When You Break The Rules, You Get Into Weird, Unexpected Situations. Here’s How You’ll Know You’re In One.

These words I have heard over and over again:

Oh, I’ve never seen anything like that before.

As in the time I brought my cell phone to the AT&T store with a crack in the screen. They asked me, “Did you stab this phone with a knife?” I told them, No! What am I, a maniac?

And then I heard words I would hear many times in the years since:

Oh, well then I guess I’ve never seen anything like that before.

Or the time I was in China, trying to get the right press credential for the Olympics. I was a student and a freelancer and I didn’t live in the same time zone as the newspaper I was writing for. This made the Chinese confused. On a half-dozen occasions, a government employee told me:

Oh, I’ve never seen anything like this before.

Or just this weekend, I was on the phone with the company handling the payroll for Stry.us. Since all my reporters are employees of Stry LLC, we have to go through some fun government hoops to get the team paid. The thing is, the LLC is registered in Maryland. We’re doing business in Missouri. We’re not actually making any money. And my entire team has permanent residences out of state.

So, yeah, you can guess what I heard when I was trying to get the payroll forms filled out:

Oh, I’ve never seen anything like that before.

This is the kind of stuff that happens to me all too often. It happens because I am decidedly weird, and I cause trouble, and I tend to do things that normal people would not do. Stry.us is one giant case study in what not to do.

With Stry.us, I was told:

Don’t quit your well-paying job!
Don’t start your own media company!
Don’t go into a passion project without a safety net!
Don’t start a business if you don’t know anything about business!

And they were right. They were all right. I mean, what I did was stupid. Crazy. Possibly the dumbest thing I could’ve done.

It’s also the single biggest decision I’ve ever made, and the one that’s gotten to me where I am today, and the one that I would make every single time. Even knowing all the crap I would go through, I’d do it again, absolutely.

But I’m also aware that I operate in a world quasi-divorced from reality. There are no cubicles in my world. There is very little normal in my life.

There is — as a friend told me a few days ago — probably something very wrong with me. And maybe that’s a good thing.

I’m someone who tends to make up his own rules, and I know that I will — from time to time — run into a situation where other rules actually apply. And where I will have to obey said rules, because they have consequences.(1)

What I try to keep in mind is:

1. I believe I can get it done, because I always have.

2. Things have gone wrong before, and I’ve always come out okay.

I’m always thinking about what I’m aiming for with a crazy new project or idea. I know what I want to accomplish. I know things are going to go wrong along the way.

And I know that I will do things, far too often, that will lead people will tell me that what they’re seeing is something that they’ve never seen before.

For the most part, that probably means I’m doing something right. I’m challenging the system.

There are times when I am flat out wrong. And in those cases, I’ll be the one getting challenged on it. Advisors/friends will tell me, You actually can’t do that! And then they’ll grab me by the collar and tell me again: Dan, you can’t do that. We know you like to push the bar, but for legal/ethical/health-related reasons, you simply cannot attempt this.

Which is good to hear, actually.

“Oh, I’ve never seen anything like that before” is different. When you hear it, it means that you’re trying something very unusual. The person telling you this knows that whatever you’re doing isn’t impossible. But they also haven’t seen anybody stupid enough to attempt it before.

Often, when I hear those words, the person will look up at me and silently ask themselves: Is this guy dumb enough to try this?

And the answer is often: Yes, yes I am.

Weird? Unexpected? Yeah, it happens when you start building a world that you really want to live in.

Get used to it.

  1. For tax reasons, or because the Chinese could deport me, etc etc.