. Create and wait for those.

  43. Travel is wonderful, but do not try to use it to run away from facing the important questions head-on.

  44. People only share 1% of their lives publicly. So don’t let Instagram (and people’s selective sharing) make you sad.

  45. “When the student is ready, the master appears.” You are an agent of your own life, and yet.. some of the things you most desire cannot be brute-forced into reality, often because they are not external. Perhaps you haven’t yet found your life partner because there is still a little tinkering to be done on yourself.

  46. It is possible - and sometimes really worth - fixing broken relationships (of all types). If you feel like something ended for the wrong reasons and you miss it, you should put your ego aside and give it a sincere shot.

  47. Speak well of people behind their back and criticize them (if you have to) to their face.

  48. Deliberately expose yourself to more randomness. Enjoy seeing if you can break something about your model of the world.

  49. Let your heroes teach you about general strategy and incite you to do great things, but do not attempt to replicate their exact execution.

  50. If you know you’ve made a mistake and it’s not too late, you should consider yourself incredibly lucky and go fix things immediately.

  51. Don’t do things that compromise your integrity. It is - per the definition of the word - what makes you whole.

  52. Fun is not only reason enough, but one of the best reasons to do something.

  53. If you often tell people you’re not good at something, decide if you want that to be the case of the rest of your life or if you want to try to become good at it.

  54. You’ll be surprised at how good you can become at most things if you apply yourself to it for a year or two. Try it and tell me.

  55. A few subjects worth taking one class in at some point in your life: dance (especially before wedding season), public speaking and / or stand-up comedy, cooking, wine (so you can at least distinguish between more than just white vs red). Knowing just a little bit more than nothing here will feel great and goes a long way.

  56. Go on more road trips.

  57. Keep note along the way of things that you will want to share with your children (even if you don’t want children).

  58. The world is scary, random and unfair. The world is wonderful and kind and always conspiring in your favor (as Coelho would say).

  59. Never let events or people extinguish your fire and love for living. You are alive when you are burning.

  60. Your intuitive voice is the one that is correct.


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