Annual Reboot: 52 Questions to Reflect and Reset

Summary

Let me guess. You meant to do a proper year-end review. Maybe even had a few tabs open for weeks—a half-written journal entry, some color-coded plans, a quote from Seneca, perhaps.And now it’s January. For some of us, the only reflection so far has been noticing how quickly the first week disappeared.Over the years, I’ve built and rebuilt all kinds of systems for reviewing the year. At one point, I created a questionnaire with 126 questions. I cleared my calendar, brewed good coffee, and sat down like it was a quarterly board meeting for a startup going through an existential crisis.Still, I’d end up overwhelmed by the sprawl of it all—the travel patterns, the intimacy hiccups, the spreadsheet rabbit holes. What started as reflection quietly turned into a full-scale audit.So this year, I tried something else.I didn’t aim for comprehensiveness. I aimed for contact. Just sitting with the year as it was, without forcing it into categories, lessons, or tidy conclusions.This is what remained once I trimmed the process down to its spine. Fifty-two questions. Just the ones that kept earning their place.Identity & Life Direction (8)Looking back1. What belief about myself no longer serves me?2. What did I say yes to out of fear?3. What part of me grew stronger this year?4. Which moments challenged how I see myself and what did they reveal?Looking ahead5. If I knew I had three years left, what would I make time for this year?6. What mindset shift would bring me closer to that version of myself?7. What kinds of actions would create that mindset?8. Which habits would someone living that way naturally adopt?Emotions & Inner Life (8)Looking back9. What emotion or mood visited most often last year?10. When did I feel most alive?11. When did I feel most anxious, and why?12. What helped me feel emotionally grounded when everything else was spinning?Looking ahead13. What feeling do I want to experience more often?14. What moments tend to invite that feeling in?15. What emotion do I w...