I Designed My Career to Be Unemployable

I've sat in meetings with just about every C-suite role. They all listened to me, believed some of what I said, and some still decided they didn't want somebody like me on the team. I can't say I fault them, but I once did. They could see there was a chance I'd stir something up. Maybe I'd say something off color or pitch a crazy, harebrained idea. And they could see that trying any of it might cost them.

At first I didn't get it. It took people like Cara Steinmann, my wife and my friends to help me understand why people pass on me. When Cara came on my podcast, she put it plainly.

"The very definition of having an employee is that you get to control what they do," she said. "And people like you and I are very hard to control. And that makes sense."

She's right, and now I get it. I've never been a great employee. I always change the plan mid-project, and I tend to catch things that are off before anyone else does. One of those habits once cost me a job.

The $15,000 website

I was hired to build a website for a company, and before I'd been paid anything, my first meeting was with the software guys who ran its booking system.

I realized pretty quickly that something was wrong. Their software broke the rules for handling credit cards. It sent customers' card information to their own servers first, and then on to the payment processor. I sat through the whole meeting asking poking, prodding, prying questions, and I got a really bad feeling about it.

As soon as we hung up, I called the owner. "Hey, I think this shit is super illegal," I told him. "I'm not going to put my name on this website."

So I lost a $15,000 website. The owner was very thankful, and the whole thing blew up for them once they reached out to the software company, which wasn't really a company. It was a dude in a van, traveling around the country.

None of that made me any money. But that's how my brain works. I pick everything apart as it's happening, and that time, I was the one who couldn't be part of it.

It has to work both ways

In those C-suite meetings, it goes the other way. When somebody passes on me, the reason changes from one meeting to the next. Sometimes a lot comes out in one conversation: an off-color comment, a crazy idea, how long it would take to bring me along, and what it would cost to try any of it. Together, that kills the deal. Other times it's just one thing.

Those are just the things I notice, and I don't hold any of them against anybody. What I'm looking for now is the right fit, and it has to work for both of us.

The right client understands that somebody who picks everything apart is what they need. And whatever we build together has to be something I can put my name on. That website never was.

You need a little bit of crazy in you to want crazy me working with you.