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Business & Work ● January 2010

Being your own boss is about being your own employee

Starting up a business from scratch isn’t easy. Yet, there’s a romantic myth that most people believe about the freedom you gain from becoming “your own boss.” No impending wrath from The Man or any pressure from the people above you. While the freedom is something I crave (else I wouldn’t still be doing this), you’re probably wrong about why I crave it.

Going off on your own isn’t about becoming your own boss. It’s about becoming your own employee.

You can jump real high on a sunny day whether or not you are your own boss. Trust me.

Everyone is their own boss

The reality is, everyone is their own boss at their job—almost all the time. When I worked in corporate America, I set my schedule between now and the next deadline. I decided how I’d order every small task from here to the finish line. How I approached a problem was entirely my own. By and large, I decided when to eat, go to the bathroom, think hard, think slow, and not think at all. All the time between meetings and check-ins, you are your own boss.

If ever the day comes when I’m back in the clutch of a real “boss”, I’ll do the same. So will everyone else. Some people just don’t realize they are their own boss almost all the time.

Freedom is being your own employee

When your off on your own, the freedom comes from being your own employee. And it’s not for everybody. It requires you to be disciplined enough to listen to your new boss (you). And given the amount of people who eat, smoke, drink, and play Xbox too much (and wish they didn’t), being your own employee is clearly hard, hard….hard work. As a free employee, it’s just too tempting to disobey your own inner-boss.

Going off on your own means your free to choose how things will play out; But things only play out well if you’re a great employee. Every great company became great, not because their founders were great bosses at first, but because they were their own best workers at first. Later on, they hired great people to take their place so they could be great workers at something else.

The right answer is yes. But, it’s the wrong question.

Find other people good at being their own employees

A nifty trick to starting up your own business, but avoiding the discipline of being your own boss? Partner up with people who are good at being their own employees too. That way, you can occasionally decide to boss each other around a bit. That’s why there are personal trainers, shrinks, and AA meetings. Everyone needs those moments where someone else is in charge of their day so they can recoup the discipline to be their own employee again.

There’s something nice to the occasional fall back on having a real boss (who is not you) who might better motivate you to work hard. Ask anyone who truly works for themselves and they’ll likely admit they wouldn’t mind the occasional day where they just do what others want them to.

So, to anyone who really wants to start their own thing, I urge you to practice being a great employee at your current job. That’s what really will decide things. Then, come in with that same mentality when you start your own thing. Become your own employee, not your own boss.

Originally published Jan 13, 2010 at We Are Mammoth. Go to the next essay in Business & Work, “Building an ISV on top of a client business”.