Life Of Work With Leslie Stephens

by | Jul 2, 2020 | Interviews | 0 comments

Leslie Stephens is the VP of Content at popular lifestyle blog Cupcakes and Cashmere, where she manages all blog content. Prior to working at Cupcakes and Cashmere, Leslie served as an Assistant Editor at Food52 in New York City.

Today, we talk to Leslie about her success finding niches where she can stand out, her top tips for aspiring writers, the art of giving and accepting feedback, C&C’s response to BLM, her top sleep tips, and more.

I was looking at your LinkedIn yesterday when I was preparing for this interview and it occurred to me that if someone was just looking at your resume they might think, “She has been preparing for the role she has now for her whole career. It’s just been this straight line!” What has it felt like for you?

When I got to college, I knew I wanted to do something in English or Journalism, but there wasn’t a specific major at Wellesley, so I really tried to do internships that honed into journalism. At first I wanted to be a book editor, and I really just followed that route to the max. I worked at Candlewick publishing, which is the cutest children’s publishing company in Boston. Then, I took the Columbia Publishing Course after graduating.

 While I was there, I realized I was way more interested in editing food books, specifically cookbooks, than novels. There were some people who were in the course who were like, “I want to edit the next great American novel,” and I just realized that wasn’t for me. Half of the program was traditional book publishing and the other half was online media and magazine publishing. I was one of basically two people in the entire program who was excited about the online media part. It was really a lot of aspiring fiction editors. We had the Editor-in-Chief of Bon Appetit and the editor of BuzzFeed news and these other really exciting people come to lecture, and I was the only one who wanted to line up to talk to them. I ended up interning at Tasting Table while I was at that program, and then just wiggled my way into the food publishing world.

It sounds like you were noticing that your interests didn’t really align with your peers in a way that ended up being really great for you.

Completely. I realized that I was interested in this specific niche of where food meets online journalism, and I leaned into it.

You interned a lot in the beginning of your career. Tell me about your experience of being an intern.

I think that you can either prioritize the “college experience” when you’re in college and join a bunch of clubs and really lean into that, or you can go out and get professional experience. I was so freaked out about getting a job after college that I poured all of my attention into getting a job after graduation. This worked in my favor in some ways, because when people looked at my resume I really think that the internships were more valuable to than where I’d gone to school and what I did there, but it also meant that I didn’t really enjoy college in the same way a lot of people did. My junior year of school, I was literally working 40 to 50 hour weeks, because I had a campus job at the financial aid office, and then I was going into Candlewick Publishing four days a week, and then I was working at a Lucky Brand on the weekends. I’ve had some really good and some really not good internships, but overall they were a vastly positive experience.

This also means that when I’m hiring editors who are right out of college, I’m always looking to see if they had an internship experience or if they started something themselves, or if they took the initiative in some way that was outside of the protective college bubble.

What advice would you give to the people on the other side who are managing interns?

I think it’s important to always have open communication with any interns you hire. Of course, there’s going to be grunt work that all interns have to do. I think that that’s just part of any internship or entry level job. I made so many press mailers at Candlewick. Sometimes I spent 40 hours a week stuffing envelopes. But then within that were these really valuable things. For example, I had the experience of writing the cover copy that went on the back of a few books. That was the kind of thing that I could actually show for my work. Yes, there is going to be this fair share of menial tasks that interns have to do and somebody has to do it and they should be eager to do it. But it’s key to also provide projects or other opportunities to make the internship worthwhile.

Do you have go-to interview questions that help you identify great team members?

We are really looking for people who know the brand inside and out. I always ask questions like, “What could we be doing better? What are some of your favorite pieces on Cupcakes and Cashmere? What are articles that have really resonated with you?”

The community that Cupcakes and Cashmere has created naturally is a really interesting community that I’m always drawing inspiration from. I think our readers are some of the most incredible people. I’m always trying to make sure that applicants actually know the brand, that they have actually been a reader and they’re not just applying blindly to a job. I feel like as long as you have that foundation, and a good work ethic, for the most part, other skills can be taught. I can help an intern become a better writer, or teach them some other work skills, as long as they’re enthusiastic, a hard worker, and know the brand really well.

What are some misconceptions that readers of Cupcakes and Cashmere or just readers of blogs in general might have about the work that you and your team do?

The biggest misconception is how much work goes into it. We’ve pulled back the curtain a bit recently, because readers are craving authentic content. Especially with Instagram stories, there’s no other way to do it than to really share what’s going on in your life. But there’s still this element that most people don’t understand: just how many hours go into a single post. There are things that we want to appear effortless, of course, but just like with any company there are so many emails and meetings and planning things that go into literally everything that is published.

What’s the most challenging part of your job?

