10 Important Questions to Ask to Make This Holiday Season Actually Enjoyable

Julio Vincent Gambuto
4 min readNov 6


Each Monday, Julio Vincent Gambuto presents “Modern Muting” — a weekly Medium story series dedicated to helping readers step back from all the bullshit of modern life, create quiet, re-evaluate, then go forward boldly. It’s 500 words a week of “self-help meets the system.”

Get off autopilot this holiday season. No other time of year hits our buttons and smacks our triggers quite like the holidays. Sucks to talk about this at the top of November (!), but from this vantage point in the calendar we have breathing room and can start to actually plan for joyful holidays instead of ones full of utter nonsense. Here are some helpful questions to ask as you think about the weeks and months ahead:

  1. What worked well last year that we want to repeat? What didn’t?
  2. Was I really rested after the holidays last year? Was I full of joy and satisfaction, having spent good, quality time with friends, family, people I love? Or was it a shitshow? If it was the latter, why? What would need to change to make it not a shitshow? (Be honest. These questions and answers are just for you.)
  3. How much travel time did I allot? Was it enough? Not enough? Also, how much rest time did I allot after the actual holiday? None? Do I want to change that this year? Is it possible to do so?
  4. Did I take enough time off from work? Can I take more? Should I take less? What was expected from me at work? Will that be expected this year? How do I need to plan to make sure work doesn’t get in the way of enjoying some downtime? Also, did I communicate my schedule well to those that rely on me, my work, my projects? How can I be crystal clear with colleagues, clients, co-workers, etc. about my schedule?
  5. Whom did I see? Who was in my life, in my calendar, at my table from Thanksgiving to New Year’s? Are these the most important people in my life? The ones I enjoy the most? Who was missing? Who can I bring back into my life this year? Who should come out?
  6. Are there any conversations I can have now — not at the turkey table or as we trim the tree or light the menorah — to make the holidays more enjoyable? Now is the time. Pick up the phone.



Julio Vincent Gambuto

Author of “Please Unsubscribe, Thanks!” from Avid Reader Press at Simon & Schuster // Now available in US and UK //