03/14/2026
Stuck in the Middle With You
There is a stage in business that almost nobody talks about.
Small businesses can work.
Larger businesses can work.
But the middle can be exhausting.
Over the years in my career I have seen many small businesses operate successfully, and I have also seen larger organizations run very well. The businesses that seem to struggle the most are often the ones stuck in between, especially under the weight of administration.
When a business is small, the owner usually carries most of the responsibilities. You do the work, send the invoices, manage the clients, deal with the problems, and keep everything moving. It is a lot to handle, but when the scale is small enough it can still be manageable.
When I say “large,” I do not mean corporate scale. I mean large enough, relative to a small business, that you can dedicate people to administration. Maybe someone spends a portion of their week on billing, payroll, scheduling, and coordination. Maybe you have a dedicated administrative staff member. Either way, those responsibilities are no longer sitting entirely on the owner’s shoulders.
The middle is where things get difficult.
That is the stage where the business has grown enough to become complex, but not enough to properly divide the responsibilities. The owner ends up taking responsibility for everything. Billing. Payroll. Human resources. Business development. Client relationships. IT problems. Deadlines. Deliverables. And often the actual hands-on work too.
I have been through that stage myself.
I started as an independent contractor, subletting office space from another accountant. If something needed to be done, I did it. Over time the business grew. I added an assistant, then more professionals, then support staff. It was progress, but it also created a new kind of pressure.
I found myself stretched too thin.
Not because the business was failing, but because it had reached that uncomfortable middle. Too much complexity for one person to manage well, but not yet enough structure to relieve the pressure.
Eventually you realize something important.
Working harder is not the answer.
The shift has to be in how you see your role. It means finding the right people, training them, trusting them, and allowing them to build their own skills while you step back from trying to do everything yourself.
That is easier advice to give than it is to follow.
But the middle is not a place you can stay forever.
Sooner or later, you have to decide.
Go big, or go home.
