“Expect to be Graded on This.”
That’s the title of the very first chapter of the book, The Perfectionist’s Guide to Losing Control by Katherine Morgan Schafler.
When I first read it, pen in hand and ready to read, I literally laughed out loud. She knows exactly who she’s talking to.
In the book, Schafler, who worked as an on-site therapist at Google for many years, walks us through the different faces of perfectionism. There’s classic perfectionists (reliable and detail-oriented to a fault), intense perfectionists (singularly focused on one sharp goal), parisian perfectionists (who spike on deep connections with others), procrastinator perfectionists (who excel at the art of preparing for the thing vs. doing the thing), and messy perfectionists (who feed off new ideas and fresh starts more than finishes).
I read the book right when it came out and promptly texted a dozen friends who I suspected might relate. In a fortuitous Internet dream come true, I slid into the author’s DMs and she agreed to join us in person for a very special book club, one that eventually became less about the book and more about group therapy for me and all of my similarly high-achieving perfectionistic friends, paralyzed by one thing or another, holding back forward progress.
Things like:
“It will never be perfect.”
“What if I can’t reach the top?”
“What if I lose the people I care about?”
“What if I pick the wrong thing?”
“I’m just not ready.”
That last point—“I’m not ready”—reminded me of a recurring dynamic I’ve observed in how perfectionism influences career paths. At the time, I was dedicating most of my fractional work cycles to projects in crypto and web3, fields that, like many emerging tech industries, tend to skew heavily male in representation. While the number of organizations focused on bringing more women into the space is certainly growing, one week I had two conversations about how people landed jobs in crypto that highlighted a striking difference in approach.
In one conversation, a male friend shared how he pivoted from education to crypto. He casually mentioned his curiosity about the ecosystem to another friend, who then invited him to a happy hour. There, he met a founder in the space, and shortly afterward, he was hired—eventually becoming COO at that organization.
In the other conversation, a female friend told me about the great effort she’d been putting into making crypto feel more accessible and welcoming for women. She started a DAO for crypto-curious female professionals, where she led skill-building workshops, hosted crypto 101 lessons, and facilitated peer feedback on resumes to help members prepare for jobs in the field.
This difference in approaches—one informal and opportunistic, the other deliberate and structured—struck me as potentially emblematic of a larger pattern. Are women spending more time preparing, while men focus on figuring things out as they go? If so, does this dynamic mean that the most emerging and cutting-edge fields will consistently skew male-dominated? More importantly, can we break free from this pattern of perfectionism and reimagine how people enter these spaces?
The Pattern of Perfectionism
Schafler’s book resonates with themes from Reshma Saujani's book, Brave, Not Perfect, where she shares her journey of breaking free from societal expectations of the so-called perfect, “good girl" prototype to pursue more ambitious goals in two messier, real world arenas: Politics and entrepreneurship.
That women are more likely to self-identify as perfectionists is likely not a surprise. But, the margins aren’t by as much as you might think (72% of women vs. 65% of men self-identified as perfectionists, according to one study).
Regardless of gender, this trend toward perfectionism has intensified over the past few decades, with socially prescribed perfectionism (ie: the idea that you have to be “perfect” to gain approval”) increasing among college students by 32% between 1989 and 2017.
That said, it’s hard (impossible, maybe) to untangle where the internalization of this mindset begins and ends vs. how much of it is shaped by societal expectations. And for whatever reason, perfectionism as a mindset seems to shape the female journey of leadership and success across many contexts and archetypes.
From Taylor Swift:
I'm damned if I do give a damn what people say.
No deal
The 1950s shit they want from me
I just wanna stay in that lavender haze
To Barbie:
You have to never get old, never be rude, never show off, never be selfish, never fall down, never fail, never show fear, never get out of line.
It's too hard! It's too contradictory and nobody gives you a medal or says thank you! And it turns out in fact that not only are you doing everything wrong, but also everything is your fault.
And even lyrics sung by the character Alice Paul, one of the leaders of the women’s suffrage movement, in Suffs: The Musical:
She sounds just like my father
Please Alice, have some sense
Don't you know that no one likes a girl who's too intense
Don't get so defensive Alice, don't be so aggressive
Settle down, you're too obsessive
I've heard it many times before
But I don't wanna hear it anymore
These cultural touchpoints all highlight the same underlying theme of the relentless societal expectation for women to maintain a perfect exterior. Whether it’s Swift railing against outdated stereotypes, Barbie grappling with impossible contradictions, or Alice Paul confronting the pushback against her intensity, the message is clear: Women are held to a standard of polish and composure that leaves no room for chaos—or humanity.
Clearly, there’s a disconnect. If men and women experience perfectionism in near-equal numbers, yet these themes dominate the female narrative, perhaps the difference isn’t in the perfectionism itself but in the pressure to keep it contained.
That’s why the title of this seminal book, The Perfectionist’s Guide to Losing Control, is such a powerful call to action. Chaos, after all, is the antithesis of order—and losing control is an act of rebellion against perfectionism’s constraints.
It begs the question: How can you introduce a little bit of chaos?
Permission to Lose Control
About a year ago, I traveled upstate for my solo annual planning retreat. This tradition has become a cornerstone of my professional rhythm—I use the time to reflect on the past year and set goals and objectives for the year ahead.
But last year, my retreat didn’t go as planned. On the very day I was supposed to leave, one of my education projects hit a panic button chaos moment. It pulled me into superhero mode, and I spent half the weekend on phone calls, triaging the situation, and crafting backup plans B and C to ensure the students still had a meaningful learning experience.
With this recency bias hanging over me, forward-thinking planning was impossible. Every time I sat down to write, instead of goals and aspirations, I found myself dredging up story after story about times I felt failed by the education system—moments from my life that had clearly left a mark.
By the end of the weekend, I realized something surprising: I was still pretty mad about it all.
About two weeks later, I happened to be at another event where I ran into the book’s author, Katherine Morgan Schafler, in person. When she asked how I was doing, I told her about my recent weekend retreat upstate, and the surprisingly angry undercurrent of the essays and stories that I apparently needed to spend the time writing out.
She listened thoughtfully and then asked a question that stopped me in my tracks: “What if you gave yourself permission to be angry for a whole year?”
I laughed at the absurdity of it. I’ve never thought of myself as an angry person. The idea of intentionally sitting with that emotion—let alone for an entire year—felt irrational, even reckless.
But, just for fun, I decided to give it a try. So I started blasting femme rage anthems on repeat. I’ve let my patience dwindle to a threadbare fuse. I’ve said exactly what I mean, even when it wasn’t the nicest thing or what people wanted to hear. I will admit that sometimes this has not gone as well as it could. Eh.
I’ve also channeled some serious Office Space energy: In my head, I shove imaginary computers out of windows, smash laptops against desks, or fling plates onto sidewalks. But I’ve also taken it a step further. I’ve been to a legit rage room in Brooklyn—multiple times—to actually smash computer parts to bits. It’s…kinda nice, actually. You ought to give it a try.
What I’ve learned is, permission to feel angry isn’t about losing control entirely—it’s about letting go of the need to keep everything contained. And sure, maybe smashing up an old printer or a few Ikea plates (in a controlled environment!) can actually be a very good thing.
So next year, I’ll ask you the same question: What if you gave yourself permission to get a little angry? What small act of rebellion would you try? Count yourself off if you have to. 3…2…1…let go.
