This might be what’s holding you back

Life, Philosophy / /

Lately, I’ve been immersed in the diaries of Etty Hillesum.

What unfolds on those pages is one of the most radical shifts in perspective I’ve ever seen. You watch her go from restless and frustrated to calm, confident, and courageous—in the span of just a few years, and under the shadow of the Nazi regime that would eventually claim her life.

“I really must become simpler,” she writes. “We have to become as simple and as wordless as the growing corn or the falling rain. We must just be.”

What struck me most, as I read, was how much she sounded like a Stoic—specifically, Marcus Aurelius. And yet, there’s no evidence she ever studied Stoicism. One of the many parallels I found was this reminder they both wrote to themselves: Uncomplicate yourself. Be free of calculation and pretension.

Then I thought: no calculations. Have no calculations.

I’ve been repeating this to myself for the past month, and it’s been freeing. Not that I think of myself as “calculated” in the usual sense, but I can be calculated with myself. Sometimes I do things that are irrational, either out of superstition or as a way to relieve anxiety and feel in control. I’ll go back and forth in my mind, debating what something means or doesn’t mean, what will happen or won’t.

But now, when those thoughts creep in, I remind myself: no calculations. And I move on.

Isn’t it wild how much power our thoughts have over our life? If you think your life is crappy…it’s only because you think your life is crappy! Our stories are reality.

The other day, Courtney went to the dentist and told me how uncomfortable she felt for the first fifteen minutes. While the dentist was poking and scraping, Courtney was saying to herself, “It will be over in twenty minutes, and then you can feel relief.”

But then she thought: or I can just feel relief now.

She repeated it—I can feel relief now—and little by little, she relaxed.

That shift—changing the story we tell ourselves—reminds me of something Billy Oppenheimer recently shared:

After finishing college, Ezra Koenig took a job teaching middle school in Brooklyn. Outside school hours, he poured his energy into Vampire Weekend, the band he started with friends from college, where he served as the lead singer and guitarist.

“At that phase of my life,” Koenig said, “I was pretty unhappy. I enjoyed parts of being a teacher, but I stressed constantly, thinking, ‘Oh, I didn’t choose this. This isn’t my dream or passion. The band has to take off. My dream has to materialize.’ Everything felt very high-stakes.”

He found himself constantly preoccupied with what would make him truly happy.

“I really wish I could go back and tell myself, ‘Being a teacher would be fine too.’ I wish I could relieve some of that stress and say to myself, ‘Being a teacher is important too. If the band makes one album and you come back to teaching, that can be a really rewarding life as well.’”

Vampire Weekend did go on to become a huge success, and Ezra is genuinely grateful for where he ended up. But looking back, he sees how unnecessary all that pressure was. He could have found happiness on either path—whether as a musician or as a teacher who plays music on the side.

“There’s the belief that happiness only comes from achieving your dreams. The concept of dream achievement is such a double-edged sword. Because the paradox is that most people’s dream, including mine, is really just to be happy. When you strip away all the specifics, the dream is to be happy.

I’ve now met so many people in my life. I’ve met people who are infinitely more successful than me, who are some of the most stressed-out, miserable people you can imagine. And I’ve also met people who’ve watched opportunities come and go but are deeply happy.”

He learned that the state of his mind shapes the state of his life.

“I think that’s why I now have that impulse to go back and tell myself, Vampire Weekend or teacher in Brooklyn—on both paths, it’s about your attitude.”

It’s about the story you tell yourself.

“Obviously, both could be rewarding because you see that being a musician and a teacher are both incredibly fulfilling jobs for many people.”

Whether it’s getting a handle on OCD, or feeling okay at the dentist, or finding satisfaction right now, in this moment…the thing holding you back might be the story you’re telling yourself.

Books Read This Month

Favorite Books, Reading / /

Etty Hillesum: A Life Transformed by Patrick Woodhouse
The more I read about Etty Hillesum, the more in awe I am of her. This book deepened my understanding of what shaped her spiritual awakening—and I still don’t have the words to do it justice. There’s so much I want to say about it, and about Etty, but at the moment it would just come out as word vomit. (Case in point: the other day I asked Courtney to come to my office and she assumed I wanted to read her another Etty passage.) So for now, I’m holding back until I can write about it properly. Suffice it to say: this book is brilliant. (Also, the section on Etty in Enduring Lives: Living Portraits of Women and Faith in Action by Carol Lee Flinders is worth the price of the whole book.)

So Gay For You by Leisha Hailey and Kate Moennig
I love a good memoir, and after reading a sample of this one on Amazon, and laughing out loud, I bought it on the spot. It opens with Leisha Hailey recalling the moment she first heard about a new TV show that would eventually become The L Word:

“I was at a barbecue in the Hollywood Hills talking to an ex of one of my exes (in keeping with gay tradition) when she mentioned the lesbian pilot. “Oh, did they finally find Amelia Earhart?” I asked. She chuckled, which made no sense to me, since I was genuinely invested in the aviator’s whereabouts.”

I really enjoyed this book. It reminded me of one of my all-time favorite memoirs, High School.

