We’ve all had those moments—where we replay a conversation we wish went differently, a job we didn’t take, a dream we didn’t pursue, or a relationship we let slip away. And in those quiet, vulnerable moments, a heavy whisper often shows up: “I should’ve… I could’ve… I would’ve…”
Regret has a way of chaining us to the past, keeping us stuck in a loop of “what ifs.” It’s one of the heaviest emotional weights we can carry. Whether it’s a missed career opportunity, a failed relationship, or simply not showing up as your best self when it mattered most—regret doesn’t just linger; it festers.
But here’s the truth: regret may visit, but it doesn’t have to move in. You don’t have to be a prisoner of the “should have, could have, would have” mindset. There is freedom. There is grace. And yes—there is redemption.
Let’s unpack the burdens of regret, why we carry them, and how to finally let them go—so you can start living fully in the now.
Part 1: The Nature of Regret—And Why It Hurts So Much
Regret is a complex emotion. It’s not just sadness or disappointment—it’s sadness plus self-blame. It says, “I’m not just hurting; I’m responsible for my own hurt.”
Psychologist Neal Roese, Ph.D., author of If Only: How to Turn Regret Into Opportunity, describes regret as “the emotion of self-reflection, an opportunity to learn from our past mistakes.” But while regret can be a teacher, for many of us, it becomes a tyrant—haunting our decisions and limiting our future.
Regret whispers things like:
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“If only I’d taken that job, I’d be further ahead.”
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“If I had said yes instead of no, maybe we’d still be together.”
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“I wasted years doing something that never fulfilled me.”
And the deeper truth behind all of it? Regret often comes from a place of not trusting ourselves—or not believing that God can still bring beauty out of brokenness.
Part 2: The Different Faces of Regret
Regret shows up in all shapes and sizes. Some people carry career regret, others carry relationship regret, and some wrestle with personal regret—moments when they weren’t who they wanted to be.
Let’s look at the most common types:
1. Career Regret
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Not pursuing your passion.
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Staying in a job for security while your soul was dying inside.
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Passing on an opportunity out of fear.
“The only thing worse than starting something and failing… is not starting something at all.” — Seth Godin
2. Relationship Regret
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Letting go too soon—or holding on too long.
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Choosing pride over vulnerability.
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Not saying “I’m sorry” when it mattered.
3. Personal Growth Regret
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Knowing you could have done better but didn’t.
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Letting fear or insecurity dictate your choices.
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Losing time to distraction or comparison.
4. Faith Regret
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Walking away when things got hard.
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Not trusting God’s plan and trying to write your own.
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Feeling like you wasted seasons by not listening to His voice.
Part 3: The True Cost of Regret
Regret isn’t just emotional—it’s spiritual, psychological, and even physical. Studies from the National Institutes of Health show that unresolved regret can lead to anxiety, depression, and even sleep disorders.
It drains your energy, clouds your decisions, and poisons your self-esteem.
“Regret is an appraiser of our past. But it should never be the architect of our future.” — Dr. Brene Brown
Let that sink in.
When we let regret sit in the driver’s seat, it begins making decisions for us. We get overly cautious. Or stuck in perfectionism. Or avoid risk at all costs. And slowly, life begins to shrink.
But that’s not what God wants for you.
Part 4: The Biblical Truth About Regret
Here’s the raw and redemptive truth: regret doesn’t have to be the end of your story. God doesn’t waste pain—and He certainly doesn’t waste your past.
Romans 8:28 reminds us, “And we know that in all things God works for the good of those who love him, who have been called according to his purpose.”
Notice it says all things—not just the good things. That includes the missed opportunities, the bad decisions, the detours, and even the self-inflicted wounds.
Regret is real, but so is redemption.
Part 5: 7 Practical Steps to Break Free from Regret
Let’s move from theory to action. Here are steps you can take starting today to release regret and reclaim your peace.
1. Acknowledge It Without Shame
Regret doesn’t define you. It simply reveals where growth is still needed. Own the emotion—but don’t own the identity.
📝 Takeaway: Journal about one major regret and identify what emotion is really behind it: fear, guilt, anger, disappointment?
2. Learn the Lesson, Leave the Luggage
Ask yourself: What did this teach me about myself, others, or life? Then, take the lesson and leave the weight behind.
📝 Takeaway: Write down 3 positive outcomes or wisdoms you gained from that regretful situation.
3. Talk It Out With a Safe Person
Sometimes healing comes in conversation. Whether it’s a counselor, coach, pastor, or trusted friend, don’t carry the weight alone.
📝 Takeaway: Schedule a conversation this week about the regret you’ve been silently carrying.
4. Refuse to “Should” Yourself to Death
The words should, could, and would are red flags of regret. Replace them with “Next time, I will…” and start creating forward movement.
📝 Takeaway: Rewrite your regret narrative with empowering language: “I now know…” or “In the future, I choose…”
5. Make Amends Where You Can
Not all regrets can be “fixed,” but some can be healed through humility and action. An apology. A reconnection. A closure conversation.
📝 Takeaway: Is there someone you need to reach out to? Write the text or email—even if you never send it.
6. Trust God With What You Cannot Change
This one is hard. But faith steps in where control ends. If you believe in a God who restores and redeems, you can rest in knowing that He can still get you where you’re meant to be.
📝 Takeaway: Pray this short prayer: “God, I surrender my past to You. Use it, redeem it, and help me to walk freely into what’s next.”
7. Take One Bold Step Forward
The best way to silence regret is to live boldly. Do something today that your future self will thank you for.
📝 Takeaway: Sign up for the class. Start the business. Make the phone call. Apply for the job. Stop waiting.
Part 6: Regret vs. Responsibility
Let’s be clear: There’s a difference between regret and responsibility.
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Regret keeps you stuck in the past.
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Responsibility empowers you to shape the future.
We’re not saying “just move on” or pretend like it didn’t happen. We’re saying: own your part, release the rest, and walk in grace. There’s a difference between learning from your past and living in it.
Part 7: Expert Voices on Regret
Here’s what the professionals have to say:
“Regret doesn’t remind us that we did badly. It reminds us that we know we can do better.” — Kathryn Schulz, author of Being Wrong: Adventures in the Margin of Error
“People’s biggest regrets tend to be not the things they did, but the things they didn’t do.” — Dan Pink, author of The Power of Regret
“The most freeing thing you can do is forgive yourself. Not because you’re perfect, but because God’s grace is.” — Dr. Caroline Leaf, cognitive neuroscientist
Final Thoughts: You’re Not Too Late
Let’s end here: It’s not too late. You’re not too far gone. And your best life isn’t behind you—it’s ahead of you.
Your story doesn’t end with regret. It begins with the choice to release it.
Let go of the “should have, could have, would have” and step into “I can, I will, and by God’s grace—I am.”
There is freedom waiting for you.
Bonus: Daily Affirmations to Break the Regret Cycle
Start your day with one of these simple truths:
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“I release the past and receive today’s grace.”
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“I am not my mistakes. I am what I choose next.”
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“I trust that God can restore what I thought was lost.”
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“My future is not limited by my past.”
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“I walk in wisdom, not shame.”
Share This. Someone Needs It.
Regret is one of the most universal human emotions. We all have something we wish we could go back and redo. But we don’t have to stay stuck there—and neither does someone you love.
💡 If this post spoke to you, share it. Tag someone who needs to read it. Let’s help each other get free.
