I know what it feels like to hold cash in your hand as a kid and sense something bigger than money. The first time this happened I was around ten years old. What I felt wasn't greed, it was possibility. Like the world had just told me something true about itself. I spent most of my life chasing that feeling without fully understanding what I was after.
My dad wasn't around much, and my mom was preoccupied with her health. Early on, I figured out how to take care of myself. I cut lawns, worked construction, pumped gas, and bartended through college. I wasn't special. I was just hungry and paying attention. Every job taught me the same thing in a different language: see the system, find the gap, step in.
I majored in computer engineering and discovered programming the way some people discover a second language they already know. It wasn't technology I loved. It was the feeling of seeing something broken, having the tools, and knowing how to make it better. That process became the lens I carried into everything that followed.
My first real job was at Microsoft in the late eighties. The company was still young and the energy was electric. I went from bartending and student loans to a six-state sales territory and stock options I had no real grasp of what they could become. The promotions came, the relocations came, and most of all, the money came. What didn't come was a clear sense of who I was underneath it all.
I was performing and approval was the currency. Do good work, get the reward, look for the next reward. I told everyone what they wanted to hear, and I was good at it, and exhausted. Some years later, I quit a senior position at the corporate office and moved to the mountains thinking the scenery would fix something the work never could. It didn't.
My best friend and I had talked for years about starting a company together and we finally did. We built something real and launched at MacWorld. We checked the website that night from our hotel room and found two orders waiting. We were ecstatic. Building something from scratch and watching someone else find value in what you made — I still can't fully describe it.
Our company was growing rapidly until the Great Financial Crisis hit. The products we built were luxury items and sales dropped off a cliff. My partner's health was suffering, and my finances weren't in good shape, but there was still work to do. I stayed behind to sell off the inventory and meet our obligations, then shut down the company. My final act was to declare personal bankruptcy.
While I was winding down the business, my mother sold her house and moved in with me. A month before she was supposed to close on her new place, my older sister unexpectedly passed. She left behind two young boys and a husband who wasn't much of a father. We canceled the condo contract and Mom stayed. I became her caregiver for the next five and a half years.
I was carrying bankruptcy, a failed business, years of emotional baggage, and caregiving all at once. I was an emotional wreck in a way I had never allowed myself to be before, feelings oozing out of every pore, unable to stop crying, and not knowing what was happening to me. For a man who had spent his whole life holding it together, I was terrified.
I rebuilt the way I knew how — trying to make things better. From the outside it looked like restoration, and by most measures, it was. But the core pattern was still intact. The performance, the approval seeking, and the fear of being truly seen, all of it running quietly underneath everything I was building. I didn't see it.
Then I felt it again, that old familiar pull, the one that says this is it, this is the thing. I stepped into the opportunity and made another all-in commitment. The work and team was real, and for a while, I felt genuine purpose. I believed that completely, or told myself I did. When it collapsed, I was left dumbfounded. Somewhere underneath it all, I had known I was repeating a pattern. That's the hardest part to admit.
For as long as I can remember, my body had been trying to tell me something. I had tension in my shoulders and neck that turned out to be anger and a dropping sensation in my solar plexus that felt like a lack of safety. I had done serious work on myself in therapy and coaching, years of it, but the patterns kept repeating despite my efforts. After that last all-in attempt, I gave myself over to wanderlust. No destination, no plan. In the quiet, something integrated, and for the first time I wasn't leading with my mind. What had seemed separate started to converge, and for the first time, I could see the source of my pattern and how it had been running everything.
I started performing young. My parents were distracted and performing was how I got their love and attention. I carried that programming into every situation I encountered for the rest of my life without questioning it. Underneath it all was a misbelief I never examined: if people saw who I really was, they wouldn't like and accept me. The word authentic cracked something open. The three years that followed were some of the hardest of my life and the most rewarding. What crystallized on the other side was undeniable. I stand revealed stopped being aspirational and became the only thing worth choosing.
I chased approval because I hadn't learned that worth built from the outside is borrowed and worth built from the inside accumulates. I'm not the same man who declared bankruptcy, or the one who moved to the mountains to outrun himself. What I found on the other side is a man I recognize, grounded and rooted, able to show up with love and compassion, and equally able to hold a firm boundary.
I'm still on the path. Still doing the work. I still make mistakes, sometimes the same ones. But I know how to find my way back. That's enough.