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A Chat with Leslie Stephens about Social Media Addiction, Her Novel, and Living Alone
And most importantly: listening to your own voice when it comes to scary decision-making.
If you’re reading Wallflower Chats, you’re likely already a fan of Leslie Stephens and her always-relevant, always-engaging newsletter, Morning Person, which presents obsessively curated picks along with essays around “living an intentional and well-entertained life.” Her voice is warm and generous, like a good friend offering great advice and recommendations. Who doesn’t need a (morning) person like that in their lives?
I first met Leslie when I cold-pitched her a piece for cupcakes and cashmere. I’d always been a fan of her thoughtful writing (along with thousands of others), and knew we’d have a lot to say to each other. Since then, our editor-writer relationship (which I miss deeply) has morphed into a friendship where we cheer each other on and gush about our babies (her sweet dog Toast and my sweet daughter E). Though we’ve never met in person, she’s one of the people that makes my life a happier place.
What I love about Leslie, aside from her unfailing kindness and on-point book recommendations, is her ability to be fearlessly honest about what she’s going through. Let me tell you, as someone who has published online herself: that public vulnerability is hard. But it’s also what makes her such a great writer and conversationalist. Below, we talk a little about turning thirty, pivoting careers, and resisting societally imposed milestones.
Hi Leslie! I dove into your newsletter this week and I loved it. You always have the best recommendations. I was just about to put on Anaïs in Love (Hulu).
That movie came at the time that I needed it. It’s about a woman in her 30s who’s examining her life and her relationship. It’s similar to The Worst Person in the World, which I saw in February. After the movie, I started sobbing so hard. I was like, “What is this?” But Anaïs in Love is really good.
I can't think of anyone who has their finger on the pulse of everything like you. I know you're not an editor anymore, but you just have such an editorial eye. Have you always had that?
It’s funny you say that because I don’t think of myself that way! On the one hand, I really don't think that I could name every Kardashian. I have absolutely no idea what is happening in pop culture sometimes. But I have always been obsessed with asking questions and figuring out how to do things better. And I'm always excited about what movies and shows are coming out.
This past year has been such a time of change for you. I would love to know what you were thinking when you shifted from your VP of Content job at cupcakes and cashmere to counseling school.
I have always made decisions by ruminating on them on the back burner. But I’m not always doing it consciously. It’s like an itch in the back of my mind. I started to feel that way with cupcakes and cashmere. It was, for a time, a place where I loved working. I liked elements of the job, like the creative output. But I had been at the company for five years, and it was no longer challenging or exciting to me in the way that I wanted.
So while I was reading a terrible self-help book one morning, I saw a simple question on the page: If you could be doing anything, what would you be doing? At that moment, I had an immediate vision of myself doing talk therapy on a trail. I love nature and I love interacting with people. I've always been interested in counseling and have gone to therapy on and off my entire life. And that was that.
I had the vision early in the morning, and by the time Jonah woke up at 7 a.m., I said, “Okay, I'm going to counseling school.” Ecotherapy is a type of talk therapy that is offered as a certificate program at some colleges, including a school in Portland, where I already knew I wanted to live. It all came together.
I remember you saying that part of what prompted your career change was the social media addiction you were seeing, which is often in contrast to how people relate to nature. Is social media addiction still a part of your scholarship now?
I’m in an addictions track in my program, where most people are studying substance addiction. I went into counseling school with such a specific idea. While living in L.A., which is a very social media-centric city, I had a front-row seat to how dangerous overuse of social media can be. I kept seeing the unhappiness and anxiety created by the apps, not just by the people who consume them, but the people who are creating that content. They were compulsively checking Instagram, even though they know that even the act of scrolling can create a lot of anxiety. But long story short, as I learned more about topics within the mental health world, social media addiction became just a part of what I was interested in. I see it now as less of the root issue of things and more of a symptom of other struggles.
I find that the moments when I most spiral are the ones where I'm leaning on that validation you get from social media.
It’s that quick dopamine hit. The times I rely on social media are the ones when I feel uncomfortable, like if I’m standing in line at the bank and have nothing to look at, or if I’m stressed and under a deadline. People compare social media to a pacifier, which is a really apt comparison. And in that respect, it's not dissimilar to other types of addictions, where people have some sort of discomfort in their life and then reach for a substitute.
I know you're writing on your novel too, in the midst of your studies. You’re now represented by an amazing agent. And I'm so excited, I can't even tell you. Can you talk to me about the process of working on a novel?
