The vulnerability of entrepreneurship

I’ve had a raft of conversations this month with founders who are looking back over their shoulder.

One came across a job posting that looked so attractive, almost alluring! Another just started daydreaming about what it would be like to get a nice, cushy corporate job. (With benefits!)

I get it.

I had those fantasies for at least the first ten years after I went out on my own. I even spent six months here and there working for one client exclusively.

When we work for ourselves, it feels vulnerable. If (or when) I screw up – I’m the one who’s going to pay the price. When I work for someone else, I (imagine) that I won’t feel so vulnerable. The self-doubt that haunts me in my sleep will just vanish. (Won’t it?) Instead of worrying about the whole enterprise, I could “do my job” and go home.

If I worked for someone else, I wouldn’t have to take every piece of client feedback personally. I wouldn’t wake up in a cold sweat thinking about receivables. I could figure out how to deal with the “Sunday night scaries” instead of the “every night scaries!”

But we’ve been down this road…

Remember, we left cushy jobs working for someone else to start this place, didn’t we?

What didn’t I like about that?

• No autonomy? I had to show up for boring meetings and pretend to be busy all day.
• Unclear direction? I remember how hard I worked on that thing, only to have my boss dismiss it.
• Oh, and speaking of my boss – how will I go work for someone else?

I’m not trying to be dismissive of the option. Maybe it’s the right option for you at this time. There’s no shame in that. Benefits are nice to have, even a 401K!

I just want us to be honest. It’s a trade-off.

In a corporate job, there’s a place to hide – you won’t always feel so vulnerable. There may be fewer ups and downs (depending on your boss and the organization). And you will have to put up with crap bosses, unclear direction, and irrational demands.

Either side of that road has plusses and minuses, but staying in the middle of the road will get you killed!