85. Questions I Ask at Year-End
AKA How I capture the nuance of a year in my life.
☕️ the main thing
In corporate America, a good chunk of mental energy is spent at year-end on performance evaluations and such. Completing some form of self-assessment against one’s stated goals is common. Anyone in a supervisor or manager role has to compose performance evals for every member of their team. And large companies prefer to conduct this dance formally and structured, usually with some HR oversight.
I’ll be honest: That whole process is one thing I do not miss from my corporate experience. Not even a little bit. In my case, there were years when I also participated in committees where we compared one individual’s performance against another to see who came out on top. I understood why it was necessary then and wanted to be part of that process. I no longer do.
Thank heavens I don’t have to rate another human being. Ever. (That is my goal for the rest of my life.)
Having said that, I do sit down for my annual reflections in December.
The first year after leaving corporate, I simply replicated the process I’d followed for many years, answering the same questions, assessing myself the way I’ve always done. Soon though, that format felt restrictive, the questions irrelevant. I started to futz with the process to make it my own.
For a time and with the goal of simplifying, I cut it down to three questions. But those felt too high-level and general and did not capture the nuance of a year of my life.
Other people’s processes — those who weren’t doing it for their jobs — were helpful as I cobbled together a new process for myself. I copied some and refashioned others to meet my needs.
Eventually, I came up with a list of 21 questions (I know!) that I go through every year. I’ve completed these questions in one sitting, but I prefer extending it over a few days and allowing myself to sit with my responses.
I’ve been following this format for several years now. It’s battle-tested, I feel, and I’m comfortable sharing them with you. Even if you don’t complete all 21 questions, perhaps there are a handful that you can include in your year-end reflection.
Here you go:
1. What did I create this year?
2. When did I feel masterful or skillful?
3. What did I try to avoid?
4. What was the hardest part of the year? How did I meet that challenge?
5. What were the biggest decisions I made this year?
6. How did I practice my values?
7. How did I grow? What skills did I learn? How did I use my strengths?
8. What new relationships emerged?
9. What takeaways did I get from major interactions this year?
10. What opportunities did I create for myself?
11. What new habits did I cultivate?
12. What habits did I break?
13. What new things did I try?
14. What was most fun and enjoyable?
15. When did I feel most proud of myself and why?
16. How did I do with my commitments?
17. How did I meet my intentions?
18. What goals did I achieve?
19. What goals or projects did I not achieve and why?
20. What lessons did I learn this year? Which is the most important?
21. On a scale of 1-10, how proud am I of myself this year?
A short explanation of that last question.
During the first few years after leaving corporate life, I struggled from the lack of external validation. I had lived in a world where I was constantly evaluated and rated and compared against peers. Admittedly, I liked the game and did very well playing it. Leaving that world was a shock to my system, and I felt the absence of bosses patting me on my back. For a bit there, I didn’t feel proud of myself anymore. It was a long hard slog to get out of that pit. Question #21 is a reminder to recognize my own accomplishments and that there’s so much to be proud of.
“There’s a poignant autobiographical question: if I’d done a different job, would I have been a different person? And the answer must be yes.” How Your Job Shapes Your Identity
“That answer will actually get you somewhere. It’s the question that can change your life. It’s what makes me, me and you, you.” The Most Important Question of Your Life
📣 hear hear
“It's a dangerous business, Frodo, going out your door. You step onto the road, and if you don't keep your feet, there's no knowing where you might be swept off to.” — J.R.R. Tolkien, The Lord Of The Rings
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