What No One Ever Tells You About Being Your Own Boss

Sure, it's all flexible schedules and elastic-waist loungewear, but there's also some under-discussed nuance that comes with going it alone.
Courtesy of AMC

All this week, ELLE.com will be unpacking what we've dubbed the Work Life issue—as in, the tricky subtext that informs everything other than the actual mechanics of the jobs we're paid to do.

In 2010 Intuit predicted that, in the next 10 years, 40 percent of the American workforce will be free agents, including contract workers, part-time workers, freelancers, and individual suppliers. (Forbes puts this figure at 50 percent by 2020.) Soon enough, cubicles, bosses, and workplace-appropriate attire will be an ancient archetype for practically half of us. Autonomy will prevail.

I've never had an office job—not because I never sought one out, but because I was unable to find a full-time gig in the competitive field of journalism. As such, I'm unfamiliar with the ways of work besties, salads in plastic bowls, and speaking in a hush, monotone voice to conceal personal conversations; I'm untainted by fluorescent lights and fickle HVAC systems. The entirety of my professional life, about 10 years now, has been spent as a freelancer, master of my days, minder of my thermostat.

In this way, I am your future. As such, I'd like to share with you my existentially fragile—and yet still wholly awesome—experience with being my own boss.

Let's start by acknowledging that we work for a lot of reasons. The most basic one is money, yes, but underneath that need lies the human instinct to have something to do, someone to be. For many of us, the responsibilities and communities offered to us by our workplaces provide this. Work facilitates self-actualization; it's a vehicle through which we contribute to the world while working on ourselves. For those of us able combine passion and profession, this is even more the case.

So, what happens to the self when the office holiday bash is a party of one?

Let's start with the downsides. Among the more obvious ones are loneliness and rusty people skills. On the occasion that I do have to work collaboratively, I find myself impatient, stubborn, and resistant to talking things out. My inner fascist emerges, and I can't help but think about how much more efficiently operations would run if there were just one capable person in charge rather than trying to accomplish things by committee.

I also have nobody to get dressed for in the morning. This may sound trivial, but it is not without its consequences. The exercise of choosing an outfit each day is an act of self inquiry, an opportunity to better understand how we are seen by others, and how we are seen by ourselves. Sure, my daily wardrobe of half-tucked tees and slouchy pants—would you really wear non-elastic waistbands if you worked at home?—saves me a lot of money on clothes, but it also denies me the pleasures we can achieve through self-presentation.

In her ode to the workplace in New York magazine, Jennifer Senior talks about the office as an opportunity for object permanence—the idea that something continues to exist even when we are not right in front of it, the opposite of "out of sight, out of mind"—in our otherwise chaotic and unstable lives.

"In other cultures, you may have a very large family home that provides you with memories—you associate it with experiences and relationships and people. It's a landmark. But in a society as mobile as ours, we run the risk of never having that permanence," Sue Ashford, a management professor at the University of Michigan, told Senior.

Because we are social creatures, wired to be connected to something larger than ourselves, such object permanence is an important part of our identities. As a freelancer, it's easy to feel during a dry spell as if nothing is of any real consequence. I've certainly had moments of feeling spiritually aloft when I work hard on something I believe in and then…crickets.

Of course, it's easy to find affirmation online, which is also dangerous. I have no doubt that too much of my life is mediated through the digital realm. I consider promoting my articles and essays part of my responsibility as a modern writer and, as such, most of my work-related interactions take place on Twitter and Facebook. It's possible to do this with dignity, but it's also very hard. Most days I feel like a turn-of-the-twentieth-century newsie, shamelessly hawking my own goods in a crowded town square.

Offices provide us with a community of peers who know us as individuals and have witnessed our humanity, and therefore are likely to give us the benefit of the doubt when judging our work. The Internet is a hotbed of quick takes and misguided assumptions—and so often I find myself choosing between fighting back and ignoring something, the latter of which can be read as not caring. I often long for a nod or smile from a respected colleague, whether it's for trying or succeeding. It would be far more satisfying than another RT or Facebook like. This type of scrutiny is especially tough for writers, but anybody who primarily engages with the world via the Internet is victim to this part.

Now for the upsides. Practically speaking, freelancing makes being a working mother significantly easier. I have the freedom to adapt my schedule to my child's needs without letting anyone down. I can toss the chicken in the oven and then get back to work. I have no commute, which affords me approximately two extra hours a day to get everything done. Yes, in some ways this is a surrender: Workplaces fail to accommodate parents, but instead of forcing the system to change, many of us are going out on our own. Still, the convenience can't be overstated.

And then there's the solitude, which for me is the best part.

In Harper's magazine last month, Fenton Johnson explored "the dignity and challenges of solitude." When examining the work of some of his favorite artists, writers, and musicians, he "recognized that they and I had something in common—a deep core of aloneness, a desire to define, explore, and complete the self by turning inward rather than looking outward." This idea could be extended to suggest that the permanence many find in the workplace is found by some of us within ourselves.

For women, solitude is a radical act. The concept of being my own boss and pursuing my ambitions without guilt (or having to sacrifice having a family or material comforts) is pretty extreme when put in historical perspective. Our traditional role as caretakers and minders of the domestic realm meant that we had little time to dedicate to the pursuit of self-discovery. For most of history, a woman's mind was not considered worthy of such cultivation. I'm not proposing freelancing as a finite solution to the myriad problems surrounding women in the workplace—but I am suggesting that, for some women, those like myself, it can be a real gift. It's both a corrective of the past and a steadfast commitment to the idea that a single woman just might be the only hierarchy she needs.

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