Quit your job. Close your company.

Well, at least for a few hours.

There have definitely been days where Steven Slater, most famous for having one the most unbelievable quitting stories, has been my spirit animal.

For those that don’t remember, Steven is the Jetblue flight attendant who had had it. After a particularly rough day (after I assume what was a particularly rough period of time), this gem of a human got fed up, grabbed some booze, pulled the emergency slide and gloriously exited into 15-minutes of fame and eternal notoriety.

The fantasy of it all! Imagine, rather than logging into Headspace to do the 3 Minute Crisis Breathing Exercise, you just go fuck it, say your mind, pull the shoot and sashay away.

It’s pretty baller.
And totally impractical for most of us.

But that frustration he felt? Damn that’s real. It doesn’t matter if you’re working for someone else or hustling your own jam, some days just suck. And in my own experience, despite the suckage, in the past it was all too easy to get trapped in the treadmill of the path I “should” be on, even though that “should” was sucking the soul out of me.

When I started my company my biggest fear wasn’t around failure (although that definitely loomed); my biggest fear was that the company would do well and I would lose myself in it. My biggest fear was that I would wake up one day realize that I wasn’t on someone else’s mindless treadmill, but, even worse, that I had built my own.

So, I started a yearly ritual of giving myself real permission to close my company. Here’s how it works…

Every December during the holiday break, I blocked off a half a day to think uninterrupted. I would take that time to ride a motorcycle to a state park in Florida and spend a few hours at a picnic table with my journal.

From the moment I got on my bike, I would start to tell myself
“I’m walking away.”

I rolled that sucker around in my head. Repeated it several times. Got through the initial “yeah right” reaction. Felt it. And then, when it really soaked in, I processed it.

For me processing means writing. And for a few hours, I would write about all the reasons why I’m walking away. I’d dig into the stuff that nagged me about the company and my work, made my blood boil or just made me sad.

I wrote about what I’d need to arrange in the company and also what to do in my life emotionally, financially, practically to walk away. I wrote about what kind of job I’d take next. I wrote until the idea settled in me, until it was pretty much real.

And then, once I had planned out my fabulous next phase of life, I’d ask myself: Do I really want to do this?

For three years, I didn’t.

But as I rode away from those afternoons, journal filled with thinking, I gained a lot.

Every year I gained the confidence that I was doing what I really wanted to be doing, that I’m not just on some treadmill of momentum. Keeping the company open was an active choice, not an act of inertia. And as someone that has suffered from the addiction to that treadmill and inertia in the past, that intentionality is gold.

This exercise also helped me gain clarity on the things that made want to walk away. Writing about the real problems, the daily annoyances, the stupid crap that tempted me to say fuck it, brought them to light. And when they’re in the light, I could see them. Deal with them. Create solutions to them.

And the company was always stronger for it.

December 2017 was interesting. Because while the company was still open and thriving, this past year I had unexpectedly took another job, leaving my company in capable hands. (Yeah, didn’t see that coming. But it happened.)

In taking this new job which is filled with tremendous new challenges (and also moving across the country), I committed to myself that I’m not even allowed to question whether I want to leave for two years. To do this job the way I want to do it, I need to be heads down for awhile.

I understand the contradiction in what I’m writing. I’m advocating for an annual “quit” moment while simultaneously saying I’m not going to do that for a couple of years. But life has different phases, and the thing that helped me stay soul-happy in one era of my life isn’t a tool that I’m choosing to use in another era. I think that’s okay. Whereas I find tremendous power in rituals, I don’t think they’re useful when they turn into rigidity.

But I can easily anticipate that in the future, the annual quit moment will come back into play. Just not right now.

So this past December I still rode a motorcycle to state park in Florida, but this year I took a nap on a bench. I think I got some side-eye from nice families because of my leather and snoring, but hey, you gotta do what the soul needs.