As a nocturne, my regrets tend to visit me in the early hours of the morning. Over time I have become accustomed to it. That familiar punch to the gut as my mind served up a highlight reel of every stupid thing I’d ever done. The business partnership that imploded because I was too proud to listen. The words I said to my husband that I can never take back. The strain that my selfishness put on my young marriage that almost ended in divorce. And literally every embarrassing moment ever.
Maybe you know this feeling. That suffocating weight of regret that seems to get heavier with each passing year. The way your mistakes feel more real at 3 AM than your accomplishments ever do in daylight.
I used to think these midnight reckonings were punishment—my mind’s way of making sure I never forgot how badly I’d screwed up. But after years of wrestling with my demons and finally finding some peace, I’ve learned something different. Those 3 AM wake-up calls aren’t torture. They’re invitations to finally heal.
If you’re reading this with your own catalog of regrets weighing on your chest, I want you to know something: you don’t have to carry this load forever. I know because I’ve been exactly where you are, and I’ve found my way through to the other side.
Why Everything Feels Harder After 40
There’s something brutal about hitting our forties. Suddenly, every choice you’ve ever made gets put under a microscope. You start seeing the patterns, the missed opportunities, the ways you’ve hurt people you love. It’s like someone turned up the volume on your inner critic.
I remember looking at my life at 38 and feeling like I’d wasted half of it. Every road not taken seemed to mock me. Every relationship I’d damaged felt like proof that I was fundamentally broken.
But here’s what I’ve learned: this isn’t happening to torture you. Your brain is actually trying to help you grow. It’s just doing it in the most painful way possible.
When I finally stopped fighting these feelings and started listening to what they were trying to tell me, everything changed. Those regrets weren’t just random emotional debris—they were guideposts showing me exactly what needed healing.
The Three Ghosts That Visit After Dark
In my journey through self-forgiveness, I’ve noticed that regrets tend to show up in three main flavors, each with their own special brand of torment:
- The Things We Did – These are the biggies. The affair. The lie that spiraled out of control. The time you chose money over family. The words spoken in anger that can never be unsaid. These regrets whisper, “How could you have done that?”
- The Things We Didn’t Do – The dreams we abandoned. The chances we didn’t take. The love we didn’t express. The risks we were too scared to attempt. These whisper, “What if you had just been brave?”
- The Ways We Lost Ourselves – Maybe the most painful of all. The times we betrayed our own values. When we stayed silent when we should have spoken up. When we let others define who we were supposed to be. These whisper, “Who are you really?”
Understanding which ghost visits you most often is the first step toward making peace with all of them.
Why Your Brain Won’t Let This Go
I spent years wondering why I could remember every detail of my worst moments but struggled to recall my achievements. Turns out, there’s actually a reason for this bad joke.
When we replay our mistakes, our brains literally experience them as happening right now. That’s why a divorce from ten years ago can feel as fresh as yesterday’s argument. Our minds are trying to protect us by keeping these memories vivid—but instead of helping, they keep us trapped.
The good news? Our brains never stop growing, even after 40. Every time we choose compassion over criticism, we’re literally rewiring our neural pathways. It takes practice, but we can train our minds to respond to mistakes with curiosity instead of cruelty.
Breaking Free from the Mental Prison
For years, I have walked on the regret treadmill, expending enormous energy thinking about my mistakes but never actually getting anywhere. I’d replay conversations, reimagine scenarios, and torture myself with “what ifs” until I was emotionally exhausted. Did i cry? Maybe.
Breaking free from this cycle was one of the hardest things I’ve ever done. It meant learning to catch myself mid-spiral and ask different questions. Instead of “How could I have been so stupid?” I started asking “What was I trying to protect or achieve back then?” Instead of “I’m such a failure,” I began wondering “What can this teach me about who I want to be now?”
It wasn’t instant. There were days I fell right back into the old patterns. But slowly, gradually, I learned to be curious about my past instead of just critical.
The Four Truths That Set Me Free
Truth #1: Context Changes Everything
The first breakthrough came when I stopped judging my past self by what I know now. When I made those mistakes, I was working with different information, different resources, different levels of emotional maturity. I was often scared, overwhelmed, or trying to protect something I thought mattered.
This doesn’t excuse harmful behavior, but it does help explain it. Understanding why you made certain choices is the first step toward forgiving yourself for making them.
Truth #2: Every Mistake Contains a Gift
This one took me the longest to accept because it felt like I was minimizing the harm I’d caused. But gradually, I began to see how my biggest failures had become my most powerful teachers.
That business failure? It taught me humility and showed me what I truly valued. The affair that ended my marriage? It forced me to confront how I’d been avoiding intimacy and taught me what authentic love actually looks like. The times I’d chosen fear over courage? They showed me exactly who I wanted to become.
Our mistakes don’t define us—how we respond to them does.
