On Regularity and Bill Simmons

6 minute read

It’s been over two months since I’ve written anything in this space which is exactly NOT how to begin an essay but hopefully you’ll bear with me for a bit. As a closet neurotic, though some might think the door has been yanked off the hinges, one of the habits I am intimately acquainted with is of self-improvement through habit. We all have these nebulous ambitions of “doing something better” but without the necessary habit of actually doing those things, we tend to revert to our natural inertia of laziness and cookie consumption. One of the great analogies for this problem is The Rider and The Elephant where our conscious mind is represented by a tiny rider on top of an elephant and our unconscious reptilian cookie loving mind is represented by a huge elephant with the power to go where he wants. The key to change is managing those two entities in ways particular to each. Often, a component of that change is the replacement of inertia with habit which is something I firmly believe in. Discipline before mastery and all that.

But those things aren’t what interests me today. Instead I’m fascinated by the modern phenomenon of people who have some habit, particularly of writing, and turn that into a career. Pre-Internet, if you wrote in a journal every day, you were either a author or a teenage girl, the Venn diagram of those two groups being quite similar. Today, writing on a blog every day can turn you into a media empire assuming you have the requisite audience for your voice. I think about this because it became public two weeks ago that Bill Simmons will no longer be writing anything for ESPN. For those unfamiliar with the Simmons canon, he started writing a sports blog about 20 years go when the Internet was still largely driven by AOL CDs and flamewar chat rooms. He wrote about Boston sports and developed a big enough audience that ESPN hired him. Think about that for a second. He was writing a blog before blogs were really a thing and he did it so often and with enough interest that ESPN hired him. If you enjoy sports and writing, surely that’s a dream job, one you effectively created by perseverance and talent.

From the lowly Page 2 where ESPN originally put their edgy, non-mainstream voices back in the day up to running Grantland where they put their edgy, non-mainstream voices today, Simmons became a power house at ESPN all the while writing and podcasting in a very similar manner to how he started. If you read a post of his from 2000 and one from today, they are remarkably similar. Along the way he also created and spearheaded 30 for 30 which is one of the best things ESPN has ever done. Oh and did I mention he makes around $5 million a year? It’s not too much of a stretch to say he turned a Blogspot.com blog into a career worth $5 million a year. This is our modern day Sam Walton.

There are others who have done the same thing. Ree Drummond comes quickly to mind as someone who took a blog and turned it into a wildly popular media career. There are likely others I’m unaware of. Partly, this is winning at the internet lottery. There are probably thousands of other regular writers out there in internet land who are just as entertaining who never even rise above the level of “the friends and family audience” which can be rewarding but usually not in the same way $5 million is rewarding. In my long and storied internet surfing career, I have read some very funny or poignant or whatever else interests me writers who never started working for the Food Network or running an entire division at ESPN. Part of it has to be luck and fortune and rubbing the right Buddha’s belly.

But I can think of zero writers without that passion and perseverance and habit who went on to work at ESPN. The only way to find your voice and thus your audience is to write, though voice and audience are not linearly related unless you are James Joyce. Simmons cranked out 3000 word articles and essays at an insane pace. This was partly due to his apparent chronic case of diarrhea of the pen, an affliction I regularly share and one that never really abated even with the strong antibiotics administered by the masters at ESPN. But even that works in the favor of today’s aspiring Simmons clones because you can always turn more words into fewer words with some decent editing. Rarely can you do the opposite. He once wrote 2500+ words about the power of E-Bay for God’s sake.

When you look at the ascent of writers like Simmons or Drummond, it’s important to see the interaction between the author and the audience. One of Simmons’ ongoing article themes is the mail bag where he answers emails from actual readers. This is a genius way to expand an audience because everyone likes to see their name in lights, even if it’s the lights of a no name blog in a dusty corner of the internet. And if it’s on the front page of Grantland, well that’s icing on the cake. Very few artists can ignore the audience entirely and more often than not, it’s a symbiotic relationship not unlike a theater performer. Today’s blog writer gets immediate feedback with all the pros and cons that come along with it. Immediately knowing that you’ve hit a chord with your audience is invaluable if you are building a marketing platform.

One of the keys to building an audience beyond the obvious ability to say some thing interesting is regular content. An essay a month probably isn’t going to cut it unless you are Gore Vidal. Of course, not all of the output needs to be for public consumption. Most writers have a journal for ideas, experimentation and basic brain dumps. But if you want to move out of the dusty corner of the internet you currently live in, you need to write more. Simmons wrote a weekly NFL column for years that made an attempt to pick the winners of that week’s games. I faithfully read Simmons’ NFL picks essay every week for years. That kind of regularity does two things. One, it builds anticipation in your audience. If your readers know they can count on an interesting piece on a topic they enjoy every X number of days, you are going to be far more successful. Two, it creates a habit, one that gets harder to break as it happens more and more often. These two things feed off each other in a very positive way.

It seems that regularity is good for the bowel and for the budding artistic career. Maybe next month’s post can examine how to make that possible. PS. You now have the ability to sign up for notifications when I actually do write something. If you’ve liked my stuff in the past, feel free to sign up in the column over there on the right. Oh and tell you friends I’m hilarious. I’ll try not to disappoint you too terribly.