“I can’t make more money unless I hire somebody. And I can’t see how to afford somebody. So I’m stuck.”
A client said this to me with the precision of a woman who had run the numbers a hundred times. She wasn’t wrong about either half. She was only wrong about the conclusion.
If you’re circling the decision of hiring your first employee — or your first VA, or your first contractor — and every lap ends at “stuck,” this is the catch-22 talking. Let’s take it apart.
Why the hiring math always comes out “no”
Here’s the calculation most owners run: current revenue minus new salary equals less money for me. Framed that way, hiring is a pay cut, and no reasonable person volunteers for one.
But that math compares the cost of help against your business as it is — a business capped at the ceiling of your personal hours. The honest comparison is against the business that becomes possible when your best hours come back to you. What would ten reclaimed hours a week produce if they went to the work only you can do — the clients, the offers, the price conversations? That number belongs in the equation, and it’s almost always bigger than the salary.
Unhired help doesn’t show up on any spreadsheet, but you pay for it every month — in growth that didn’t happen and energy you didn’t have.
Start smaller than “employee”
The phrase “hiring your first employee” makes the decision sound like marriage. It doesn’t have to be. The ladder has lower rungs:
A few VA hours a week. Inbox, scheduling, invoicing — the bottom of your list, handled for less than the cost of a nice dinner.
A contractor for one defined thing. Bookkeeping. The website. The newsletter. One container, one invoice, no payroll.
Then, when the relief has paid for itself, the bigger step — with evidence instead of fear driving the decision.
Start where the risk feels survivable. The point isn’t the org chart. The point is the experience of being helped — because that experience is what dissolves the catch-22.
The block under the spreadsheet
Because here’s the quiet truth: for most women I coach, the hiring hesitation was never really the money. It’s control — nobody will do it like I do. It’s guilt about paying someone before paying yourself properly. Sometimes it’s the worth question in disguise: who am I to have staff?
The spreadsheet is where those feelings go to look respectable. That’s why we work both layers at once — the practical plan for the first hire, and the beliefs that made “stuck” feel safer than “supported.”
What she said after
The client from the top of this post? She eventually made the hire she was sure she couldn’t afford. The word she used afterward — her word, not mine — was “liberated.”
Not “broke.” Not “regretful.” Liberated. The catch-22 was never a locked door. It was a door that opens from a direction she hadn’t been shown.
If you’ve run the hiring math a hundred times and always land on “stuck,” bring the spreadsheet — and the feelings underneath it — to a free 30-minute conversation.
Free · 30 minutes · Zoom or phone