Do You Have Regret or Reasons?

Grief can run you, or it can refine you. Your call.

Bear with me here, this one’s going to be personal.

I woke up for the second day in a row from dreams about “the one who got away.” Now, in full transparency, that was over 20 years ago, and I’m now a middle-aged woman who bears nearly no resemblance to the immature young Marine I was then, so the chances that he was actually “the one” are slim to none. Nonetheless, he lives on in my mind, all these years later, as the thing (person) I messed up.

I was having a conversation yesterday with a coaching client who’s struggling with a transition in his life that’s fraught with lots of heartache, grief, sadness, and confusion. He’s a highly-respected man at the peak of his successful career–a living reminder that the deep realness of emotional agony happens to all of us, no matter what we achieve and the position we occupy in social and political circles.

I talked with him about grief–about what happens the moments after we pull the plug on something that’s been on metaphorical life support. We all have them. Maybe it’s a startup that you invested your life savings into and, despite your best efforts, watched disintegrate. Maybe it’s your 20-year marriage that slowly turned into a battlefield. Maybe it’s a child who disowned you. 

Regret. That’s what they all have in common. Regret about our choices. Regret that we didn’t “see it coming.” Regret that we didn’t do enough. Regret about how we showed up, or didn’t. Regret that we made the “wrong” choice.

Regret and grief are familiar bedfellows.

I shared with him that I still hold onto my story about “the one who got away.” It’s a part of my life development that has shaped who I am. But the emotional and mental space that I allow that story to occupy within me determines whether I live with regret or reasons. Living with regret means living in the past, fixated on things I cannot change, beating myself up. Regret keeps part of us stuck–part of us that persists under the surface no matter how high-achieving we are. 

Reasons are what emerge when we stop grasping at the past and start learning from it. My story about “the one who got away” isn’t neat or noble. I was young and dumb, and I made choices that hurt people. At some point in our lives–actually, throughout our lives, at different levels of intensity and impact–we all do. But over time, I turned that regret into a reason: a reason to lead with honesty, even when it’s uncomfortable. I can’t change what happened, but I can let it shape how I move forward, and that’s what turning regret into growth looks like. 

Grief is natural and necessary. Pulling the plug hurts. Loss hurts. But beyond that is choice about the stories we tell ourselves and others about what happened, what we experienced, and what we want our lives to look and feel like beyond the threshold of finality. We can hold on to regret, or we can turn our grief into reasons and reminders for doing it differently next time.

It’s the “growth mindset” we talk about in leadership circles, applied to deeply emotional human experiences. Feel the feelings, then use the lessons for good. What is this experience here to teach you? How is this experience–no matter how painful–serving your highest and best development? It’s hard to tap into when we’re in the thick of it, but when the dust settles, the choice is yours.

The people I work with are often the ones everyone else assumes are fine. From the outside, they look successful, composed, and in control. But underneath, they’re carrying real grief, regret, and emotional weight they rarely get to name out loud. What I’ve learned is this: those private struggles don’t have to break us—they can become the very reason we lead with more clarity, depth, and humanity. You don’t get to choose whether struggle shows up, but you do get to choose what it becomes. Regret or reason. Stuck or shaped. Choose reason.