Why founders are stuck in the middle

Most business owners are still doing work they should’ve delegated years ago.

They’re fixing customer issues, approving invoices, and troubleshooting staff problems — busy, exhausted, and secretly wondering why the business never seems to “level up”.

The business owner pyramid

Every business owner lives in one of three layers:

1. The bottom: The doer

Solves daily problems. Answers questions. Puts out fires. Feels productive… but becomes a bottleneck.

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2. The middle: The manager

Delegates some tasks but still gets dragged into the weeds. The business works, but only because you’re working.

3. The top: The owner/leader

Makes a small number of high-impact decisions. Builds systems that run without them. Allocates capital and talent. Thinks ahead.

The fastest-growing, highest-value businesses? Their owners operate almost entirely at the top.

The problem is that most business owners are stuck somewhere between the manager and the doer.

When you’re buried in day-to-day operations, you lose altitude. You can’t see the strategic decisions that actually move the business forward — opening a second location, hiring a GM, pivoting product, killing the wrong customers.

Most problems in your business aren’t yours to solve

Every time you step in to fix something, you train your team to rely on you. If you:

Call the upset customer yourself

Redo the proposal because you can do it faster

Micromanage every manager

…you’re reinforcing that you live at the bottom of the pyramid.

Move up the pyramid

The big decision that you know you need to make is uncomfortable. Calling an employee and firing them to serve the company is not easy. Hunting for a new office or opening up a second location is not easy.

Working on that one enterprise deal that’s going to bring in three months of revenue instead of smaller projects from prospects that are willing to buy now is tough because it’s uncertain, and it takes time.

It is much easier to get in the weeds and work 70 hours a week on the stuff that you know won’t move the needle in a large way.

Most business owners know this, but they are afraid to tackle what they need to tackle.

I know many business owners who purposely ignore the hard decisions and elect to toil away at the small stuff that doesn’t matter. PURPOSELY. They get a false sense of productivity at the bottom, and they’re using that to neglect the big, uncomfortable stuff.

In short, they are afraid.

Leading a company is hard for three reasons:

Many times you have to make decisions that hurt people you care about.

You will be disliked despite the fact that you’re doing your best to serve the most people.

You will be misunderstood and you won’t be able to defend yourself on every decision you make.

Your job this week: work on getting out of the weeds. Tell your manager that you aren’t available — “I won’t bail you out here. You are on your own, so make the call”.

Focus on the big stuff. The uncomfortable stuff. Make that big decision you’ve been procrastinating on.

It is your job as a leader, and it is why they pay you the big bucks.

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