06/02/2026
I was talking with a business owner recently about taking a vacation.
We weren’t discussing retirement or an extended absence. The conversation centered around something much simpler. Could he get away for a few days and truly disconnect from the business?
Just a vacation.
A real vacation where the phone stays in your pocket, emails go unanswered for a few days, and the business continues operating without constant check-ins.
The owner laughed and said something along the lines of, "That sounds nice, but that's not how this business works."
I've heard that response many times over the years.
What I've found interesting is that most owners don't say it with frustration. They say it as if it's normal. The business needs them. Customers need them. Employees need them. Questions need answers. Problems need solving. After enough years, it simply becomes part of running the company.
I’ve never met an owner who said they wanted to become the bottleneck. Most of the time they’re simply trying to help the business succeed. Years later they wake up and realize that every major decision, customer issue, and difficult problem somehow found its way back to their desk.
Most business owners don't wake up one morning and decide to become the bottleneck. They get there by being good at what they do.
That's one of the reasons I find these conversations so interesting. What starts as a discussion about taking a vacation often turns into a discussion about something much bigger.
