I was a kid the first time I remember drowning in regret. Something I said at school, some small social misfire, and I lay awake certain I had ruined myself for good.
I hadn't. But the feeling never really left. It just kept finding new material.
I regretted whatever I believed I had done to make my father leave when I was twelve. I regretted my awkward, anxious adolescence, the kind of anxiety that makes a kid feel like an outcast inside his own skin. I regretted joining the Air Force instead of going straight to college. I regretted never chasing a science degree. I regretted relationships. I regretted career choices. Always, underneath all of it, the low hum of regret.
Wow. This post is a downer. Stay with me. It turns, I promise.
Because here is the thing about a life built on regret. It caves. Mine did, spectacularly. Regret was never really about any single decision. It was a state of mind, another word for shame, and that shame haunted almost all of my childhood and most of my adult life. The things I did to hide from it, or to quiet it, are what eventually brought the whole structure down.
Which is how I ended up in prison, swimming in an aquarium of regret. Confined, breathing my own poor choices, circling the same water.
It took about two years inside before something cracked open.
I realized that, apart from the pain I caused others, I had nothing to regret.
That one exception is real, and I hold onto it. I hurt people. I carry it gently now, not with the old shame, but I do not pretend it away.
Everything else, I finally looked at squarely. Young Doug, the one I had been condemning for decades, made some bad choices in his early twenties. So does almost everyone in their early twenties. Young Doug did not choose mental illness. And when it got bad, really bad, he checked himself into the hospital. He sought his own care. He directed it.
Young Doug earned a master's in social work. He set himself on a path toward improving mental health systems, work opportunity, and disability rights. Who cares that he never wanted a science degree. Those choices carried him to the Texas Capitol, doing real policy work. They put him in front of a classroom at the University of Texas, teaching that policy to students.
Sitting in that cell, my only real regret was that I had never once looked up at my own wall. I never saw the degrees hanging there. I never looked around at the young child, the wife, the house I owned, the job with room to grow. I had spent a lifetime regretting a man who, it turned out, had built a life worth being proud of.
My only regret was not realizing, years sooner, how little I truly had to regret.
So I decided to stop. Not to manage regret. To stop doing it.
I named the life I wanted. I pictured, in detail, where I hoped to stand five years after my release, on every front. And then I did something strange. I started living that future in the present, as if it were already here.
Every letter I wrote to my daughter from prison was me living the close, loving relationship I intended to have with her. Not someday. Right then. How I showed up for my prison job was me investing in the career I intended to build. I stopped waiting for the future to arrive and started making it real in the same moment I imagined it.
Five years after I walked out, all of it had manifested. And I do mean all of it. Across the board.
Twelve years ago this week, I walked out of that prison. I have been thinking a lot about the man who walked out, and about everything since.
I cannot name a single thing I would change. Not one. And especially not the mistakes, because those have served me better than almost anything else I own.
A podcaster asked me recently where I want to be in five years. I told him the truth. Right where I am. I get paid to do the work I would do for free. I have a wife I adore and two daughters, one of them recently adopted. It is a rich, rewarding life.
None of that means it has been smooth. I still have mental health challenges. The stress of building a business has, at times, put real pressure on my sobriety. I stumble. But I do not regret the stumbles anymore.
I have simply become someone who sees the future he wants and lives it in the present, on purpose, so that he never ends up staring in the rearview mirror at everything he wishes he had done.
Because that, honestly, would suck.
If there is a version of your future you have been putting off until you are ready, until things settle, until the timing feels right, consider this your invitation to stop waiting. Name it. Then live the joy of that future life in the present, as though it were already yours.
I would love to hear what you would name.