How to Regret Better
I often talk about regret with my clients as one of the hardest emotions to sit with. That would’ve, should’ve, could’ve feeling can take up residence in the gut like a sharp, stubborn rock. Regret keeps us up at night, replaying conversations, choices and actions we can’t redo. The job we didn’t take. The words we wish we hadn’t said. The love we didn’t surrender to.
Regret is uncomfortable and, yes, profoundly human.
But instead of clinging to the idea of living life with no regrets, what if we learned to embrace them? What if we used regret as a kind of compass for better living?
Why Regret Hurts So Much
Regret is different from sadness or disappointment because it comes with agency. We had a choice and we blew it. Or at least, we think we did. If we had no say, there’d be nothing to regret, only acceptance or resignation. The thing is, humans are built for self-determination. We crave the freedom to make our own calls, steer our own lives and own our decisions, even when those decisions lead to regret.
Regret stings because it lives at the intersection of control and loss. We feel it when we believe we could’ve done something differently. That classic “I should have known better” loop can shake our confidence and make us question our judgment.
You could call it the price of agency. We love autonomy, but it comes with fine print: Sometimes, we’re wrong.
Research backs this up. An NIH meta-analysis found that people’s deepest regrets usually revolve around education, career and romance, those big-ticket areas where we get to make meaningful choices. And over time, it’s what we didn’t do that tends to haunt us more than what we did. In other words, inactions linger longer than mistakes.
When Regret Sticks Around
Regret doesn’t just live in your mind; it settles into your body too. One study found that people asked to recall regrets before bed took significantly longer to fall asleep than those who didn’t. No surprise there.
Regret can tighten the chest, shorten the breath and send the mind into endless replay mode. Dan Harris, author of 10% Happier, says our inner voice of self-blame can “own us” when we’re not aware of it. Sound familiar? Harris’ TED talk called, The Benefits of Not Being a Jerk to Yourself, is worth a listen.
The goal isn’t to silence your inner voice. It’s to notice it, name it and decide what to do with it.
How to Optimize Your Regrets
Author Daniel Pink studied more than 15,000 people in 105 countries for his World Regret Survey and found that nearly everyone experiences regret. Only one percent said they never do (which, honestly, sounds a bit suspicious). Pink argues that regret, when handled well, can be one of our most constructive emotions.
It can sharpen judgment, clarify values and improve decision-making. As Pink puts it:
“Our goal should not be to minimize regret. It should be to optimize it.”
Here’s how:
1. Name It
Unacknowledged regret has power. When it lives in the background, it’s running the show. Bring it into the light. Write it down. Be specific. Maybe you didn’t go back to school when you had the chance, or you hurt someone you cared about.
Ask why it still bothers you. What story are you telling yourself about it? You can also talk it out with a trusted friend or therapist. You’ll probably find that regret feels smaller once it’s spoken out loud.
2. Forgive Yourself
Replaying old scenes like a personal blooper reel won’t change the ending. It just keeps the wound open.
You can’t rewrite the past, but you can change your relationship to it. Try saying, “I was doing the best I could with what I knew at the time. I release myself from this suffering.”
Self-forgiveness isn’t pretending it didn’t matter. It’s deciding that self-torment isn’t productive and that you deserve to move forward. Think radical acceptance.
3. Move Forward
Regret is a tough but honest teacher. It shows us where we weren’t aligned with who we want to be. It says, “You can do better next time.”
Think of it as tuition in the school of hard knocks. What did each regret teach you about your values or priorities? What small change could reflect that lesson today?
You’ve already paid in pain. Don’t walk away without the learning.
The Myth of “No Regrets”
You’ve seen the tattoo: No regrets. It sounds bold, but it’s bad psychology. To live with zero regret would mean never reflecting on your choices—or worse, never caring enough to.
The goal isn’t to erase regret; it’s to work with it. To turn it from something that owns you into something that guides you. Regret can remind us to be brave, to speak up, to take chances, to apologize and to tell the people we love how we feel while we still can.
We can’t change the past.
But we can let it change us.
If you want to talk, we’re here to listen.