How I Started and Why I Stopped

In 2003, I traded the life of a touring musician for that of an MBA candidate. The transition was abrupt: I toured California with Suzanne Vega in early August and started school by the end of the month. To put a finer point on it, I went from standing on stage at the Fillmore Auditorium – where people clapped for me every three minutes – to circling up in a conference room with the aspiring captains of industry who comprised my “cohort” for the semester. It didn’t soften the blow when one of them figured out he had seen me open a sold-out show for Todd Snider earlier that year. What had I done?

Actually, there’s an easy answer to that question: I’d taken the first steps toward becoming employable before it was too late. I was 33 and had been pursuing a career in music for about eight years after moving from California to New York City in late 1995. Prior to that, I’d been a college student and indoor volleyball player; after college, I’d been a construction worker, European traveler, ski instructor at Club Med, and – very briefly – professional beach volleyball player. During that time, and indeed since about 5th grade, I’d harbored musical ambitions, and following two of my best friends to New York seemed like a decisive way to finally pursue them. 

At the time, I’d written slightly more than zero songs. That is to say, I had a few fragments from college and the year after – and even performed one at an open mic at the Albion Bar in San Francisco – but they didn’t amount to anything. More precisely, they approximated songs: sad imitations of what I thought good songs should sound like. In New York, while wandering around, I came up with a few lines that felt real, and before long two or three complete songs that weren’t totally embarrassing. I still remember where I was – on the Upper East Side between the 6 train and the palatial home of a high-school kid I was tutoring for my job at The Princeton Review – and how I felt when this first not-terrible song started coming together:

The Hotel Di Medicis on the Rue St. Jacques

I started going to open mics, and fell in with a group of songwriters who met weekly at Jack Hardy‘s West Village apartment to present new compositions for feedback (I still recommend writing a song a week for as many years as possible as a surefire way to develop your craft). After not too long, I was able to book “entry level” gigs at the Fast Folk Café, the Sidewalk Café, and the Bitter End. I met an agent around a campfire at the Rocky Mountain Folks Festival and he helped me land my first out-of-town engagement, opening for Dan Bern at Rutgers University. I graduated to better NYC gigs – Fez, the Mercury Lounge – played regularly at the original Living Room on the corner of Stanton and Allen, and worked my way onto the East Coast touring circuit with regular opportunities at Club Passim (Cambridge, MA), the Iron Horse Music Hall (Northampton, MA), the Tin Angel (Philadelphia, PA), and elsewhere.

I got to know Suzanne Vega at the Hardy meeting, and she came to see me at the Living Room right when I was starting to feel comfortable on stage. Consequently, when I proposed myself as an opening act for her California shows in May 2001, she knew I was up to the job. That made one of us: her gigs were at the Knitting Factor in LA (500+ capacity) and the Fillmore in SF (1,200+ capacity), and I’d performed for 500 people once but never more than that. I felt and apparently seemed nervous in LA but got it together in SF, where I received a bad review but also an encore and an invitation to open more shows. Eventually, I opened for Suzanne all over the U.S. and Europe for more than a year and also played the Newport Folk Festival.

Valentine’s Day (Cologne 2002)

By 2002, it could have been argued that I was at or near the top of the heap, at least in my neck of the up-and-coming singer/songwriter woods. But, of course, it’s not that simple. I made decent money opening for Vega, and sold lots of CDs at the shows. But small-club openers paid $50 and that’s what I went back to when the Vega tour ended. Also, unfortunately and somewhat surprisingly given how well I went over most nights, I wasn’t building an audience of my own or attracting interest from “the business.” I can tell you rejection stories until the cows come home, and posit any number of plausible explanations, but I’ll leave that for a future blog post.

The long and short of it is, I’d crossed over into my early 30s, and couldn’t see how my music career was going to become sustainable. Some artists I knew had grown their audiences quickly with the help of labels and managers and etc. who showed no interest in me. Others had developed their careers by building up slowly through years of touring. That was an option, since I liked touring and had a solid foundation, but what happens if you chase the dream for ten years and still don’t have much to show for it? It occurred to me that now might be a good time to pull the ripcord.

During the Vega period, I relocated from NYC to San Francisco to Iowa City, where I lived with my fiancé, who attended the Iowa Writers Workshop. Really, there’s only one way to change careers in a Midwestern college town, where there’s not much in the way of industry. I took the GMAT – which wasn’t that intimidating because I’d been a test-prep guru in my 20s – was accepted by the business school at the University of Iowa, and started thinking of myself as someone who might after two years be a candidate for a real job. 

Before school, there was one final West Coast tour with Suzanne Vega. I didn’t waver, even when I played the Fillmore for the second time, or when Suzanne connected me with Judy Collins’s label, which might have been willing to release my next album. In hindsight, I might have been enamored of a new challenge, which constituted a major learning opportunity and could lead in a bunch of interesting directions. To this day, I’m proud of changing direction so extremely, even if I was headed in the wrong direction relative to what I really loved doing. 

I didn’t have a terrible experience in business school. Although I didn’t exactly fit in with the other students, many of whom were younger and politically conservative – I received a joke award at a year-end banquet for being liberal – they were good people and smart and I learned stuff. My resumé was an impediment at first, because it said “singer/songwriter” and nothing else, but I eventually nailed down an internship and then a full-time job with the help of two guitar-playing marketers at a natural products company in a cornfield outside of Cedar Rapids. After three years, I moved back to the San Francisco Bay Area with my wife and young son and worked for Clorox, where I marketed Formula 409 and Glad plastic containers. The transformation was complete…

I value my 10+-year sojourn in the business world. I was sometimes viewed as eccentric, which was personally satisfying after years of feeling fairly conventional relative to other musicians. There was also a sense of accomplishment associated with intellectual exercises and getting things done. Most importantly, I internalized principles that have made me a more competent DIY artist now that I’m spending more time on music again: strategic thinking, planning and organization, creative best practices, etc. If I’m better at marketing myself now, I probably have Clorox to thank, though it had a dark side. Here’s how I felt about corporate life on bad days: 

I Think I’ve Taken Enough Shit From You This Year

Would I have made it work if I’d stuck it out? Some of the people I started with – most notably Josh Ritter, Mary Gauthier, and The Weepies – have pretty great careers. Others have kept it going with varying levels of success, and many have moved onto other things. I moved on with a vengeance, but eventually inched back with an eye toward spending as much time as possible engaged with the creative process. For the record, my second act is about writing more and better songs and sending them out into the world. I hope you’re listening, but I’m trying not to worry about it too much.