I watched the movie Young Washington the other night, and I have to tell you, I wasn’t expecting a history movie to hit quite so close to home. I figured I’d get some powdered wigs, a few battles, maybe learn something about the man whose face I’ve been looking at on dollar bills my entire life.

Well, I got a little more than I bargained for.

The movie takes us back to George Washington’s younger years, long before he became the man we know from the history books. He’s a young officer, eager to prove himself, and his first major assignment goes terribly wrong. People die, including someone he cares about, and he returns home carrying the weight of what happened.

And just when you think the poor man has been through enough, life hands him another helping of heartbreak. Then his mother, who isn’t exactly a hugger, says something that stopped me in my tracks.

I’m paraphrasing here, because I was a little too busy trying not to cry to write it down. But the message was essentially this:

Failure can become your legacy, or it can become your greatest teacher.

The rest, as they say, is history. Literally. Well, hello, life lesson. I thought I was just watching a movie.

That one line stayed with me because I think most of us have a mistake or two tucked away somewhere that we’d rather forget. And yet, somehow, we keep pulling them out, dusting them off, and reminding ourselves of everything we wish we’d done differently. Sometimes for years.

When Regret Rides Shotgun

I’ve noticed something about regret, both in my own life and in conversations with the women I work with.

Most of us are pretty good at keeping our lives moving. We’ve built careers, raised families, managed businesses, solved problems, and handled situations that would have sent our younger selves running for the nearest exit.

We’re capable women. We know how to get things done.

But that doesn’t mean we’ve made peace with every decision we’ve ever made.

In fact, I think some of us have gotten so good at moving forward that we don’t even notice the old regrets riding along with us.

Picture regret sitting in the passenger seat of your car. It doesn’t necessarily grab the steering wheel, but it certainly has opinions about where we’re going.

And wouldn’t you know it, the minute something new comes along, it leans over and says, “Are you sure about this? Remember what happened last time?” Oh, yes. Thank you for bringing that up. Again.

Maybe it’s a business decision that went sideways, a real estate deal that fell apart at the closing table, or a professional opportunity we passed up because the timing didn’t feel right.

Maybe it’s something more personal. A relationship we stayed in too long, words we wish we could take back, or years spent working so hard to build a successful life that we missed some of the moments that made it worth building.

And for those of us who are used to being the dependable one, the problem solver, the woman everyone calls when something needs to get done, those memories can carry a little extra weight. When we’re accustomed to getting things right, the times we didn’t can be awfully hard to reconcile.

I know I’ve caught myself revisiting mistakes that nobody else seems particularly interested in discussing anymore. Meanwhile, I’m over here mentally preparing my closing argument for a trial that ended years ago.

Apparently, regret didn’t get the memo.

Maybe Regret Has Something to Tell Us

Now, I don’t believe regret is necessarily a bad thing. I know, I know. After everything I just said about that annoying passenger in the car, you might be wondering why I’m defending it. But hear me out.

When we regret something, it’s often because that experience mattered to us. Maybe we cared deeply about the outcome. Maybe we disappointed someone we loved, or acted in a way that didn’t reflect the person we wanted to be.

Regret can help us recognize what we value, where we might need to grow, and what we’d like to do differently the next time around.

There’s wisdom in that, even when the lesson comes wrapped in a memory we’d prefer to leave unopened. The trouble comes when we keep replaying the experience long after we’ve learned what we needed to learn. That’s when regret starts acting less like a teacher and more like a ghost.

A good teacher helps us understand what happened, gives us something useful to work with, and eventually sends us on our way.

A ghost, on the other hand, has absolutely no respect for boundaries. It moves in, rearranges the furniture, and makes an appearance at two in the morning when we’re trying to sleep. And somehow, we’ve gotten used to having it around. We might even be setting an extra place for it at dinner.

What If We Gave Regret a Different Job?

Here’s an idea that’s helped me look at old mistakes a little differently. What if we stopped giving regret so much authority over the stories we tell ourselves?

Think about how often an old experience becomes the opening line of a new possibility.

“I’d love to start another business, but you know what happened with the last one.”

“I’ve thought about putting myself out there again, but after that relationship…”

“I’d really like to try something different, but I’m not sure I can handle another disappointment.”

Before we’ve even had a chance to explore what might be possible, we’ve invited the past to explain why it probably won’t work. 

And the past, bless its heart, is always happy to offer an opinion. Maybe it’s time for a little management restructuring.

We can keep the lessons we’ve learned without letting those experiences narrate every new chapter of our lives. I like to think of it as giving regret a new job title.

Instead of making it the narrator of our story, we can make it a consultant.

A consultant brings experience to the table. We can ask questions, consider the advice, and appreciate the perspective. But at the end of the meeting, we get to make the decision. And if the consultant keeps repeating the same story from 2017, we’re allowed to thank it for its input and move on with the agenda.

Washington’s early failure didn’t disappear from his story. By every account he carried it the rest of his life. But he picked himself up and went on to face more challenges, make more decisions, and grow into the leader we remember today. The experience became part of what shaped him.

