I’m sitting in my office at Date-Line Digital Printing – the company I co-own in Fairbanks, Alaska – trying to figure out how I should introduce myself to someone who has never met me and has no clue what I care about. I guess it all starts with this:

I’ve never been very good at following the rules.

It’s not that I think rules are unnecessary, it’s just that so many of them seem to make it more difficult for people to do their very best work and take unusually good care of those around them.

No bueno.

In 2005 I had no idea what I didn’t know about running the company I had just bought into. I had been running operations at Date-Line Digital Printing for a few years and felt like I had a pretty good handle on what it meant to keep the machine moving forward. That belief coupled with the thought that owning the company seemed like a great way to keep my job was all I needed to make the single largest purchase in all of my 29 years on the planet seem reasonable.

It would take a few years for the dust to settle and the truth to surface:

I had no idea what I was doing.

I was actually pretty great at ensuring the trains ran on time, metaphorically speaking, but as an owner it was my job to lead and I wasn’t doing much of that at all.

By late 2009 I had coasted us right up to the precipice of disaster. Sales had suddenly dried up and so had our cash reserves. The business was facing an extinction level event.

Staring down complete financial has a way of waking you up.

I immediately altered a few business practices that should have been addressed months (or even years) ago and I had the unenviable job of looking one of our 3 employees in the eyes and telling them we couldn’t afford to have them on the payroll. Except that wasn’t the whole truth.

The whole truth was they didn’t have a job because I was terrible at mine.

It was a punch in the gut to realize that a person I cared about was unemployed because I hadn’t been the leader they needed me to be. It was clear that I would have to level up (and fast) if I wanted to honor the responsibility I had to take care of the people who looked to me for leadership.

That seemed like a tall order for a college dropout.

The issue was I began to develop all these irreverent and lofty ideas about the kind of small business I wanted to run but I was incredibly self-conscious about what “smart” business people would think about my obvious naivete. I had these crazy notions about preparing employees for their next job, treating customers like actual human people, and contributing something meaningful to the community even if it hurt our bottom line. I was crazy enough to think contributing something meaningful might be what the bottom line was for.

Spoiler alert: I did it my way.

I decided that the only thing worse than failing on my terms was succeeding on someone else’s, so I decided to start breaking any of the “rules of business” that prevented me from building the kind of organization I wanted to run. (This did not extend to the rules set forth by the IRS. I followed those rules to the letter.) I started making waffles for my staff once a month, our sole policy became “when in doubt, take unusually good care of people”, and we started giving away thousands and thousands of free thank you cards.

And then our weird business became an award-winning weird business.

Suddenly our practices stopped feeling so weird and I started writing about them because I wanted others with similar sensibilities to know they weren’t alone. Those blog posts turned into speaking gigs which turned into an ebook which turned into an invitation the stage at TEDx, which turned into running a Leadership academy, which turned into my whole life being different.

I backed into my very best work.

It’s a trip to think back on the kid who dropped out of college after 6-weeks and had absolutely no idea what he was going to do with his life. So far he’s done okay, but he’s not even close to done.