Thank you! There's still a long road ahead, but I began writing my novel in 2017 and wrote the entire thing in hour-long increments before work, between 6 a.m. and 7 a.m. My book takes place 40 years in the future, across multiple perspectives and timelines, so there was also a lot of mapping the outline on flashcards in the beginning. Writing the "shitty first draft," as Anne Lamott calls it, was the fun part—I hand-write everything, then transcribe it. Editing it has felt much more like "work," but it's rewarding to see how much better my book has become with every draft. I'm exploring themes around how we create meaning and conflate self-optimization with meaning. It takes place at a wellness retreat!
That sounds like a fun landscape to explore. There's just so much language around wellness, and it's an industry that commands so much power, especially for women.
Yeah. There’s this line where practicing physical and mental health is so important. But there's also the line where it becomes more of a compulsive pursuit, more about becoming well, rather than actually being well enough to enjoy life.
Is there a pivot you have to make to write fiction versus nonfiction?
The biggest thing for me about writing fiction is that it requires so much creative thought. There are certain things that I'm able to write, like an essay for school, that follow a really strict formula, and needs less energy from me. With fiction, I've always only been able to write it first thing in the morning.
It makes sense. Your mind is withdrawing from dreamland and you're still in that beyond-the-veil state, so it leads to weird thoughts, which I think is important for writing.
And it's a chunk of time that I have before I get distracted. But I always set these lofty goals of working all day on my book. I say: I'm going to start in the morning, and then I'm going to break for a walk and lunch, and I’ll keep going into the evening. And I literally never keep that schedule.
You’ve accomplished so much, and you recently turned 30. I'm curious, how are you feeling now? And what's your vision for this next decade?
Truthfully, I have absolutely no idea. I've written in my newsletter about my separation from my husband, Jonah, which I'm still very much in the process of figuring out. I had always planned my life meticulously. Throughout my 20s, I hit every single one of those milestones. And after moving to Portland—the city I want to live in for the rest of my life—after buying a house and adopting a dog, the next step was having kids. But there was something that stopped me. Maybe because it was the final thing on my checklist? And having kids is also a completely permanent decision in a way that buying a house is not.
I’m also in a counseling program that encourages a lot of self-reflection. All these things made me slow down for the first time in my life and look at the decisions that I've made, and why I've made them. I realized that many of my choices have been governed by the feeling that I should do them. Things started to unravel for me after that. And what's interesting is that I recently realized that I used to think of 30 as ancient.
Right. Me too. Social conditioning!
You hear so many times that if you don't meet a partner by a certain age you’re an old maid. Plus, there are lots of feelings around fertility for women.
I recently learned the etymology of the word spinster. It comes from women who spun wool for a living—spinners. They were financially independent and didn't need to get married. Then it became a pejorative, this sense of women not needing husbands.
I think it's the threat of female power.
With my separation, I'm not yet at the place where I'm conceptualizing it as a permanent split. We're privately figuring that out in a way that has felt compassionate on both ends. But the separation confuses the people I talk to—and me, too. They ask, “So you're telling me you're married to the kindest person you've ever met, one who's your best friend and one who is ready to commit to all these things with you? And you're questioning that?” It can feel so backward to do that. But after I wrote that newsletter post, I got hundreds of responses from women with their own stories about separation, echoing my questions.
When I say I'm choosing to be alone right now, that also goes against what we're told to want. Societal norms are about finding a partner so that you can avoid being alone. But for me, right now, I just need to make sure that whatever I choose is because I am truly hearing my own voice.
Top three books of the year: I've been reading Infinite Jest for the past two weeks, and can't even remember what it felt like to read a book before I started this one. But! I loved The Marriage Portrait by Maggie Farrell, A House Between the Earth and the Moon by Rebecca Scherm, and Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin. Was also very moved by How Should a Person Be? by Sheila Heti, which isn't new but came to me at the exact time I needed it.
Best thing you ate this week: Romel Bruno's fried chicken sandwich, at a pop-up at Well Spent Market in Portland!
Last thing that made you laugh: My friend Bri and I get the giggles at the least opportune moments in class, to the level of disruptive middle schoolers. There's something about our dynamic where we bring that out of each other, to the point that we've almost been told not to sit together. In a Master's program. Earlier this week, I confidently delivered what turned out to be the completely wrong answer to a professor's question, realized it as soon as I glanced at her, and we lost it.
Weirdest celebrity crush: I've never been a boy band person, but a few years ago I had a sex dream about Aaron Carter that I really cannot explain.
Next dream travel destination: So many! I would love to go to Japan or hike the Milford Track in New Zealand. Also eager to visit more National Parks!
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