My 2022 Recap. Lessons I Learned The Hard Way

When I started out on my entrepreneurial journey, I made a commitment to share my education by posting on LinkedIn. Once, twice or in many cases several times a week depending on things I felt important to share. I have held to this commitment for seven years and along the way conducted a lot of experiments with long form, short form content, videos and memes. The noticeable benefits that accrued are; My writing improved dramatically. It has helped me organize my beliefs and outlook based on first principles. Opened a door to discover my authentic self (which was both liberating and confidence boosting) and extended my creative range.

As an entrepreneur, the last 7 years have also been the hardest years in my life. Filled with a fair share of pain and disappointment. It has stretched me beyond my comfort zone and at times psychologically crushed me. It has been an agonizing bootcamp that deconstructed and rebuilt me. The journey has provided invaluable lessons. And when you subdue your ego (which typically wants to blame others for misfortune) and open your mind to learn, you experience epiphany and lose fear.

For my 2022 recap, I have distilled the some of the hard lessons learned along the way, both personal and professional. Each could easily be a short form essay. But part of the art of writing is being concise. So I leaned on the help of those much more perspicuous than me. To be clear, these are not my words, but those of others - I saved them because they encapsulate, with exceptional brevity, what I learned from my own experiences. This is not an exhaustive list by any means, and there is no ranked order - what binds them together is how often I recognize them now and how often time plays as a central concept.

1.Nature's got nothing but time. Regardless of what games you play, nature always wins. Nature just runs the clock out on you. Every time. (The greatest gift is time doesn't stand still: the greatest curse is time doesn't stand still.)

2. Time does not just burn all assumptions, it razes them, then poisons the well and plows salt into the ground.

3.What you seek to optimize will eventually optimize you.

4. Game changers are never announced. They come silently to change the game. You never see a game changer coming, that's why they are called game changers. They don't ring an alarm bell to tell you they are coming.

5. Even the most complex simulation model on earth, requires a break. (Nothing can survive without sleep, or blinking)

6. Good decision makers aren't good at making great decisions. They're good at not making bad decisions.

7. People will forget what you did, but they'll never forget how you made them feel.

8. The joy of missing out > the fear of missing out.

9. Success is about the ability to handle failure. Be a success at failure.

10. The smartest kid in the class is not in the class, or even enrolled in the school.

11. It's broken long before it breaks.

12. When you have nothing left to lose. That's when you know you've won.

13. In complex systems, when you maximize the benefits, you maximize the harm as well. You don't get to pick only the benefits.

14. Be aware who sets the rules in the games that you choose to play. If they can change the rules to benefit them, find another game.

15. When you know the arguments against your point of view better than those who make them is when you become an expert.

16. Know that you don't know. Real life is about managing what you don't know, not learning what you don't know. (Life is composed of second order effects that are unknowable because "rules", if they exist, can be bent or broken.)

17. The essence of upstarts and disrupters: You can't stop someone that can't be hurt or hurt someone that won't be stopped. They don't kneel to budgets and deadlines.

18. Simple, yet elegant, design creates more brand equity than any amount of marketing budget can possibly buy.

19. A sign of growth is having more tolerance for discomfort. But it’s also having less tolerance for bullshit.

20. Who you are is not your fault, but it is your responsibility.

21. You don’t find your ground by looking for stability. You find your ground by relaxing into instability. (Variant of # 16)

22. The biggest life hack is to become your own best friend. Everything is easier when you do.

23. What you hate most in others is usually what you hate most in yourself.

24. Real confidence looks like humility. You no longer need to advertise your value because it comes from a place that does not require the validation of others.

25. Finding your true self is an act of love. Expressing it is an act of rebellion.

26. Your mind doesn’t wander. It moves toward what it finds most interesting. If you want to focus better, become more curious about what's in front of you.

27. You can't life-hack wisdom. Do the work.

28. When religion was pervasive, the criteria of demarcation of science was obviously clear. Religion is the compliment of science not the competitor.

29. Some become scientists to help humanity. Others do it because they want to wear a lab coat and boss others around.

30. Your words are meaningless because anyone can reproduce them. Your actions, on the other hand, are not.

31. Improve the process to improve the outcome, but don’t worry too much if the outcome isn’t perfect. "Amateurs practice to get it right, professionals practice until they can't get it wrong". (the essence of becoming a master artisan or Takumi)

32. Wisdom is born out of empathy and compassion. Not the accumulation of knowledge.

33. When you DON'T get a straight answer. That's more informational than getting an answer. It tells you everything you need to know.

34. If you do get an answer, the follow up question to the answer is: What's the cost of the answer?

35. If you can’t subdue your ego and listen to people better than you, you were doomed before you even began.

36. It's supposed to hurt. That's how you know it's worth it. Pain is part of the process. It will purify you.

37. Speed beats power. Positioning beats speed.

38. A shitty apology doubles the insult.

39. Committees can't observe and then make effective decisions because their opinions are constantly in their way.

40. To be popular add to the consensus/narrative, to help society leave it behind and explore

41. Number of employees - like number of artists, number of scientists, number of thinkers - is a completely useless metric.

42. When things don't go well it's because we didn't plan enough. Typically it is the opposite: we planned too much and then held ourselves captive to a plan that turned out to be wrong for all sorts of reasons.

43. Deadlines are moments of communication around the *outcome* we are trying to achieve, rather than an estimate for how long it will take to build something in the blind. It's a budget for how long we can invest time in trying to find a solution.

44. Maps >> Plans. Road maps/journey maps/story maps = opportunity exploration. Opportunities do not bake in the assumption that you are right, unlike plans.

45. If you have to negotiate, time > money.

46. This graph, in reality, is actually exponential and is the equivalent of the first law of thermodynamics in business and in life.

47. This guy understood, better than anyone else, the importance of time in all ventures in business and in life. Unfortunately the concept is lost on many who only view this literally.

48. Complexity responds to competence, not authority.

49. Avoid falling into this mental model. "They don't know ... (how brilliant I am)"

50. Technology is above all things defined in terms of newness, which not only makes it disruptive of pre-existing power, but destructive of itself —?a sort of anti-power that only guarantees change. The true failsafe. The ultimate reset.

51. Supposedly it takes 10,000 hours to become an expert at something. Not quite, it takes 10,000 iterations. Replicating the same outcome 10,000 times. It is a commitment to build expertise in a particular skill or set of skills.