The Toughest Leap You’ll Make – and How to Land It
Let’s face it: no one talks enough about the financial growing pains small business owners feel when they’re ready to scale. Sure, the bootstrapping phase gets plenty of spotlight — you, a dream, a laptop, a lot of late nights, and maybe you’re starting in a garage (a classic) or you have a dog cheering you on as you figure things out. Sound familiar?
You grind through the early days, figuring out who your customer is, how much you can charge without making people sprint away, and how to deliver on what you promised without collapsing from exhaustion. You keep overhead low, cobble together systems that “work for now,” and celebrate every win — because every win feels like surviving another round of business Hunger Games.
But eventually, if you’re doing it right, the “just me” model doesn’t cut it anymore. You add an employee or contractor here, a piece of software there. Maybe a couple more employees who do the actual work while you go look for more. Revenue goes up, overhead creeps up, and you start feeling like you’re getting somewhere.
Until you hit that moment.
The “Am I Really About to Hire Overhead?” moment.
Hiring your first real manager, COO, or right-hand person isn’t just a financial transaction. It’s personal. Because here’s the truth: the money to pay them? It’s coming directly out of your own pocket.
You’re not bringing them on because you have piles of extra cash lying around. You’re bringing them on because you know you can’t keep doing everything yourself — but the leap requires some real-world sacrifice. Maybe a smaller salary for yourself for a while. Maybe fewer owner draws. Maybe tightening the belt at a time when you’d really rather loosen it.
It feels scary because it is scary.
But it’s also exactly how you go from “owner-operator” to “growth generator.”
If you’re standing at that ledge, staring into the unknown, here’s how to make the jump with a little more confidence (and a little less heartburn):
1. Ask an Expert (aka: Fractional CFO or Accountant)
Don’t wing this one. Seriously.
Work with a numbers pro who can map out your potential future — the “If I invest X now, here’s where it could lead” kind of path. Pro forma statements, cash flow projections, stress tests. Boring? Maybe. Necessary? Absolutely.
You’re about to swap “gut feeling” for “strategic planning” — and that’s exactly what growth generators do.
We’re not talking bookkeeping finances – but planning for the future financial projections. Maybe it will help you to ‘see’ where you could be in the future, once you get through this financially challenging new step of hiring your first ‘overhead’ employee.
2. Know Your Processes (and Yourself)
Before you hire your second-in-command, take a hard look in the mirror. What do you love doing? What drains the life out of you? Where is your Zone of Genius? Don’t give up that work! Find someone that complements your skillsets and helps to round out the company oversight.
Sketch out your processes. Get painfully clear about what you want to delegate and what you’re not ready to hand off. Hiring your ‘twin’ will have you duking it out over who does what. Make it easy on yourself – and your new manager/overhead person – and find ways you can work together without competing.
Know your strengths. Know your needs. Then find your complement, not your clone.
3. Lean on Your Tribe (Because Lone Wolf Syndrome is a Trap)
Making these decisions in a vacuum is brutal.
That’s why small business owners in CEO Peer Groups like my Intentional Growth Circles thrive — they’ve got a confidential, experienced peer group in their corner. Folks who’ve either faced the same leap or are gearing up for it. People who get that “I’m about to spend my vacation money on a COO” panic.
Real talk. Real feedback. Real support.
You don’t have to do this alone. (In fact, if you’re serious about growing, you shouldn’t do this alone.)【】
Final Thoughts
The path from owner-operator to growth generator isn’t a straight line. It’s a series of calculated risks, gut checks, and “oh wow, did I really just do that?” (good and bad) moments.
But here’s the thing: the real magic happens when you’re willing to invest in future you. The you who’s not juggling every role and wearing every hat. The you who’s building something bigger than your own two hands can hold.
Plan. Act. Learn.
And remember — that leap? It’s not a free fall. It’s the first big jump toward the business (and life) you’ve been working for all along. Here’s to intentional growth!
