In fact, over 15 years of owning my multimedia marketing and production agency (sold in late 2024), I had a lot of bosses – better known as, “clients.”

At any given time, I had 20-30 active clients who served as my bosses. All with different personalities, needs, wants, expectations, and demands. Whether they were a $5000 client or a $50,000 client, they wanted to believe – and I made sure they did – they were either my only boss or at least my most important one at the time. Some call this “managing up,” I call it “respect for the relationship.”

Most days, I would “meet” with 5-6 of those bosses, shifting mental gears, skillset and knowledge base from one to the other, knowing that we could be fired (lose the client’s business) or promoted (more work or referrals) depending on how we responded to each of those bosses. Proudly, our client retention rate at Red Apples Media was exceptional, and they had proved to be our best advocates in bringing on even more bosses in the form of reviews, testimonials and referrals. I believe this critical balance is an extremely valuable asset that translates exceptionally well in an organizational environment, particularly if there are dotted line reports.

All of that said, I do admit that one of the greatest advantages of “being your own boss” is a degree of flexibility in your schedule. However, as the primary driver of revenue, new business and client relationships, my time off might also have a financial impact during the time I was away. More importantly, good leaders build teams that keep “the machine” moving in your absence with little to no infringement on your time away from work.

So, if you’re thinking about going at it and being your own boss, I would caution and remind you, we all work for someone — and sometimes, many someones.