Is there a glass ceiling in the freelance world, or is it just scaremongering?

I’ve been seeing a lot of pieces lately about how the pursuit of entrepreneurship, or simply going freelance, isn’t solving the problem of the glass ceiling. This is a discussion that most definitely needs to be had, especially as millions of jobs slowly get phased out every year to become contract and freelance positions when women already face major disparities in salaried work.

Having spent my entire career in boys’ towns mixed with coming of age in a time when virtually all labor is being devalued, I have a lot of mixed thoughts and feelings about this based on both experience and observations.

Woman in a suit propping up a ceiling

I was pointed to this NY Mag piece bluntly titled “Going Freelance Won’t Solve Your Problems”. The author’s experience definitely should not be discounted, nor should that of the other women who she interviewed where they had everything happen from attorneys taking this “Oh isn’t that cute that you started this business! Is this meant to pay for your kids’ after-school activities?” attitude to men who literally ask her to take less money for doing the same job.

She also makes the observation that freelance men make a stunning 50% more than freelance women do. My research provided some REALLY dismal statistics:

Wow. That’s pretty depressing.

But also angering for many reasons. Statistics never tell the whole story, so here’s my take on this phenomenon.


First, we need to stop discouraging women from taking risks, period.

Women are not socialized to take risks the way men are. We need to end this like, 50 years ago.

We’re told to go for the sure thing even if that “sure thing” winds up stabbing us in the back. Even if that supposedly stable and secure path winds up holding us back in numerous ways!

And it starts early! When I was growing up, there weren’t a whole lot of female role models I had for going off the beaten path, especially in something like game development which was still a totally new field. I looked up to Roberta Williams obviously, but in terms of my immediate family and neighborhood I was only shown women who aspired to get jobs and/or husbands: not strike out on their own.

Society really programs women to be risk-averse for the most part. It’s been true of personal finance, and true of many other facets. I’m not saying that there’s no risk-averse men out there but when it comes to way that we’re socialized, in America at least? Women are really told to go for the sure thing and therefore to not expect much if they want go to their own way. No risk = no reward. It’s time to change this.


Women are socialized to be overly agreeable and this also needs to stop.

Let’s look at traditional employment for a second because of the way that women have different expectations shoved on them in the workplace: office housework, for instance. If you don’t do things like take notes during meetings when that’s not your job, make coffee, and plan office birthday parties, then you’re not a team player and this will count against you in many ways. But then if you do go ahead and do these things, it holds you back in a different way because the men in the office aren’t expected to drop what they’re doing for these kinds of things and it takes away time from your real actual work and there’s opportunities you can be missing. But women are stuck doing this crap because of this incessant programming to be too agreeable. 

You know, when a man won’t take crap from a boss he’s assertive and standing up for himself. He’s smart if he negotiates a salary. But the second a woman does these things, she’s a bossy bitch who could be a problem and is called entitled if she demands more money– even if office housework is now being baked into her actual job that has nothing to do with changing the coffee filters or “helping” a co-worker to the point that she’s missing out on important meetings or conferences.

For women who’ve worked mostly rank-and-file jobs where you have to constantly dole out “Yes, sir/ma’am” and “I’m sorry”, it’s very hard to break out of this constant state of agreeability which is often driven by fear. Fear that you’ll anger the person who signs the paycheck and therefore lose your job, because if you just lean in then you may face accusations of being too “bossy” or disagreeable.


Close the confidence gap.

In addition to the very real wage gap, there is also a confidence gap. Many female freelance writers feel that there is definitely a gender disparity when it comes to professional writing, and their proposed solution? Pretend you’re a white man.

Confidence issues know no bounds when it comes to race and gender, but let’s face it: just like how American society tells women not to be risk-takers and only go for the “secure” path, it also does NOT encourage us to be confident about everything from our body image to what we can do– because we’re given this schizoid message that we need to love ourselves and be proud of our abilities, but then we can’t have *too much* bravado or else we’re arrogant.

Um, fuck that so hard.

BE PROUD of what you’ve accomplished. Don’t downplay your deeds. Don’t go too far in the other direction and embellish them either, but women have a tendency to downplay themselves so as to not intimidate the men in the room: whether’s understating your intelligence, earnings, or sheer ferocity.

Granted, some of this is generational rather than gender-specific given how many of us have had to dumb down our resumes when a better job wouldn’t take us, and that takes a toll. A toll that can unfortunately still bear down on you upon going freelance.

If you are not feeling really confident in yourself or abilities, it’s definitely not going to make you want to take any risks or step outside your comfort zone. And despite how far society has come, this is another social more that hurts women: that expectation to be passive and agreeable, which heavily contributes to said confidence issues.


