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Jonathan Coulton.
Jonathan Coulton.

With all the emphasis on science, technology, engineering and math, better known as STEM, many people would be satisfied with a high-paying career in software development, with rising opportunity and good benefits.

But Jonathan Coulton willfully abandoned his career writing database software for executive recruiting firms in 2005. He had just become a father for the first time. As his paternity leave matured, so too, in a way, did Coulton. While he always loved music, he never saw music as a path toward anything.

As with many people who find themselves surprised by a career, all the ambitions of youth were lost in the striving and concentration required to hold the job and succeed at it. This time off to care for his daughter helped Coulton realize that his software career was a choice. It was a choice he was no longer willing to make.

“I wanted to a set a good example to my children. I wanted to be the person I wanted to be, someone willing to take chances—a person who didn’t live with enormous regrets,” he recalled. “I had this baby. I only had a limited time to make big career mistakes. I told myself, ‘Make the big mistake before the baby is old enough to be embarrassed by you.’ ”

If someone asked him in high school what he what he wanted to be when he grew up, the answer would be, “a musician.” After college Coulton moved to New York and did not become a musician. “It was very unclear how to become a musician,” he said.

JoCo 2016
Photo Credit: Brian Irwin

“I held a lot of ‘non-career jobs.’ I was in a couple of bands. I worked for a record label. I thought it would be good to be close to the industry,” he said. “This was the early and mid-90s. The Internet hadn’t really changed the music industry yet. The old record industry was still a hit-based economy. You had to prove to people that you were worth their investment. I wasn’t able to do that, and wasn’t really able to even try.”

He explained, “It’s a very daunting thing to confront the machinery when the starting question is, ‘How do you justify yourself?’ It’s a really horrible place to start. I was scared and I was intimidated.”

So the software career.

And then the Internet happened. MP3s. Blogs. Podcasts. Self-publishing became a viable option.

Coulton left the software job and started posting songs to the Internet every week. Mostly his songs, a few covers here and there, all recorded in his home studio. These were the days before iTunes let in independents. Before Bandcamp. He posted files to a page for free. He created a tip jar for a while and then created his own storefront.

He found a following.

“A few of the songs had viral moments. By the middle of 2005 people were buying the MP3s.” Coulton leveraged early analytics, triangulating towns where MP3 buyers lived to decide where he should book a gig.

Within the first year, he had not replaced his software salary, but had enough success to cover his babysitter and to keep food on the table. He decided not to look back.

He did, however, hold on to a very important lesson from his previous career where he worked up to, and through, the dot-com bubble and burst.

“This company was really making up their own rules. I had friends who were getting huge stock options at startup companies. They were getting rich. I was asking myself, ‘Why aren’t we a start-up company?’ And then the dot-com bubble burst and I was glad we weren’t. What I learned was that these guys were doing this thing they wanted to do, this thing they felt competent doing. They didn’t chase after things, and they worked hard, but it was a business they created because they enjoyed it. They tried to minimize the things they didn’t want to do. It wasn’t about getting rich; it was about getting satisfied.”

Coulton thrived in the emergent indie music industry. He now applies the rule-making rubric to his own business, which has grown from weekly song posts and few gigs into an enterprise that includes an annual cruise for fans.

2016 Sea Monkeys
On the 2016 JoCo Cruise. Photo Credit: Steve Petrucelli

The path toward the high seas proved serendipitous. “If you put yourself out there. If you work with enough people, and if you have enough exposure to your work, opportunities come your way.”

Coulton asks questions, plays music and tell’s jokes on NPR’s “Ask Me Another.” He writes the weekly “previously on” songs for CBS’s SciFi political spoof Brain Dead. Coulton noted that Robert and Michelle King, creators of Brain Dead and the Good Wife, do things because it is fun. “People forget they can make fun a priority.”

Jim Boggia & JoCo.
Jonathan Coulton and Jim Boggia. Photo Credit: Michael Bain

In March 2017 Coulton will launch his seventh cruise. The cruise evolved from touring. Coulton’s booking agent, who also represents Paul and Storm, asked, “Hey, what if you guys did a Cruise? Barenaked Ladies does a cruise and they seem to have some success.”

They held a poll to see if anyone would be interested. The first cruise attracted 350 fans who shared the boat with other cruisegoers. The 2017 cruise charters Holland America’s ms Westerdam.

Waving pic by Mark Barrington (2)
Photo Credit: Mark Barrington

The cruises have evolved from performances and hanging out with Coulton and his compatriots, to near convention-on-the-sea status that includes comedy, dance parties, cocktail parties, karaoke, gaming, time with writers — and, of course, music.

“Calling it a convention is pretty close to what it is. Many of us have been to conventions so we only try to do only the fun things. It has become its own community of people who have been several times. We are all fans of the same kinds of stuff. We get together and share experiences. We get to literally commune with a community of fans. We get to bask in it for a week.”

Jonathan Coulton, Greg "Storm" DiCostanzo and Michael Ian Black
Jonathan Coulton, Greg “Storm” DiCostanzo and Michael Ian Black. Photo Credit: Steve Petrucelli

Coulton is very hands-on. He, along with Paul and Storm, and personal assistant Drew Westphal, book the talent and plan the agenda. Reflecting back on his software career, Jonathan shared, “working in a team is hard. Spending almost a decade at the software company, sometimes managing people, taught me a lot that I apply to managing my own fan group.”

“The nice thing about my job is I get to wear many hats. I get to be purely creative, to write songs and sing them, but I also get to work on some business stuff. It’s nice to be able to change gears when you want to. It’s nice to diversify so you aren’t going to the same place every day doing the same thing. You never know what you’re going to get. You can cause some parts of your life to expand or contract depending on what you are interested in. Being entrepreneurial is a very rewarding lifestyle.”

The 2017 cruise includes a wide range of talent including Aimee Mann, Adam Savage, Matthew Weiner, Wil Wheaton, Rhea Butcher, Cameron Esposito and Redshirts author John Scalzi.

“My favorite thing is the collaboration, getting all these people together and seeing what they do. Everybody these days does a podcast so they record and interview each other. There are a bunch of panels and Q&A sessions where they talk about stuff. I don’t know what it’s going to be this year, but last year, all the musicians, while we were onboard, rehearsed and organized a little David Bowie tribute for the last night of the cruise. They did eight David Bowie covers. For instance, Comedian Paul F. Tompkins sang Under Pressure, with Janet Varney. Amiee Mann on base. Ted Leo on guitar. It was just very cool to see people cross-pollinate in that way.”

And if you are wondering about the role of software in managing all the details, the answer is that Coulton and his team hold a weekly conference call and they share an Excel file with several worksheets in it that tracks what they are working on and where they are. “Sometimes it’s just good to talk to somebody on the phone,” he said.

Too often people feel trapped by work, not empowered to make the trek that will slam their vocations and avocations together. But Jonathan Coulton found that taking the risk to expose his art to the world, along with a lot of diligent work, deliver his dream job. He gets to control his own destiny and have fun doing it.

What have you done to bring your vocation and avocation closer together today? It’s always karaoke night somewhere.

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