The first piece of professional advice I ever received came on my 4th grade Career Day. My classmates and I were encouraged to “grow up and do something we’re passionate about”. A message profoundly simple and perfectly suited for an audience of inquisitive 10-year-olds.
After mulling over my options, I figured I had two choices: I could either grow up to be a professional Ninja Turtle or I could grow up to work in sports.
After college, I moved to Chicago and met a young, energetic entrepreneur named CK—a former SEC linebacker who had just launched a start-up that specialized in navigating high school athletes and their families through the collegiate recruiting process. I had long ago given up my dream of becoming a Ninja Turtle, so working in sports was my sole remaining chance to fulfill the promise I made to my 4th grade self.
I joined CK’s team and, along with a few other brave ground-level hires, off we went to revolutionize how high school athletes get recruited. Together, we poured everything we had into our shared mission. After several mergers and two major acquisitions, what began as a simple dream to help families in a time of need grew into the largest athletic recruiting firm in the country, employing over 5,000 former college athletes and helping over 100,000 prospects a year find and finance an opportunity to play their sport at the college level. The year I left the company, we had 13 former clients taken in the NFL draft.
As is often the case with young businesses, I was fortunate to wear many different hats on our ascent to the top. Each new stage of my career presented an exciting new chance for professional growth. At different stages of my career, I traveled the country facilitating athletic camps, led large sales teams, oversaw product development, and managed call centers, just to name a few.
I championed a company-wide diversity and inclusion initiative and served as the chairman of the business’s Leadership Council. At 28 years old, a well-known publication recognized me as an up-and-coming star in Chicago’s vibrant tech scene. At the time I left the business, I was overseeing a sales operations division that served over 1,000 employees.
In hindsight, I feel like those early professional years were chosen for me. Like many young people, I had been conditioned from a young age to follow a particular script:
Step 1—Go to the best college possible, even if it means accruing a massive amount of debt.
Step 2—Find a stable job with benefits, a retirement plan, and advancement opportunities.
Step 3—Work hard, pay your dues, and contribute to the company retirement plan.
Step 4—Ride off into the sunset as a happy and financially stable retiree.
This version of professional growth was all I was ever taught. It molded me into the quintessential corporate grinder—highly ambitious, perpetually chasing the next job title, raise, or opportunity to distinguish myself. It was like running a race with no clear finish line.
When it was all said and done, I was nearly 40 years old before I stepped back and really began to question the path I was on. On the surface, I appeared to be a resounding success. I was working for a great company in an industry I loved. I had amassed an array of valuable corporate experience and was respected by my peers. I was on the exact path I was always conditioned to covet, but something still didn’t feel right. Something was ‘off’.
The first issue was that despite making more and more money, I didn’t seem to be retaining any of it. Every time I got a promotion at work, my first reaction was to elevate my status by purchasing something new.
‘Make more, spend more’ is an easy trap for a young professional to fall into. We live in a world that glorifies material things, so our natural inclination is to operate at the peak of our financial limits. My house, my car, everything I owned was at the very ceiling of what I could reasonably afford.
For years, I felt like the next promotion or next pay raise would catapult me into a more stable financial situation, but the more money I made the more of the same things happened: I accrued more debt, paid more taxes, and fell further behind Chicago’s cost of living curve.
Whatever strain I felt on my finances paled in comparison to what I was feeling inside. The higher up the corporate ladder I climbed, the less fulfilled I felt as a professional. As the years went on and my contributions to the business piled up, I grew more and more resentful —not of CK or of the company I worked for, but of the institution of employment itself. Once I had enough tread on my tires to appreciate my own worth, I became disenchanted with the idea of working hard to make someone else rich.
After a heavy dose of soul-searching, I abandoned my corporate job at the height of my career to redefine myself as an entrepreneur. As the first of many new business ventures to follow, I took what I learned as a recruiting “matchmaker” to open a franchise matching making firm in Chicago, IL.
In 2018, I applied my 20 years of experience to develop a framework for franchise investigation known as “The F.R.E.E.D.O.M Perfect Match Method”. My methods, which were later published in the 2024 book, Franchise Freedom: 7 Steps the Finding Your Dream Business, have helped thousands of aspiring business owners navigate their franchise search with confidence.
Business ownership transformed my life for the better —so much so that I now consider it my professional calling to help others chase that same sense of fulfillment.
