It feels like this chapter has been building for years. I didn’t start my first business until 2023, after a corporate reorganization sent my career skidding off the track. But the spark started much earlier.
In the early 2000s, a group of friends and I tried to build a business. We shared a love for technology, board games, and fantasy. We were convinced we would create something brilliant and eventually sell it to Microsoft.
What we actually had was enthusiasm and a lot of late-night brainstorming sessions. What we did not have was a plan, funding, or much direction. The project never became a real company, but it planted an idea in my mind that entrepreneurship was possible.
For the next two decades, I built a steady corporate career. I worked in Big 5 consulting in the 90s, then in finance and the stock markets, and later on projects supporting the Defense Department and state and local governments. I took on large responsibilities and delivered results. Long hours were normal. Late nights and weekends came with the territory.
Once I even left a Texas Rangers game to troubleshoot a critical issue that kept me working until three in the morning. At seven the next day, I was presenting the solution to the customer. I took pride in being the person people could rely on when things got difficult.
Then 2022 happened.
A restructuring split apart the division where I worked. My boss went from running the entire group to managing only a fraction of it. A new leader stepped in above me and gradually began reducing my responsibilities. I noticed the warning signs but convinced myself things would eventually stabilize.
They didn’t.
One afternoon she asked if we could move my staff meeting so she could speak with me. When HR joined the call, I already knew what was coming. Fifteen minutes later, I was out. No dramatic moment. Just a clean break and a polite corporate “thank you for your service.”
If you prefer racing metaphors, it felt like Fernando Alonso’s crash at the 2016 Australian Grand Prix. One moment everything is moving at full speed, and the next you’re tumbling through the gravel trying to understand what just happened.
Or, staying true to the nautical theme of this blog, my schooner hit the shoals at full speed. The hull cracked and I went straight into the cold water.
The job hunt did not offer much of a life raft. I had several interviews early on, but the wave of tech layoffs at companies like Microsoft and Meta flooded the market with candidates. Competition increased overnight. I was interviewing at the Director level, which meant my salary expectations no longer matched what many companies were willing to pay.
Each interview ended the same way. A polite message thanking me for my time and letting me know they had decided to move forward with someone else.
In the middle of all this, I had an introductory call scheduled with someone named Deborah to talk about entrepreneurship. The night before the meeting, I almost canceled. I was ten years from retirement and what I wanted most was stability. A business sounded like the opposite of that.
But I had plenty of time and nothing to lose, so I kept the call.
That conversation changed everything.
Deborah did not try to sell me anything. Instead, she asked thoughtful questions and challenged some of the assumptions I had been carrying for years. Together we explored several possibilities, including home improvement businesses, a beauty salon concept, and even the coaching work she was doing.
The coaching idea stood out immediately. With my background in Scouting and years of helping people grow in their careers, the role felt natural. A few months later, I became a franchise owner with The Entrepreneur’s Source and started a new career as a Career Ownership Coach.
Coaching also gave me the push I needed to finally start this blog. I had considered writing for years while working in IT, but I never had the momentum to begin. The only thing I had settled on was the title: Here Be Dragons.
Now I spend my days helping people explore new possibilities for their careers and their lives. Writing feels like a natural extension of those conversations.
Some posts support the work I do with clients. Others are meant for people standing where I once stood, trying to figure out what comes next after a career runs aground.
Over the past few years I have also become a genuine believer in entrepreneurship and franchising. I do not sell the businesses I introduce people to. My role is to help people explore their options and understand what might be possible.
For some, business ownership creates time freedom. For others it provides deeper personal fulfillment. Sometimes it leads to financial independence. Occasionally it delivers all three.
Now, nearly three years into this journey, my wife and I are preparing to launch another business together.
The adventure continues.
If you are reading this, there is a good chance you are preparing to set your own sails. You might still be studying the charts or checking the horizon before the next turn.
Either way, I am glad you are here.
