“I Think I’ve Always Been an Entrepreneur,”

I thought to myself the other day, on a run down my favorite street in the neighborhood. Just as I had that thought, I heard a quiet voice from behind me, yelling out “Water! Water! Water!” I looked and, yes, there was a little boy sitting in front of a table selling bottled water to passersby. Sweat was pouring down my face and I wanted to keep going, but I had to stop to say hello to this little boy. I didn’t have the money to buy a water from him but I wanted to take the time to encourage him for his efforts. I told him to keep it up. What I didn’t tell him was that he reminded me of myself.

I too used to set up shop on my front lawn, yelling out sales calls to passersby. It began on Nantucket, selling powdered lemonade and Chips Ahoy cookies taken out of their package and put on a nice plate. Sometimes I would even paint shells and sell them. Sometimes I would end the day with cups filled with cash, others I’d leave with pockets full of sand. But every summer, I would get out there with my little stand and wait.

I’ll never forget going into the shoe store in town one year and paying for a pair of blue flip flops—worth $20—all in coins. While the cashier looked at me like I was crazy, I could only beam back pride, for I had earned every penny I put on that counter. It went on from there. I started babysitting, and put up posters around ‘Sconset advertising my skills. I remember walking around with a wallet so fat with cash that it couldn’t even fit into my back pocket. I started a savings bank in my early teens and have slowly been adding to it, bit by bit. I have almost always had a job and I have almost always brought my entrepreneurial sense to that job—finding a way to make whatever business I worked for just a little bit better.

I think I’ve always been an entrepreneur.

Which is why, I thought to myself running down the street drenched in sweat, I’ve always struggled in the mainstream. It’s why I went to three different colleges, why I wandered the world looking for my purpose, and why I’ve still struggled to find it. I’ve struggled in the mainstream idea of success—that classic “go to a good college get a good job make a good living” notion—not because I am not meant to be successful. Not because I don’t have talent, or creativity, or a solid work ethic.

I’ve struggled because I’ve been trying to use that talent, creativity and work ethic in the wrong places. I’ve been trying to shove myself into someone else’s box or business, rather than thinking of what I uniquely bring to it. Rather than creating my own.

So, I am grateful to be here doing just that—whacking through the weeds of what it means to be an entrepreneur, a small business owner, and an artist, all at the same time.

This blog will uncover just that, and more, in my journey of building a business, one step at a time.

Thank you for coming along for the ride.