Permission to Fail
Failing is as much a part of freelancing as bragging about working from home in pajamas. But we don't all fail equally.
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Six and a half years ago, when I decided to leave my reasonably secure full-time newsroom job to hurl myself into the erratic world of freelance writing, I thought I had a good idea of what the challenges would be. I expected it to be hard, but surely I’d be fine.
I knew I’d have to network relentlessly and hustle every single day. I’d have to know when to put the pressure on and resend a good pitch, and when to take my foot off the accelerator. I’d have to be agile and toil away to meet tight deadlines. Sometimes, I’d have to accept assignments that were boring or stupid or didn’t fill me with joy, just to keep my foot in the door. I’d have to tolerate the insult of late payments (not to mention payments that were far too low for the effort involved) and the headache of clumsy admin systems. And I knew that quite often I’d have to just Suck. It. Up.
About all of this, I was correct. It turns out all of those things really are required to stand out in the increasingly crowded labor force of independent workers. But above all, the thing that you have to be truly excellent at—the non-negotiable skill at which you have to excel—is failing: failing to land the pitch, failing to get paid, failing to get noticed at all.
Failing, it turns out, is as much a part of freelancing as bragging about working from home in pajamas. It happens all the time and, at least from what I can tell, it doesn’t notably let up—even as the assignments become more frequent and the compensation slowly ticks up. Most recently, I was reminded of this when no fewer than 16 publishing houses rejected my latest book proposal in the span of just two weeks. “It’s a nice idea,” the chorus seemed to go, “but not for us.”
Over the years, I’ve become better at not equating professional failure with personal defeat, but it’s not easy. I’m proud of the work I do, and that pride means that what’s professional is inextricably linked to what’s personal. Compartmentalizing can feel really hard.
But here’s the consolation: I’m not alone. Many of my fellow freelancers have told me about experiencing this same rollercoaster of emotions and that, like me, they’ve had to work hard to shrug off the thoughts that come with the recurring “no thank yous” (if you get a response at all)—thoughts like, maybe I’m not very good at this; maybe it’s time to try something else. And of course, this is also true of industries beyond journalism: The contract worker in marketing who didn’t get her contract renewed, the graphic designer who spent 10 hours on a proposal only to have it rejected. You get the idea.
This consoles me because it’s evidence that I’m not the odd one out. It frustrates me, because it’s sad that it’s so systemic. And another reason it frustrates me? Failure and rejection hits differently depending on who you are.
Welcome to the latest gender gap. This time it’s personal.
One Person’s Failure…
A few years ago, Claudia Goldin, a professor at Harvard who won the 2023 Nobel Prize in economics, spoke on a panel at the University of Chicago about a seemingly strange phenomenon.
At the time, women accounted for about one-third of undergraduate students in the discipline of economics, yet they only made up about 14% of full professors in departments that grant Ph.D.s in economics.
The explanation was simple: Women were dropping out of the field at a much higher rate than men. But the ramifications were terrible. “There are two males for every female Ph.D., three males for every female assistant professor and associate professor, and six males for every female full professor,” Goldin said at the event.
The real question therefore was, why were so many women dropping out?
The panelists offered a variety of ideas: Men might have more effective mentors and role models than women, Goldin, Alessandra Voena—who at the time was at the University of Chicago and has since moved to Stanford—and Veronica Guerrieri—of Chicago’s Booth School of Business—theorized. And women, they seemed to agree, are also not only competing with a tenure clock like their male counterparts, but with a biological clock. After all, having a child almost always means taking time away from research, study and teaching.
But there was another reason Goldin floated. Women undergrads who get less than an A- in a foundational economics college course, are more likely to give up economics as a course of study altogether. The same does not hold true for men.
“If they get below an A-, women are less likely to pursue economics, and the fraction who eventually major in economics drops,” explained Goldin. By contrast, “The guys, you could hit them over the head with a baseball bat, and they would still stay in economics.”
In other words, for many women, failure to reach a certain goal is prohibitive. It’s a message that you’re not welcome here. It really stings.
As for men? Sure, a lower grade might be suboptimal. But does it constitute a major barrier on the path they’ve already decided to take? Probably not.
The Blame Game
Other research corroborates what Goldin and her peers observed.
Academics from Brazil, recently wrote that in academia, “when faced with rejection, women are more likely than men to give up on submitting a paper in the following year.”
In the same article, they reference research showing that, in math competitions, women are less likely than men to keep competing if they lose the first or second round. And similarly, one study they mentioned that related to the Dutch Mathematical Olympiad, found that girls who did not make it to the second round of the competition were less likely than boys to try again next year.
