Let’s be real: regret is messy. It’s that annoying friend who shows up uninvited, eats all your snacks, and then has the audacity to criticize your life choices. And yet, you let it hang around because part of you thinks, “Maybe I deserve this punishment.”
Newsflash: you don’t.
Here’s the thing about regret — it’s loud, but it’s also lazy. It never tells you anything new. It just keeps hitting “rewind” on the same old memory, like you don’t already know how the story ends.
And the more you play along, the more regret convinces you that you can somehow negotiate with the past. You can’t. Time machines don’t exist. And even if they did, let’s be honest — you’d probably make new mistakes anyway.
So if you want to stop obsessing over regrets, you’ve got to flip the script.
Step One: Stop Romanticizing the Past
One of the biggest traps people fall into is the “What if” game.
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What if I had taken that job?
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What if I had left that relationship sooner?
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What if I had spoken up when it mattered?
Psychologists call this counterfactual thinking — obsessing over alternate realities that never happened. The problem is, our brains love to edit those realities into highlight reels. The job you didn’t take suddenly looks perfect. The relationship you lost seems like it could’ve been forever.
But here’s the truth: that alternate path had its own problems. You just never lived them. When I work with clients stuck in “what if” land, I often ask: “And then what?” It forces them to imagine that even the “better” choice wouldn’t have been flawless.
That mental shift pulls regret out of fantasy mode and back into reality.
Step Two: Recognize That Regret Means Growth
Here’s a perspective shift most people miss: regret is proof of progress.
Think about it — the only reason you regret something is because you know better now. If you were still the same person you were back then, you wouldn’t feel regret.
Research backs this up: psychologists like Daniel Gilbert (author of Stumbling on Happiness) have shown that regret often grows out of our evolving values. It’s not a sign of weakness; it’s evidence that you’ve grown, that your standards have changed.
So instead of saying, “I should’ve known better,” try: “I didn’t know then, but I do now.” That subtle reframe takes regret from being a punishment to being a milestone.
Step Three: Give Regret a Job — or Fire It
Here’s what I’ve seen over and over in my coaching work: when people don’t know what to do with regret, it takes over. It drains energy, steals focus, and keeps you stuck in the past.
The way out isn’t to ignore it — it’s to give it direction.
Ask yourself:
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What is this regret teaching me about the kind of life I want now?
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How can I use this memory as a reminder to act differently today?
I once worked with a client who deeply regretted not repairing his relationship with his father before he passed. That regret haunted him — until he realized it was actually a signal. It pushed him to be present with his own children, to never let silence become the family norm again.
Regret didn’t disappear. But it got repurposed. It became fuel.
And if regret refuses to take the job? Fire it. Some regrets serve no purpose. You don’t have to keep carrying them.
Step Four: Practice Self-Compassion
This one is harder than it sounds. People love to hold themselves to impossible standards. But here’s the reality: every single person you admire has regrets. The difference is, they’ve stopped letting those regrets define them.
Self-compassion isn’t about letting yourself off the hook. It’s about remembering you’re human. You’ll make mistakes. You’ll make choices you wish you could redo. That doesn’t make you broken — it makes you alive.
Neuroscience even supports this: studies show that people who practice self-compassion recover faster from setbacks and make healthier decisions moving forward. Why? Because shame paralyzes, but compassion mobilizes.
The Bottom Line
You can’t stop regret from knocking. It’s part of being human. But you don’t have to let it move in, rearrange the furniture, and eat all your leftovers.
The path to happiness isn’t regret-free living — that doesn’t exist. The path to happiness is refusing to obsess over regret, and instead, using it as a teacher.
Regret can either be your jailer or your guide. The choice is yours.
So the next time regret shows up, don’t obsess. Ask it a better question:
“What can you teach me today that will make tomorrow lighter?”
Because happiness doesn’t come from erasing the past. It comes from owning it — and moving forward with less baggage.