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I Moved Into My In-Laws’ Basement at 38 years old.

Entrepreneurship is a game full of choices.

It was what anyone could’ve expected; a period of collective peace and jubilation in the early weeks. My daughter’s grandparents were thrilled to have her causing a cute ruckus throughout their home. My wife was optimistic that being front and center with her mother would spark some relationship repair.  Meanwhile, my dog and I tried to be on our best behavior. We were grateful that we had a place to call home for a couple months. A couple months turned out to be half a year in total and a pretty turbulent ride for us all.

I was free. Well, more like free falling and looking for my rip cord.

“So what are you gonna do?” “So what do you do now?” These were questions I received regularly during our stay in Blackstone, Virginia.  It’s an interesting question to have to answer at 38 years old; especially after just quitting a job that had me in the mid 100K compensation range.  “I’m not sure” and “I don’t know” often yielded puzzling looks and vague support. I had never been in this situation before. I was in full control of my life.  No boss. No superior. No one to come home and talk about at the dinner table. I was free. Well, more like free falling and looking for my rip cord.

Flybys Media:
Don’t worry, I’ll come to you.

I set up a makeshift office at my father-in-law’s storage facility building.  It was there I would browse the internet for hours, perusing bright shiny objects, educational courses, and the gear I would need to be a renowned photographer. I mean… videographer. I mean…marketing consultant. No matter what flavor of the week it was, my ambitions all involved spending money in an effort to be taken seriously as an entrepreneur.

I was running in mental circles and selling things from our two jam packed storage units.  I was paying for new career shortcuts and because of that I would win! It was all a racket as you might expect.  I returned much of what I purchased or sold it on eBay once I saw that I couldn’t and shouldn’t have had these items.  I never said this out loud, but internally my self narrative was “I’m a Marine. I can learn and succeed in ANYTHING.”

Clearly what I wasn’t learning was that my wife’s and my plan to “crush” debt was actually going in the opposite direction.  She was not bringing in what she had expected financially and somehow her ability to get things done was worse than ever. The environment was just too chaotic and it became evident that unresolved issues were being exacerbated by this living situation. While conscious of it all, we both just tried to be conveniently aloof.

September approached and something amazing happened despite my poorly strategized departure from working full time. A CEO I had met via LinkedIn the previous year, randomly reached out to me. They coincidentally were going to be in New York during a time I had planned on being there as well. A couple weeks later, we met at a bar in Manhattan for 20 minutes. After some laughs and career chat, I was somehow presented with an offer I couldn’t believe:

  1. I was going to be mentored in videography and storytelling by the Vice President of the CEO’s digital team; a 28 year veteran of media production.
  2. The digital team would document the CEO’s efforts to help a veteran who chose life over money and was starting his career over from scratch.
  3. I would be documenting my business lessons and spreading it to my LinkedIn veteran network of approximately 700 people; number I thought was massive.
  4. I was offered a salary! This was completely unexpected.

Things happened quickly, but I was energized. I felt like a boxer who’d been getting beaten all fight and then miraculously landed a knockout blow. Now I could answer what I was doing with confidence and vivaciousness. After all, a CEO chose to help me.  We could now move out of my in-laws’ home as some things had become truly visceral. We could reestablish ourselves on the right track, and the rest would be history.

Traveling across the ocean in the belly of the beast

My wife and I traveled to Sicily via Space- A travel; a wonderful perk for military retirees. A few days later I would pay to fly out and meet the CEO and VP in the United Kingdom as they were there for a conference. I could think of no better way to kick things off than documenting the beginning of this unique adventure overseas!

IT WAS A DISASTER.  I flew myself across the pond only to be let go from the project. A project about me. A project that hadn’t even started. Stay tuned. Sometimes the help you’re offered is not the help you need.


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