The Overachiever's Trap: Why Trying Harder Is the Thing Standing Between You and Peace
A bestselling writer on the uncomfortable truth: the dream life you're chasing may be the thing keeping you from the life you have
The Big Idea: Trying harder isn’t a virtue. Often, it’s a trap. The relentless pressure to do more, be more, and never quit isn’t a path to the dream life. It’s a path to burnout, self-erasure, and a life spent chasing a mirage.
Why It Matters: We inherited a story: winners never quit. That story has a cost, and most of us are paying it quietly.
Try This Today: The next time you catch yourself thinking, I should be doing more, pause and ask: Who taught me that? Was it actually your own desire—or a standard you absorbed from social media, work culture, family expectations, or the general pressure to “have it all”? Sometimes the first step toward self-acceptance is simply noticing which expectations were never really yours to begin with.
These ideas come from How to Stop Trying: An Overachiever’s Guide to Self-Acceptance, Letting Go, and Other Impossible Things by Kate Williams . Kate is a novelist, journalist, and New York Times bestselling ghostwriter who has written for Elle, Cosmopolitan, Women’s Health, and Shape, among others. Read on for 5 of her big ideas.
1. Trying, and trying again, is killing us.
Gen X and millennial women were raised to believe that all we had to do to “have it all” was try. This messaging has gone into overdrive in the last couple of decades with the ubiquity of social media and the rise of influencers. Everywhere we look, we are being told that if we want it bad enough and are willing to do whatever it takes, then our dream life is within reach. But making your dreams come true isn’t just a matter of work. It’s also a matter of circumstance, opportunity, luck, and a million other things outside of our control.
However, this is rarely acknowledged by those encouraging us to just keep going. So, we blame ourselves for not being able to achieve the perfect life that we’re told is possible. No matter how hard we’ve tried or how much we’ve worked, we assume that it has not been enough. For me, this hit full force when I was trying to have a second child. Over the course of three years of trying, I went through multiple miscarriages and failed fertility treatments. I was growing depressed, and the cycles of hope and disappointment were making it hard to enjoy the rest of my life. I was so focused on what I wanted that I couldn’t appreciate what I had. And yet, when I decided to stop trying, a lot of people couldn’t understand this: I hadn’t exhausted all of my options, so why didn’t I want to keep going?
As a kid, one of the first life philosophies I was ever exposed to was that winners never quit and quitters never win, so I became that kitten clinging to a branch. I hung in there, no matter what. I white-knuckled my way through life because I was scared that quitting would mean I was weak. This isn’t a path to your dream life. This is a path to burnout and exhaustion.
If we want to enjoy life and pursue what really matters to us, we have to make perseverance a choice, not a habit. We have to stop trying so hard at everything and reserve our trying for things we really, truly care about. This means that sometimes we have to quit. We have to stop being the kitten and learn to let go.
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2. Internalized misogyny is messing with your head.
Living in a misogynistic society has taught us that certain types of women, and certain characteristics in women, are more valuable than others. From early on, we’re told that these are the types of women that matter: nurturing women, caregiving women, selfless women, nice women, pretty women, and thin women. We learn to tamp down everything about us that doesn’t fit into these molds because we want to matter, too. As a result, so much of our trying isn’t even about trying to achieve or succeed. It’s just about trying to be who we think we should be, instead of letting ourselves be who we are.
Misogyny has given us fat-shaming, victim-shaming, slut-shaming, mom-shaming, and a whole cornucopia of other socially acceptable ways to keep women in line. The real tragedy is that we internalize all of these and turn this lens of judgment on ourselves. No matter how good we are, we’ll probably never feel like we’re quite good enough. Career women are particularly susceptible to internalized misogyny because we’ve been told that so many of the attributes necessary for success—assertiveness, advocating for yourself, ambition—aren’t feminine traits. The irony is that, even as we’re failing to have it all, we still feel guilty for trying in the first place. We feel like our careers aren’t something we can be proud of. Instead, they’re something that we need to make up for.
“Even as we’re failing to have it all, we still feel guilty for trying in the first place.”
When I became a mother, I felt like I had to try extra hard to be perfect, because the fact that I had a career I cared about meant that I already had one strike against me. This wasn’t just in my head—I’ll never forget that when I was looking for childcare so that I could keep writing, a female relative reminded me that some women write when the kids are in bed. Also, when we see career women portrayed in pop culture, their career is presented as merely a misguided attempt at a meaningful life. The 1987 classic Baby Boom is a prime example of this—no coincidence it was one of my favorite movies growing up—but you can also see this in contemporary films like Babygirl, which imply that women only become professionally ambitious because some other part of their life is lacking. As a result, many of us harbor shame about our careers, which only makes us try harder at work and home to make up for it. There’s no magic laser gun that vaporizes internalized misogyny, but the more we become aware of it, the less we allow it to drive us to keep up with impossible expectations.
3. Productivity is patriarchal, and that’s a problem.
Our culture is obsessed with getting more done, and we are told that the key to happiness is figuring out how to do more. But our productivity problem isn’t that we need to do more. Our productivity problem is that there is too much to do.
This is especially true for women. Over the past couple of generations, as our culture has shifted to put more responsibility on women outside the home, duties inside the home have not shifted to make up for that. More than three-quarters of women in the United States between the ages of 25 and 44 work outside the home, yet women still do two and a half times the unpaid labor as men. This is part of the paradox of being a woman in the 21st century. We’re constantly being told that our unpaid work—nurturing and caregiving—is our most important work, yet this same work is consistently diminished because it is unpaid. Capitalism only truly values what makes money, which is why even in 2025 you’ll hear people say, “Yeah, but what does she do all day?” when talking about a stay-at-home mom.
Productivity is a trap. It’s a game we can’t win. Emphasizing productivity leads us to prioritize quantity (getting as much done as fast as possible) over quality (enjoying ourselves while we do something meaningful), and we end up feeling like we’re missing out on our lives.
We have to get comfortable with the mess of letting things go undone and confront the gender biases that have loaded our to-do lists. We also have to stop praising men for doing the bare minimum. Just because he is not lying down in front of her car when she tries to drive to work in the morning does not mean he is being supportive.
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4. Acceptance isn’t settling.
We live in a world of more and better, where we’re taught that we should always be trying to do better, be better, and have more. We think we should never let ourselves get comfortable with who we are or what we have because that might mean we are settling for less. We’ve been taught that anything less than perfection is settling, so we think we can only accept something if it is perfect. This belief applies to ourselves.
However, acceptance isn’t a declaration of perfection, it’s simply acknowledging something for what it is and deciding to no longer devote time and energy to trying to change it. When you accept something, you admit to yourself that perfection does not exist, so there’s no point in holding out for it. When you settle, you tell yourself that perfection does exist, just not for you, so you’d better take whatever old crap you can get. Acceptance is abundance, and settling is scarcity.
“You are allowed to be who you are. You are allowed to have flaws.”
As long as you fear acceptance means settling, you will continue trying to be someone else and have something different. More often than not, when you’re trying, you’re buying. This is why motivational influencers are always telling you not get too comfortable. This isn’t because comfort is bad for you. Comfort is bad for them, because if you get too comfortable with yourself, then you’ll stop buying their online courses that promise to make you into someone different. You are allowed to be who you are. You are allowed to have flaws. You are allowed to be human. Yes, even if you’re a woman. There is no better person for you to be than the person you are, and there is no better life for you to live than the one you have. It’s not settling to believe this.
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5. It’s not bad to feel good.
Women are constantly being sold things that are supposed to make them feel better and make their lives easier, and the assumption behind these messages is that we feel bad and that our lives are hard. Even though they are often correct, this messaging teaches us that it is normal to feel bad about ourselves. After a while, we start to feel that it is dangerous to feel good because doing so might leave us out of step with our peers. Think of the iconic scene in Mean Girls, where Cady Heron commits the huge faux pas of thanking someone for a compliment rather than vehemently denying it. Yeah, Mean Girls is a satire, but it’s funny cause it’s true. When I was growing up, a popular slumber party game was to sit in a circle and each say something we hated about ourselves. It was literally a competition to see who found themselves the most deplorable.
Women are often taught that self-deprecation is a form of politeness (as a million pop songs will tell you, the good woman is a humble woman who doesn’t know she’s beautiful), and we also use it as a defense. We point out everything that is wrong with us because we don’t want someone else to do it first. However, while this behavior might start as a way to fit in, after a while, we begin to believe what we’re saying: that we’re too fat or too old, our house is a disaster, and we can’t do anything right.
It is a great and evil irony that we live in a world that tells us that the more we hate ourselves, the more lovable we become. But we can decide to love ourselves despite the consequences. Self-love and compassion is where we can try harder. We don’t have to think we’re the best. We just have to stop believing we’re the worst.
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All such good reminders.
Trying more stops working because of the law of diminishing returns. None of us can escape it, no matter how much we may be exceptional in other ways — it’s the glass ceiling that will actually never shatter.