10 Books on the Light (and Dark) Side of Obsession
My favorite reads on the blurry line between loving your craft and losing yourself.
Hi friends,
I’ve been devouring all those year-end book posts lately (Todd Kashdan, Brad Stulberg, and my friend Justin Steinfelder all have great ones).
I’m always on the lookout for new books. But even more than that, I think I’m just looking for a connection. I get so deep in my own little world of reading that it’s nice to see what everyone else is up to.
Unsurprisingly, many of my favorites revolve around people who are obsessively passionate about something. Since “Obsessive Passion” isn’t exactly a standard bookstore category yet, I made my own list for you. Some are new-ish. Many are not. But I loved every one of them.
It is interesting that many of these are about topics that, on the surface, I care nothing about. That is what passion does: it draws us in. It doesn’t matter if I don’t personally feel a connection to stargazing or acroyoga; I want to hear why you love it. And every one of these authors does an amazing job putting that love into words.
I hope you discover at least one new book from this list, and maybe even allow yourself to go down a rabbit hole of a new passion.
Stephen Florida by Gabe Habash
Passion: Wrestling
I hesitated to include this one at first. On one hand, it’s a masterpiece. But given my own background in grappling, this hit a little too close to home. It gets into the mind of a wrestler whose whole world revolves around his sport, showing the undeniably negative side of passion.
There’s a line that actually haunted me:
“I could never have guessed that wanting one thing for so long... finally getting my hands on it could not feel really different than it felt all along.”
Don’t get me wrong; it may show the negative, obsessive side of passion, but the writing and the way the author gets into his character’s head is just astounding.
Get it here.
Carrie Soto is Back by Taylor Jenkins Reid
Passion: Tennis
I’m a huge Taylor Jenkins Reid fan — she writes characters better than almost anyone — but the way she gets inside this character’s head is astounding even for her. It follows a tennis star whose whole identity is wrapped up in winning.
Like Stephen Florida, it shows the danger of obsession, but — and this is one of many reasons why I loved it — she actually matures through it. It captures the struggle, and the joy, of being absolutely in love with your craft. Just brilliant.
Get it here.
What I Talk About When I Talk About Running by Haruki Murakami
Passion: Running (and writing)
I’ve never been a runner. I honestly hate running! But this is one of the only books that truly captures the relationship between sweating and creative work.
I’ve always felt that my training and my writing were inseparable—that I couldn’t do one without the mental energy of the other—and Murakami puts that feeling into words better than anyone else.
But really, I love this book because it makes me feel less weird about my need for solitude. Read this, and tell me if it doesn’t sound exactly like me:
“I’m the kind of person who likes to be by himself... I find spending an hour or two every day running alone, not speaking to anyone, as well as four or five hours alone at my desk, to be neither difficult nor boring... I could always think of things to do by myself.”
Get it here.
The Animators by Kayla Rae Whitaker
Passion: Animation
This book proves a theory I’ve always held: a story can be about any craft—even one I know nothing about — and still feel universally relatable if the author nails the obsession behind it.
The characters here are deeply, messily in love with animation. It captures the highs, the struggles, and that specific “good kind of passion” where the work consumes you in the best way.
I just loved this quote (it perfectly describes that flow state we all chase):
“I know a day of work has been really good when I have to look up from the board and recall who I am and what I’m doing.”
The Correspondent by Virginia Evans
Passion: Letter writing
I actually had a pen pal from another school growing up. We’d write each other about our lives and swap photos from summer vacations. Even when email took over, I tried to keep that spirit alive... until somewhere along the line, I just stopped.
That is why this book hit me so hard. Sybel, the protagonist, views her letters not just as a hobby, but as her life’s true work.
As she writes:
“My letters have been far more meaningful to me than anything I did with the law... The clerkship was my job; the letters amount to who I am.”
Reading this actually convinced me to resume my own letter-writing practice (I’m aiming for one a week). That is the cool thing about reading about other people’s passions—sometimes, they give you permission to reclaim your own.
Get it here.
