Transitions are difficult. However, I have three times decided to make major career transitions without being forced into them by external factors.

My most recent transition has been the most difficult choice to make. About two years ago, my business partner and I decided it was time for me to end my day-to-day involvement in the business we had started together. I finally completed the transition a few weeks ago, freeing me to begin something new.

David Waring and I, co-founded Fit Small Business in 2013. Fit Small Business is an educational website for small business owners. While I hate terms like “work spouse”, David and I shared a very intensive relationship often spending 10 hours a day together. In 2017, I would say our relationship was “rocky” and we were frequently having disagreements on matters large and small. For me, our problems came to a climax when the company reached a $3 Million run rate. I was excited, ecstatic, and wanted to celebrate. We were now legitimately a “multi-million dollar” revenue company. David was disappointed. He thought our growth rate should be much higher and did not want us to have a complacent attitude after achieving this milestone. We decided it was time to separate.

In deciding to separate, David and I had two concerns. We wanted to act honorably towards each other and we did not want the change to hurt the business. After much discussion, we decided that I would be leaving the role of co-CEO while keeping my financial interest in the company. For a few months, we agreed that I would be staying on while we hired an executive team and to familiarize David with the parts of the business which I managed. 

While David and I were hiring an executive team, a funny thing happened. Annual revenues grew from $3 million per year to over $16 million. David became more energized about the business. In fact, he began to start our weekly all-hands company meeting with listing the developments that he was excited about. Our relationship got better. The less actively that I participated in the business, the more actively he sought my input. I was enjoying working with David again. 

However, I started to hate my job. We had become a large company with almost 200 people working with us globally. My days had become a never ending series of meetings. Instead of hopping on sales calls to help close deals, my days were filled with lawyers, accountants, and bankers. We had become a “real company” and that did not best suite the way I liked to work. Two years after David and my originally decision, I have finally stepped out of all operational duties and assumed the mantle of non-executive chairman.

“What do you want to do next?” said a friend to me about a month ago. I shared with him an idea that I had been noodling over the last couple years. I am a big believer in talk therapy and have personally experienced the benefits. I think many people would benefit from going to therapy. In fact, I know many people that want to try therapy. However, their experiences finding therapists have been horrible. The process of finding a therapist has been so unpleasant and difficult that many gave up on finding a therapist. There is something broken. I am hoping to fix this process. 

The company is only a few weeks old. We have started to do interviews with both therapists and those who recently entered therapy. There is not only a problem finding a therapist but, therapists have a problem receiving poor quality referrals. If you have ideas, suggestions or well wishes, I can be reached at .