The most challenging part of my job is staying excited and inspired. It’s weird to call it a “challenge,” because it’s a challenge that I really enjoy. I think that my life is better because I’m always asking myself, “How can I do something better? How can I seek out inspiration? How can I turn this into a post?” I’m really lucky that that my challenge at work is to seek out inspiration, and to distill it in a relevant way that’s interesting for people to read. But it’s nevertheless a challenge to be constantly be asking ourselves, “How do we grow? How do we learn? How do we adapt to new technologies?”

You and your team seem to channel this enthusiasm and curiosity about the world. I imagine sometimes you just don’t feel like showing up that way to work. How do you reenergize that side of yourself?

Just like with everybody at work, like there are days where I feel extremely motivated and then there are days where I just don’t feel motivated at all, and I’m not feeling inspired. The only thing that I can do then is take time off from the creative part of my job. I’m lucky that I do have enough parts of my job that are not necessarily just creating content but involve planning bigger partnerships or working with sponsorship brands, or just responding to emails and don’t require this element of creativity.

It’s been really important for me to remember to do little things like turning my phone off during the weekend. I see Instagram as the extension of the blog in our team members each have separate personalities on our personal Instagram accounts. It’s almost like if you want bonus blog material, you can follow us there. I sometimes feel this responsibility to always be posting and always be inspiring and always giving tips and recommendations, but whenever I remember to just turn off and recharge, then all of a sudden I have 500 new ideas.

When what used to be a personal portal into social media is now blog bonus content, do you feel like it’s harder to express yourself?

It’s interesting because I think that my “personal online brand” is so in line with Cupcakes and Cashmere and a lot of that is because I came into the space and came into social media always reading and following Cupcakes and Cashmere. I would say that one thing that I don’t share as much on my social is showing sort of the messy parts of life. I always ask myself, what do I come to Instagram to see specifically? I’m usually coming to get tips and inspiration from people. And so every time I’m posting a story on Instagram, I’m asking myself, is this valuable to somebody else? Is this something that is an activity that they can do or products that they can buy that would make their lives better?

I don’t want to spend that much time on Instagram, so I just want the good stuff. What’s the easy dinner you’re making? What is the tea you’re drinking? What do you buy for your house? What candle do you like? That sort of thing.

I want to talk about writing a little more. You’ve written that you’re living your dream of getting paid to write, which isn’t easy to do in this media environment. How do you practice the craft of writing?

I write all day, every day – at least it feels like that some days! I reserve mornings before work for creative writing. I do my fiction writing then, and that’s just something that is for myself. It’s something that I’ve never shared publicly, and I’ve never submitted my fiction anywhere, but it’s sort of this creative outlet that I think also helps fuel other creative outlets. Then during the day at work I am writing nonfiction about my life. I really enjoy doing both. My favorite thing that I do at work is writing a post. I just love it.

You mentioned earlier that you can help teach new Cupcakes and Cashmere contributors how  to write. What are some of your tips for someone trying to write a great personal or informative post?

There are two tips that I always come back to with writing. Of course, there’s a baseline of being clear and concise. That’s just a basic foundation for writing. But I’m also always asking myself, why would somebody care? What is somebody taking away from this? Just like a college essay, there should be a clear thesis for every post. It could be something simple, like: “Here is the dinner that is absolutely fantastic and you have to make this tonight.” Or it could be: “I’m struggling with anxiety, and here’s my approach to it currently.”

The second thing is I am always watching to be sure I’m not falling in love with my own writing. I think that this is something that a lot of people do, and that’s how you get writing that is way too flowery or full of adjectives. People will write a sentence, myself included, and be like, this is beautiful. I heard David Sedaris say on a podcast that anytime he catches himself thinking this is a beautiful sentence and he falls in love with it, he deletes it, because it means that it’s usually not. So I do that now, and I remind myself that if I’m falling in love with my own writing and being a little bit too self-congratulatory, it’s probably not as good as I think it is.

Two other little tips for any aspiring journalist or contributor. One: tone is really important. Whatever outlet you are writing for, read at least 15 posts from that website and get the tone in your head before you start writing for them. It’s a subtle thing, but it is very noticeable as an editor. And then secondly, I usually find that with post introductions, I will write a first draft and almost always end up deleting the first one or two sentences. I’ll delete something like, “On Sunday morning, I was thinking to myself how much I love making pancakes.” Just start with the pancakes. I made pancakes. Here are the pancakes.

One of the things that’s really hard to do in any workplace is give feedback and take feedback. Is there a specific way that you do that in your work or things you’ve learned to do for both giving and taking feedback?

In general, always lead with the good. Don’t forget to tell somebody how much you appreciate the work they’ve done. It’s so easy to immediately say, “Here are the two things that need edits.” This is true especially when we’re all working so quickly. I always seek to remember to lead with what I like about a piece because it can often go unsaid.

