Essay Collections That Make You Necessarily Uncomfortable

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Jaime Herndon


Jaime Herndon finished her MFA in nonfiction writing at Columbia, after leaving a life of psychosocial oncology and maternal-child health work. She is a writer, editor, and book reviewer who drinks way too much coffee. She is a new-ish mom, so the coffee comes in extra handy. Twitter: @IvyTarHeelJaime

I love essay collections. Maybe because they allow an opportunity for lots of different topics to be addressed in one book, or because my attention span is better suited to it, but for me, there’s nothing like diving into a new set of essays. The collections I love best are the ones that sometimes make me put down the book to marvel at what I just read, that demand I go slowly and examine each essay. These are the ones that can leave me reeling halfway through a piece or make me want to order copies of the book for several friends (or even not-friends, depending on the topic). They’re the books that make me rethink some things or reflect on beliefs or assumptions. They’re not always easy to read, but they’re always worth it.

We are living in a world where politicians and parents don’t want their kids to be “uncomfortable” — in the classroom, in the bookstore, in the library. And excuse my language, but that’s bullshit. Education and books are supposed to make you uncomfortable. Supposed to challenge you and make you reconsider long-held beliefs that perhaps need to be evaluated. Supposed to provide information for you to explore, examine, and reflect upon — and then form your own thoughts. Growth is not comfortable — even physically, we have growing pains in childhood. If we are always comfortable and never reconsider or evaluate anything, we don’t get anywhere.

This list could have been so much longer — books like Tomboyland by Melissa Faliveno, Minor Feelings by Cathy Park Hong, and A Mind Spread Out on the Ground by Alicia Elliott are among the collections that I’d add, as well. These books are powerful, they make you think, and they (hopefully) lead you to make changes in some sort of way, whether it’s with yourself or in the larger world.

cover of Some of My Best Friends by Tajja Isen

Some of My Best Friends: Essays on Lip Service by Tajja Isen

Social justice and the language of social justice are everywhere — but are they really? Or are these buzzwords with no follow through or real action? Isen takes these issues on, writing about quick fixes that don’t really move the needle or make a real difference with larger systemic issues but which everyone holds up as “progress.” She writes about diverse representation within the literary world, colorblind casting, and inequality in the justice system, among other topics. Combining personal experience with social and cultural critique, filled with dry wit and honesty, these are essays that are important and timely, holding up a mirror and making you think.

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Looking For An Enemy: 8 Essays on Antisemitism edited by Jo Glanville (August 16th)

Antisemitism has been rising again, and it’s too easy to brush it off as something that only happens on the right/alt-right. This essay collection from a variety of Jewish writers explores antisemitism on the right and the left, as well as its place in the far-right. Whether it’s politics or “social justice” activism or antisemitism in different countries and the forms it can take, these thought-provoking essays have the power to shake up your thinking about antisemitism and hopefully take action against it.

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Escape Into Meaning: Essays on Superman, Public Benches, and Other Obsessions by Evan Puschak (August 30th)

At first glance, this may look like a fun and smart essay collection — which it is. But it’s also a group of essays that can raise some uncomfortable questions or thoughts, like discussing our enmeshment with the internet and social media, or the topic of certainty and whether experts know things for certain, and what to do with the uncertainty that comes from experts disagreeing. (And even further, critical examination of the information we’re given.) At the very least, these essays will push you to think more deeply about certain topics, and that’s always a good thing.

cover of Eat Up! by Ruby Tandoh

Eat Up!: Food, Appetite, and Eating What You Want by Ruby Tandoh (July 12th)

GBBO alum Tandoh writes about food — enjoying it and appreciating it, wholly and without shame or hesitation. In this book, she explores the “wellness industry,” fad diets, food snobbery, categories of “good” and “bad” food, mental health, and much more. Filled with honest, smart essays and lots of commentary and recipes, this is an essay collection that is nourishing in a multitude of ways. The essays urge readers to step outside preconceived notions about food and wellness, and to rethink our relationship with food.

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Sure I’ll Be Your Black Friend: Notes From the Other Side of the Fist Bump by Ben Philippe

This memoir-in-essays is a funny, insightful book that sneaks up on you to give you blunt truths of being a Black man today. Phillipe writes about his immigrant childhood, college during Obama and then adulthood with a Trump administration. His honesty and humor, paired with social commentary and straight talk about race, stereotypes, and racism, make for an important and compelling essay collection that draws you in and leaves you thinking about what you just read.

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The Art of Teaching Children: All I Learned from a Lifetime in the Classroom by Phillip Done (July 26th)

While this essay collection may not make people explicitly uncomfortable, I hope it will spark some rethinking of certain attitudes and assumptions in the classroom. Done writes about his decades in the classroom, working with children, and challenges of the field. He discusses the obsession with testing, how some teachers kill the joy of learning and reading, and how “smart” can look different in different people. Perhaps most importantly, if something’s not working, he writes about teachers looking at themselves before assuming it’s the student. This is a book about learning, not about school. About relationship and connection. At times, that feels downright revolutionary in education.

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People Love Dead Jews: Reports From a Haunted Present by Dara Horn

The title alone is enough to stop you in your tracks or cause an awkward silence within conversations — and that’s the point. Horn writes about her travels, her personal life, and her research and asks the questions like why are people so fascinated by dead Jews, and never living Jews? Why are people so willing to explore the Holocaust and never present-day hate crimes against Jews or issues facing them? Her resulting material is raw, honest, and not always comfortable to read — but necessary just the same.

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Body Language: Writers on Identity, Physicality, and Making Space for Ourselves edited by Nicole Chung and Matt Ortile

Bodies and their assorted functions and issues are typically topics that people tend to shy away from — in conversation, sometimes in writing — or are hesitant about it. In this anthology, the essays are about the stories our bodies tell: fertility treatments, disability, sports, sex, injuries, illness, race, violence — each essay is so different and the topics are wide-ranging. They look at what it means to be in our bodies and how they’re seen and treated, the expectations and assumptions, the stereotypes and behaviors. Uncomfortable at times, these honest and reflective essays will make you think about your own body and how you relate to it and perhaps even provoke some change.

If you’re looking for even more essay collections to explore, check out this post on recent essay collections not to be missed and this list of 100 must-read essay collections.