Ann Friedman: how long have you been self-employed?
Eight years. EIGHT! My business is a third grader.
AF: Before you went freelance, did you aspire to work for yourself?
Only in a fantastical pipe-dreamy kind of way. It seemed so fun! Like an episode of that show about a freelance NYC cartoonist, Caroline in the City. (Oh, soooo 90s!)
AF: What made you take the leap into self-employment?
It was not my choice initially. I was laid off, a by-product of the 2008 housing crash. The economy troubles trickled down to the mid-size design studio I was working and during this time they tried to grow too quickly and had to let a sizable portion of the staff go one day. There were no hints the company was in trouble. This was going on city-wide so I knew it would be hard to find another FT position right away, so that’s how I decided to go for the pipe-dream. At this point, I had about 1.5 month’s rent and a severance package of one month’s pay to my name, plus a pile of student loans, some pressing dental needs, and had made no other preparations in starting a business.
AF: What were your biggest complaints or issues with working a staff job? Have those problems gone away now that you’re self-employed?
The first place I worked in Chicago was run under an iron-fist level of management. They read our email and heavily monitored internet use as well as our time. The pay was miserly and there were some stunningly bad relationship dynamics that they tried to patch up by making everyone do personality tests and then leaked the answers people gave, yielding much gossip. That, and the issues related to my autonomy are much improved now, though I still work all the dang time.
The only other issues I’ve run into have stemmed from being the only female in a space, or on a team/project. Like the time, one of my guy workmates photoshopped my face onto the body of a swimsuit model and emailed it to the whole company. You know, cause, jokes are funny. </sarcasm> Gender issues still come up from time to time, because we live in a world where sexism still exists.
At this point, I don’t think I would “fit” in very many offices anymore. I’ve seen and heard too much bullshit through friends or experienced it personally to have much faith in that system. It would have to be someplace with an unusually flexible, non-traditional, non-hierarchical set-up with lots of women and gender non-conforming humans, people of color, queer folks, parents, and all ages of people who are empowered to make decisions about all aspects of the place. Such places do exist, but they are few and far between. I hope for more change here, for everyone’s benefit.
AF: Are there any struggles related to being self-employed that you feel have to do with your gender?
Anyone who isn’t a white cis guy tends to be more interested in my work, but generally, there is a struggle to be taken seriously. People won’t ask me about work and yet they will routinely ask my partner about his business. Cool, but it would be even cooler if people switched that habit up a bit. I’ve heard lots of women convey this. I’ve been also brushed off by lawyers or other business-adjacent professionals I’ve tried to hire. They’re all, “aren’t you cute with your little business”. Excuse moi, you don’t know what kind of money I might have for you. Same goes for negotiating fees. My women clients very rarely push back about my fees, but it happens with more frequency if I’m contacted by a male-driven business.
AF: Do you identify as an entrepreneur?
I don’t typically apply the term to myself, but I don’t reject it outright. It is technically true by dictionary standards. But it’s hard not to hear it without a heaping dose of over-confidence and snootiness (insert monocle and yacht). It’s also one of those words I can never spell correctly on the first try. Not my style. I use “self-employed” the most often because freelance doesn’t convey the grit and hustle it takes to start, grow, and maintain a business.
AF: I’m sure people seek advice from you about self-employment. Do you advise other women to go freelance? Why or why not?
Work is hard regardless if it’s for someone else or for yourself. It’s a tough haul to cobble together a growing freelance income just like it is to land a FT gig that isn’t soul-sucking.
I do advise women to go freelance, but with caveats, because it’s not for everyone. The financial risks are super real, but also it requires much alone time and constant self-governance. Some do better with the firm structure a 9-5 gig affords or do their best work among teams. Zero shame in that! However, there are lots more excellent business resources available now than when I started so it is possible to learn as you go. Other women-run businesses are critical to befriend, having a crew has been major through the hardest parts. And finally, no one talks about this, but so many small businesses are in debt and it’s not the end of the world nor is it something to be ashamed of. It is possible to have a successful business and be able to manage debt at the same time. ’Tis the American way, it seems. I recommend this book to everyone who has non-variable income. It fundamentally changed my entire relationship to money which in turn majorly impacted my income.