30 Questions for my 30th Birthday

Here's what I'm asking myself about writing, entrepreneurship, and living your best life.

In my 30 years of life, one thing has defined me more than anything.

Just ask my parents, siblings, friends, and fiance: I ask a lot of questions.

From the curious (Why?) to the accusatory (Seriously… WHY?), few things excite me more than great questions and the answers they lead to.

Today is my 30th birthday (Woohoo!) I have little wisdom to share. Instead, below is a list of 30 questions I’m asking myself about writing, entrepreneurship, and living your best life.


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For my last birthday request, I want to know: What are your favorite questions to ask?


  1. What were my biggest challenges 6 months ago? 2 years ago? And how do I feel about those things today?

  2. What good decisions did I make this week?

  3. What poor decisions did I make, and how do I avoid them?

  4. What am I grateful for?

  5. Am I excited about the journey I’m on, or just the destination?

  6. What excites me most about the future?

  7. How do I find more balance between deep work (writing) and audience growth (social media)?

  8. What am I not saying that needs to be said?

  9. If money was not a factor, what would I do with my life every day?

  10. How do I be more present with my fiance, Mary?

  11. Am I actually ambitious, or do I just WANT to be ambitious, and therefore I try hard? And is there a difference?

  12. What would it be like to live in a multi-planetary society?

  13. What legacy do I want to leave behind?

  14. What do I want to be remembered for?

  15. Why am I so lucky?

  16. What if I doubled the amount of time I spent writing?

  17. If I achieve everything I think I want, will I still be happy?

  18. When will I write my sci-fi book? HOW do I write my sci-fi book?

  19. If I had to teach an alien how to write, where would I start?

  20. What would this look like if it were easy?

  21. Would I be prepared to handle a major tragedy in my life?

  22. When will “enough” be enough for me? What’s my true goal post?

  23. What would my life be like if I 100% believed in myself?

  24. How can I better balance work with family and friends?

  25. If I could only work two hours per week, what would I work on?

  26. If I knew I was going to die in 1 year, what would I write about?

  27. If I could no longer write, what would I do with my life?

  28. Am I thinking big enough?

  29. What am I taking for granted?

  30. If I died today, would I be satisfied?


Finally, thank you for being a part of my life. I never thought I could get so much satisfaction from interacting with people I’ve never met in real life, but you have proved me wrong.

Most importantly, you’re helping me build the life I’ve always dreamed about. So again, thank you 🙏

Cheers,

Ben