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DWYSYWD (Or: How being unreasonable with my word changed my life)

Updated: Oct 18, 2020

After drinking and partying my way through college, I took a job waiting tables at Damon’s Grill my first job out of college. The same restaurant for which I’d stood at the host stand in high school. Three and a half years, fifty thousand dollars, and I’d moved 10 feet.

I worked at Damon’s for nearly two years after school, impatiently waiting for my big break. Where were the opportunities? (it was 2008, there were none) What happened to the life I was supposed to live? The job I was supposed to have? The money?

I remember when my future father in law offered me a job as an assistant to the general manager at a truck dealership, I told my fellow waiters and this one girl, Lacey, was shocked. Shocked that I’d gotten an office job, sure, but more than that shocked that I’d waited tables for so long if I had had a degree all along. She didn’t believe me at first, that I’d graduated college, because why the hell would I be waiting tables? She thought the same as I did, that a degree was the skeleton key to the life we were promised.

So I got that office job. Assistant TO THE General Manager. And I waited there too. I followed the directions I’d been given. I updated the website. I learned SEO and optimized everything. I took photos of trucks to show them online. I hated trucks. I knew that I was destined for better things. I had a creative writing degree from a university, and I was supposed to be a writer. My friends were off in Chicago, or the coasts, and living high and making bank. My boss at the truck dealership, one time, saw my paycheck for the week ($250) and confessed he was embarrassed. I wasn’t embarrassed until he said that, but after that every time I got a check I felt ashamed.

School had come so easily, just get your stuff done and the grades take care of themselves. 3.0 is fine, most kids do worse. I got a 3.0 mostly-drunk, which is pretty much like a 4.0 sober. I knew I was smart, capable. Why didn’t they see that? Why didn’t my boss? The world? I wanted more out of life, now two years out of school, but I couldn’t figure out how to get started.

A friend of my mom’s took me out to dinner, one of those dinners that your mom arranges which makes you a charity project. But I listened to this one, for some reason, as a middle-aged guy told me about the power of my word. How if I was willing to develop an unreasonable relationship to my word, I could have everything that I wanted. How if I was willing to take responsibility for that, and that only, just my word, everything would change.

That middle aged guy, that mom-arranged blind date, changed my life.

The power of my word

“Handle them carefully, for words have more power than atom bombs.” Pearl Strachan Hurd

The idea was simple. Just do what you said you would do. Always, without fail, without exception, even when it means moving heaven and earth. Even when it means driving five hours round trip to go to a ninety-minute class every Tuesday night after work. Even when it doesn’t make sense. Even when fill in the blank. If you said you would do something, you did it. End of story.

That’s it. Just do whatever you say. Match up your actions to your words, and that’s it. This simple concept, once I’d gotten the hang of it, would prove to be the engine that drove me to starting companies, raising millions of dollars in venture capital, leading a team of 100 people, and more.

It took practice. At first the market value of my word was a bucket of week-old compost. I would say so many things, to other people, to myself, and then when it came time to deliver on them I’d find some way out. Some justification why I never really meant what I’d said, or why it didn’t matter anyway. These were the hurdles I needed to clear. The practice was simply, in all cases, do it anyway. Because I said I would.

But it’s pointless. It’s dumb. I don’t want to. Nobody cares if I do. Chatter chatter blah blah blah. Do it. You said you would.

When you start living this way, you learn real quick what not to do. You learn right away not to give your word about ANYthing. I think that was progress for me, because I started to see just how much I had been flippantly throwing it around. I’ll come out tonight. I’ll do it tomorrow. I’ll call you right back. I’ll ask for a raise. The minute I committed to honoring everything I said I would do, it became overwhelmingly clear that the only possible first step, the easy hack, is to just stop saying I’d do anything.


