From Spiderman Costumes to Missed Opportunities: Lessons Regret Taught Me
If I were ever granted wishes from a genie, one of them would be this: to live my life over again—but with all the knowledge and experience I’ve gathered so far. Just imagine the possibilities. Oh, the mistakes I could avoid.
Like the time in kindergarten when I was too afraid to ask my teacher for help untying my plastic Spiderman costume so I could go to the bathroom. That fear didn’t save me twenty minutes later in the play area.
Or all those awkward teenage moments when I couldn’t talk to a girl without forgetting how to speak English entirely. What exactly was I so afraid of?
And here’s one that really stings—I had a shot at buying a three-bedroom condo in San Diego back in 1999 for $111,000. I passed on it. Today, it’s worth over $350,000.
So yeah, I could go on. But the point is, I don’t really relate to people who say they have no regrets. I do. Plenty. But I’ve learned not to let those regrets define me. In fact, I’ve learned how to use them to my advantage.
Not long ago, I found myself on the outside looking in on full-time employment. I’d been planning for over a year to take a course in clinical hypnosis with Dr. Michael Yapko. It was a serious investment. And then, boom—I lost two-thirds of my income.
We were in the middle of a house renovation. My wife had just given birth to our first child. Money was tight. Everything about the situation screamed, “Don’t do it.”
But that’s exactly why I did.
I thought about all the times in my past I had talked myself out of opportunities like this. And I didn’t want to add one more regret to the pile. So I invested in myself.
That decision changed everything. Since completing the training, I’ve helped clients experience real transformation. Like the adolescent client who came to me just after being hospitalized for suicidal threats. After a guided imagery session, they learned healthier coping skills. Two sessions later, we had nothing to talk about—because they were thriving. No medication needed.
Another client—a woman with severe OCD—was trapped in a cycle of compulsive cleaning that was wrecking her marriage and career. One hypnosis session brought immediate relief. Over the next week, she cleaned only twice. That may not be everyone’s outcome, but it’s not rare either.
I share these stories not to boast, but to show how regret, when used wisely, can push us forward. We’re constantly told by marketers that we’re missing out—and they bank on our regrets. So why not use that same emotional force to improve your own life, instead of someone else’s bottom line?
Here’s how:
Believe it’s possible to change. You’re not stuck. The average Baby Boomer held 11 jobs between the ages of 18 and 46—back when job security was still a thing. Change is not only possible, it’s normal.
Use regret as fuel. Let it motivate you instead of shame you.
Focus. Start small and specific. Regret in relationships? Try expressing appreciation for something mundane—like thanking your partner for paying the power bill. Just that. Today.
Regret not being more social? Start by saying “hi” to coworkers and asking about their weekend.
Feel disorganized? Put on some music and declutter your office. Toss the easy stuff first.
Inconsistent exercise habits? Start with your bedtime routine. Seriously. Turn off the TV, put down your phone, get some sleep. Your mornings—and your energy—will change.
I’m not saying it’s easy. But it is doable. You might as well use your regrets for good—after all, someone else already is.
So here’s where you come in:
What’s one regret you’ve been avoiding that could actually guide you toward growth?
What small, specific action can you take today to begin rewriting that story?
Who might benefit from your transformation if you chose to act now?
Your regrets don’t have to hold you back. They can become the very reason you move forward.