I started my 20s a few months after the biggest heartbreak of my life. I had spent the previous five years as the lead singer of a band that I started with my closest friends when I was 14. We played for five years, developed a great following around Texas and toured the country three times. I booked our tours and managed the band because there was nothing else I could imagine myself doing other than playing music with my best friends – the guys I had gone from junior high to high school with, graduated with, moved to Austin with and grew into an adult with.

 

In 2002, we returned to Texas from a six-week tour with bands that we looked up to, who were on a record label that we dreamed of being on. It was the biggest thing that ever happened to us. And when we got home, we went our separate ways. A couple of weeks after that, I found out that really meant that those separate ways were the one I would go and the one that the rest of the band would go without me. They started a new band and wrote new songs. I had lost the thing I had spent nearly all of my teenage years on. And on top of that, I had lost the best and only friends I had since junior high. I would turn 20 years old alone and in my shitty hometown with absolutely no hope or direction.

 

I fell into a pretty bad depression. Had I peaked at 20? What could I possibly have to look forward to that would top touring in a band? Around this time, my dad told me something I will never forget. “Michael, you’re twenty years old, you have enough time to start over ten more times.” Honestly, I don’t think that advice clicked with me then as much as it does now and has over the last decade.

 

I went back to college to become a history teacher and my brother and I started a zine on our college campus. After two years, I decided that, at 22, I was not ready to do the same thing for the rest of my life. So, I started over. All I wanted to do was write. I loaded up everything I owned in the van I had bought for my band to travel in, and I headed out to Los Angeles. Forty minutes into the trip, the van broke down. Eight hundred dollars and three days later, I was back on the road. Two hours away from L.A., it broke down again. I had gone too far to turn back and give up. I knew, at that time, Los Angeles was exactly where I needed to start over. So I ditched the van at a junkyard, got a U-Haul and finished the trip. The two years I spent in L.A. were two of the most productive writing years I’ve ever had. And, I learned a lot about myself while I was there. I became more confident and I learned that I do have some talent.

 

In 2007, I decided I needed a break from L.A. and my girlfriend at the time had gotten a writing gig in Nashville. So, I started over. I was 24 and moving across the country. I landed a job as a booking agent at a small indie singer-songwriter/Americana label. It was a dream job and I was making more money than either of my parents were making. It didn’t take long for that job and the relationship that took me there to run their courses. At the end of 2007, I started over.

 

At 25, I moved in with my brother and his family in Corpus Christi, Texas – the “big” city about 45 minutes from our hometown. My brother had turned that little zine we started in college into a monthly alt-news publication. Being back “home” felt like I had failed. Those feelings I had after my first band break up were coming back. I went back to writing for our magazine, which I had always loved doing. And, I started doing stand-up, which I was too intimidated to do in L.A. Around Halloween of 2007, I did my first open mic and within a few months, I was opening theater shows in front of 400 people. But it still wasn’t enough. Less than a year later, I started over.

 

In July of 2008, at 25 years old, I enlisted in the U.S. army as a combat photographer/videographer. It was the biggest mistake I’ve ever made. In fact, it’s the only one of my crazy spontaneous decisions that I actually refer to as a mistake. When anyone asks why I joined, I say it’s because I was bored. That’s partially true. I needed some direction – something to give me a sense of purpose.

 

I felt like I still hadn’t topped the first band, so I did the most extreme thing possible. And, as a writer, I figured, what could possibly be more inspiring than war? I would go on a few deployments, document the war happening right in front of me, and then I’d come home and write about it. I was going to be the next Hemmingway or Vonnegut. Right? I lasted a year. Never got deployed. Never did anything, really. I realize that the military works out for a lot of people, but I was just not one of them. I always joke that I’m so bad at commitment that I even found my way out of the army. In 2009, I started over.

 

At 26 years old, I moved back to Corpus Christi, Texas, back to our magazine, and back to being directionless and hopeless. A year passed before I decided to go back to college. I only had a year-and-a-half left, so I figured, what the hell? I went back as a communication/media major. In the fall of 2011, I got an internship at Comedy Central in the digital media department, working with The Colbert Report and The Daily Show web team. I spent five months in New York and then went back to Texas for one final semester. I graduated from Texas A&M University – Corpus Christi in May of 2012. I was 28 years old and it was time to start over.

 

By the time I graduated, I had already interviewed and gotten hired at Comedy Central in the same department that I interned in, but for different shows. In June of 2012, I moved to New York and started my first real career. In the year-and-a-half at the job, I’ve been promoted, nominated for a couple different awards, and, earlier this year, I won an Emmy. Sure, maybe I finally topped those teenage tours in my first band. But how the hell am I supposed to top an Emmy?

 

I suppose early success – or success in general – can be seen as a blessing or a curse. I can understand how it is a blessing – I’ve continued to work my ass off over the years because I couldn’t have my crowning achievement be a two-and-a-half month tour that my band went on when I was 17. But, I never look at it as a blessing. I’m constantly thinking of it as a curse because I always feel like I have to top the last thing. Yes, it inspires drive, but it also drives me crazy.

 

I’ll be 31 this year. During the day, I toil away at one of the biggest media corporations in the world, and then I come home and sit right back in front of my computer to work on my things. I’m about fifteen thousand words away from finishing my first novel, and I’m currently trying to organize a non-profit that will take bands and comedians on tour to military training bases.

 

My hope is to make the adjustment into military life a little easier for those young kids who have left their homes and everyone who cares about them for the first time in their lives. It’s a little ridiculous how everything I did in my 20s – touring, writing, booking agent, even the military – is coming together to form what I hope to be doing in my 30s and 40s. And if that doesn’t work out, I guess I can just start over.

 

Musician, novelist, photographer, Emmy winner.

Facebook Twitter YouTube