34 Lessons on The Way to 34

I’ve come to recognize that I’m really hard on myself. My inner critic has developed into an expert in what Steven Pressfield would label "resistance"- that voice whispering “you're not good enough, you need to be doing more”. There’s almost a twisted sense of pride that I feel in admitting that, but it’s honestly just debilitating.

I was at a live podcast recently where Andrew Wilkinson mentioned something that stuck with me- “Most successful people are just a walking anxiety disorder harnessed for productivity.” Tim Ferriss has also acknowledged something similar: “I want to be easier on myself, but I worry that if I do that, I will lose whatever magic, if there is such a thing, that enables me to do what I do”.

Finding a balance between striving and acceptance has been difficult for me. Looking back, I see that I was desperate for “success”, yet I never properly defined what it was I was chasing. I think I somehow thought that quickly achieving in another area would allow me to move on from the pain of not realizing my lifelong dream of playing in the NHL. I’ve struggled with it for years, holding onto everything so tightly and taking everything so seriously, to the point where my body refused to accept the built up stress any longer, leading to a panic attack and hospital visit. That’s when I admitted I couldn’t “effort” my way through life, and started seeing a therapist regularly for the first time- I feel like I’ve gained a super-power of insight after each session.

“If we’re not regularly, deeply embarrassed by who we are, the journey to self-knowledge hasn’t begun.”

— Alain de Botton

As I set out to reflect and put some thoughts together leading up to my birthday this year, I forgot that I had already done something similar when I turned 29. On my morning run yesterday, all of these thoughts mixed together in my mind and I decided that for my birthday, I need to gift myself kindness- remember how to have some fun. There’s a great book title by Kamal Ravikant that serves as a good reminder here: “Love yourself like your life depends on it”. In it, he asks an important question that I’ll end with:

“If I loved myself, truly and deeply, what would I do?”

To celebrate another year of life, here are 34 pieces of wisdom I’ve come across filtered through thousands of books and notes over the years, reminders to myself more than anything else:

  1. Inspiration is perishable and extremely valuable. When it comes, act immediately and build momentum. Amelia Earhart has a quote that I like related to this: “Always think with your stick forward.

  2. You need to develop your own version of a feedback loop, a system for tracking how you’re doing over time. For me, I have an in-depth annual review, and quarterly I grade myself in 3 major areas: Health - Wealth - Wisdom. The sub categories I review quarterly are: Family, Marriage, Parenting, Friendship, Nutrition, Training/Sleep/Meditation, Finances, Business, Home, & Happiness.

  3. Something I keep written where I’ll see it every morning is a final piece of advice that my Grandpa gave to me before he passed: "Live with integrity, humility, bravery and honesty. Have the knowledge to accomplish your goals, and the wisdom to do so with respect and love."

  4. “I’m not entitled to have an opinion unless I can state the arguments against my position better than the people who are in opposition. I think that I am qualified to speak only when I’ve reached that state.” - Charlie Munger

  5. “Strong opinions loosely held” (via Marc Andreessen). You need strong convictions, but you also need to be able to adapt in light of new information.

  6. Something that took me a long time to realize: don’t worry about organization of thoughts and notes initially. Instead, build up the material, let it accumulate. No thought is too small to jot down. Keep detailed notes, as often things often only make sense looking backwards. To connect the dots, you have to collect a lot of them.

  7. Seek wealth, not money or status. Wealth is having assets that earn while you sleep. Money is how we transfer time and wealth. Status is your place in the social hierarchy. - Naval Ravikant.

  8. "A calm mind, a fit body and a house full of love. These things can not be bought. They must be earned." - Naval Ravikant

  9. An interesting thought exercise that has had a big impact on me in the past year from “A Happy Pocket Full of Money”: Meditate on the eternal moment of Now: Everything that can possibly happen in the universe, everything that can possibly be created, the past, present and future, are all running all at the same 'time' in one huge field. Your consciousness and awareness are awake to only a small section of this field at any one 'time' and as you move them about from one point to another, you experience 'time', experiencing a sensation of past, present, and future. The field itself does not experience time; it only experiences an eternal process that is always happening all at one go, Now, Here, Always, All Ways.

