5 • 715 Ratings
🗓️ 26 September 2025
⏱️ 10 minutes
🧾️ Download transcript
Sometimes Jay Schwedelson skips the marketing hacks and just gets real. This time he shares a personal story about nearly missing out on the love of his life and the lesson it left him with: regret is far heavier than failure. It’s raw, funny, and surprisingly relevant if you’ve ever hesitated before taking your shot in business or in life.
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Best Moments:
(01:09) The biggest turning point in Jay’s life that reshaped how he thinks about work and risk
(02:42) The sting of seeing someone you care about happy with someone else
(05:16) The bold move at the bar that changed everything
(07:45) Why you only need 10 seconds of bravery, not a lifetime of courage
(08:32) The torture of living in the land of what ifs
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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson
Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson
Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/
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| 0:00.0 | Welcome to Do This Not That, the podcast from marketers. We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode. We also keep it short, like this intro. Let's check it out. |
| 0:16.0 | We are back for Do This Not That podcast presented by Marigold. And normally I come on here and I say, hey, stick this in your subject line or do this on a social media post and you'll see all this amazing stuff happen. But I wanted to share something that really has stuck with me. And it's this concept of regret is worse than failure. You know, I've been writing this book, which has made me think about all these big life lessons |
| 0:38.9 | I've learned and I feel total imposter syndrome. |
| 0:41.0 | I feel like a clown doing it, |
| 0:42.6 | but it's really got me thinking in all sorts of different directions |
| 0:44.9 | about moments of my life that have really been |
| 0:47.4 | a big deal for me. |
| 0:49.1 | And probably the biggest moment in my life |
| 0:50.8 | that happened was how I met my wife |
| 0:54.1 | and then also how that translated to impacting |
| 0:56.8 | how I think about work and business and everything else. And hopefully, you know, after you hear |
| 1:02.0 | this nonsense, you're like, you know what? Regret is worse than failure. And you can incorporate that |
| 1:07.2 | into everything that you were thinking about. Maybe you do that already, but I'm so intentional about it now because it really has transformed |
| 1:14.0 | things. |
| 1:15.0 | So what is that even mean? |
| 1:15.2 | What am I talking about? |
| 1:17.0 | So here's the story you didn't ask for. |
| 1:19.1 | Here's how I wound up meeting my wife. |
| 1:21.9 | So I've been married to Allie for 22 years. |
| 1:25.8 | She's the most incredible human being on earth a billion times smarter than me. |
| 1:30.1 | She's a dermatologist. She's the most amazing human. I have two great kids. One's a freshman in college. |
| 1:35.7 | One's a senior in high school. Greatest human beings alive. But it all almost didn't happen. |
... |
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