Episode
The Secret to a 50-Year Career Is Being Willing to Lose It – Ohio Governor Mike DeWine
- Podcast
- Is This Working?!
- Published
- Aug 26, 2026
- Duration seconds
- 2816
- Processing state
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- https://episode.flightcast.com/01M0X2PW7VZ3CFSR6DQGYTBBAM.mp3
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Summary
"You have to be willing to fail." That's Mike DeWine, the man who's held just about every role in Ohio politics, including US Senator, a job he ran for four times. First, he lost. Then he won. Then he won again. And then he lost. After that second loss, DeWine came home to Ohio where everyone congratulated him on a great end to a great career. Well, almost everyone. His wife Fran, who he met in the first grade and has now been married to for fifty-nine years, said, "you're not done unless you tell yourself you’re done." DeWine wasn't done. Next, he ran for Attorney General of Ohio and won. Then, he became Ohio's Governor, a role he finishes this coming January. So Connor sat him down for an exit interview on topics including: whether the American Dream can survive the AI revolution why the worst thing a leader can be is the smartest person in the room DeWine's thirty-year history of humanitarian work in Haiti his secret to remaining stubbornly optimistic (hint: have eight kids) Plus: the box of chocolates in sixth grade and the line his whole career comes down to: "Work is the price we pay to achieve what we want. No shortcuts." If you're looking for hope from someone who's been in the trenches for the past fifty years driving actual change, this episode is for you. CHAPTERS: Chapters 00:00 The career nobody wins by accident 00:06:53 Learning to lose — The 2006 Senate defeat 00:10:03 Never be the smartest person in the room 00:13:31 59 years — The partnership that started in first grade 00:21:41 Is the American Dream dead? 00:26:55 AI, critical thinking, and muddling through disruption 00:31:48 30 years in Haiti — Why he keeps going back 00:36:47 Springfield and the eating dogs rumor 00:38:30 What's next — Leaving the governor's mansion 00:41:03 Work is the price we pa…