Entrepreneurship: Sometimes Work Is Just Work

If you're lucky enough to do what you love, you'll work every day of your life

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The other day I was leafing through my diary, looking for my notes on the holidays last year, and I came across my goals for 2014. Among them was this, noted in large letters: “Make our jobs fun.”

At the end of last year, Maddie and I were paging around through job listing at various large online women’s publications, looking at the kind of jobs we’d do if not working for APW. And one or the other of us commented, “You know most of these jobs are probably really not fun, right?” We’ve both done our time working in creative jobs in New York City, and we know that there is a long tradition of bosses who are both crazy and unrealistic, who scream at you, and who send you scroller text messages (not the good kinds). And then there is the other kind of creative job in New York—the kind where your actual job is boring and corporate, the product just happens to be theatre, or indie movies, or blog posts… but you’re paid a fraction of what other people doing boring corporate jobs are paid.

Because we know that, our goal for this year was to make our jobs magically awesome.

Since it’s the end of the year and I’m here to give you an honest accounting, I’d say we basically failed at that goal. Not failed like we made our jobs miserable. (We didn’t. They were lovely job-like jobs.) But our attempt to make our jobs somehow glitter filled and like flying through the air on a unicorn was… a bust.

Do What You Love?

“Do what you love, and you’ll never work a day in your life.”

I had this quote pinned up at my first real-life-grown-up-job-with-benefits-at-a-theatre-company that I got at twenty-five. It was pinned up on the wall on the inside of the storage closet that they had cleaned out so a co-worker and I could sit inside it all day and work on grant proposals. Every time I looked at the quote, it tortured me. Because even though I’d taken out a tiny loan to work through a nearly unpaid internship to get a job at a theatre company, I was working in an actual closet. My bosses were a dysfunctional mess of three kinds of crazy who were all angry at each other, and I was updating paragraphs in last year’s grant applications while incorporating passive aggressive notes from my nicest boss in track changes.

For all that I’d been broke for years, trying to find work in a creative field that I loved, every moment felt like grinding, painful work. It was awful.

No, But Serial-ly

This year, I’ve been thinking a lot about the way our work lives can cycle through thrillingly creative work and more humdrum work-a-day work. Even when we’ve found careers that we love, not every moment (or week, or year) is the kind of moment that warms our hearts and feeds our souls. Sometimes work is just… work. And while that sounds terrible, in reality, it’s a good thing. It takes a lot of emotional energy to do the kind of work that feeds your soul, 365 days a year. And sometimes you just want to do a little data entry while listening to Serial, and maybe have time to debate it afterward with your co-workers.

Living in the Bay Area in the middle of an out-of-control tech boom, I’ve found that there are two distinct narratives around entrepreneurship. One, though it has a bunch of high-flying rhetoric layered on top of it, is more or less all about money. It’s about, “leveraging” and “disrupting,” “funding rounds” and “exit strategies.” It’s less about the idea (or hell, the actual profit), and more about how much money you can pull down from VC firms and angel investors, and what plans you can come up with to sell your company for… a few billion. (Or, if that fails, burn it to the ground and move on to your next company and VC funding round, till the music stops.)

The other entrepreneurship narrative—the one that lives all over the Internet—is the narrative of constant passion and love. If we’ve left our jobs to set up our own shops, the story goes, every single thing we do should be infused with our deepest ethics, and every project we take on we should take on because it comes from a place of undying passion. (Not only is this not actually possible, working this way gets so unhealthily connected to your work that every time some Internet person tells you they hate what you wrote, your world falls apart. Instead of just shrugging and getting back to… your job.)

The problem with both of these (rather extreme) narratives, not to mention the quote I had on my office wall at twenty-five, is that it glosses over the fact that, sometimes, work is just work.

Work, Sashay, Shante (Repeat)

Even though we mostly failed at the “make our jobs extra fun” goal, it was hardly all failing for me this year. I also picked a verb for 2014, and apparently (because yes, I’d forgotten) that verb was “flourish.” This was coming off 2013, a year I started on maternity leave with a one-month-old baby. My goal that year was a somewhat more unofficial “survive.” Which we did, and I’m proud of. But for 2014, with a one-year-old, a newly relaunched website, and a really stressful year behind us, I wanted to flourish, both at work and at home. And I did, APW did, and the whole staff did.

The trouble is, flourish is a messier verb than you’d think. It involves a lot of wading around in the mud, getting dirty and frustrated, and then all of the work of growing. And while having flourished is delightful, actually working at flourishing is exhausting.

And that’s what work was like this year. Everyone on staff worked their asses off and grew (into new positions, longer hours, and more responsibility). We had fun moments of flourishing: nice meals out, fancy outfits, our regular and requisite trips to Salt Lake. And while our jobs were like work and not like play, we did try hard to be nice to ourselves and each other whenever we could. We had work lunches on the water, where I insisted Maddie order oysters on the company dime. (Because why not?) When we traveled, I made sure we got awesome hotel rooms and the company paid for everything from baggage handling fees to fancy room service. (Because if everyone is working hard, you should get fancy toast a few times a year.)

But our day to day was often an exhausting slog. And for a staff full of people who really enjoy each other’s company, there were countless times when we clearly just wanted someone else to meet their goddamn goal, or deadline, and stay out of our hair already. There were weekends where we couldn’t bear to think of talking to each other because OMG SO TIRED OF WORK.

Like What You Do

The torturous quote I had on my desk at twenty-five is a lie. If I had to rewrite it for myself, I’d rewrite it this way: “Do what you love, and you’ll work every day of your life.” Why? Not because work isn’t still ultimately… work. But rather because when the job is good, you’ll go to sleep thinking about how you can do it better, and wake up ready to give it another try.

I’d say my goal for 2015 should be rest, but it’s pretty clear that would nothing more then self-delusion. So maybe my goal for 2015 is simpler: more room service, more oysters, and much, much more work. To me, that sounds like perfection.

This post was sponsored by Squarespace. The Squarespace mission is to provide creative tools that give a voice to your ideas and help take some of the work out of…work (you can find out how the new Squarespace 7 makes that even easier by clicking right here.) To get you started, Squarespace is offering APWers a 10% discount on yearly subscriptions when you use the code APW14 at checkout. Click here to start your 14-day free trial.

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