When I started “living my dash” I had no idea I was doing it.

I grew up in a small town in Connecticut and started working at the age of 14 on a farm, making ice cream cones and pizza for kids birthday parties. When I turned 16, I got my first real job as a Sandwich Artist at Subway. I had no idea at that moment, I was changing my life.

I worked at Subway all throughout high school and made lifelong friends there. My best friend Tim and I were inseparable, and it was hard to imagine what life would be like once we both went off to college.

When it came time for me to pick a school, I found myself completely unprepared to “leave the nest” With my parents help, I chose to go to a small state school in Massachusetts (Go Owls!!) not far from my hometown.

Throughout college, I would return to Subway on the weekends so I could work and Tim and I could catch up on life. At this point, our boss, Steve, had started a venture of buying and flipping Subway shops.

One weekend, instead of Tim and I returning to the flagship store to work, Steve asked if we could meet at a different store to help him with the transformation. Over the next year or so we began meeting at different stores and helping the staff get back in shape. Steve would work on the physical transformation of the shop, while Tim and I would work with the staff.

During my sophomore year in college, we got a call from Steve that I’ll never forget:

“Bad News: I sold the Enfield store, Good News: I bought a store on Maui. You guys coming?” With a million thoughts going through my head, I wasn’t sure how to respond, but I knew the answer was no. We were poor college kids! We couldn’t afford a trip to Maui!

As time went on, Steve persisted. He got an apartment with beds for us. He bought a jeep that we could drive while we were out there. Then came the icing on the cake: He emailed us plane tickets leaving a few days after we were done with school for the summer, under the condition that we would work to pay him back.

So off to Maui we went! We spent a summer there, followed by a winter break. Once we graduated school, we decided to surprise Steve and make the move there. In July 2005, along with Tim’s girlfriend Mimma, our friend Hank and two of our cars, we all packed up and left the mainland!

Much to our surprise, Steve called us days before we left, letting us know he sold the Maui Subway and was headed back to Connecticut after we had already left!

From there, with a little panic and scrambling, Tim and Hank landed a job at Blockbuster (yes, that’s right, Blockbuster was still a thing!) Mimma was an elementary school teacher and I worked as a manager for a local surf shop (shout out to Maui Built!!)

We spent an amazing year on the island of Maui. Hank returned home after 8 months, Tim and Mimma came back after 12, and I stayed for about a year and a half.

And it was that experience that set the tone for the rest of my life. The best part? I had no idea yet….