Charlotte Lieberman's career path has been anything but traditional. After studying poetry and initially planning to pursue a Ph.D. in English, a viral article for Cosmopolitan set her on a trajectory into the world of freelance writing. Fast forward through roles at a digital wellness publication, various mental health organizations, and navigating the peaks and valleys of freelance life, Charlotte found herself wanting more collaboration in her work, and built up a portfolio of work as a copywriter and digital content strategist. She now leads a team of UX writers at JPMorgan Chase.

Intrigued by the twists and turns of her professional journey, we sat down with Charlotte to learn more about her experience transitioning from literary writing to a corporate creative role, dealing with burnout, and her advice for others forging their own paths as creative professionals.

Charlotte Lieberman: It was kind of this weird, lucky fluke. I had studied poetry, and my creative writing professor put me in touch with the editor-in-chief of Cosmo right after I graduated — they were friends. The editor-in-chief of Cosmo was fascinated by hookup culture, so I ended up pitching an article for them about my experiences dating in college. It went viral. It gave me this glamorous illusion of the freelance writing life because it so quickly became a reality, but it was an unrealistic start because I had this connection right off the bat.

I got a really splashy debut — a photoshoot, invitations to be on panels, the whole nine yards. It was kind of the apex of what you want as a freelance writer. But my subsequent articles were a lot less sexy, got a lot less attention. I had decided I was going to pursue freelance writing because that first viral article gave me so much momentum and felt so good. But I had to fall down a bit after that start.

Lieberman: I got my first  full-time job as an editor a year later at a digital wellness publication called mindbodygreen. I loved it. I was working with writers all day — collaborating and connecting with people, editing other people’s writing, curating features about relationships, mental health, and well-being. But it was also more strategic than just exploring my own ideas: part of my role crossed over with marketing because there was an e-course platform on the site, so the stories and articles were a way to encourage people to buy courses.

A year later, I wanted to go back to writing more of my own work and was craving the flexibility of working for myself. I had made a bunch of contacts in the wellness world and also built up more of a marketing skill set at that point. So from there, after I left the job, I was able to market myself as a freelance copywriter while continuing to pitch and publish my own stories — most of which were about mental health.

The crucial point that got me from freelance writing to where I am today was landing a job at an online therapy company called Talkspace. I was hired as a marketing copywriter, but because it was such a small team when I started, my role had a lot of crossover with product and user experience aka UX. A lot of my challenges were around how to translate the brick-and-mortar therapy experience onto a digital app.

So I was working closely with clinicians, product people, and that gave me the background in product and UX that is now in my current role at a bank, which is really different.

Lieberman: If I'm being totally honest, not really. I think particularly because in my current role, I'm mostly managing people. The blessing and curse is that once you're managing in a field you're equipped to manage in, you kind of stop doing the actual thing you're prepared to do.

As a people manager of a UX writing team, I don't have as much of a hands-on impact on the experiences being created. My own writing muscles are a bit weaker than they could be.

That said, the more diplomatic answer is that there is some relationship between creative writing like poetry and UX writing. With poetry, you're thinking about economy of language, connecting with your reader, invoking something for them.

In my experience, I do think marketing as a discipline is a lot more creative than UX. Marketing is about invoking emotions and compelling people to take action, whereas in UX, the user has typically already “bought in,” so you're just supporting them through the experience they’ve already agreed to. The constraints are also often much greater in UX writing, because you're working closely with technology teams.

Lieberman: Honestly, burnout was a large part of why I got my current full-time job. I had been freelance writing but also doing consulting to have multiple revenue streams, so it was kind of two hustles at once.

I'm sure many people can maintain a full-time job plus a side hustle as a writer, but I didn't even really have that vision in mind. I was also going through a very painful breakup in 2022, dealing with logistics like health insurance and being partially financially dependent on my ex-partner.

When I found myself on my own, suddenly needing to pay to live alone in a New York City apartment and get health insurance, I was just kind of like, "I need a full-time job where I can show up, do what I need to do, and then not have to deal with myself so much." I've sort of been in that continued phase for a couple years now.

