Dec 26, 2021 • 15M

#53: Turning over a tough year

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Helping product leaders scale up effectively without burning out. Build a product that matters, an org that is effective *and* healthy, and a fulfilling career.

Some short thoughts on how to review and close out a tough year, and set ourselves up for a powerful, generative new year.

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Completion questions: remembering and reviewing

"Remember" questions

  • What was your favorite music playlist?

  • Who was your favorite artist?

  • What was your favorite song?

  • What was your favorite concert?

  • What were your favorite photos?

  • What were your favorite videos?

  • What was your favorite movie?

  • What were your favorite articles?

  • What was your favorite travel?

  • What were your favorite experiences?

  • What was your favorite speaking, teaching, awards, or recognition?

  • What were your favorite memories?

  • What was your favorite restaurant?

  • What was your favorite meal?

  • What was your favorite first meeting?

Past year calendar review

This is an exercise I learned from Tim Ferriss, and it's great. If you do nothing else, I'd do this.

Simply put, you go through the entire past year on your calendar, and make a list of the people, activities, and commitments that triggered peak positive/negative emotions on a weekly or monthly basis. Then, find the 20% of each list that produced the most reliable or powerful peaks. Proactively schedule the positive ones now, and avoid/reduce the negative ones.

Areas of life review

Look holistically across your life. Don't solely focus on your career. I tend to go through the following eight areas of life:

  • health & wellbeing

  • creative expression & fun (hobby, travel, adventure, etc)

  • wealth / finances

  • relationships (family, friends, romance, other)

  • personal systems (habits, routines, processes) & personal development

  • career/mission/work

  • emotions / spiritual

  • mind

For each area, I ask the following five questions (I don't necessarily answer all of them every time though):

  • what was accomplished?

  • what wasn't accomplished?

  • what worked?

  • what didn't work?

  • what was missing?

Lastly, I like to have a freeform section that is just "is there anything else I need to say about this to feel complete?" I'm often surprised at what comes out here, so don't underestimate this question.