Why I Traded in “The Dream” to Work for Someone Else

Sometimes the dream doesn't play the way you expect it to

apw-squarespacewoman sitting on a tree with a camera

Eight years ago, I was a newly pregnant college student in my last semester at university, working toward a dual degree in sociology and global studies (and a minor in art history, no less). I really wasn’t sure what exactly I intended to do with the degree, really, except maybe talk about art in fabulous international cafes while studying all the people who walked by. So when two friends of mine started a wedding photography business, I thought, “Oh hey! I wonder if I could do that, too?” Better yet, I thought that if I could do that job, I could also be home with my baby when he or she was born.

working for yourself isn’t everything

Fast-forward a few months and it turns out that, yes, my lifelong interest in hobbyist photography meant that I had developed a bit of an eye for capital-m Moments. My habit of following people around and taking notes with my eyes (aka being nosy as fuck) meant that I was good at finding those moments without people realizing I was there, and both of those skills are crucial parts of being a wedding photographer. A few months later, another friend asked if I would help her shoot a mammoth of an eight-hundred-guest wedding, and after that we started our own business.

The first few years were amazing: We shot so many weddings in such a small amount of time. Navigating the world of business was tricky, and we had our fair share of disputes (see also: having a business partner is hard), but we dove into the world of weddings, loved it, and it loved us right back. In those first three years, we made enough money to support ourselves and our families and travel a bit, and we met countless incredible couples. Additionally, I took on various editing and writing jobs in that time period, and though I wasn’t making hundreds of thousands of dollars a year (and sometimes things were still tight), it was enough to support my family while my husband dabbled around in different jobs, and it was enough for us to get by.

That’s kind of the dream, right? At least, it is if you read any number of articles online, all decrying the idea of working for anyone other than yourself. But the truth is, for every time I’ve read that the only way to be fulfilled by work is to be your own boss, I have a real-life example of how working for someone else has been more fulfilling.

sometimes “the dream” looks different in reality

Then, a year ago, we decided to move from Oregon back to the southern US, where we live today. Six months later, I got an email from Meg (yes, that Meg, the EIC of APW, who is also a longtime Internet friend—we met through another website that I worked for), asking if I would be interested in working three to five hours a week to help APW out during her maternity leave. As I have always aspired to work on the Internet (seriously, since I was fourteen in 1999 and that first AOL CD landed in my mailbox), I jumped at the chance—plus, three to five hours a week in a field I had plenty of experience with? That’s not much. So I added it to my workload, happily filling in when needed, and getting to know the APW team of Najva, Keriann, and Maddie in the process. We completed our move, and when Meg came back from maternity leave, she asked if I wanted to stay on. My husband didn’t have a job yet, and #workontheinternetgoals persisted, so I said yes. Color me surprised (and so pleased) when three to five hours a week turned into ten by year’s end, then fifteen, and then twenty… and now I find myself on track to be full-time with APW early next year.

Somewhere between hours ten and fifteen, I realized that, OMG: I kind of loved this working for someone else thing. And by kind of, I mean a whole, whole lot. But every time I talked to someone at APW about taking on more hours, I would get a little nervous—what if the Internet mysteriously vanishes? What if APW folds? What if I hate being part of a team, or I don’t like being on the hook for content and hours?

the hard knocks of self-employment

I think most people who go into business for themselves do so because, more than anything, they crave that special kind of freedom that self-employment offers. Even when it’s stressful as all get-out, and you’re pulling fifty-hour weeks to get everything finished, you know in the back of your mind that a few weeks later, you’ll be solely in charge of how you spend your time again. Even when you’re paying taxes and kicking yourself for not putting away the 30 to 40 percent you should have to pay the IRS right away (just me?), you know that payment plans exist and the IRS still likes you as long as you get them their money. Even when you have those random nights where you’re up until 2 a.m. editing because your kid just needed you to hang all day and all night, you realize that, oh hey: I have the luxury of being able to hang with my kid all day and all night (you know, if you want to).

I know I was definitely one of those people: Self-employment sounded like the dream because it would mean I was responsible for me, and that’s it. It also meant that I would have all of this time to go to those ballet classes I kept wanting try out (except I never actually did). What I didn’t realize about working for someone else, or at least about working for someone the way I do now, is that there’s a special brand of security that comes with not having to make all of the decisions yourself. I didn’t realize how light my shoulders would feel when every major—or even minor—business decision wasn’t on me. I didn’t realize how cool it is not to be concerned with budget, not having to drive three hours one way for a wedding every weekend, or how cool it is to know that if I have my hours as 1 p.m. to 4 p.m. on a Thursday, that’s all I have to work, and then I can walk away. The idea of leaving work at work was foreign to me until I got a boss, and now? Guys, I love leaving work at work.

I also love that in a culture where it often feels that we are inundated with articles and commercials and movies and even billboards that tell us what we need to do is go out on our own, start our own business, run our own show, I’ve found a lot of contentment while working for someone else. Sure, I know I’m expected to be online and available for a certain number of hours a week. Yes, I answer to one or two people at any given moment, and yes, there have been days where I would rather be outside instead of poring over endless comments… but every time I see a piece bemoaning not being your own boss, I find that I no longer agree. Sure, I’m not convinced I would fare well in a strict corporate office environment (especially not those that still place heavy restrictions on colorful hair and tattoos), but I’m responding quite well to knowing that it’s not all on me, all the time.

When it comes right down to it, I get paid (well, even!) to regularly write about my opinions on my favorite playground (the Internet), and then other people, who are generally kind, intelligent, and thoughtful, tell me their opinions on my opinions. And then we go back and forth, round and round, and I love it. At the end of any given work week I am often tired, run down, and looking forward to pouring a hefty glass of Tempranillo, but I’m also giddy, excited to talk about what I’ve been up to, and ready to hit the ground running on Monday. Let’s just say that when I was shooting thirty to forty weddings a year, I didn’t exactly greet Monday with quite the same gusto.

looking to the future

Of course, I do still have my photography business, and I’m even still booking weddings. The difference is that I’m not pouring money into advertising, and I’m not aggressively marketing. I have a steady paycheck that comes twice a month, and now I can choose to shoot up to five weddings a year (or maybe ten). I’m not sure if I’ll ever be fully comfortable with the idea that the Internet is truly my work space (seriously: what if it really does mysteriously vanish?!?), but… I’m looking forward to trying to get there.


This post was sponsored by Squarespace. This year we are partnering with Squarespace to bring you a series of career conversations about what it means to be a woman with hustle in 2016. If you’re in the market for a new job or looking to explore your options, one of the best things you can do for yourself is create a home online where you can show off your work in the form of a portfolio site, an online resume, or another hub where you can display just how awesome you are. Squarespace provides the creative tools that make it easy to build your online home beautifully, even if you’ve never made a website before and have no idea where to start. In conjunction with our career series this year, Squarespace is offering APWers a 10% discount on your first purchase when you use the code APW16 at checkout. Click here to get your website started today with a free 14-day trial from Squarespace.

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