  10. “The best work ethic requires a good rest ethic.” Work hard, but learn to manage your energy.

  11. A few related ideas: “The fact that I’m me and no one else is one of my greatest assets.”- Haruki Murakami. “Be your unapologetically weird self” and “embrace your funk”.

  12. Kindness is free and opportunities for it are everywhere- if you notice something worth a compliment, say it out loud.

  13. Discipline = Freedom

  14. When someone tells you something is wrong, they’re almost always right. When someone tells you how to fix it, they’re almost always wrong.

  15. Having a child has increased my bar for commitment to things and my unwillingness to waste time. These moments aren’t just being taken from me- they’re stolen from my little girl as well.

  16. Something that will make you feel both powerful and woefully inadequate: your little girl staring at you expecting you to have all the answers.

  17. Learn as much as possible about incentives and motivation. Especially in a business context, train yourself to ask “what is this person’s intention, and what do they want out of this”. If it feels like you’re being manipulated, you probably are.

  18. Tools are only as good as what they allow you to accomplish. The best system is one that works for you- ensure regularly that it’s actually working and producing results. What have you actually built with it? What have your systems allowed you to produce?

  19. The first principle is not to fool yourself – and you are the easiest person to fool.” - Richard Feynman

  20. The mundane and everyday can be unbearably beautiful if we really pay attention.

  21. Develop a strategy for when you’re feeling down, stressed or anxious- it can be really difficult in the moment, so having a checklist of sorts to return to can be helpful. One thing I’ve found helpful is to send out what you need- love and energy. Help someone, send a friend a text or compliment. Learn to reliably shift your state.

  22. Keep your identity small (via Paul Graham)

  23. When travelling or at a concert- put your phone away. You’re never going to go back and watch that crappy quality video. Let the experience be the reward and fully inhabit the moment.

  24. “I’m divine light hidden in a human form” - Mike Posner

  25. Make friends among the eminent dead”. Read widely, and learn from the best of what others have discovered. Old problems have old solutions. There’s a quote here that I like from Machiavelli- “at night, in the austere silence of his studio, he engaged in solitary, literary conversations with the ancient scholars.

  26. Two potentially conflicting ideas: “how you do anything is how you do everything” and “what you do is more important than how you do it, and doing something well does not make it important.

  27. The standard pace is for chumps (via Derek Sivers). Things like curriculum are organized around the lowest common denominator so that everyone can keep up. Learn to question assumptions and reason from first principles.

  28. Use your tools- don’t let them use you. Some of the smartest people in the world are working 24/7 on new ways to distract you and keep you glued to a screen. Don’t rely on willpower alone, and develop strategies to use your devices wisely.

  29. There are no shortcuts to understanding yourself better, and no one can do the work for you.

  30. Observe your rhythms and learn to communicate them. In marriage, mistakenly assuming your partner knew something (or should have known something) can be one of the biggest sources of conflict. Your partner can’t read your mind, and honest communication solves a lot.

  31. Behind mountains are more mountains - failure or success are never permanent, things are always in a state of flux.

  32. For high pressure situations, simple mantras are a good way to calm your mental state (stop it from spinning out of control). “Calm Controlled Confident” is what I used through my hockey playing days. “Steady Strong Smile” is what I now use during cycling or running.

  33. For all difficult projects or events like a marathon, when you’re 90% done, there’s 50% left. That’s also where the pay-off waits. Sometimes in a writing session, you sit there for 59 minutes and it’s the 60th minute where things start to flow. In a marathon or Gran Fondo, it’s the final 5 or 10k stretch where you’re really tested and learn the most.

  34. “The object isn’t to make art, it’s to be in that wonderful state which makes art inevitable” - Robert Henri. Seek states of flow.