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What Have Been Your Best and Worst Decisions?

A Personal Perspective: A look back that can yield a better future.

Peggy Marco, Pixabay, Public Domain
Source: Peggy Marco, Pixabay, Public Domain

We can learn a lot about what to do next by looking at what we did before. At each life stage, what were your best and worst decisions, and lessons learned?

It may help to evoke your ideas to see a sample. It’s a composite drawn from my clients.


Best decision: To be bookish even though it meant I had few friends. It taught me to realize that I can be more self-contained and still have friends as a small yet significant part of my life.

Worst decision: To not rebel against getting confirmed. Even at age 13, I was sentient enough to know there were better uses of my time than going to confirmation class. Lesson learned: Question convention. Don’t necessarily rebel but don’t necessarily fall in line.

Teenage Years

Best: Dating Michael. I chose him over edgier types. He was smart, sweet, well-adjusted, and attractive. A wise choice.

Worst: Not going to the prom because it was expensive. Lesson learned: It’s worth spending on important one-time opportunities, even if you have to overpay a bit.

Young Adulthood

Best (tie): Going to Chicago State and living with my parents. Not only did my parents save a fortune, from what I hear of dorm life, I was better off at home.

Best (tie) I avoided the college’s drug culture in favor of getting super-involved in extracurricular activities: I volunteered at the college’s peer counseling center, played on the field hockey team, and joined the college choir. Lesson learned: Even though being overscheduled can be stressful, it’s really beneficial, fun, and a distraction from my worry-wart personality.

Worst: Taking the three years to get my master’s in teaching. Too much was theoretical and very little has been useful. Yes, the piece of paper got me a bump in the salary schedule, but I would have been better off spending the three years on other activities.

Later Adulthood

Best: Quitting teaching and becoming self-employed. Teaching was just too draining and I would have hated working in some bureaucracy: They move slowly, I’d have limited agency, and I’d too often have to bite my tongue.

Worst: Donating to a large charity. They didn’t use the $5,000 for the purpose I specified. I’ve since learned that such mission creep is common in large organizations.

Reviewing those lessons learned, that “person’s” major takeaway might have been to, in his or her will, to replace that organization with a smaller non-profit s/he feels s/he can trust more.

So, now, review your list of best and worst decisions and lessons learned. As a result, is there anything you want to do differently?

Consider all aspects of your life: What would you like to change about your work life? Your relationships? Your money? Your physical health? Your mental health? Your recreational life? Even the meaning of life?

I read this aloud on YouTube.

Other posts in this series of personal growth self-inventories are The Museum of You and The Half-Hour Autobiography.