40 Reflections on Life at 40

As I turn 40 years old today, I am reflecting on the lessons I’ve learned in love, (work) life, and the pursuit of happiness. Some of these are borrowed. More than a few are clichéd. Nearly all have their roots in failure.


1. Daily gratitude and appreciation should be at the heart of a good relationship.

2. If you are suffering heartache, acknowledge it and pamper yourself however you need it (as healthily as possible). New jeans and new bedsheets work especially well.

3. If you’re only pining for or wanting to get back together with your ex when you’re lonely or feeling low, you’re missing companionship, not necessarily that person. The feeling of wanting to be with someone should come from a place of strength, not sadness.

4. If someone tells you that you’re too good for them. Believe them — emphasis on leave them.

5. I never had a relationship where I took things too slowly — and more than a few that ended because I rushed into it.

6. As powerful as they can be, words come easily. Actions are harder and carry more meaning.

7. It’s true that we accept the love we think we deserve.

8. Don’t go to bars with the expectation you’re going to meet your next boyfriend — you’re bound to be disappointed at the end of the night.

9. Some love interests aren’t there to be your boyfriend, partner, or spouse; they are there to remind you of what’s worth waiting for (aka “The Matthew Smith” rule).

10. The first year of marriage was harder and more work than I expected. The new level of commitment — like going from a 10x10’ room to a 10x10,000’ room — required a deeper willingness to work on myself and be the best husband I could be.

11. When you’re in a relationship, sleeping on the couch isn’t always a bad thing. Sometimes you just need it.

12. Someone told me recently that marriage isn’t 50/50. It’s 90/10 and you take turns. That seems right.

13. After more years being single than I wanted, only two rules held up for dating: 1) work on yourself; and 2) have frequent interactions with lots of people at the quality level you would want to marry (frequency + quantity + quality). Both are hard in their own way.

14. Don’t settle in love. Hold out. It’s worth it.


15. People always remember how you start and leave a job. Handle both with care.

16. Life is cumulative. The harder you work in high school, the better college you can go to, which is more likely to help you get a first job you don’t hate as much.

17. Yes, and… Life is not totally linear. There’s no guarantee that your hard work will result in a better college or job. Or that you can’t return to a path you once left.

18. In my second job out of school, I stressed out about the direction of my career. I put too much pressure on myself to “get it right.” I wish I’d known then that what I needed was simply more experience. What I did mattered less than how I did it.

19. A candidate for public office who answers the question “why are you running” by talking about herself, and not her community or a greater injustice, is more likely to lose.

20. Twice I’ve taken the job that pays more but brings less daily joy — and my career and life suffered. In contrast, when I was paid less by a job I loved, I was more passionate and worked harder — thus increasing my success and, in time, paycheck.

21. The world gets increasingly less black and white with each new experience, especially with each loss and failure.

22. Starting my own business was scary as hell, and totally the right decision for me at that time. Once the entrepreneurial spirit was in me, there was no turning back — and I’ve yet to regret it.

23. The idea of a self-made man or woman is laughably short-sighted. We have all benefited from those who came before us and the greater public infrastructure.

24. We white people (especially men) need to listen more to people of color. The world will be a better place if we do.

25. In work and life in general, don’t pull up the ladder behind you. Reach down and help the next generation / person trying their hardest to make it in the world.

26. My mother-in-law was right: never underestimate the power of a hand-written thank you note.


27. If given the choice to go out or stay home (barring sickness), go out.

28. If given the choice to go/live abroad (barring sickness), go.

29. I spent most of my teens trying to be someone else — and every day since trying to shrink the space between what’s inside and how I express it. Decades later, it still requires constant effort.

30. Lasik/PRK eye surgery is truly as life-changing as they say.

31. Dave Matthews was right: it’s not where but who you’re with that really matters.

32. Start using moisturizer in your 20’s.

33. Health — like love and life — is only fully appreciated when it goes away.

34. I often paint my toe nails for the reaction I have at the gym after taking my socks off and have a flash of “that’s not right.” Twenty years after coming out, that guy is still in there.

35. Sandwiches at lunch in your 20’s become salads at lunch in your 30’s.

36. As Carmen taught me, crying isn’t a sign of weakness; it’s healing the pain and weakness we’ve already felt.

38. Ice your knees after running, even if they don’t hurt.

39. Drink the good wine today. There’s no guarantee you’ll get to drink it tomorrow.

40. Details matter. There was no 37 in this list, and thus 40 is actually 39.

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