Why I Left My Dream Job to Open a Food Truck

Why I Left My Dream Job to Open a Food Truck

I once wrote to MLB.com CFO Ed Weber that I would “gladly drive 477.52 miles round trip” from Penn State to the MLB.com offices in New York City to discuss my candidacy for a summer internship.  I sent him a letter the old fashioned way, in the mail, and threw it in a FedEx box along with a Penn State t-shirt (Weber is an alum).  My thought: A FedEx box would look important, and the box would land right on Weber’s desk.  I got the idea from my Sports Marketing professor, and taking his advice ended up paying major dividends.  Two weeks later, I had an interview.  Two months later, I walked in to the MLB.com offices for my first day working at my dream job.  Nothing could stop me.

My job got me everywhere my high school warning-track power couldn’t: Spring Training, the All-Star game, the World Series.  I was in the middle of my favorite sport, surrounded by future stars and players I had grown up watching.  On top of that, I got to help jump start the MLB social media department with a group of people that would become some of my closest friends in New York; a group that would stick together for almost 5 years. I had responsibility. I had access. I was lucky. I was happy.

And then I left.

Knowing that, a lot of people have asked “Why?”

“Why leave your dream job?”

“Why leave baseball to work 24/7 in an industry where most businesses fail?”

“Are you f**king crazy?”

My answer has evolved over time, although every response I have given has been the truth.  First, there was an opportunity. With a family that has been in the seafood industry for a large portion of my life, I grew up around fresh lobster.  When I shared this lobster with friends or colleagues, their response was often the same: “This is incredible, where do you get this stuff?”  That response surprised me, mostly because I was living on the East Coast, and these people knew their seafood.

The lightbulb turned on.

I already had relationships with people who could help me get fresh lobster; a foot in the door in an industry that was hard to get into.  Although I had an extreme passion for lobster rolls and food trucks, I had never really taken the idea of combining the two seriously.  Now, it was different.  I had a passion for a product that I knew there would be interest in, and ties to a city that I felt lacked options for a good lobster roll: Chicago.  Opportunity doesn’t often knock, but I felt like in my case it knocked, opened the door, and sat in front of me until I acknowledged it.

The second major reason this truck came to fruition was something that I was admittedly against in the beginning.  When I decided to move forward with my idea to open a food truck, two of my closest friends approached me about coming on board.  There haven’t been many good things said about mixing friends and business, and I was not a fan of the idea from the start.  Still, they pushed me to at least think about it.  The thought process for that decision is a much larger discussion, but at a certain point, I decided that the pros outweighed the cons, and that decision has proved to be one of the best I’ve ever made.  As a new business owner, I can’t tell you that making this move is best for everyone, or even most people, but for me, having two people that I can trust, who keep me motivated (and in line), and who I enjoy showing up to work with everyday, has made all of the difference.

So here I sit, just a few months after we opened our doors, thinking back at why I started this crazy journey in the first place, and a quote from the great Dr. Seuss comes to mind:

“Sometimes the questions are complicated and the answers are simple.”

I am doing what I love, in one of the greatest cities in the World, with two of my best friends.  So back to that complicated question:

“Why leave your dream job?”

I didn’t leave my dream job.  I found it.