When enthusiasm turns sharp, jokes land wrong, and leadership asks us to listen instead of defend. There’s a particular kind of mistake that doesn’t come from malice. It comes from momentum. From energy. From wanting to prove yourself capable, strong, valuable. From caring—just a little too loudly. Natalie once shared a story with me that still sits heavy, in the best way. She was early in a season of leadership where she was energized and eager. She wanted to show she could

Every Fourth of July, I find myself thinking about the story of our country. Not the polished version. The real one. A story filled with breathtaking victories and heartbreaking failures. Moments of courage that changed the world. Moments of injustice that still leave scars today. Times when we stood together, and times when we pulled ourselves apart. Yet somehow, through all of it, we kept moving forward. Not because we were perfect. Because we refused to let imperfection be

It's been a while since I've written. But last week, I was reminded why The Damaged Leader exists. I recently had the honor of helping a former teammate navigate a crossroads in her career. She was facing a decision that many of us eventually encounter. One path offered a predictable journey - success, stability, comfort. The other path led into the unknown and required her to bet on herself, trust her experience, and remain committed to the things that truly drive her forwar

Recently at Topgolf, a large portion of the sales team was laid off. Good people. People who worked hard. People who showed up every day with enthusiasm. People who rolled with constant change and constant corporate punches. People with talent, relationships, goals, families, bills, and lives outside of the office walls. Much of it did not seem connected to them personally. Consumer behavior changes. Companies restructure. Priorities shift. Budgets tighten. Entire industries

I’ve been sitting with this feeling lately, and I can’t quite shake it. It’s not that work isn’t getting done. In fact, from the outside, everything probably looks fine. The emails are going out, meetings are happening, and the numbers are still being chased like they always are. If someone were to look in from the outside, they might even say things are working. But something feels off. It’s subtle at first. Not loud enough to call out, not obvious enough to pin point. Just

I was sitting with my business coaches - a husband and wife duo who coach together in a way that feels less like a session and more like a conversation you didn’t know you needed. They see things differently, maybe it’s the two perspectives. It hits different. Not louder. Not more complex. Just… clearer. If you ever want their contact, I’ll share it. They’ve been impactful in ways I didn’t expect. In the middle of that conversation, they asked me a question that didn’t feel

A reflection on betrayal, broken trust, and choosing who you become after. I was a good leader. Not perfect, but deeply invested. I cared about my people. I spent time helping them grow, explaining the why, creating space for questions, for mistakes, for learning. I believed in development, not domination. I believed leadership was something you gave, not something you took. And then someone on my team decided they should have my job. They didn’t come to me. They didn’t ask f

Betting on Yourself, Losing, and Choosing to Start Over Anyway There’s a certain kind of pain that comes from doing the brave thing. Not the “I tried something new and it didn’t work” kind. I’m talking about the big swing. The one where you bet on your family’s future. You pack up your life, move across the country, and tell yourself, “This is our next chapter.” And then six months later… it’s gone. My wife was recently let go from her executive role. The very role that broug

There’s a moment in leadership that almost no one talks about. It isn’t loud. It isn’t explosive. It doesn’t come with a raised voice or a slammed door. It comes quietly with tears trapped behind marble eyes -- when you realize that hope is no longer a strategy. This isn’t about someone making a mistake. Or struggling. Or even failing. This is about someone who isn’t bought in. Who is disrespectful in subtle and obvious ways. Who doesn’t try. And worse -- who has no interest

There’s a moment every leader dreads. That sinking, stomach-twisting realization that feels like heavy weights around our ankles dragging us deeper into the chilling ocean's darkness: I mishandled that. Maybe it was an impulsive reaction, a decision made in haste, or a conversation where words became weapons instead of bridges. And in that moment, a whisper creeps in, one that haunts every damaged leader - Maybe I’m not cut out for this. But here’s the truth: ALL LEADERS FAI

There are moments in our life that truly shift what we think or feel about a person or a thing. One of my fondest memories, yet a memory that cruelly slices my very soul - oddly enough invoked by a smell. My deepest embarrassments surface when I smell fried chicken. To this day, I don’t eat fried chicken because it brings this life changing moment roaring back into my head like a derailed freight train. It was 1989, I remember the day, etched into my mind like an over-used

I Didn’t Have Time to Write... And I Beat Myself Up for It. There are days—weeks, if I’m honest—when the words don’t show up on schedule. The idea sits there. The post waits to be written. The cursor blinks like it’s disappointed in me. And instead of grace, I reach for judgment. You should have made time. If this mattered enough, you would’ve written it. What kind of writer doesn’t write? What kind of leader doesn’t show up consistently? That spiral is familiar. Comfortable

Last weekend my wife and I went to a three-year-old’s birthday party.You know the scene. Frosting everywhere. Balloons. Kids sprinting full speed with zero awareness of furniture or the adult legs they’re slamming into. In the middle of all that, I started talking with some new friends and, like these things usually do, the conversation drifted to work. There must have been fifty people in the house, but I had real, honest conversations with four of them. Here is who I met:

I’ve moved more times than I can count. Each new home has its own story - its quirks, its corners, its “almost perfects.” And each time, when I walk into a new kitchen, I notice the backsplash. There’s something satisfying about those clean, deliberate lines. The soft sheen of tile, the light grout perfectly placed to brighten the space. Subway tile is a popular choice for a reason. It’s timeless, functional, and easy to clean. The design is straightforward - neat rows, rep

Developing others is often depicted as guiding someone through a smooth, well-paved road to success. But for the damaged leader, the journey is far from a flawless highway. It’s more like navigating a well-worn vehicle down a rugged, winding road full of potholes, detours, and unexpected breakdowns. As leaders, we’ve been behind the wheel when the engine sputtered, seen warning lights flicker, and had to steer through rough terrain using nothing but grit and a little bit of h

Working at Minus 5 Ice Bar in Las Vegas taught me an unexpected lesson about leadership and pain. Picture this: I'm handling crystal-clear blocks of ice, crafting experiences for guests in a venue where everything – from the walls to the glasses – is made of ice. Then it happens. A tiny shard of ice, no bigger than an eyelash, finds its way under my skin. The initial shock is sharp and intense. My hand reflexively recoils, and for a moment, all I can focus on is this minuscul

Last week was one I used to look forward to every year: our annual summit. Coming together as a sales leadership team, spending coveted...

It might seem strange at first—comparing leadership to a “silly old bear” with a penchant for honey and simple-minded wisdom. But if you really think about it, Winnie the Pooh, with his unassuming charm, embodies the essence of what it means to be a damaged leader. His imperfections, his moments of uncertainty, his deep reliance on those around him—these are not weaknesses. They are what make him an exceptional leader. As damaged leaders, we often find ourselves learning from

The first time I heard the term, I thought it was just another corporate buzzword. A flavor-of-the-month idea cooked up in some boardroom...

Prayer for Mercy There were 42 assorted pills, different sizes, different colors contrasting brightly against the whiteness of my hand, on a different day it would have reminded me of skittles, or maybe M&M's after they added some new colors. The square bottle of water was sweating on my nightstand and for some reason that mattered, I did not want a water stain on the wood. Now I look back and wonder why it mattered to me so much. I shook the pill slightly, dropped one a