[Editor’s note: David Wilson fronts the Cowboy Dave Band, which makes its way back to Nebraska this Thursday — at Uncle Ron’s with Jason Boland and the Stragglers — and Friday — at the Zoo Bar.]

by David Wilson

It was at a truckstop along I-80 at about three in the morning when I realized that I had officially found myself stuck in the middle ground of a musical lifetime.

See, you start out practicing every week in a garage, burning with passion and anticipation as you work your day job and try to write truck-driving songs that will one day save the world. That’s the first step. Then comes the middle ground. It’s that nearly unavoidable step between having a steady day job and paying your bills by playing music. This is the three-step process.

The middle ground is where you find yourself in the back of a John Deere green shuttle bus, parked between two semis, trying to sleep on a flat air mattress at three in the morning. Big trucks make weird noises all night, and when you combine that with coming down from the high of playing a street dance in Hartington, Neb., and building up excitement for your first-ever show in Chicago, it’s hard to sleep. But when you’re driving to Chicago for little to no money, a flat air mattress in the back of a shuttle bus is a pretty good option for sleeping accommodations. Just don’t accidentally leave your doghouse bass player at said truckstop. That’s another story for a different time.

Anyway, so as far as I can tell, there’s no way to skip this middle step (short of winning the lottery or signing a major label deal). The middle step is where you break out of your hometown, hit the pavement and scream your existence to the world. Unfortunately, I haven’t found it to be a very lucrative step. It’s the step where you drive 1,768 miles roundtrip to Houston to play one show for $200. It’s this continuous step of leaving your comfort zone to play venues in other states over and over and over again, until slowly, you work your way to being the headliner, and eventually (hopefully), you find yourself making enough money to pay for your trips, and theoretically, one day, your bills.

You can’t skip this step.

There was a Thursday where we played on a sidewalk on East Campus, and then drove straight through to Jackson Hole, Wyo., for a show with BR5-49, the single greatest band of all time. We got paid $0.00 for that show in Wyoming. But it was a good show. And I would do it again. Actually, that was eight years ago, and I’m still making insane band-routing decisions of this nature. I’m not saying I’ve been fully committed to the middle step for eight years, but I’m definitely stuck. Not sure what my problem is, but I believe it to be an addiction of some sort.

Speaking of hitting the road, you can catch me amid this middle step on Friday, Sept. 21, at the Zoo Bar in downtown Lincoln, Neb. I’ll be bringing my now-Denver-based group of honky-tonk pickers to Nebraska for the first time. Let me know if we can sleep on your couch. We’ll also be playing Uncle Ron’s with Jason Boland and the Stragglers on Thursday, Sept. 20.

Boland, I might add, is a phenomenal example of a self-made success. I’m pretty sure he busted out of that middle step in less than eight years. I remember him telling me about how he started by lining up shows opening for the Great Divide throughout Oklahoma and beyond until he was headlining those same venues.

That makes me feel a little better about chasing down shows throughout the Midwest and South with musicians I look up to.  Maybe one day I can pay the favor forward (and start paying the bills). Until then, I’ll keep sleeping at truckstops. Even though big trucks make weird noises at night.

A purveyor of honky-tonk music, Nebraska native David Wilson fronts the Denver-based Cowboy Dave Band, and works endlessly to put the western back in country and western. Connect with him via Twitter and Facebook and at CowboyDaveBand.com.