Truth #3: Healing Requires Action, Not Just Reflection
For years, I thought self-forgiveness meant just thinking differently about my past. But real healing happened when I started taking action. Sometimes that meant making amends where possible. Sometimes it meant changing patterns in my current life. Often, it meant using my hard-won wisdom to help others facing similar struggles.
The point isn’t to “earn” forgiveness through good deeds. It’s about letting your growth become visible—to yourself and others.
Truth #4: You Get to Rewrite Your Story
This was the most revolutionary realization of all: I am not my worst chapter. Yes, I did those things. Yes, they had consequences. But they are part of a larger story that’s still being written.
Instead of seeing myself as “the person who had an affair,” I began to see myself as “someone who made a terrible mistake, faced the consequences, and became more honest and faithful as a result.” Same facts, completely different story.
My 8-Week Journey to Self-Forgiveness
When I finally committed to healing, I gave myself eight weeks to see if real change was possible. Here’s what that journey looked like:
Weeks 1-2: Getting Honest I started by simply acknowledging what I was carrying without trying to fix it. I wrote letters to myself about my biggest regrets, treating my past self like a friend who’d made mistakes, not an enemy to be punished.
Weeks 3-4: Understanding the Why. This is where I dug deeper into the context of my choices. What was happening in my life? Was there anything I was afraid of? What did I think would happen if I acted differently? This wasn’t about making excuses—it was about developing compassion for someone (my past self) who was doing the best they could with what they had.
Weeks 5-6: Taking Action: I made amends where I could. I wrote letters (some sent, some not). I had difficult conversations. Finally, I made changes in my current life that reflected what I’d learned. Not to earn forgiveness, but to honour the growth that had come from my pain.
Weeks 7-8: Sharing the Journey The final step was sharing my story—first with trusted friends, then more broadly. Not because I thought everyone needed to hear it, but because keeping secrets about our growth maintains shame. When we share our healing journey, we give others permission to begin their own.
The Lies That Keep Us Stuck
Along the way, I had to confront some persistent lies that kept me trapped in guilt:
“What I did was unforgivable.” If you’re seeking to change and grow, you’re already demonstrating exactly why you deserve forgiveness. The fact that you feel remorse proves your goodness, not your badness.
“I should have known better.” This assumes you had access to wisdom, emotional resources, or information that you clearly didn’t have at the time. It’s like expecting your 20-year-old self to have the judgment of your 45-year-old self.
“The damage is permanent.” While some consequences can’t be undone, our response to them creates new possibilities. I’ve watched people build beautiful lives and relationships after devastating mistakes. Redemption is always possible.
“No one will ever forgive me.” You can’t control others’ forgiveness, and trying to will drive you crazy. Focus on becoming someone worthy of trust and let others make their own decisions.
The Unexpected Gifts of Self-Forgiveness
The journey to self-forgiveness gave me gifts I never expected:
My relationships got deeper because I stopped hiding parts of myself out of shame. When you’re honest about your struggles, people feel safer sharing theirs.
My decision-making became clearer because I wasn’t paralyzed by fear of making another mistake. When you know you can survive and learn from failure, you become braver.
My empathy expanded exponentially. When you truly understand your own capacity for poor choices, you develop profound compassion for others’ struggles.
I became a safe person for others to confess their worst moments to, because I’d learned to hold space for human imperfection.
Most surprisingly, I discovered that my greatest contributions often came through sharing my struggles, not my successes.
Your Imperfect, Beautiful Life
Here’s something our culture doesn’t want you to know: your struggles might be exactly what the world needs from you. The story of how you survived your darkest choices could become someone else’s lifeline.
We’re taught to hide our failures and showcase our successes, but real connection happens in the messy middle—where we’re all just humans figuring it out as we go.
Your mistakes don’t disqualify you from love, success, or happiness. They qualify you for deeper wisdom, greater compassion, and more authentic relationships.
Where You Start Today
Self-forgiveness isn’t about forgetting what happened or pretending it wasn’t wrong. It’s about changing your relationship with your past so it can inform your future without controlling it. If you’re ready to begin, start small. Pick one regret that’s been haunting you and ask yourself: “What was I trying to protect or achieve when I made that choice?” Write down your answer without judgment. Just curiosity.
That’s it. That’s where healing begins.
Remember: You are not your worst moment. You are not your biggest mistake. You are a human being capable of growth, change, and redemption. Your past has shaped you, but it doesn’t have to cage you.
Those 3 AM visits from your regrets? They’re not coming to punish you. They’re coming to be healed. And you—imperfect, struggling, beautifully human you—have everything you need to do that healing work.
The only question is: are you ready to begin?
If this resonates with you and you’re ready to begin your own journey of self-forgiveness, know that you’re not alone. Every step toward healing is an act of courage, and the world needs your whole story—struggles and triumphs alike.