Avoid the Groundhog Day Syndrome—Break the Cycle of Repeating Mistakes

Norm ran his courier business with heady ambition in the go-go eighties, chasing the $100-million mark that promised validation. But looking back, Norm saw that each time he hit a wall—bad acquisitions, ignored warnings from advisers, the thrill of risk run amok—the aftermath looked eerily familiar. His phone would start buzzing with anxious calls from employees and creditors, his office’s stale air heavy with unshed words. Norm would freeze, avoiding conversations, racing from crisis to crisis instead of pausing to reflect.

When his company fell into bankruptcy, Norm faced a brutal reckoning—his need for speed and scale cost not just profits, but the livelihoods of hundreds. The mistake, he realized, wasn’t just one bad deal; it was a cycle. As years passed, Norm slowed himself down by always listening to dissenters longer than felt comfortable, and by pausing whenever a sense of déjà vu crept in. He even began to keep a log of warning signs—stress, pressure, overreliance on his own gut—and would regularly debrief with a trusted partner before making big moves.

Behavioral research confirms that self-awareness, feedback loops, and open dialogue can disrupt our tendency to repeat errors. The brain often defaults to patterns, but conscious reflection and peer input create new pathways for better decision-making.

Start by honestly reviewing two or three big decisions from your recent work or school life—what familiar patterns come up? Note down any common warning signs you notice, such as recurring stress or ignored feedback, and be specific. Share your findings with someone honest and experienced, and invite them to help you brainstorm different approaches. By making your cycles visible and choosing to break them, you’ll open the door to more thoughtful, less painful paths forward next time. Try the reflection and conversation step this week.