I'm no longer in an acute grief phase, but I do feel like I’ve had to piece my life back together a bit. As we know, creativity doesn't really thrive when you’re in survival mode. So it's been a combination of burnout, plus grief, plus depression. I'm in a better place now but I'm still figuring it out.

Lieberman: I think so, yeah. I think I'll write again too. I just need to reconceptualize my relationship to writing, which used to be oriented around workaholism and achievement. I feel like I needed to demolish my previous way of relating to writing in order to rebuild it, and I'm just not at the rebuilding stage yet. Eventually, I want to find a creative path that is motivated by genuine desire rather than ambition.

Especially in the age of social media, endlessly packaging yourself and waiting for validation, it can all feel like a trap. So I still write poetry, and to me, that feels like a more pure form of writing. It's never been about getting external validation. As a result, I've maintained more of an appetite for it.

Lieberman: I think it's important to just recognize how hard it is to be creative while also expecting to live comfortably, especially in an expensive city. I think I used to feel gaslit by this image that I could be a freelance writer but also should be able to go to hip restaurants all the time and be super comfortable financially. I mean, it’s probably possible, but it's hard without generational wealth or financial support from somewhere else.

I think what can happen, or what happened to me, is you say, "Okay, I want to write, but I also want to prioritize my comfort." That was helpful for me to verbalize, but the compromise of those priorities can actually end up bending you into a bit of a pretzel. You can end up commodifying a certain type of writing that will build your platform or earn income. But then you start to lose sight of what you actually want to be writing.

Bottom line? I think it's about being really honest with yourself about your priorities and finding ways for your creative practice to be fully your own, even if that means keeping your day job for financial security and maintaining strict boundaries around it. It's a constant push and pull but giving yourself permission to create on your own terms is so important.

Lieberman: What I found hard about publishing articles is that it's difficult to stay true to the sorts of things you want to be writing and also get published in mainstream publications. Editors have a vision for what they want, and unless you have a really close relationship with an editor who trusts your writing and taps you for a story they think you should do, you often end up bending yourself into what you think publications want.

If it were up to me alone, I'd probably write lyrical essays with poetic elements, personal elements, and some literary elements. Maybe I could get those published in a literary magazine, but then fewer people would read them. Does that matter? I don't know. It didn’t occur to me at the time I was pitching a lot. When I was hell-bent on having a more popular type of writing with a bigger readership, I felt myself contorting to what I thought publications would want. Through that process, I kind of lost contact with what I even wanted to be writing.

With poetry, I'm inspired by the freedom. I can write about my corporate job, my sex life, what I ate, my Zoom meeting, my Google calendar, my dirty AirPods, anything. There are no real rules or constraints. That freedom is what keeps drawing me back to poetry as a medium.

Lieberman: I really liked the hustle and the dynamic nature of freelancing. It's kind of like cooking — I enjoy the stressful parts. I like that oil in the pan is getting hot while I'm chopping something I have to sautée before checking the oven. The constant multitasking and juggling of projects and priorities really worked for my sensibility.

I also think an integral part of freelancing is trusting that things will work out. I've found that existentially helpful as a way of learning to be in the world — recognizing that you can't control everything. As a freelancer, you're never really sure where your next project is coming from, but you have to trust that something will come through. And it usually does, but the unpredictability can be both exhilarating and demoralizing.

Lieberman: I try to identify everything that I have found anxiety-provoking in work culture and not do those things. For example, I don't believe in the culture of work being everything, or the mentality of getting things done at all costs. I think it's unhealthy when people feel like they need to alert everyone when they step away from their desk or have a doctor's appointment.

I try to promote the idea that if you have an appointment, feel free to just let me know you have something going on, no big deal. I've had people ask me if they could go to therapy during work hours, and I always say, "Do whatever you need to do." I don't believe in surveillance culture as a manager.

My hope is that people feel more motivated when they don't feel punished for taking care of themselves. I'm not their therapist, but I try to model the way that I want to feel at work and create an environment where people feel emotionally supported within the appropriate boundaries of a manager-employee relationship. A lot of it is about leading by example and showing that it's okay to be human.

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