When is it Time to Change Scenes?

Updated: Aug 29

By Executive Scheduling Associates CEO Mitch Santala -


A close friend I love has traveled a circuitous route to business success. When I say he is successful, I'm referring to the fact that an international firm just acquired his insurance technology startup for millions. I find his journey unusual and intriguing, including how he navigated the forks in his road where he had to choose among career options.


Act #1

His career began as one of the most gifted musicians I know. He plays multiple instruments, including the melodious but seldom heard dulcimer. In addition, he is a singer, composer, orchestrator, and bandleader. But he hit a wall pursuing this first ambition.


"I love music," he told me. "But music-making didn't work out the way that I thought it would. The experience trying to support myself and my family as a musician was brutal. I lost a lot of money, and I saw dreams squashed."


Act #2

He said his second career launched by necessity.


"While I was a musician, I began working in the insurance industry, helping employers find the benefits they wanted for workers. I talked with employees and their families about their needs. In the process, I discovered the rewarding feeling of uncovering the best benefits for them. Slowly, a new passion developed that ran alongside my love of music, the joy of helping people meet their insurance objectives."


I responded, "So you became a broker to take care of your family. And you discovered you were good at this new way of serving people."


Then came another turning point for Garrett that is the most interesting to me. Should he settle into a comfortable routine as a successful broker or, well, I'll let him tell you the story.


"I was going to play it safe", Garrett continued. "I was working for another broker. We planned for me to take over their business at some point. While I still longed to return to being a broke musician, I committed to my wife that I wouldn't risk my family over that love. Then, at the last minute, these broker friends pulled back their offer and sold their business to someone else. It was a devastating experience. But that pain led me to a much better place."


I love this type of perspective on life and work. Career #1 tanked but Garrett found genuine joy in something different. Dream #2 fell through his fingers, and, undaunted, he pushed on to a third plan that turned out even than the last. Here comes the part about the startup that sold for millions.


Act #3

Garrett continued, "I discovered while working at my friend's brokerage house how challenging it was for insurance providers to process the data points that create insurance programs. If our common objective in business is to meet needs, I was staring at a big one – finding a better way for insurance providers to analyze customer coverages."


I thought as I listened to Garrett, thus begins a familiar story. Someone who doesn't think of himself as an entrepreneur begins to think entrepreneurially. Garrett had begun the search for that better way.


“I saw a new way via software,” he said, “to help insurance carriers, the principles of this industry, develop proposals and quotes for their products. Whereas the inner workings of that enterprise were complex and messy, I thought I saw a solution.”


Here is my point. Sometimes when the safe places in our lives get blown up, the best alternative is to risk and innovate, to make something happen out of nothing. To change the scene. To create the next act. Garrett did so in a one-person office with no initial investors. Now his vision is a multimillion-dollar business, doubling revenue during the past several years, serving insurance carriers with the most prominent brand names around the globe.


If, like my friend, you just experienced a career blow-out, take heart. Maybe something much better is around the next bend in the road.


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