If you’re getting clients who lowball you, you’re looking in the wrong places.

The NY Mag piece discusses a designer getting pushback about her fees from men considering her services, but not from women. I’ve gotten pushback about my fees numerous times also predominantly from men but sometimes from women, and these attempts were so numerous that I actually had a post about this I initially planned to make public then decided not to once this stopped happening to me.

Woman asking for money from angry man with wallet

How did I do it, you ask? I got off those shitty race-to-the-bottom bidding platforms and refuse to work for content mills that pay less than one cent a word. I did not stay in that “I HAVE TO take this shitty gig to pay my bills!” mindset and kept looking and trying until I found something better than those content mills.

It takes time to work your way up to those vaunted $1-2/word posts if you’re in the market for well-paying writing work, but you have better options than bidding against someone in Cambodia on Upwork who will write that 50,000 word e-book for pennies on the dollar.

Oh, and when someone also asks me to lower my fees for them, I already know they’re not worth dealing with. I am not an employee at a publisher where I have to take whatever client they stick me with. I can show that person the door the second they start balking about my rates. I already know that this client is going to demand roast free-range duck for the price of a McNugget, and anyone they refer me to is also probably going to be similar.

Getting pushback about your fees is a freelancer rite of passage. It sucks, but that’s how you learn how to avoid shitty clients who will make your life miserable anyway. And it’s also your cue to look elsewhere for clients!


There’s other gender-neutral aspects of running a business that many people making the shift simply haven’t learned yet.

I side-eyed the bejesus out of this paragraph of that NY Mag piece:

“Women who go freelance are likely to find a lot of their work problems repeated outside the confines of their salaried job — without an HR rep or sympathetic co-workers to lean on. Couldn’t get your boss to give you a raise? Try negotiating several times a month, for each new job you take on. Can’t get your co-workers to take you seriously in a meeting? Try getting a client to approve revisions when they’re only dealing with you. Want more time with your kids? Watch as work bleeds into every corner of your day. Many of the problems of traditional employment are magnified, not reduced, by working for yourself.”

Negotiate several times a month? Yeah, if you’re on those shitty platforms that make your life miserable, or you waste time on bad leads. Otherwise, if you’re negotiating with many new clients then this is a good problem to have. Decentralizing your income is where it’s at because if one client dries up you have others to tap.

This also honestly depends on what kind of work you do. Writers can get very or semi stable work at Writer Access, where they take care of all the client management aspects and when you’re on the dashboard you already have an idea of how much you’ll get paid and therefore determine if it is worth your time. For designers and professional services it’s different, but if you’re a consultant you’re apt to have more flexibility because you choose what kind of engagements to offer and what projects to take on.

As for work bleeding into every corner of your day, this only happens if you let it.

You have to learn how to prioritize and outsource. Refusal to delegate, whether it’s a business or personal task, is what causes so many freelancers to just self-destruct. Because yes, in the beginning I was working more than I’d ever worked at any full-time job– but the other day, I reveled in the fact that I was able to do some work in the morning then I wanted to enjoy the amazing summer day, just because I can. I went for a run in my gorgeous neighborhood then went to the city and ate tacos in the sun, found a coffee shop and worked on Clam Chowder Hub Run, then got a free feed courtesy of Venture Beat because I’m at that point of my career. I finished my writing work when I got home, but not before I answered emails and reserved more writing jobs on the way back.

Come on, virtually NO job is going to offer that kind of awesome quality of life.

(If you’ve got kids, you likely angrily sputtered at that last sentence in that above paragraph so I highly recommend reading Wealthy Single Mommy because she explains how she does it all and makes bank in the process, and shows how other successful single moms did the same.)

But I’ve met other entrepreneurs and freelancers without children who talk about how they work all the time and while I go through spells of this myself, it took some practice to get my time management under control. That is something that business owners of all genders excel and fail at. By telling women that working for themselves is going to be this never-ending toil and they should just stick to a desk job, it’s making these articles look like ploys to just keep us locked down in miserable and inflexible jobs that don’t pay enough. Fuck that noise.

In closing, while a lot of valid concerns are being addressed in women picking up a greater part of freelance work– especially writing– I think that this kind of scaremongering is really unwarranted and does not help us shatter the glass ceiling both in and out of traditional employment.

It’s going to take massive social changes so I beg of you, if you are female or female-identifying and work for yourself in some capacity PLEASE be a good role model to the young girls in your life, and encourage them early to be confident, true to themselves, and unafraid to reach for the stars. A constant stream of “Yes, sir/m’aam” and “I’ll do the job for $250 since you don’t want to pay $500!” after years of being brainwashed to be agreeable is no way to make a living or live a life.

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