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What Musicians Teach Us About The Challenges Of Being Your Own Boss

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In the Academy Awards-nominated movie Inside Llewyn Davis, viewers spend a few days with an aspiring musician in the pre-Dylan New York City folk scene. By the end of the movie, Llewyn is homeless, penniless, careerless and friendless. What’s more, he’s had his butt kicked. Crouching on the ground, Llewyn puts his hand to his injured side and wonders: how did I manage to sink so low?

Whatever the answer, he’s got mostly himself to blame. When you work for yourself, as do musicians and a growing sector of the economy, you bear the responsibility for how your career pans out. And it’s not always an easy burden to bear.

In the next decade, according to the 2013 MBO Partners State of Independence in America workforce study, 50% of the work force will have spent some time as an independent worker. This means they will have been at some point self-employed, an independent contractor, business owners, creative professional, consultant, temp, entrepreneur or freelancer.

In many professions, working independently is a relatively new option. But some professions have always been independent. Artists, writers and musicians have been opportunistically organizing their careers around various activities, gigs and projects for generations. That’s why Smashing Pumpkins drummer gives drum lessons, Gwen Stefani has a fashion line, and Akon owns own a diamond mine. American Idol winner Taylor Hicks patches a living together by performing live five nights a week at the Paris in Las Vegas, releasing an album every two or three years, managing a handful of rental properties and being part-owner of Saw’s Juke Joint, a barbeque-and-blues bar in Birmingham.

We all know about the benefits of independence: you can craft a career path around your interests and unique skills, you don’t waste time on meaningless office conversations and you can experience complete alignment between who you are and what you do. But we don’t know as much about the psychological challenges of working on your own.

A study led by University of Michigan professor Susan Ashford has examined this issue by interviewing dozens of artists, writers, graphic designers, consultants, and other people working on their own. Ashford found that independent work raises a host of existential issues that people who work for organizations don’t have to deal with.

“People bemoan many aspects of organizations: they’re rigid, they kill creativity, you’re a cog in the works,” Ashford told me. “But one of the things that organizations also offer you, through some of those same structures, is that you’re a part in a bigger whole.” When you work for an organization, if you don’t show up on a given Tuesday, somebody will notice. But if you work at home and you don’t show up at your desk, no one might notice. Or care.

As a result, independent workers experience a kind of existential anxiety. Without external reminders of their worth, they find themselves pondering, “Is what I do valuable?” and “Why and I doing this?” As one participant in the study said, “Working in an office you have a huge support system, even if it’s just hanging around the Xerox machine. … You [don’t] have this kind of loneliness and this idea that there’s nobody out there.”

Ashford’s team found that to make their work life psychologically sustainable, independent workers craft physical and social spaces that infuse their work lives with a sense of meaning. To ward off existential anxieties, they connect to place, routine, people and purpose.

Connecting to space means designing a physical working environment that facilitates work. The best design is based on independent workers’ insights into their work processes and what kind of space is best for their productivity. One independent worker they studied felt most generative working in her bed, while another built an eight by ten feet shack in his yard to work in. “I can concentrate more when I don’t feel that my mind is expanding in a large space,” he said. “If I could work in a closet that would probably be best of all.” In organizations we often don’t have choice about our physical space. Working independently presents an opportunity to tailor your workspace to your needs.

Connection to routine is the practice of doing some things the same way every day. Although flexibility is the reason so many people want to work on their own, complete lack of structure can be debilitating. As study participant noted, without a routine, you life feels arbitrary: “You wake up, anything could happen, and there are no outside forces to force you, or even any times to even influence at all to make different kinds of decisions… there’s not even a distinction between day and night really.” A sequence of activities performed in the same way every day creates momentum for getting into work mode.

In the documentary, History of the Eagles, Glenn Frey reveals how he learned the secrets to successful songwriting by witnessing his neighbor Jackson Browne’s routine: “I knew I wanted to write songs, but I didn’t know exactly, did you just wait around for inspiration, you know, what was the deal? I learned through Jackson’s ceiling and my floor exactly how to write songs, because Jackson would get up, and he’d play the first verse and first chorus, and he’d play it 20 times, until he had it just the way he wanted it. And then there’d be silence, and then I’d hear the teapot going off again, and it would be quiet for 20 minutes, and then I’d hear him start to play again … and I’m up there going, so that’s how you do it?” Browne had a routine that was as predictable as clockwork, and Frey did well by embracing it.

Connection to people is the practice of connecting to those who encourage us and remind us that our work is valuable. One writer in the study talks to his publisher every day. Others turn to friends and significant others to provide regular reminders of why what they do is worthwhile. Musicians rely on their band members as reminders of their common purpose. This might be one reason musicians in bands are less likely to die than solo performers.

Connection to purpose is a way to ward off feelings of meaninglessness. As one study participant said, “The dark night of the soul is really the existential question of, you know, am I making a difference?” To answer that question, independent workers remind themselves why it is that they chose to work on their own. They recall their unique vision or mission statement for their careers. And they think about the positive impact their work has on others. In 2006, two miners trapped in the Beaconsfield Mine collapse were given food and water through a 90 millimeter hole. Asked what else they wanted to have while they waited to be rescued, the miners asked for an iPod loaded with Foo Fighters songs. Band member Dave Grohl was so moved by the request, he wrote a song for them. “I was really touched,” he told NPR’s Terri Gross, “To feel that something that I do could perhaps help someone in a situation like that... It changed the way I look at what I do to feel like your music is making a difference in someone’s life.”

Many people consider working for themselves to be the highest form of career self-actualization. According to a recent study, 72% of Millennials, the youngest cohort of the labor force, would like to be their own boss, and 74% want flexible work schedules. The MBO Partners study found that 77% of independent workers are committed to staying that way. But when you disconnect working from belonging you are quite literally left on your own. Making independent work sustainable requires proactively creating work spaces, routines, positive interactions and a clear sense of purpose to deal with the lack of an organizational support system.

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