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Discussion Guide

Why You Keep Making Bad Decisions — Kimani Upshur, M.Ed.

For book clubs, small groups, and reading circles · Free to copy and share

About the book: You're not stupid. You're predictably wrong. Every bad decision follows a pattern — the same cognitive traps, the same emotional shortcuts, the same predictable errors. This short book names the patterns behind your choices and shows you how to build a decision system that holds up in real life. (The Made Simple Framework · upshurunlimitedllc.com)

Questions for discussion

  1. The pattern, not the person. The book opens: "It is not a character flaw. It is a system flaw." Think of a decision you keep repeating. What pattern — not what personal failure — explains it? (Introduction)
  2. What a decision actually is. How did the book's definition of a decision differ from how you usually think about choosing? (Chapter 1)
  3. Emotion at the wheel. Describe a decision you made while angry, afraid, or excited that you later regretted. What was the emotion really deciding for you? (Chapter 2)
  4. Overthinking. The book says overthinking is not careful thinking. Where in your life does "thinking about it more" actually make the decision worse? (Chapter 3)
  5. Biases. Of the cognitive biases in Chapter 4, which one do you catch in yourself most often — and what's a recent example? (Chapter 4)
  6. Stress and pressure. How do your decisions change when you're tired, rushed, or under pressure? What guardrails could you set in advance? (Chapter 5)
  7. The sunk cost trap. Name something you're still funding — with money, time, or loyalty — mainly because of what you've already put into it. What would you tell a friend in the same spot? (Chapter 6)
  8. Framing. Take a live decision your group or family is facing and state it two different ways. How does the framing change the answer you lean toward? (Chapter 7)
  9. Decisions you can live with. Using the regret-minimization idea — yourself at eighty, looking back — which current decision looks different from that distance? (Chapter 9)
  10. Your decision system. The book ends with building a personal decision system: pre-committed rules that protect your choices from mood and impulse. What's one rule you'd adopt this week — and what will you do about the cost of not deciding? (Chapter 10 + Final Chapter)

For the leader

  • The book is short by design — most groups can read it in one sitting and discuss it in a single 60–90 minute session, or take one question per week for a season.
  • No preparation needed beyond reading the book. Questions follow the chapters in order.
  • Group copies & bulk orders: kimani@kimaniupshur.com · More from the Made Simple Framework: upshurunlimitedllc.com

Get the book: Why You Keep Making Bad Decisions by Kimani Upshur, M.Ed.