Regret Is Your Greatest Teacher: How to Learn From the Past and Build a Future You Love

Ever looked back on a missed opportunity and thought, Ugh, what if? Well, you’re not alone—and that feeling of regret might actually be one of the best tools for growth. I had the privilege of chatting with New York Times bestselling author Daniel Pink about his book The Power of Regret—the book that gave me the final push to launch this very podcast!

Dan breaks down why regret gets a bad rap in our culture of toxic positivity and how it can actually help us make smarter choices. He conducted a massive study (we’re talking 26,000+ regrets from people in 130 countries!) and uncovered four core types of regret that shape our lives.

We got personal, talking about boldness regrets (yep, like not shooting your shot), connection regrets, and even my own struggles with juggling career, parenting, and ADHD. Spoiler: being kind to yourself is key.

Instead of fearing regret, Dan suggests we flip the script—treat it as a guide, not a life sentence. Because in the end, regret isn’t about what we did. It’s about what we didn’t do. So, if you’re stuck in what could have been mode, this episode will help you leap forward. Tune in now!

“Regret clarifies what we value and instructs us on how to live.”
~ Daniel Pink

In This Episode:
00:00 Introduction to the power of regret
04:24 Understanding regret and other negative emotions
06:48 Types of regrets: research and findings
14:46 Regrets about career and boldness
17:32 Acknowledging foundation regrets and moving forward
25:17 The importance of self-compassion in overcoming regret
26:26 Daniel’s top life regrets and how he overcame them
28:11 Practical steps to overcoming regret

Connect with Daniel Pink:
LinkedIn:  / danielpink  
Website: https://www.danpink.com/
Instagram:   / danielpink  
Daniel’s Book, The Power of Regret: https://amzn.to/33G8WF8

Connect with Maureen Wiley Clough:
Instagram:   / itgetslateearly  
Website: https://www.itgetslateearly.com/
LinkedIn:   / maureenwclough  
Facebook:   / 100088694515585  

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