Prevent Regret by Taking Risks

Man standing on a small ledge on the side of a mountain overlooking a mountain range

“I wish I would’ve…”

No one wants to mutter this on their deathbed. That’s the type of statement that screams “regret.”

Having regret isn’t bad, necessarily. Like, I regret not studying abroad in college. I regret not having learned how to surf when I lived in Hawaii. Now, my life is great despite not having these experiences, but because I’ve had some regrets, I now look at my choices a little more carefully for the tradeoffs and the YOLO moments.

In Daniel Pink’s new book, “The Power of Regret,” he has categorized four types of regrets that we have:

1. Foundation Regrets – Choices that would’ve impacted our stability, like “I wish I would’ve invested in Apple stock,” or bought a home in our 20s.

2. Boldness Regrets – Choices that required us to be courageous, like moving cross country, or taking that job offer.

3. Moral Regrets – Choices that could undo bad behavior we demonstrated, like picking on someone in middle school.

4. Connection Regrets – Choices that could correct the lack of care and attention we gave to someone we cared about.

In my work, I focus on helping people with “Boldness Regrets” – helping them make courageous decisions today that they want to do, but are afraid to tackle. Things like: leveling up in their career, taking on a new initiative, starting an interesting side hustle, or pursuing their wildest dreams.

We’re hardwired to do big, bold things. The interesting thing is that life kicks the crap out of us, and we learn that “playing it safe” is a good way to stay in the game. (I wrote about the “Play it Safe Paradox” in Bet on You.) Here’s the deal: playing it safe keeps you in the game, but it doesn’t let you win the game. 

I talk to people all the time: many of us want to win. What gets us feeling victorious in life? Taking risks that are on our hearts and in our minds.

I think of risk-taking as regret prevention. And here’s the deal about risks: you can start today. Small changes, over time, produce sustainable and transformational change.


–   If you want to change careers, start talking with people and learning about the variety of options in front of you.

–   If you want to downsize your house and live in a tiny-house community, join an online Facebook group to see what that’s all about.

–   If you want to run a 5k, get off the couch and go for a walk.

Everyone – and I mean everyone, even Taylor Swift, Usher or Patrick Mahomes, starts inexperienced. Sure, they might have natural talent, but talent only gets you so far. As grit expert Angela Duckworth shares, effort always counts twice as much as talent. So, don’t focus on what you lack – focus on what you have.

What are you waiting for? Go out and do epic things! Stop thinking about the “I wish I would’ves” and start saying “I’m doing this because I can.”

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PS. And if you want to change careers, no need to do it alone. When you invest in my eCourse, Now It’s Time for You: How to Lead Your Career Transformation, you join a learning cohort who’s got your back. Doesn’t that sound awesome?