The Profile Dossier: David Sedaris, the Writer Fusing Humor with Pain

“Everything’s funny eventually.”

“Everything’s funny eventually.”

It may take days, months, or years, but humorist David Sedaris says the day will come when you’re able to laugh about it. He has become a master at turning pain into humor. As one reporter put it, “He says the quiet parts out loud.”

When he’s in a traumatic situation — such as getting tested for cancer — he reminds himself that he can write about this later. Writing becomes a refuge.

“You should celebrate if you get fired from a job or if your house catches on fire, or you lose a limb that’s not your writing arm,” he says in his MasterClass. “Make the most of it.”

And Sedaris is no stranger to darkness. His mom died suddenly during treatment for lung cancer and his sister Tiffany committed suicide in 2013. He wrote an essay about the family’s complicated relationship with Tiffany titled, ‘Now We Are Five.’

In an interview about his sister, Sedaris says, “I could not have saved Tiffany. If you don't want to take your medication, there's nothing anyone can do. There's not a single day that I don't think about her, though. She was a remarkable person.”

Sedaris has had an illustrious career as a humorist and best-selling author, but he had a long road to where he is today. He held a number of odd jobs, from working at I-HOP to dressing up as an elf at Macy’s. He drank, he did drugs, and he smoked cigarettes, which he has largely given up.

But there was one constant in his life: Writing. He recorded his observations in his daily diary for decades, which became his refuge. It was that diary that served as inspiration for many of his popular personal essays, including, SantaLand Diaries, Now We Are Five, and Letting Go.

Here’s what we can learn from one of the preeminent humorists of our time about the power of observation, navigating difficult familial relationships, and living a full life.

(Photo Credit: Anne Fishbein)

READ.

On developing thick skin: One of Sedaris’s biggest gripes with young people is that they are too easily offended. Meanwhile, he lives for the awkward, anger-inducing moments. If those didn’t exist, what would he write about? This is a fascinating look at the delta between what people will laugh at in private versus what they feel comfortable laughing at in public.

On becoming the ‘American Alan Bennett:’ Sedaris wasn’t exactly an obvious success story. His writings became popular when he started sharing personal stories of humor intertwined with pain and trauma. In the 1990s, his stories of family life and of working as an elf at Macy’s department store during Christmas season turned out to be exactly what people wanted to read, and his popularity increased. Here’s how he learned to further develop his cutting, dry-witted style of writing.

On his sister’s mental illness: Sedaris’s sister Tiffany committed suicide after years of mental illness. In this Q&A, he talks about the difficult relationship he had with her and the rest of his family, why he chose to continue writing about them, and what happened when he came out to his parents and five siblings.

LISTEN.

On why he keeps a daily diary: For pretty much his entire adult life, Sedaris has kept a diary, dutifully keeping notes of everything he encounters on a daily basis. Often, those daily observations are the ideas that transform into his personal essays. “In order to record your life, he says, “you sort of need to live it — not at your desk but beyond it.”

On living a full life: In this podcast interview, Sedaris explains how he was almost attacked on stage over a joke, why he didn’t have an ID card for the longest time, and how flying in a plane isn’t what it used to be.

POLINA’S TAKEAWAYS.

The extraordinary is found in the mundane: Sedaris is a master at turning everyday moments into masterfully funny stories that connect with nearly every human who comes across his work. His secret is that he envisions himself as “part of a story,” and his best advice is to let that story unfold. One time, he was on a train in Paris, and an American was talking to his friend in English, when he told her this about Sedaris: “Be careful, that guy is a pickpocket.” Of course, Sedaris could’ve interrupted him and told him he was not a pickpocket and that he was also American, but that would require him to interrupt the story. Sometimes, he says, let life unfold, become an observer, and tune into your surroundings until they feel like a story. Resist playing on your phone because it acts as a shield between you and an entire treasure trove of story-like moments. To write about the world, he says, you have to live in the world.

Avoid ‘small talk’ questions: Sedaris despises what he calls ‘small talk’ questions: “How was your weekend?” or “How about this weather?” They’re empty and shallow questions with no meaning. While in conversation with a stranger, he’s asked the following questions: “Have you ever touched a monkey before,” “Do you know a lot of doctors,” and “Have you ever run for office?” Those “big talk” questions can lead to deep conversations, which then lead to ideas, which then lead to an amazing piece of writing. “As long as I’m having encounters with people, I want them to be meaningful to the extent that they can be,” Sedaris says.

Realize that money is just a tool: When Sedaris was asked if he had any guilt or embarrassment about having a lot of money, he responded with: “I think I am pretty good at it.” Sedaris says money comes with responsibility. “Give it away. Be generous,” he says. “Find your younger self and make a difference in that person’s life. And you’re supposed to spend money if you have it. You’re not supposed to just keep it all.”

QUOTES TO REMEMBER.

“Even if nothing much happened, I still have a lot to say about it.”

“Writing gives you the illusion of control, and then you realize it's just an illusion, that people are going to bring their own stuff into it.”

“You can't brace yourself for famine if you've never known hunger.”

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