On Solitude by Montaigne
I love the way Montaigne writes. (He is the inventor of the modern essay, after all.) He follows his curiosity wherever it leads, flowing from one thought to the next like he’s having a conversation with himself. But what really makes this worth reading is the wisdom inside. It’s like eavesdropping on someone who’s thinking things through in real time—and stumbling on truths that still hold up centuries later.

Still Writing by Dani Shapiro
I loved this book. It’s full of writing wisdom, yes, but more importantly, it’s full of encouragement. One idea that especially stuck with me was about lowering the stakes: a writer friend of Shapiro’s set out to write a short, bad book. That was the goal. No pressure, no perfection. Just a short, bad book. It ended up winning a Pulitzer Prize.

The Daily Stoic by Ryan Holiday and Stephen Hanselman & A Calendar of Wisdom by Leo Tolstoy
No matter how many times I read these books—at this point, it’s probably five or six times each—I always discover something new. When I first read The Daily Stoic in 2016, it felt like a launching pad for the rest of my life. Nine years later, I’m still learning from it. It’s written in a page-a-day format, and this year Courtney and I have been reading a page aloud together each night after dinner. A Calendar of Wisdom has been life-changing, too. I picked it up for the first time in 2019, and now I read a page each night before bed. Somehow, the insights still land as if I’m hearing them for the first time.

The courage to let people watch you fail

Creativity, Life, Philosophy / /

The courage to let people watch you fail

In the 1850s, before she became a pioneer in education, religion, and women’s rights, Rebecca Mitchell’s life was turned upside down. Her husband died, leaving her with two small children to raise. Under Illinois law, a widow couldn’t inherit her husband’s property—it all went to the government. Everything she owned, right down to the clothes on her back, was no longer hers. If she wanted it back, she’d have to buy it.

Rebecca had dreams of becoming a minister, but women weren’t allowed to… well, do much of anything. Her second marriage ended in separation, and by 1882, with her two sons grown and a sense of opportunity pulling her west, she and her teenage daughter boarded a train for Idaho. When they arrived, the only shelter they could find was a shed—just warm enough to keep them from freezing. And yet, in that tiny shed, Rebecca started a school, eventually squeezing in 40 students.

Determined to expand, she set her sights on a larger building that could serve as both a school and a church. For two years, she worked tirelessly to raise the funds. When the chapel was finally built, it housed the school and the school district she had helped establish.

But Rebecca’s ambitions didn’t stop there. She continued founding schools in neighboring communities, and by 1891—now in her fifties—she turned her attention to the government.

After fighting for and winning women’s suffrage in Idaho, she took an even bolder step: she applied to be chaplain of the Idaho legislature, something no woman had ever done. The men were baffled. They said they had never heard of such a thing.

“Why not do the unheard-of thing?” Rebecca asked.

And that’s the question, Sharon McMahon writes: Why not do the unheard-of thing?

“Humans aren’t so much afraid of failure as they are of having people watch them fail,” McMahon continues. “The shame doesn’t come from not scaling the summit, it’s from the people who judge you for not having succeeded.”

Rebecca knew that judgment well. She had been criticized for her failed marriage, for starting a school, for daring to believe a woman could be a chaplain, and for refusing to retire. When she didn’t get the chaplain position, the judgment only intensified. But she didn’t stop. A year later, in 1897, at the age of 64, she got the job. Letters of congratulations poured in from across the country.

After she died in 1908, The Idaho Republic paid tribute to her legacy, calling her “ever ready to proffer the hand of aid and the voice of sympathy to the needy and distressed.” She had lived a life of self-sacrifice, courage, and unstoppable determination in pursuing justice.

More than a century later, in 2022, Idaho unveiled a bronze statue commemorating women’s suffrage. The Spirit of Idaho Women stands tall, a graceful figure with a hand stretched out. “Behind her,” writes McMahon, “stand twelve sets of shoes, those of the generations of women who came before, each decade of suffragists treading the path to enfranchisement. In her hand, she extends a shoe to the women of the future, inviting them to continue in the work that was begun by those with the courage to let people watch them fail.”

Don’t ask, tell

In the 1980s, Leonard Mlodinow was beginning his career as a physicist at Caltech. He was given the freedom to research whatever he liked. At first, this sounded great—complete freedom. But it soon became clear he had a problem: he didn’t know what to work on. He became increasingly anxious. String theory was popular; should he study that? What about that other theory gaining traction? That would be good to research, right?

Desperate to figure it out, he sought out Nobel Prize winner and fellow physicist Richard Feynman and asked him for guidance. After some probing, Feynman finally said to Mlodinow, “Look, selecting a research problem isn’t like climbing a mountain. You don’t do it just because it is there. If you really believed in string theory, you wouldn’t come here asking me. You’d come here telling me.”

If you let others decide what’s “acceptable,” you’ll never get to the good stuff. And that, Elizabeth Gilbert warns, is the real tragedy. “Your life is short and rare and amazing and miraculous, and you want to do really interesting things and make really interesting things while you’re still here.”

So go for it. Do the unheard-of thing, the thing that lights you up.

Tell people what you’re going to do—and have the courage to let them watch you fail.

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