You Don't Have People Anymore: The Support Staff Reality Nobody Talks About

Let me be direct about something I’ve watched trip up multiple talented educators who’ve made the leap to entrepreneurship: the support staff problem.

Here’s the pattern I keep seeing. The people who typically leave schools to start their own businesses are senior administrators or heads of school. These aren’t assistant teachers or department chairs making this transition. They’re people at the top of the organizational chart.

Why does this matter? Because these are the people who had “people.”

You know what I mean by “people.” I’m talking about the support system and support staff that came with your position. Need to schedule an appointment? Someone handles that. Document needs proofreading? There’s someone for that. Administrative task that needs completing? You delegate it.

When you go out on your own, that entire infrastructure vanishes overnight.

Suddenly, every single task defaults to you. Schedule that appointment? That’s you. Proofread this document? That’s you. Handle this administrative detail? Also you. You don’t have people anymore. You are the people.

I’ve watched several colleagues make this transition and struggle with this reality in ways they never anticipated. They were brilliant educational leaders who could manage complex institutions, but they found themselves drowning in the minutiae they used to delegate without a second thought.

This isn’t an insurmountable problem. But it is a problem you need to solve before you make the transition, not after you’re already struggling to keep your head above water.

Here’s what I encourage you to do: Before you leave your current position, conduct an honest audit. Catalog every bit of support you rely on during a typical week or month. Write it all down. Every task someone else handles for you, every administrative detail that gets taken care of without your direct involvement.

Then ask yourself the hard questions: Which of these tasks can I realistically handle myself? Which ones do I need to outsource to a virtual assistant or contractor? Are there other solutions I haven’t considered?

This exercise might feel tedious, but it’s critical. You need to know exactly what you’re taking on before you’re the only person available to take it on.

The freedom of entrepreneurship is real. But so is the reality that you’re now responsible for everything. Plan accordingly.