Regret has a funny way of casting a long shadow over our lives, doesn’t it?
You might be moving along just fine, and then out of nowhere, those pangs of “What if?” sneak up on you.
I used to think regret was a sign I’d failed. After all, if you regret something, it must mean you did it wrong—or so I told myself.
But over time, I’ve realized that regret can actually be a powerful compass. It not only shows you where you’ve been but also points you toward where you need to go next.
For me, that wake-up call came when I decided to end my marriage. I was in my late 30s, working long hours in digital communications, and trying to keep my home life afloat. Leaving my marriage felt like the right choice at the time.
But afterward, I was flooded with doubt. Did I give up too easily? Could I have tried harder?
In the midst of all these questions, I found myself grappling with a new identity: I was now a divorced single mom, trying to navigate both a career and parenting on my own. The regret felt enormous.
Interestingly, though, that regret became the nudge I needed to rediscover who I am and what I truly want out of life.
Instead of letting it define me in a negative way, I started asking, “What can I learn from this?” When I decided to shift my perspective, everything began to change.
Now, here I am, writing for DM News, offering up some insights that might just help you turn your biggest disappointment into your greatest asset. So let’s dive in.
A moment I wish I could redo
We’ve all had those moments in life we wish we could press “undo” on.
Maybe it’s walking away from a stable job too soon or distancing ourselves from someone who mattered.
My regret might seem obvious—going through a divorce is rarely anyone’s Plan A. But I’d be lying if I said it wasn’t more complicated than that.
For me, the real regret wasn’t the act of leaving; it was ignoring all the small warning signs that led up to it, signs that maybe there was a deeper change I needed to make in my personal life.
Just a few months after the dust settled, I found myself aimlessly scrolling online job boards late at night. My son was fast asleep, and I felt this gnawing sense of having missed something fundamental.
My entire professional life had been in digital communications, but I realized I wasn’t enjoying it anymore. It was as if the divorce had pulled back a curtain, revealing a deeper dissatisfaction that had been hiding in the background for years.
I regretted staying in a routine that no longer served me, and I wished I had trusted my intuition sooner about pivoting to something more fulfilling.
That regret forced me to sit down and confront the real question: “If I could redo this part of my life, what would I change?”
And the answer was shockingly clear: I’d shift my career to something that allowed me to help people directly, combining my knack for communication with my passion for understanding human behavior.
It was a scary leap, but one that ended up guiding me toward writing about psychological insights and career advice. Even though the journey was filled with moments of self-doubt, my regret became my fuel for meaningful change.
The hidden power of facing disappointment
What if I told you that disappointment, at its core, could be your greatest teacher?
As Sheryl Sandberg once said, “We cannot change what we are not aware of, and once we are aware, we cannot help but change.”
The awareness part is key here. Regret is like a neon sign pointing to something that needs your attention. Often, we avoid reading that sign because, let’s face it, who wants to dive headfirst into feelings of failure?
But here’s what I’ve discovered: true growth happens when we allow ourselves to feel that wave of disappointment and then ask, “What is this here to teach me?”
Sometimes, the lesson is about setting better boundaries. Other times, it’s about recognizing your own strength.
In my case, it was about having the courage to step off one path and onto another—no matter how uncertain that new path might be. Because disappointment isn’t just a pit stop on the way to something else—it can be the map you use to find a more purposeful route altogether.
I’ve also noticed that embracing regret often goes hand in hand with giving yourself permission to be human. We tend to forget that each choice we make is based on who we are at that exact moment—our knowledge, emotional state, and personal circumstances.
So in some ways, regret can reveal how far you’ve come. When you look back and think, “I wish I’d known better,” perhaps that’s a testament to how much you’ve grown.
Another voice that’s really helped me frame this is Stephen Covey, who said, “Between stimulus and response, there is a space. In that space lies our freedom and power to choose our response.”
If we treat disappointment as that “space,” we might uncover a hidden reserve of inner strength we didn’t even know existed.
Finding meaning in what feels meaningless
I get it—when you’re in the thick of regret, it can feel pointless, like you’re stuck replaying a scene in your mind that’s never going to end differently. It’s tempting to let hopelessness creep in.
But I believe there’s a silver lining to this kind of emotional low point. It pushes you to re-evaluate what really matters.
After my divorce, I poured myself into journaling, which started as a simple outlet for my thoughts. Over time, that journaling became the seed of what would eventually become a new career in writing.
This shift from “meaningless” to “meaningful” didn’t happen overnight. It was the result of small, consistent efforts to align my daily actions with what I truly valued—my passion for storytelling and a desire to help others avoid the pitfalls I had experienced.
Once I let go of the idea that my life had to look a certain way by a certain age, I found a different kind of freedom. It’s like that Seth Godin quote: “If it scares you, it might be a good thing to try.” The fear I felt in forging a new career path was a good indicator that I was on to something that mattered.
I must stress here how perspective shapes everything. When disappointment strikes, it can feel like life’s arbitrary punishment. But often, it’s an opportunity to peel back layers and figure out what’s truly important to you.
That’s the beauty of regret—it offers a moment of clarity. You see who you were, who you are, and who you want to be next.
Strategies to turn regret into purpose
Now, let’s talk about the practical side. How do you actually pivot from sulking in regret to channeling it into a higher purpose?
First, name it. Acknowledge your regret for what it is. If you’re too busy beating yourself up or denying the problem, you’ll never address the root cause.
Write it down, talk it through with a trusted friend, or even speak it out loud in the mirror if you have to. The point is to give shape to that regret so it doesn’t fester in the background.
Second, break down the lessons. Reflect on the “why” behind your disappointment. Is it teaching you something about your job, your relationships, or how you handle stress? Get specific. The more precise you can be about what you’re learning, the easier it is to make real changes.
Third, set a new goal inspired by that lesson. If your regret reveals that you’ve been ignoring your passion for ages, maybe it’s time to carve out an hour a day to explore it. Or if you realize you need more balance, start by setting strict boundaries around your work and home life.
The idea is to transform the negative energy of regret into positive momentum toward something better.
Last but definitely not least, practice self-compassion. The moment you choose kindness toward yourself is the moment regret stops being a weight and starts being a stepping stone.
Remember: your worth isn’t diminished by what went wrong. If anything, you’re stronger for coming face to face with it.
Wrapping up
It’s amazing how a single regret can open the door to profound self-discovery. For me, that deep-seated disappointment over my divorce and lingering career dissatisfaction led to a life I never could have imagined before—one filled with writing, thoughtful conversations, and a sense of purpose I hadn’t known I was missing.
Looking back, I can honestly say that regret was the catalyst I needed to build a life that aligns more closely with who I am today.
You might be battling your own regrets—maybe it’s a relationship that ended, a job you stayed in too long, or a dream you pushed aside because it felt too risky. I hope my story encourages you to see those regrets not as endpoints, but as opportunities.
Here at DM News, we believe wholeheartedly in the power of personal growth. Regret is just one piece of that journey, but it can be the piece that makes everything else fall into place.
Give yourself the freedom to look at your disappointment from another angle. Embrace it, learn from it, and use it to ignite a fresh sense of purpose.
You don’t have to stay stuck in “What if?” mode forever. Sometimes, the very thing you’d trade the world to change ends up being the catalyst for a brighter, more authentic future.
And if that’s not the best reason to welcome regret with open arms, I don’t know what is.
