andykassier

I turned 40 last week, here are 40 reflections I wrote down... On Change & Transformation 1. Blowing up my life and walking away from a successful career to embark on something much more uncertain was the most important decision in my 30s. It led to so many great things. At the time, it felt scary and foolish. Now I wish I had done it earlier. 2. You can reorient your life in a new direction quickly but the underlying rewriting of scripts and rewiring of your nervous system takes much longer than you would ever expect. 3. Following your “bliss” as Joseph Campbell has put it, is one of the most worthwhile things to do with your life. But I wouldn’t recommend it to anyone. Following what truly matters means you must walk away from parts of yourself that you love and parts of yourself that others love. This can be quite the roller coaster of emotions. 4. “The moment” when people take bold action is often a post hoc fabrication. Real change is slow and confusing. I want more people to know this so they might feel permission to embrace the slow and more confusing journey of going after things that matter to them. 5. We unconsciously adopt narratives about the shape of our lives from previous generations, movie plots, and our peers. These “scripts” are often useful but tend to outlive their purpose as we age. Much of life is about figuring out which stories to discard as you age. 6. I have two regrets from my twenties: not living in another country and not taking more risks career-wise. Both would have pushed me out of my comfort zone. It seems that life will eventually push you out of your comfort zone whether you want it or not, so you might as well do it intentionally as early as possible. 7. I’ve never looked back and regretted being more adventurous with my life. Assuming this is true still now, it means I can probably be more adventurous than feels comfortable right now too. 8. There are many rules worth paying attention to, but many more are negotiable. We live in weird times and thriving in life likely requires weird approaches. If you aren’t shaking things up in random ways, you are missing out. On Work 9. The desire to escape work is pervasive and keeps far too many stuck in less-than-ideal situations. People dream of one day becoming financially free. This is a mistake. You can’t escape work, you can only transcend it. 10. Finding your “good work,” the work that feels satisfying in the moment and satisfying upon reflection, can take years to find. But once you find it, you’ll be happy you never gave up. 11. The 14 months I spent writing my first book was the most satisfying work experience of my life. If that is the only thing of note I create for the rest of my life, it will have been worth it. 12. A “good job” can still be bad work. It’s easy to confuse a life that makes sense on paper with one that fills your heart and soul. 13. More people should try self-employment or freelancing for at least a year. Learning how to make money independently and stay productive without a boss is invaluable. 14. Time for tinkering, following curiosity, and reading about random things can feel like “wasting” time but tends to lead to interesting opportunities. 15. Burning out happens faster when working for yourself because there are no built-in limits. But this can be a good thing—it means you’ll waste fewer years doing things you don’t care about. Money & Success 16. Attaining impressive achievements feels great, and I wish people would stop pretending otherwise. The problem is you’ll get addicted to the feeling and be surrounded by other addicts too. 17. Defining success on your own terms will create tension with those around you. It is easier to succeed like those around you but more satisfying to make progress against your own secret mission over the long term. 18. Having success early in life is a blessing and a curse. It can show you that many achievements leave you feeling empty, but it also means watching your peers accomplish things you know you were capable of. 19. Having an impressive job or career is the easiest way to run from both your inner world and outer world responsibilities while still being seen as a respectable adult. 20. Money is one of the most powerful forces in the world. Never underestimate its role in shaping all of your decisions as well as those around you. 21. Making less after making a high income is a cheat code for figuring out what you value. I learned this when I went from six figures to $30k after quitting my job. 22. I spent too little when young and took too few risks. If that was true then, it’s probably true now. If you were good at saving money at 23, you’re probably still good at it at 40. 23. Money fears are the home of the deepest anxieties of life: dying, belonging, being loved, and being accepted. The happiest people I know have decided to tango with these fears directly. On Relationships 24. I’ve always found relationship advice from married people unhelpful. “Communicate,” they say. Sure. But every relationship is unique to the world you build with that person. 25. Meeting Angie felt lucky, and I don’t know what to tell people still searching other than “don’t give up.” My life changed in an instant. I’m glad I never gave up. 26. Marrying someone from another country adds permanent tension to a relationship. The mistake is trying to “solve” this. The upside is embracing the tension—it makes life more interesting. Becoming a Parent 27. I had some theories about parenting. Then I had a child. 28. Becoming a father is the most humbling thing I have experienced. The first two years have forced me to admit, “I don’t know and it’s okay” more times than I can count. 29. Anxiety about your kids is probably the most acceptable kind of worrying. But if I see everything my child does as a reflection of me, I’ll undermine the connection I hope to have with them. 30. I’ve never experienced more moments of joy and love than I have while spending time with my daughter. She is my greatest teacher. 31. I suspect having a child toward the end of my 30s makes it easier than if I became a dad in my 20s. Despite this, I am a bit sad that I’ll have “less time” with my children than a younger parent will. 32. The returns to having a great spouse with a young child are incredibly high. Having someone you can laugh with about parenting struggles is priceless. 33. It’s been sad to see so many people in my generation opt out of becoming parents. But I understand. If I hadn’t met Angie, I don’t know if I would be a parent now either. 34. Parenting has added constraints to my life, and I would be lying if I said I “had it all.” But I don’t regret this time one bit. Happiness, Life & Misc… 35. There is a state of alignment you can reach in which magical things will start happening to you. I would have rolled my eyes at this ten years ago, but now I believe it. 36. I’ve never seen a single person become happier by spending more time following politics or the news. 37. Reading history gives you more appreciation for the present. Humans have always been crazy. 38. Leisure and deep rest, the kind that recharges our soul, is a practice. And it’s incredibly hard to commit to in a world obsessed with hustle and achievement. 39. “Have you tried doing less on the problem?” is an underrated strategy for getting unstuck. Most people try to do more. 40. Writing is one of the most powerful acts in the world. It’s never too late to start. But beware: writing will expose what you truly desire.