Decks thus cleared, I gradually introduced my word back into my life. And after starting small with things like “I will do all my chores” (I was still living at home with my mom — this is probably why she arranged the dinner in the first place), and “I will make 30 sales calls every day” (AKA: I will do at least part of my job), I developed the beginnings of muscle memory. From saying to myself that I would do my chores and my job, and then simply doing them, over and over, I began to see myself as the kind of guy who would follow through. I told a group seminar I was taking that I wouldn’t miss a class, and then it was a blizzard and I had a bad day at work, and I found myself actually driving my ass two-and-a-half hours to Detroit in the snowy darkness, and then two-and-a-half hours back. The people at the class were impressed. Nobody else had a commute longer than 30-minutes. I could have stayed home and it would have been arguably the smarter decision (it took a 5-Hour Energy to stay awake the way back). But I went because I said I’d go, even though it was unreasonable to do so.

Being unreasonable

“Don’t ever diminish the power of words. Words move hearts and hearts move limbs.” Hamza Yusuf

Once I started being unreasonable, the world opened. One day I found myself telling my mom I was going to try to become a sportswriter. I said it without thought, but the moment I did I knew what it meant. I was the guy that did what he said he would do. I would become a sportswriter or die trying. I’d have to figure it out.

How in the hell could I do that? Well, I could write pretty well, so check that box. And I like sports, so check. I’m probably a shoe-in, I figured. I talked to the local paper, and they asked me for “clips,” which Google later informed me were writing samples. Published writing samples. Didn’t have those, and if he wouldn’t hire me how was I going to get them? Didn’t he get how unfair that was? I felt so oppressed. But I said I was going to do it, so if clips were the thing to do, well I had to figure that out.

I started a blog. I had it tattoo’d on my Ford Escape to make it legit. My girlfriend (now wife) Laura hated the car-tat, but it was sweet. I figured it was me giving my word to the world that I was going to make this work.

It failed. My top day in 6 months had 60 visitors, the size of my gym class in high school, and that only because I spammed the forums. People on the forum told me to shut up and go away, stop trying to be something special. I wanted to quit, but by this time I’d even told my boss at the dealership. And that car tattoo. My boss was the amazing type that cared about me as a person, beyond the job, and he suggested I take a look at high school sports. Much less competition there, so I might be able to carve out a niche. This was like a lifeline, the right thing appearing at the right time, so I went for it. I canned DSP, and started I could still keep my word, it just looked a little different.

I started writing. I invited myself to games with a badge I’d printed off at home. I had to print it on two sheets of paper, cut them out and laminate them together with a kit, back to back. It worked. Security at your average high school was lax at that time. I started covering two games per week, Tuesday and Friday nights after work (I still made my 30 phone calls per day, and did my chores). My 6th grade teacher Mr. Powers would come with me and take photos. Or sometimes my boss, or my girlfriend. I preferred my boss or Mr. Powers because they had better cameras. After diligent posting for a couple months, the people on the forums started talking about WMA on their own.

The first professional sportswriter in the automotive industry

My boss told me that the dealership was going to sponsor a high school basketball tournament called the Jam at the Van, and would I like to be the Official Website of the tournament. He was an amazing guy, and I got a taste of how websites like mine made money. I hadn’t made a dime for six months, and hadn’t really thought about it because I was creating clips to go get a sportswriting job. But one of the other media properties covering the J-at-the-V was charging the dealership $2,000 to put their name on it.

I felt like I was an imposter playing a sportswriter next to the newspaper guys. Just a kid, not worth paying. But I told myself I would get a sponsor next, and so I had to.

I asked my boss to sponsor WMA. Underwrite the whole thing. He politely turned me down, talking about budgets. I said I’d do it, so I persisted. I got creative. I asked him how about instead of money, he just let me write about sports at work? I’d put the dealership’s logo at the top of the website. I was making $250/week, so spending part of my time writing about sports amounted to a $500/mo sponsorship, a small fraction of the J-at-the-V deal, so he was in.

I thus became the nation’s first paid sportswriter employed by an automotive dealership. And I hadn’t even needed clips.

I got another sponsor. This one a university for $2,000. I told him he’d be glad he invested, so I busted my ass, wrote about three stories per week and created a West Michigan All Star Game which spiked our traffic 8x for a week in March. He was happy. I bought a cheap SLR camera with the proceeds, and relieved Mr. Powers of his duties.

The automotive collapse shut down our dealership. I remember not really paying attention to all the closed-door meetings, just merrily writing along about some late inning home run, and then there was a meeting in which