Entrepreneurs face stress of growth with first-hire decision

By JJ Rosen October 3, 2023
Entrepreneurs face stress of growth with first-hire decision

This article originally appeared in The Tennessean.

I was both excited and scared.

It’s every entrepreneur’s dream and every entrepreneur’s nightmare, and it was the biggest decision of my young career.

I was a one-person computer consulting business. With no office, no employees, and no phone line, the word “business” was an exaggeration.  I was really just a freelance computer geek doing everything from writing software to fixing printers for a handful of customers.

I was working hard, pulling regular all-nighters, and coding every weekend when I got a call to build a large software development project for big name business.

What an opportunity!  This will be a piece of cake.

But … wait.

I was booked solid and there was no way of taking on anything else by myself.  I was faced with one of the biggest decisions of my life—hiring my first employee.

It wasn’t a matter of who to hire, but whether or not to take on the huge responsibility and pressure of hiring anyone at all.

What if work dries up?  What happens to cash flow if a client is slow to pay? Will I be a good manager?

Anyone who’s started a business from scratch knows what I’m talking about.  You dream of growing from a one-person shop into a real company, but when the time comes to hire your first employee, the decision isn’t as easy as it sounds.

Next to proposing to my wife, for me, taking on the responsibility for someone else’s livelihood was the most nerve-racking proposition I’d ever undertaken.

The decision became scarier when I began interviewing potential candidates. I quickly realized that the word “employee” didn’t accurately describe what I was taking on.  It felt like too cold a term to describe the human beings that were willing to put their career in my hands.  Every person I talked to had dreams, fears, and responsibilities of their own that my tiny company might have a large impact on.

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When I finally decided to take the plunge and hire someone, my anxiety was sky-high.  It took me a full week to get a good night’s sleep as I worried about all the “what-could-go-wrongs.”

But while I was stressing out, my first-ever hire was thriving.

It didn’t take long to see that one plus one equaled three.  Not only did our small tech consulting firm’s productivity triple—but I also gained a teammate whom I enjoyed working with.  It was a win-win-win for our company, myself, and my new colleague. We all began to grow.

Thinking back, there were a few things I learned:

  • Growing from a one-person to a two-person company is a big step. Every entrepreneur I know experiences the same fears that I had.
  • It’s critical to find the right person, even if it means turning down work in the meantime. Taking time to find the best fit is worth the effort. I was lucky to find a rock star that 25 years later is still going strong.
  • It’s risky to expand, but there’s also risk in not expanding. As a “solo-preneuer” especially in a services business, it’s tough to scale to meet your customers’ needs.
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