We also have a policy that I think really helps everybody maintain their own voice where the writer of the piece gets the last say. So even though I am the editor of the site, if someone else on our editorial team or a contributor writes a post and I have edits that they disagree with, we will always try to find a compromise that works for both of us, just so that it always maintains their heart in it. We try to be careful that their opinions and their voices really shine through.

Cupcakes and Cashmere has been vocal about changes that will be made to the shop and the website’s content as a response to Black Lives Matter. What changes are you making as a company and what impact have the last weeks had on you personally?

In terms of changes we’re making as a company, Emily’s recent post is fairly explicit in its transparency, which makes me proud as an employee—you can read the changes we’re making as a company there! Personally, the last few weeks have made an enormous impact on me. It’s one thing to reckon with my role in contributing to systemic racism as a white person. It’s an entirely different thing to have to do so publicly. I am spending a lot of time learning how to be not only an ally, but an active ally and really checking myself, my privilege, and the responsibility that comes with being a person with an audience.

Has the feedback from C&C readers been constructive? How do you approach receiving feedback in this moment? In what ways has that been challenging?

The vast majority has been constructive, yes! Of course, there is a wide range of feedback, but in opening up the comments, we’re allowing in feedback that makes us uncomfortable—in a good way, the kind of way that promotes change and growth. It’s all challenging, but I’ve been eking out the difference between things that are challenging in a productive way (constructive, hard-to-hear feedback), and things that are challenging in an unproductive way (unfounded mean words).

You write about your partner Jonah a lot. You clearly have a very connected like partnership. Whether you’re talking about your wedding, your financial choices, or arranging your house, you’re both involved. I’d be curious to hear a little bit about your partnership. (Leslie and Jonah also recently got married in a socially distant ceremony.

My romantic relationships prior to dating Jonah were very one-sided. I learned that was never how I wanted a relationship to be again, I felt really controlled. Jonah had also come from a relationship that was relatively controlling. So when we came into our relationship together, we never wanted to change the other person we just want to support the other person.

I think transparency is key to everything. I think it is key to business, I think it’s key to a partnership. Always just trying to talk through things and really say how you feel and what you need in that moment can’t be overstated.

You’ve written that Jonah is the most empathetic person you’ve ever met. Are there a couple habits or things that he does with you that help you feel empathy from him?

He’s much more level-headed than me, so he’s taught me how to press the pause button before a fight. My tendency in past relationships was to blow up a tiny thing into an enormous battle. That’s how I fought with my mom growing up and that’s how I fought with boyfriends before Jonah. He’s really good at staying calm, cool and collected. I’m not a hotheaded person and I don’t get angry, but I get frustrated really easily, so I would do things like leave a fight in the middle and he’s encouraged me to stay and talk through my feelings. I had been in relationships that weren’t healthy, and you just need to train your brain to be in a healthy relationship and trust it. We know we always want the best for the other person. When we’re mad, we know we’re mad at their actions but not at the other person.

You’ve written about your struggles with sleep and what has helped you with sleep management. What are your top sleep tips for aspiring sleepers?

The biggest thing is to not do anything in your bed that’s not intimacy or sleep. If you have trouble sleeping, you need to protect that space. You can’t hang out in your bed or watch TV in bed. That also applies to worrying. When you’re stressed out, don’t stay in bed and let yourself stew. If you’re having trouble sleeping, get out of bed, even if it’s the middle of the night.

We have something that we call a “cool down period” for an hour before bed that is screen free. So we’ll play cards, or read, or do something else that is dedicated to getting ready to sleep soon.

The third thing is getting up every morning at the same time no matter what. I wake up at 6am every day on the weekends or on weekdays just to maintain that structure.

What card games do you play?

We’re really into gin rummy right now. It’s excellent. We’re having a really good time.

What are you reading right now?

I recently read The Mars Room by Rachel Kushner, which is set in a women’s prison. Now I’m reading American Prison by Shane Bauer.

Do you have a notebook and pen that you are loyal to?

I use Moleskin notebooks. I like the larger size. I always have a highlighter – I really like Sharpie Accent highlighters. My favorite pens are ones that I steal from restaurants. Restaurants have the best ballpoint pens. The one I’m using right now is from Tusk.

What restaurant are you the most excited to go to whenever restaurants safely reopen?

Meals by Genet. It’s an Ethiopian restaurant that’s in Little Ethiopia in Los Angeles and it is one of my favorites. I’m nervous for them because Ethiopian food is really communal and you eat with your hands. I hope they can survive this. They just opened for takeout. They are one of my favorite restaurants in all of LA and they are owned by an amazing woman named Genet. At this point though, I’d be so happy to be in any restaurant!

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