Open by Andre Agassi
Passion: Tennis
I’ve always thought tennis lends itself to the best psychological writing, maybe because of the isolation. When players step onto the court, they are totally alone with their thoughts. The coach has to be silent. Even the crowd gets shushed.
That pressure cooker makes for a brilliant, troubled memoir.
Unlike the other books on this list, this is actually about forced passion. It’s no secret Agassi had a complicated relationship with his talent — he was pushed by his father and often resented the sport. Yet, his inner monologue shows that he still desperately wanted to master it.
I love this book so much I’ve read it three times (and counting). I mean, just look at this line:
“What you feel doesn’t matter in the end; it’s what you do that makes you brave.”
Swoon.
Get it here.
Kitchen Confidential by Anthony Bourdain
Passion: Cooking
Oh. My. Gosh. This book!
It has been on my list for ages, but I kept putting it off—partly because I’m not overly interested in the restaurant business, and partly because it makes me sad that he’s gone.
But talk about a voice. He puts exactly what is in his head onto the paper with zero filter. It’s the ultimate proof that I don’t need to care about the topic (in this case, line cooking) to be captivated by the person doing the caring.
And then I hit this line, and felt completely seen: “People confuse me. Food doesn’t.” Replace “food” with “writing” or “training,” and that is basically my life motto.
Get it here.
The Queen’s Gambit by Walter Tevis
Passion: Chess
You probably saw the Netflix show (I did too, and loved it). But the book, published back in 1983, hits different. It reminds me why I’ll always prefer reading over watching: a camera can show you the move, but only a book can show you the thought.
In the show, the chess looks like magic. In the book, it feels like weight.
You get inside Beth Harmon’s head and realize that her genius isn’t a gift; it’s a compulsion. She plays chess on the ceiling not because it’s fun, but because she literally cannot turn her brain off.
It’s a portrait of a person who uses obsession to escape trauma, only to find that the obsession is its own kind of trap. And yet—just like the others on this list—she loves it anyway.
Get it here.
Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin
Passion: Video Game Design
I honestly didn’t think I would care about a book on gaming. But I was wrong.
This isn’t really a book about video games; it’s a book about the brutal, exhausting, life-altering work of making thingswith other people.
It captures that specific feeling of “creative flow” where you look up and realize 12 hours have passed and you haven’t eaten. But it also shows the cost. The main characters, Sam and Sadie, are arguably better at building worlds than living in this one.
There is a line in here that feels like a warning label for every perfectionist I know:
“If you’re always aiming for perfection, you won’t make anything at all.”
Get it here.
Born Standing Up: A Comic’s Life by Steve Martin
Passion: Comedy
You might assume Steve Martin came out of the womb being funny. This book proves he didn’t.
In fact, it is basically a manual on how to build a skill from scratch when you have almost zero natural talent. He didn’t rely on “being funny”; he relied on studying the math of what makes people laugh. It is methodical, obsessive, and oddly inspiring for those of us who feel like we have to work twice as hard to get the same result as the “naturals.”
This quote is the best antidote to imposter syndrome I have ever found. I read it whenever I feel unqualified:
“Despite a lack of natural ability, I did have the one element necessary to all early creativity: naïveté, that fabulous quality that keeps you from knowing just how unsuited you are for what you are about to do.”
Get it here.
What books have you read about passion, obsession, or craft that I should add to this list?
I’d love to know! Book recommendations are one of my favorite things in the whole world.
See you out there,
Krista
P.S. Do you need eyes on your writing?
I’m currently taking on a small number of book coaching clients for high-level strategy and granular feedback. If you have 50,000 words that are a mess, or an outline you’re scared to start, just reply to this email and let’s chat. I work with both fiction and non-fiction—specifically 'big idea' books and complex, aspirational novels that keep you up at night. Honestly, I love the messy middle; it’s where the real magic happens.
Such a good selection of books! Thanks for sharing
Wonderful! I love book lists. Have a read a few of these. I just put a few others on hold at the library. Thank you!