In seeking to explain these findings, the authors cite research showing that “women are more averse to losses and react differently [than men] when they fail.” They don’t go into specific details as to what these differences look like, and where that loss aversion comes from but—as ever—social conditioning may hold some of the answers.
We know that, because of social norms and mores, women are more likely to internalize failure—blame themselves, for example—than men, who, when coming up with an explanation for their defeat, might point their finger at anything (or anyone) but themselves.
Also, women are often (but not always) more prone to imposter syndrome than men, particularly in fields that have traditionally been dominated by men. After a setback or rejection, this could be exacerbated to the point of being unbearable.
Finally, studies in recent years have shown that when a woman is working in a male-dominated field and she experiences a failure or rejection, it can be conflated with the failure or rejection of all women in that field. It’s something academics describe as gender salience. An unsubstantiated premise that leads to faulty conclusions like “I guess women just aren’t good at [insert topic here].”
The Proxy Problem
Without initially knowing there was a term for it, I pondered this particular effect in the aftermath of Elizabeth Holmes’ downfall.
Holmes—as a reminder—built Theranos, which originally hailed as a brilliantly innovative biotechnology company; until it was revealed to be little more than a house of cards, propped up by hopes, dreams, lies and inflated egos.
She’d captured the attention of the world because she was a shining rarity: a woman in a man’s world. Her Icarus-like saga thrilled the global media accordingly. (Icarus flew too close to the sun.—F.D., your ed)
In the aftermath of her criminal conviction in 2022, I asked women entrepreneurs how they felt about her failure—her downfall of epic proportions—and what I heard back both stunned and horrified me. They were concerned that Holmes—despite being a total anomaly in the sense that she’s a bona fide criminal—would become a sort of proxy for young women trying to raise money or sell an idea, particularly in Silicon Valley.
I truly don’t know if this concern is justified. I’ve not encountered credible evidence of it playing out. But as I wrote last year when Holmes started her prison sentence, “if it’s the way that someone feels, then that’s an effect that’s worth considering.”
It’s also worth noting that there really is a gender double standard in effect here. Male entrepreneurs do bad things too, but the fall never feels quite as shocking or dramatic. There’s a slap on the wrist, some admonishment and they’re back to fund-raising. (WeWork’s Adam Neumann and Uber’s Travis Kalanick are great examples of this while Sam Bankman-Fried’s really was a disaster too big to ignore.)
Research by the academics Francesca Manzi and Madeline Heilman suggests there could be something to these concerns.
In a series of studies, Manzi and Heilman presented individuals with information about fictional CEOs—some were portrayed as successful, some were unsuccessful; some were female, some were male.
“We told [participants] that [a] company was seeking a replacement for the CEO and asked them to evaluate either a female or a male candidate,” Manzi and Heilman explain. “We found that the way a female (but not male) leader performed determined the impact her presence had for the women who followed.” They concluded that if a female CEO was deemed to be successful, then the chances of a woman following her into leadership were not hurt. But when a woman failed in her role as CEO, it was less likely that a woman would follow her.
Because there are still far fewer women than men at the highest echelons of business, and because gender stereotypes still portray women as not having what it takes to be competent leaders, a female leader’s gender is highly salient.
Basically, we think of CEOs who are women as female CEOs, but we think of CEOs who are men, simply as CEOs. And when they fail? A woman is a failed female CEO. Whereas a man is just a failed CEO, like any other.
Reframing Defeat
Reflecting on this, it’s clear how the weight of failure might be magnified for a woman compared with how it feels for a man. It might not seem surprising that the prospect of not succeeding is enough to dissuade a woman from ever trying in the first place. The stakes are simply too high. And yes, in case you’re wondering, of course the stakes are even higher when you’re a woman of color, a queer woman, a disabled woman, an older woman…you get the picture.
All of this is infuriating. To know that centuries of systemic inequality and conditioning has hardwired women into denying themselves the chances they deserve; chances to prove their brilliance. It’s outrageous knowing that women waste time and energy and sleep, and—yes—tears, over failures that someone else might just attribute to the stock market or the weather, or better yet, someone else’s incompetence.
But as ever, being aware of this gender gap is the first step toward combating it. A next step might be to normalize failures that are just, well, failures. Most failures are hardly cataclysmic.
The truth is, we are more than our wins and we are more than our losses. Let’s allow ourselves to be flawed and brilliant individuals, who are unafraid to try. And try again.
Mara Altman
Emily Goligoski
Emma Haslett
