Early Life: Breaking Out of the Mold

I grew up in a Catholic household that was strict, overprotective, and full of anxiety. Back then, I thought it was normal — I forced myself to live the way the church taught, even though it went against everything natural about me. It took years to realize that the box I was in wasn’t faith, it was fear. Breaking out of that mold was one of the first steps toward becoming myself.

Breaking Cycles and Boundaries

I had a father, but he never really knew who he was. He passed down the same fear-based cycle he inherited, and for years I carried it forward without realizing it. Joining a men’s group gave me the strength to start breaking that cycle — to strip away what wasn’t me and finally step into the man underneath.

Part of waking up also meant setting boundaries. And boundaries come with a cost. In my case, it led to a breakdown in relationships with my brother and sister. The same generational issues that shaped me are still shaping them, and I’ve had to step away. It hasn’t been easy, but it’s been what’s best for my kids — and for me. Sometimes the only way to protect what matters is to walk away from what doesn’t.

Sports, Power, and Pain

I’ve played just about every sport you can think of, but the one that left the biggest mark was golf — specifically long drive. Between 2006 and 2010, I ranked among the top 20 in the world for hitting a golf ball farther than almost anyone else. It was a rush, but it came with a price: torn-up shoulders, surgeries, and the reminder that strength can also bring pain. Sports taught me grit and discipline, but also that ignoring what hurts will eventually break you.

Relationships and Hard Lessons

Divorce and long-distance relationships taught me some of the hardest lessons of my life. The most important one? You have to prioritize yourself first. You can only give to others at the level you give yourself. If you’re neglecting your own needs just to please other people, you’ll never be happy. And if people can’t or won’t meet you where you are, you have to be willing to tell them to fuck off. Boundaries aren’t selfish — they’re survival.

Professional Journey

I built my career in SaaS sales, transportation operations, technology, customer success, and sales engineering. Over the years, I’ve worked in sales, in customer-facing technical roles, and in leadership — and eventually, I helped run a consulting company specializing in transportation. That role wasn’t just about consulting; it was about steering the business, building teams, and driving real results for clients.

Whether it’s optimizing routes, training front-line teams, or advising executives, my work has always been about making complex systems simpler and more effective. I’ve seen firsthand how technology can transform operations — but only if you pair it with real human expertise and truth.

Failures, Fraud, and Learning the Hard Way

Outside of transportation, I’ve tried my hand at real estate and other ventures. Some worked, some failed, and a few left scars — including getting burned by fraud. But I don’t regret any of it. Every loss taught me something I couldn’t have learned otherwise. I’m not where I want to be financially yet, but I know I’m stronger because of the tough lessons. No regrets, only growth.

Living Now

These days, I live half my life with my kids and half without. That rhythm keeps me grounded and gives me perspective. When I’m with them, I’m reminded of what matters most. When I’m without them, I focus on building for the future.

I also get to spend more time with my girlfriend than with my kids. It doesn’t replace the time I miss with them, but I’m beyond grateful to have someone so strong in my life — someone I love deeply and who loves me back. Her presence is proof that real partnership exists, and it gives me the foundation to keep growing into the man I want to be.

The world often feels fake — appearances, masks, illusions. I won’t live that way. I’d rather be broke and real than rich and fake. I believe in manifestation, but not in the Instagram version. I believe in hard work and kindness as the foundation for lasting success.

What I Believe

• Truth over appearances — if it’s fake, I don’t want it.

• Self-priority first — you can’t love others if you’re not loving yourself.

• Boundaries are love — they protect what matters and keep you aligned with who you really are.

• Real partnership matters — having someone strong to love and who loves me back proves that love built on truth and strength lasts.

• Hard work + kindness = unstoppable — that’s my formula for growth.

• Be → Do → Have — in that order.

This is me — no filters, no pretending. I’m Tommy Dorgan, and I’m here to live authentically, build relentlessly, and connect with anyone who’s real enough to walk the same path.