37 Lessons from Being 37


On Monday, I turned 38. If you’ve been following Wednesday Words, you know I use my birthday to write lessons from the prior year. Inspired by Kevin Kelly, I’ve done this for the past 7 years without fail.

To create the list, I pour over my journal entries, calendar events, photos, etc. It takes time, but it’s one of my favorite practices. And sharing them with you is a treat.

With that said, here are 37 lessons from being 37. I hope they help you in some small way.

  1. Do whatever it takes to sleep more. A few things that have (finally) started working for me: stop eating or drinking three hours before bed, keep my room cold/dark/quiet, and go to sleep around the same time each night. A little cbd helps when traveling. These changes have made a world of difference.
  2. Everyone should take an introduction to sailing course. The parallel lessons for life and work are amazing.
  3. One of the ways you can measure the richness of your community is by the age-gap between your youngest and oldest friends. The wider the gap, the fuller your life will be and the more you’ll learn along the way.
  4. Buying a home is wildly stressful. All parties involved have the power to make the transaction more delightful. Remember you’re after the same things: a good home, a fair price, and minimizing stress where you can.
  5. Book more empty days.
  6. Your mind is always bouncing between today, tomorrow, and someday. All three are ok, but the more you focus on today, the happier you’ll be.
  7. Committing to an idea before you get feedback is like sprinting through a pitch-black room — you’re going to hit something and it’s going to hurt. Feedback sheds light and confirms you’re on the right (or wrong) path.
  8. The first year of doing anything new is going to be a learning year. Give yourself extra grace for all 12 of those months. Don’t rush it.
  9. Your life moves at the pace of what & how much you want.
  10. “Disposable” items are killing us. Work to buy things you’re able to use for a long time and care for well. And whatever you’re not caring for, give away or sell. One of the best things we can do is rethink how to maintain and appreciate what we have.
  11. Career change is the new normal. Keep expanding your toolbox for when you’re ready or the time comes.
  12. The companies who teach career navigation tools will be the best places to work because their employees will feel more trust, be more engaged, and stick around longer.
  13. If you’re in any type of serious relationship, get a counselor (yes, even if you’re not engaged/married, and even if everything seems ok). If your car needs professional maintenance every few thousand miles, why wouldn’t your relationship?
  14. There are usually four steps to take before making a decision: ask the right question, gather data, summarize your findings, and then reflect on how the possible outcome makes you feel. Skipping any of these can lead to poor decisions.
  15. The success of any endeavor is based on whether or not someone can really envision the outcome. If you can’t create a clear and meaningful image, you won’t achieve your goal.
  16. Remember you can always feel better. Always.
  17. Quick ways of feeling better are usually vices. Sustainable ways of feeling better often require research, discomfort (at first), and consistency; but they’ll last. Take the time to learn what works for you. Start today.
  18. Be a loyal friend for a long time. Keep showing up. It makes for a full life and a more caring world.
  19. You can evaluate your relationship with your work based on how quickly you can switch into rest-mode. The longer it takes, the more off-balance you are.
  20. When you’re entering a business relationship with anyone, make money-discussions a normal part of the conversations. Pay attention to any yellow flags. How someone handles their money says a lot about how they’ll work with you.
  21. Address pains in your body asap. Don’t wait to get an opinion on what might be happening. Do the same for your mental wellness.
  22. When you watch athletes at the top of their game, there is a clear delineation between player and coach (or manager). As you grow your endeavors, be clear about who you want to be. You can do both for a while, but it’s unsustainable in the long-run.
  23. Worry really doesn’t help. Do what you can, and try to carry it lightly. You’ll probably get to the same outcome and feel better at the end.
  24. Don’t celebrate until it happens.
  25. If you’ve been putting off a small, important project in your home or work for a long time — just hire someone to do it. Chances are you’ll feel better having it done, and you can continue focusing on what only you can do.
  26. If you’re going to sell or pass something off to someone else, get it cleaned, fixed, polished, organized, etc. The old saying is true, what goes around, comes around.
  27. Be comfortable in dualities. Something can be scary and exciting, sad and beautiful, hard and amazing. This makes life rich.
  28. If you’re trying to decide what to learn next, make a list of what you know on the left side of a piece of paper and what you wish you knew on the right side. The gap in the middle is what you need to learn and experience next. This is the moment before your next leap.
  29. Plan annual trips. Stick to them for at least three years. Things become a tradition after three years.
  30. Don’t repeat something you don’t want to become a tradition.
  31. Ai is amazing, but it can’t dig into your past experiences and tell your stories in a way that connects with others. Learn to tell your stories well and you’ll always have a place in the room.
  32. Encourage your colleagues to take risks. The workplace should be a place of discovery.
  33. When planning an engagement or a wedding, throw out society’s playbook. It’s expensive and impersonal. Design whatever you want. It’s way more fun.
  34. The future of work and learning will look nothing like it does today. Cramming your learning into a degree and then getting a dismal 9-to-5 just isn’t it. Keep exploring new ways.
  35. If you spend more time thinking about your strengths than your faults, life is a lot sweeter.
  36. Everyone has a still, small voice that tells you exactly which way to go. It usually shows up when you’re well-rested, well-fed, and in good company. If it appears, listen to it.
  37. Write often. Review regularly. It’s the only way to really know how you’re changing (or staying the same).