When to Jump

A few weeks ago while at An Event Apart Boston, a couple of freelance web designers asked me the same question: When do you know you're ready to hire your first employee? When do you make the jump?

I didn't have a great answer. I rambled something about goals, about being realistic, and some other things I don't even remember. They probably don't remember them either.

In my defense, it's been a while (seven years) since we hired our first designer, and I haven't had to think about making that jump for a long time.

Over the last couple weeks, though, I've given the matter a little more thought, and now have what I hope is a much more useful answer.

You hire your first employee (or freelancer) when the following two statements are true:

  1. You want to.
  2. You can afford to.

That's it pure and simple.

I've met plenty of freelancers who aren't interested in hiring. For these folks, the attraction of freelancing usually has a lot to do with the freedom it brings: the freedom to make your own schedule, choose your own projects, and by-and-large answer to yourself. Hiring imposes new responsibilities that are a lot less "free". You'll have to manage someone else's schedule and priorities, even if not your own. Payday will suddenly be very important. And if you share an office, you'll probably need to stop going to work in your underwear. Sound bad? Then don't hire.

Likewise if you can't afford it, don't do it. Make absolutely sure that your cash-flow accommodates the new hire. If the cost of bringing someone onboard full-time is daunting, start with part-time or freelance and let the position grow as you earn return on your investment.

So that's my answer to the "when to jump" question, should I ever be asked it again. The good news is that the answer is simple. Incredibly simple. The bad news is that none of this says anything about how to make the jump, let alone how to do so successfully.