Private Message from E. Jean Carroll: “Don’t start an affair, start a Substack”

And other pieces of wisdom from the grande dame of advice

E. Jean Carroll (via Ask E. Jean)

E. Jean Carroll

was seeking advice. She had recently and very publicly lost her job as the famous agony aunt of Elle magazine, where for nearly 30 years she wrote the advice column “Ask E. Jean.” Like many of her peers, she was curious about Substack and the success independent writers had found on it. She wondered whether it was right for her. 

It was February 2021, and we were all still in isolation. I can only describe those days as dim, not just because of their lack of sunlight but because of how little life they had in them. This is why I remember E. Jean’s voice bursting out of my speaker (we did indeed have a traditional phone call) like confetti: “Sophia!” She didn’t quite yell it; she sang it. Typically, these discussions go something like this: I ask the writer a bunch of questions about where they are in their lives and what they want to do on Substack, and then explain how and why Substack will serve them. But 30 minutes into my call with E. Jean, I realized we had not said a word about her, but, without my even realizing how it had happened, we had talked a hell of a lot about me: my recent breakup, my relationships to writing and with my parents, my homeland, my career changes, my midlife crisis, how I liked Substack.

“Fabulous! I’ll do it!” she said. Then she had to go. 

Had I answered all her questions about Substack? More than I knew, she assured me. 

I have since learned that it is nearly impossible to ask the woman behind

Ask E. Jean

a question—about E. Jean, that is. (I had to fight to do it in private conversations but also publicly, when I interviewed her in front of a small crowd of Substack writers during a casual event at the Book Club Bar in New York.) She will somehow always manage to turn the spotlight on you, with genuine delight and curiosity.

“It is so easy to give,” John Steinbeck wrote in his Log from the Sea of Cortez, “so exquisitely rewarding. Receiving, on the other hand, if it be well done, requires a fine balance of self-knowledge and kindness. It requires humility and tact and great understanding of relationships. In receiving you cannot appear, even to yourself, better or stronger or wiser than the giver, although you must be wiser to do it well.”

E. Jean Carroll will give you sage advice because she knows, as few do, how to receive and, by that, be truly generous. “The answer is in what people ask,” she has told me. “They already know what is best for them. All I do is point it out.”

E. Jean being interviewed by Sophia in June 2022 (photo by Bryon Summers)

Here is what you should know about E. Jean: 
She has been a Miss Cheerleader USA.
She was the first woman to become a contributing writer to Playboy magazine.
She was a Saturday Night Live writer.
She has written a handful of books, including a biography of Hunter S. Thompson.
She has sued a sitting president.
Above all, she is one to risk delight. There is always a hint of a smile in her voice when she speaks. She will write emails in meter. She will sign them with: 

Ravishing regards,
E. Jean

In short, she is a legend.

I would encourage you to go ahead and ask E. Jean a question, about anything. You can do so by writing to her at E.Jean@AskEJean.com, or leave her a voicemail at 845-682-0881. 

Listen to the absolutely raw file of her witty and wonderful responses to our questions (edited transcript below).

What do you want on your tombstone? 

No. No. No. No tombstone. I have left instructions to drag my withered carcass out the door, across the river, up the mountain, behind my house, and just drop me into a stone crevice. It is a great-looking stone crevice. You’ll come and visit me. You’ll see the stone crevice. Just drop me in and leave me for the coyotes. And then when you hear those coyotes howling, it’ll be me. 

Best advice you’ve ever received. 

Oh, that’s easy. Never. Wear. Brown. Mascara. Only black. 

A mistake worth repeating. 

Marriage. Always good to try a second marriage. Or even a third marriage. A fourth marriage, hmm, that’s not a mistake. That’s a habit. 

What I’ve learned… 

Oh, have fun. Have fun. We could all be dead tomorrow. 

What is Substack in seven words? 

It is a hailstorm of brilliance. 

What is the most delicious thing about it? 

The most delicious thing about Substack is Marissa Rothkopf’s The Secret Life of Cookies. I love her Substack, and, because I love her Substack, I love all Substacks.

What has Substack brought to your life? 

Okay, we’re gonna get serious. I know what you expect me to say. It brought me new friends, stunning writing, entertainment, laughs, joy. I know that’s what you want me to say, but I’m gonna tell you what Substack really brought me: money. When Elle magazine fired me, after 27 years of writing the Ask E. Jean column, Substack saved me.

What have your Substack subscribers taught you? 

How to be brave.

Fill in the blank: Don’t start a ___, start a Substack. 

Don’t start an affair, start a Substack. The sex is better.

What is freedom for a writer? 

Everything. Absolutely everything.

What is Substack to you in one word? 

Power.​​

Private Message is a new mini series asking writers to send a voicemail to Substack’s

Sophia Efthimiatou

, head of writer relations, with reflections on what Substack brought to their life.

If you’re inspired by E. Jean and want to start your own Substack, you can get started here: