Failure is an important part of your growth and development of resilience. Don’t be afraid to fail.

—MICHELLE OBAMA, speech at Apollo Theater, 2015


I don’t fail.

Or maybe I should say that I’ve never been okay with failing. I’m a semi-reformed perfectionist— one who was once so hell-bent on being perfect that I preferred to give up on things than to try my best and potentially fail at them.

I quit swim lessons when I was six. One Saturday morning during free swim at the end of class, the teacher explained that we’d have to go underwater and open our eyes without goggles at the next lesson to recover something from below the surface. I went home and told my mother I wasn’t doing that. The chlorine would sting, and why would I put myself through unnecessary pain when Olympic swimmers could wear goggles and I never went to the pool or beach without mine? I couldn’t think of a reason or situation in which this skill would be one I’d need, and deep down I doubted my ability to keep my unprotected eyes open long enough underwater to retrieve the rings my teacher would drop into the pool for us to find. My mother asked the teacher if I could still wear my goggles, but she said no. So, I refused to go back.

I quit ballet when I was eight and a half because a ballerina came to my class and showed us what her feet looked like. She explained that when you get pointe shoes, you lose toenails and develop corns and bunions and that even breaking a toe or two is normal. I was afraid I wouldn’t be able to deal with the pain—that the second I tried to go on pointe and it hurt too badly or the dancers around me succeeded before I could, I would feel like an untalented loser. I loved dancing, I thought, so I should quit before pointe shoes were handed out and broken in. I should go before everyone could be better than I’d ever be.

I went on to quit the saxophone and the clarinet, chorus, basketball, and competitive cheerleading, though I stuck that out the longest despite feeling like I wasn’t as good or as flexible as the other girls. I even wanted to quit when I was learning to drive because I couldn’t figure out how to parallel park. And on and on it went.

At the same time, I stuck with the things I did well, the things I knew I had to do to keep up my veneer of perfection. I got excellent grades. I was an officer in student government. I was on the yearbook and prom committees, and I was in poetry club. I had the list of colleges I wanted to apply to finalized by sophomore year. I aced tests and signed up for AP classes, worked and went to church every Sunday with my family, and was a “good girl,” always making it home before curfew. I met everyone’s expectations, almost always.

As I read Michelle Obama’s memoir, I deeply related to her description of herself as a “box checker.” She writes that she got good grades and applied to the best schools and remained laser-focused on her goals. She wasn’t, as she called it, “a swerver.” And despite my streak of quitting, I was the same way. Some might have seen me as a quitter, but I saw myself as someone unwilling to take unnecessary risks. Why risk failing when I knew I could excel at so many other, more important things?

But I wasn’t exactly happy. I was always anxious and overwhelmed, and working so hard to be seen as perfect when I was so far from that ideal was exhausting. Similarly, Michelle had painted herself into a corner. She’d become the person she thought she was supposed to be—the person she thought everyone else expected her to be. And it wasn’t until she experienced major loss—the death of a close friend and her father—that she realized where all that box checking had landed her. She was “successful,” but at what cost?

When Michelle met Barack, she was at this crossroads. And meeting someone whose life had followed such an untraditional path inspired her to ask herself a new question. Instead of thinking about who everyone else expected her to be, Michelle was able to ask herself: Who do I want to be?

She went on to take some big risks, including a huge career change for herself, and of course eventually agreeing to support her husband’s decision to pursue politics. And in a swerve to end all swerves—his running for president of the United States—Michelle encountered the largest risk she’d ever taken. She was risking her very lucrative career, her children’s futures, and the life she’d imagined for herself all at once.

My crossroads came when I decided to listen to a whisper that had always been inside me, but that I’d buried again and again because the risk of failing was too great: I wanted to be a writer. This would be my big swerve—the first and perhaps only big risk I’d ever been brave enough to take. And I would (and did) fail. A lot.

Take, for instance, this very book. This is not the book I set out to write. If you scroll back through miles of my Twitter feed, you’ll see just how true that is. A very different book was announced ages ago, one that was intended to be a biography of the Obamas—both Michelle and Barack—and one I tried and failed to complete for nearly two years, spanning the pregnancy and birth of my first kid, my departure from a professional career in publishing, the COVID-19 pandemic, unprecedented civil and racial unrest, and the worst mental health months I’ve had in my whole life.

During this time, and with the help of therapy, I realized my fear of failure came from a fear of vulnerability. I had never written a book like the one I was attempting, and trying to do things I’ve never done before always puts me in a very vulnerable position: a place where someone could say “you suck” and it might be true. It was the same way I’d felt as a kid when I’d been so afraid of failing—of opening my eyes underwater, going on pointe, playing a new instrument or sport—that I’d quit. Feeling incompetent or inadequate is a very dangerous way to feel if you’re someone, like I was, who ties their self-worth directly to how good or bad they are at everything.

I feared if people found out I wasn’t perfect, they’d figure out I wasn’t valuable. And if I wasn’t valuable, was I worthy of their time, or more importantly, their love?

(The secret was, everyone already knew I wasn’t perfect. The secret was, I was loved and accepted anyway.)

But back to the book.

I wanted to quit, but I didn’t. And because that book just would not and could not work—not for me, not at the time, not in the world as it existed—I had to admit it: I had tried, and I had failed.

When my editors and I realized the book wasn’t working, we had a few conversations about why, and then decided to pivot—to move in a new and different direction. As I’d been researching the original book, I’d collected a ton of quotes by both Michelle and Barack, and I kept being drawn to Michelle’s, especially any that were about success and self-love and resilience.

The quote that opens this essay, about failure and growth, was one that had always stuck with me. I couldn’t shake the assertion that I would only grow and get better every time I failed at something. It was revolutionary, this idea that I was inherently valuable, even when I wasn’t perfect. That perhaps imperfection was a good thing—it would help me grow.

If you’re anything like me, anything like Michelle, or even the exact opposite of a box checker, I want to make sure you hear this, so I’ll say it again: You are inherently valuable, even when you are not perfect.

So, this book will not be perfect because, despite my tireless efforts to overcome my own humanity, I am not perfect. But I will be honest. And I will be open. And I hope you find some courage in these pages all the same. I hope you’ll be as touched and inspired by Michelle Obama’s words as I have been.

I’m no longer quitting when I’m afraid I will fail. I’m jumping into the pool with both eyes open, lacing up those pointe shoes, sitting down at my computer with my heart in my hands.

I’m listening to Michelle, and I’m being brave with the hope that I’ll come out the other side more resilient for it. This may be a fiasco, but this is, as Mary Oliver wrote, my “one wild and precious life.” I’m done with checking boxes. I’m taking so many beautiful, terrifying risks.

I am still afraid, but I’m doing it all anyway.

Your story is what you have, what you’ll always have. It is something to own.

—MICHELLE OBAMA, Becoming

My story starts the way most stories do: with me not knowing what the hell I was doing but thinking that I knew everything.


Copyright © 2022 by Ashley Woodfolk.