EP 69 | The Strange Emotions of Missed Upside

2026-07-14

Adam made $3,000 selling World Cup tickets and got to attend two games for free. It was an objectively great outcome. Then ticket prices doubled a few days later, and all he could think about was the additional $7,000 he could have made.

Adam and Stephen explore the strange emotions of missed upside, why our brains remember losses more vividly than wins, and how counterfactual thinking can turn success into disappointment. Adam shares the exercise that finally helped him regain perspective: writing down his financial mistakes alongside the good decisions he rarely gives himself credit for.

The conversation expands beyond money into work, leadership, and the ways high achievers quickly move past accomplishments while endlessly replaying mistakes. Adam and Stephen discuss how teams can create more meaningful celebrations, including visible records of wins, surprise afternoons off, and the possibility of commemorating every new client with a trip to Wendy’s.

TakeawaysMissed upside feels like loss.
Even when nothing was taken from us, seeing what could have happened can overpower the satisfaction of what actually happened.Our brains preserve mistakes and discard good decisions.
Failures create stories, consequences, and emotional weight. Good decisions often quietly work, then disappear from memory.Compare your losses with your wins.
Writing down both sides of the ledger can reveal how small one mistake is within the fuller story of your life.Celebration needs more weight.
A Slack message and a few emojis rarely carry the same emotional force as a failure. Teams may need tangible, memorable rituals that interrupt work and make success feel real.Keep a visible record of what is going well.
A running list or physical board of wins helps fight the tendency to evaluate a month, project, or career based only on its most painful moments.Chapters00:00 - Making $3,000 and Feeling Terrible03:48 - Loss Aversion and Missed Upside05:13 - The Exercise That Restored Perspective09:03 - Why We Remember Mistakes at Work10:17 - Midyear Reviews and Celebrating Forgotten Wins15:07 - The Power of Stopping Work to Celebrate17:47 - Why Nobody Feels Sorry for Adam19:51 - The Unexpected Joy of the World Cup22:26 - Trend Spotter: Fable, Taylor Swift, and AI24:56 - Delve Deck: Elementary School Glory29:40 - Listener ReflectionListener Reflection

What loss or missed opportunity are you currently replaying, and what wins have you forgotten to include in the story?

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2025-11-18

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The podcast for high achievers who seem to have it all, yet still feel something’s missing. Co-hosts Stephen and Adam bring humor, honesty, and a touch of mid-life wisdom to conversations about how work shapes our sense of self, and how we can reshape it to find greater meaning in work and life.

With careers spanning consulting, private equity, start-ups, and entrepreneurship, they share research-backed insights and real-world stories that help uncover new ways to drive more meaning each day. We’re excited to have you join us on this journey!