I Have Some Questions 🤔

This one's a little different...

Good morning 👋🏼 I turned 33 this week, and I wanted to do something a little different for the newsletter. Instead of sharing a list of things I’ve learned, I thought I’d share something that’s a real peek inside my mind: 33 Questions.

Not answers. Not advice. Just the questions that have been circling me lately—the ones that tug at me when I’m walking Penny or singing in the shower. The ones that show up in the middle of a rehearsal or right before I hit “post.”

My word for 2025 is Curiosity. And these questions are part of that practice. A way to stay open, to stay present. To keep making things without needing to know where they’ll land. To stay in motion, even when I can’t see because my glasses are absolutely filthy.

I’ll do some deeper reflecting at the end of this email, but for now, here’s the questions I’m carrying with me into my 34th trip around the sun…

33 Questions

  1. What would I make if I wasn’t worried about how it would perform?

  2. What would I try if I didn’t need it to be good?

  3. What’s the tiniest next step I can take?

  4. What permission am I waiting for?

  5. Where can I trade urgency for curiosity?

  6. What part of my process actually brings me joy?

  7. What am I proud of that no one else knows about?

  8. What do I wish someone else would say to me right now?

  9. Am I giving people something to connect with—or just something to consume?

  10. What’s the story beneath the story?

  11. What’s the secret only my work can whisper?

  12. What if discipline is devotion?

  13. Where can I be more generous?

  14. Where can I offer myself more softness?

  15. What is my body asking for right now?

  16. Where am I trying to "fix" myself when I could just be with myself?

  17. What have I outgrown, and am I brave enough to let it go?

  18. What’s the energy behind my effort right now—love, fear, ego, hope?

  19. What does enough look like today?

  20. How does love want to move through me today?

  21. What would happen if I let myself be fully seen here?

  22. Who am I without the story of success?

  23. What does freedom actually feel like in my body?

  24. What would it mean to belong to myself fully?

  25. What if I already have what I need?

  26. How do I make peace with the unknown?

  27. What does true surrender look like right now?

  28. When do I feel closest to the divine?

  29. How am I making space for silence?

  30. What is the “unsayable”?

  31. What if this discomfort is sacred?

  32. What would I do if I believed the Universe was conspiring in my favor?

  33. What question am I finally ready to ask?

🎭 We’re Doing It!

We officially started performances of All the World’s a Stage this week and it’s already been so interesting sharing this little show of ours with audiences.

The theater has 99 seats, so you really get a sense for what’s resonating and the overall energy of the room as the story unfolds.

We’re in ‘previews’ which means we’re rehearsing during the days, making changes to the script and the lights and anything that needs tweaking, and then performing the show at night.

If you’re in New York, and want to see the process in real time—we’ve got a seat for you! There’s $45 rush seats available an hour before every show (and if you reach out to me, I might even have a discount code I can share 🙃)

☝🏼 One last thing…

33 feels strangely significant—not quite the drama of 30, not yet the wisdom of 35, just...here. In between.

A year ago today I was in Washington DC. We visited the White House and then performed at the Kennedy Center. So much has happened since then that it feels like five years ago and also last week? My brother got married. I got a concussion that knocked me out of commission for nearly three months. I closed a tour. I filmed self-tapes and sat in waiting rooms and didn’t book a lot of things. I started this newsletter.

It's been a year of incredible highs and truly brutal lows, sometimes in the same day, occasionally in the same hour.

I've been thinking about this weird pendulum swing of being alive—how one moment you're laughing with people you love, and the next you're crying in bed wondering if this creative life is even sustainable. How you can book a show after months of nothing and still wake up with that familiar pit in your stomach whispering "but what's next?"

And I don’t know if journey gets any easier—I think we just get better at surfing the waves.

The doubt doesn't disappear. The fear doesn't fade. The struggle doesn't suddenly transform into endless smooth sailing. You just learn to build a life around it. To make friends with uncertainty. To find joy in the small victories. To celebrate other people's wins as fiercely as your own.

So here's to 33. To the highs and lows that are guaranteed to come. To the questions I don't have answers for yet. To making things and sharing them before they feel ready. To all of you who've decided, for some reason, that my weekly ramblings are worth your time.

I'm grateful you're here for this messy, beautiful, utterly unpredictable ride.

See you next week ♥️

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