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Nº184 The Desire to Inspire: 2️⃣0️⃣ Questions for 2️⃣0️⃣2️⃣0️⃣

Jon Woodroof
6 min readJan 25, 2020

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Last issue had a time theme and the circular time vs. linear time link below follows that thread.

But when I saw this list of questions passing by, I knew it’d be great to include them in a January issue.

Though, I can say: asking them throughout the year makes sense too!

  1. What was one of the moments you were most proud of in 2019?
  2. What does that tell you about what you want to spend your energy/time/money on next year?
  3. When were you genuinely surprised this last year?
  4. What was your best failure this year? (i.e. what thing that didn’t go well eventually taught you something critical?)
  5. What was your most overrated success? (i.e. something you thought would feel great that was sort of a let down?)
  6. Who really enriched your life this year in a big way? Who is someone you want to get to know better in the year ahead?
  7. What community are you a part of right now that you find most nourishing?
  8. What kind of community are you craving?
  9. What goals — personal or professional — are you releasing in 2020?
  10. Who did you feel most jealous of this year? What is that person up to that you want to bring more of into your own life?
  11. Where and with whom were you most resentful in 2019? How can you get straight about your own…

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Jon Woodroof
Jon Woodroof

Written by Jon Woodroof

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