IN GRADE SCHOOL, when my mother asked me what I wanted to be when I grew up, I recall saying “entrepreneur.” I’m sure she would rather I’d said “doctor” or “lawyer.” But the thrill of building something new and providing something of value to others has always appealed to me.
My first entrepreneurial memory was selling Entenmann’s donuts and coffee to captive motorists waiting on long gas lines during the energy crisis of the 1970s. I don’t remember if I turned a profit, but it didn’t matter—because simply trying was exhilarating. Maybe it was the idea of controlling my financial destiny that I found so appealing.
While in college, I worked at a local bagel shop. The excitement of the retail environment made the days pass quickly. I loved the action of a busy store, the people who came and went, and the independence that the extra money gave me. After college, I had a brief stint selling insurance. It bored me to tears. Cold calling friends, family and strangers was brutal. I was that guy that people hung up on when their dinner was interrupted by the ringing telephone—one that, at the time, was actually mounted on the wall.
The allure of independence and the siren of entrepreneurship kept calling me. In 1988, at age 23, I opened my first bagel store. Along with my business partner, we opened five stores over 25 years. All are still in operation today.
The business grew and grew. The excitement of sowing ideas here and there kept me awake at night and propelled me through the fast-paced days. The ideas weren’t all good, but the endless possibilities were my entrepreneurial fuel. Every idea was a potential dart to be thrown. The ideas would be first sketched out and then carefully analyzed, with the hope of controlling the aim and trajectory of each dart thrown. I just needed to be sure a wayward dart didn’t cause the kind of damage that would bring the game to an end. This is how the business ran day after day, year after year. The bagel business had become my identity.
I absolutely loved it. Until I hated it.
Approaching my 50s, I’d grown weary of the career path that had treated me so well over the prior three decades. I was mentally drained, bored and increasingly restless. To me, the business became transactional and mundane. Plain, poppy, sesame, I had built a life and a living one bagel at a time. I grew to resent the monotony of the well-oiled machine. The business was a friend in the beginning but an enemy by the end.
Something totally unexpected had happened: It became about the money. It became simply a job. Ask the entrepreneurs you meet, and they’ll tell you it’s never about the money. They’ll say that, when it becomes about the money, the passion escapes as painfully as a Goodyear tire’s slow leak on the darkest and loneliest of roads.
The jet-black hair of my youth showed wisps of gray. I was still relatively young. From the years of living a financially responsible life, I had the wherewithal to start anew. But did I have the fortitude to leave the stability of “the job”? I would constantly wrestle with the numbers, while crafting a new path, one that would require me to combine the business skills I’d acquired over the years with new skills yet to be learned. It was a path that would require total reinvention. It was terrifying.
One more idea, one more sketch and one last dart. I believed I could do it. Those closest to me believed in me as well.
In 2013, I left the bagel business to become a Certified Financial Planner. I melded my passion for helping people with my interest in personal finance to forge a new life path. After months of classwork and test-taking, I passed the required exams. I also learned that studying and fact retention gets a bit harder as we age. In true entrepreneurial spirit, I created a solo practice where I can operate how and where I choose.
My years of fiscally responsible living had given me options. And the greatest option was the chance to reinvent myself—and escape the feeling of being trapped.
Rob Solimano is a Certified Financial Planner and the founder of Angel Oak Financial, a fee-only financial planning and investment advisory firm. Rob loves teaching and learning about personal finance. Earlier in his career, he owned and operated a chain of bagel bakery and coffee roasting stores. He’s married with two grown children, and splits his time between Montvale, New Jersey, and Kiawah Island, South Carolina. Despite his career change, he’s never lost his love for fresh coffee and bagels.