I think there’s something worth considering in that for all of us.

We’re Not the Same Women We Were Back Then

There’s another piece of this that I find especially interesting. Sometimes the fear we carry into a new opportunity belongs to a much older version of ourselves.

Think about it. Maybe we tried something ten years ago and it didn’t work. We were disappointed, embarrassed, or hurt, and we promised ourselves we’d never put ourselves through that again.

Fair enough. At the time, that may have felt like a perfectly reasonable decision. But look at everything that’s happened since then. We’ve gained experience. We’ve learned to recognize situations we might have missed before. We’ve developed new skills, built relationships, survived unexpected challenges, and discovered strengths we didn’t even know we had.

Yet when a similar opportunity appears, we sometimes respond as though we’re still the woman who went through that original experience. It’s like pulling an old dress out of the closet, squeezing ourselves into it, and wondering why it doesn’t fit. Honey, we’ve grown. That’s allowed.

I think one of the most useful questions we can ask ourselves is:

“Am I making this decision based on who I am today, or who I was when things went wrong?”

Because those two women may have very different answers. The woman we are today has the benefit of everything we’ve learned along the way, including the lessons that came from the things we wish had turned out differently. And wouldn’t it be a shame to go through all that growing only to keep making decisions as though none of it happened?

Three Ways to Stop Letting the Past Make Our Decisions

So how do we begin loosening regret’s grip? I don’t think we need an elaborate process, a forty-seven-page workbook, or a complete renovation of our emotional haunted house. Sometimes a small shift in how we look at an old experience can help us find our footing again.

Here are three places we might begin.

1. Ask what the experience taught us.

Rather than replaying every detail of what went wrong, let’s see if we can identify the lesson in one simple sentence.

Maybe it’s, “I learned that I need to trust my instincts sooner.”

Or, “I learned that saying yes to everything eventually means saying no to something important.”

Perhaps it’s, “I learned that I need to ask for help before I’m completely overwhelmed.”

We can acknowledge that an experience was painful while also recognizing that something useful came from it. And once we’ve identified the lesson, we can begin putting it to work in our lives today.

2. Separate what happened from who we are.

This one can be tricky, especially when we’re accustomed to holding ourselves to high standards.

There’s a big difference between saying, “I made a poor decision,” and deciding, “I’m someone who makes poor decisions.”

One describes an experience. The other turns that experience into an identity.

And when we repeat those kinds of statements often enough, we may start treating them as facts.

I’ve found it helpful to pay attention to the words we use when we talk about ourselves, especially when we’re remembering something we’re not particularly proud of.

We can take responsibility for our choices without making one chapter of our lives the definition of the whole book.

3. Give ourselves permission to try again, starting small.

Sometimes we imagine that moving past a failure means we have to jump right back into the very thing that frightened us. But who says we have to do that? If a business venture didn’t work out, maybe the next step is exploring one small idea instead of launching an entirely new company.

If a relationship ended painfully, perhaps we begin by accepting an invitation to coffee rather than worrying about whether we’re ready for another serious commitment.

If we’ve been dreaming about writing a book, maybe we start with one page. One conversation. One appointment. One small decision.

We can build confidence through experience, and those smaller steps give us opportunities to discover just how much we’ve changed. The goal is to begin making room for possibility again, at a pace that feels right for us.

Don’t Let the Ghosts of Your Past Spook Away Today’s Gifts

With Halloween just around the corner, I’ve been thinking about how appropriate it is that we call these old memories the ghosts of our past. Some of them really do have a way of showing up when we least expect them.

We can be having a perfectly lovely day, minding our own business, when suddenly an old memory wanders in and starts rattling its chains. And there we go, questioning ourselves all over again.

But here’s what I believe:

The Power breathing you is greater than any circumstance, situation, or condition.

That includes the circumstances we wish we’d handled differently, the decisions we’d love to revisit, and the opportunities we didn’t recognize until they were gone. Our mistakes are part of our story, and we can learn from them without allowing them to determine what happens next.

I keep coming back to that moment in Young Washington and the choice his mother placed before him. Will failure become our legacy, or will we allow it to become one of our greatest teachers? I suspect most of us have a little of both in our stories. And maybe that’s okay.

We don’t have to pretend the past was perfect, and we certainly don’t have to keep punishing ourselves because it wasn’t. We can take what we’ve learned, appreciate the woman we’ve become, and give ourselves permission to see what else might be possible.

As for those old ghosts? Well, if they’ve taught us what we needed to know, perhaps it’s time to stop leaving the porch light on for them. We’ve got a life to live.

Let’s Talk About What Comes Next

If there’s an old mistake or disappointment that’s been weighing on you, I’d love to explore it together.

I offer a free discovery session where we can talk about what happened, what you’d love for your life now, and what one small step forward might look like.

You don’t need to have everything figured out before we talk. Sometimes a good conversation is a wonderful place to begin.

With love,

Rosemary Gibson