Twenty-Nine, Truths & Twists

I’m BACK from Nantucket, back from turning 29, and back to the fall hustle. Nothing like a week of beach bikes, seafood towers, and pretending sunscreen counts as “self-care” before returning to the hot garbage aroma of NYC sidewalks.

And while yes, it’s only August, let’s be real — we’re gonna blink and it’ll be 40 degrees, Mariah Carey will be out of her cryo-chamber, and you’ll be stress-eating turkey while checking Shopify dashboards.

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In honor of my 29th bday - I’ve decided to compile a list of 29 things that I ACTUALLY wrote in the last 2 years that could be good advice / things to read while you’re navigating your 20s/30s or whatever age you are. I’ve written nearly 100 newsletters, so.. I obviously know what I’m talking about. So, without furtherado:

The Official Trust Fun List Of 29 Things I Forgot I Wrote (That Are Actually Decent Advice)

1. Always put yourself first, because no amount of money, titles, or clout is worth sacrificing your mental health.

2. If you ever get severance, don’t just treat it like Netflix-and-chill money—use it as a launchpad to invest in yourself and buy back some time.

3. The best jobs don’t come from hitting “apply”—they come when you’re so valuable someone makes up a role just to keep you around.

4. Being entrepreneurial doesn’t mean quitting your job tomorrow; it just means creating something out of nothing wherever you are.

5. Stop pretending to have all the answers—there’s power in saying “I don’t know” and letting people actually teach you.

6. Go for a run without headphones once in a while; silence has a sneaky way of solving problems you didn’t even know you had.

7. Networking isn’t about handshakes and LinkedIn—it’s playdates for adults, and your “toy” is whatever unique value you bring to the table.

8. Check in with your friends in a real way, not just with the lazy “how’s it going,” but with the questions that actually matter.

9. Make decisions faster, because even the wrong choice will move you forward while overthinking keeps you stuck.

10. Don’t just establish a brand—establish an enemy, because people rally around conflict way more than they rally around logos.

11. Life isn’t about being positive or negative all the time; it’s about being neutral enough to keep moving regardless of how you feel.

12. The bad moments aren’t infinite, even when they feel that way—eventually they run out, and you’re still standing.

13. Remember that roses have thorns, but no one calls them “thornses”—focus on the good parts and people will too.

14. Don’t skip the customer calls; anecdotes from real people are often more powerful than the cleanest spreadsheet.

15. You’re only one LLC filing and a crappy Wix website away from calling yourself a founder, so stop waiting for permission.

16. Pick a favorite number and stick with it—sometimes the little rituals and quirks matter more than the big strategy.

17. Boring content works, cringe content works—the only stuff that doesn’t work is the stuff you never post.

18. Discounting your product cheapens it; give people gifts or bonuses instead and make them feel like insiders.

19. Treat your email list like a plant—it won’t grow if you don’t water it, prune it, and actually give a damn.

20. Your gut will lie to you more often than you think, so ask for help and don’t make every call in a vacuum.

21. If you’re in business, collect emails—there’s no bigger cheat code for building leverage.

22. Be vulnerable online, because the internet is ruthless but it also rewards honesty more than it rewards polish.

23. Working out is basically free therapy and the closest thing to legal MDMA—you need it the most on the days you want it the least.

24. Traveling will expose all your anxieties, but it will also expand your perspective in ways staying home never will.

25. Your website isn’t just a storefront—it’s the closer, the thing that takes someone from “interested” to “I’m in.”

26. Collect stories, not resumes, because the stories are what people will actually remember you for.

27. You’re never going to “make it”—there’s no finish line, and the sooner you accept that, the more fun the game becomes.

28. Anxiety is like a vampire—it feeds in the dark, so talk about it out loud and give it sunlight.

29. At the end of the day, the real point is trusting that this whole ride can be fun, even when it’s hard.

Take all of this or leave it, but it’s pretty cool to see my brain come to life on the page.

Anyways that’s it. If you live in NYC, come to my improv show in the LES on Wednesday, September 3rd. You won’t be disappointed.

Tix here.