Do the Hustle: The Year I Spent as a Touring Musician

On May 2, 2010, I grabbed my guitar, climbed on my kitchen table, and recorded my first song for YouTube — a cover of John Linnell’s “The Songs of the Fifty States.”

At that point, I had only been playing guitar for four weeks.

On March 31, 2012, I posted my 100th song to YouTube. I had been crazy enough to record one song per week for two years—and quit my job to become a full-time touring musician.

Was it a naïve decision? Perhaps. But it was not without merit. Between May 2010 and March 2012, I released three albums of original music and established relationships with nearly every nerd convention within a 200-mile radius. I was already earning money as a performing musician. I figured if I quit my job and turned up the hustle to 11, I could earn even more.

Technically, I was correct. But, there were many nights when I felt like the struggling artist. For example, at Phoenix Comicon, when the PA system stopped working in the middle of my first song and nobody could hear me. My hustle didn’t always go according to plan.

My first goal as a full-time touring member of my one-person band Hello, The Future! was to earn enough money every month to pay rent. I knew I would have to make enough to cover all the expenses that come with traveling and starting a small business, but making rent—which was $780 for a tiny room in a Los Angeles fourplex where I slept on a camping futon—seemed like a realistic goal.

And it was. I quickly started “playing out,” as they say, securing a performing residency at a Los Angeles bar and regular gigs at local coffee shops and restaurants. The nights I wasn’t playing locally, I was traveling. I got myself a Southwest Airlines credit card and started racking up the miles as I shuttled to places like San Jose, Phoenix, Portland, Seattle, Philadelphia, Washington D.C.

I made a lot of friendships and connections as Hello, The Future! What I wasn’t making, however, was a profit.

I made a lot of friendships and connections as Hello, The Future! What I wasn’t making, however, was a profit.

When I wasn’t emailing coffee shops and comic conventions or pitching venues for performance slots, I was standing behind a merch table convincing people to buy my CDs, t-shirts, and hoodies. The experience taught me how to size people up and identify what they needed in order to close the sale. Some people needed to feel like I was flirting with them. Others needed to feel like they were helping me achieve a dream. In a world where digital music is cheap, and people don’t really need to buy CDs, you have to find other reasons to make that transaction meaningful.

Who can forget the “booth barnacles,” the people who hung around my merchandise too long, creating traffic-jam lines? After more than a year of playing these comic book conventions, I was more than familiar with the type. I watched people glance at my booth, notice someone still talking to me, and step away. I remember one guy in particular, who was about to buy two albums and one of my “Life is a LARP” hoodies, but couldn’t decide whether to pay with cash or credit. Of course, I accepted both. He forgot his wallet at his table, and by the time he was on his way back, the MC called me to the stage. The sale that got away.

I was making money, but with a catch. I could afford rent—and eventually made $20,000 as a performing musician—but nearly all money that didn’t pay my bills went toward touring. Only a handful of those Southwest flights were free, and I still had to pay for food, hotels, and the taxis that got me, my guitar, and my stacks of merchandise to the venues. I also had to pay to print the merchandise, and, unfortunately, I had to pay taxes on merch sales. It baffled me that a $20 t-shirt really only put two dollars in my pocket after accounting for all production costs.

After three years of gigs, I was still only an opening act. I kept waiting for it to flip—for people to contact me to headline an event, but it didn’t happen. I knew how to hustle for work, but call any bar in the country and they’ll probably be happy to book you for a 7 p.m. slot on a Tuesday. What you really want is for the venues to call you.

As I continued to travel, hoping each gig would provide the spark for my music career to flourish, I started hustling for freelance writing jobs to pay the bills. I realized my skills at sizing up people who visited my merch tables easily applied to clients. It was, in many ways, exactly the same job: wake up, go online, ask for gigs, appease clients (who are probably the same booth barnacles I encountered), complete gigs, and wait for a modest check.

And then clients started contacting me. Not for my singing, but for my writing. It took a year to realize I would never be a successful touring musician. But I don’t think I ever would have known my pen is mightier than my guitar without that time spent on the road, freelancing on stage.

Image via NYU Local