Welcome & Thank You for Subscribing

Hi colleagues, fellow writers, and new friends!

Welcome to Hustle Culture, a twice monthly-ish newsletter centered around financial and creative guidance for working writers. If you’re looking to balance personal projects with paid work, contemplating what it might mean to freelance full time, or wondering how to pitch your ideas (writer or otherwise), you’re in the right place.

Before we dive in, a bit of background on me and what compelled me to start this newsletter to begin with.

In April of last year, with no concrete plan or proof I’d make any money, I left my secure, reliable job as a journalist to become a freelance writer. I can’t trace my desire to work and write for myself to one moment, but a hundred tiny observations that told me—despite once believing I had my “dream job”—I was on the wrong path.

I was 21 when I moved to New York to start my journalism career, with enough energy and naiveté to say yes to anything my editors asked of me. (My mom was not pleased when I went to Wall Street bars to get “scoops” from fifty-year-old men). Still, in the first few months of my job, I found that I spent two or more hours of my day pretending to work to “be online.”

I’m no stranger to the stereotypes about Gen Z lacking work ethic. My problem, though, felt to be quite the opposite: I wanted to write about many topics and experiment with form. I had the energy to work 60 hours a week. But, over five years in a few different roles, I felt more and more constrained by my beat(s) and the audience (Wall Street) I was writing for.

Left: My short stint as a TV reporter 🤭, Right: My last view of the office before quitting

It’s possible that the corporate 9-to-5 eluded me because both of my parents worked for themselves during my most formative years. My mom was a personal trainer who operated a studio gym in our San Diego suburb. And my dad, after being laid off during the financial crisis, was a contractor for a British company and worked remotely from our guest room. When I got home from school in the afternoons, my dad and I chatted while I ate Cheerios before lacrosse practice. And my mom built a schedule that allowed her to come home at lunch, throw in a load of laundry, prepare meals for dinner, and get back to the gym for her afternoon clients. I didn’t realize it at the time, but independence was being modeled to me over corporate loyalty.

Maybe I would’ve been able to push my interest in freelancing aside if I felt energized by the work I was doing. But above all else, I wasn’t proud of the kinds of stories I was writing or comfortable with what was expected of me. Rather than deliver “scoops” about the Federal Reserve or fashion companies, I wanted to write in-depth essays about things that really matter to me: climate change, economic inequality, art, and literature. And I had a very personal story to tell, one that I knew would require time and experimentation.

After a trip to Costa Rica, yoga teacher training (cliche, I know), and an internal job change that didn’t satisfy, it was clear I needed to make a big career shift. I knew that freelance writers existed, but I didn’t understand how they made it happen. How did they make enough to earn a living? What were their schedules for personal writing and how did they fit it in? How did they meet editors and find gigs? How did they avoid getting lonely? And how did they afford health insurance?

There weren’t great books or online resources that helped me understand how independent writers made money and made time for creative work. So, at the end of 2023, I sent cold emails, LinkedIn messages, and DMs to writers who appeared to have things figured out. It was the best way for me to meet established writers and plan my ultimate exit from corporate journalism.

Over the last year—thanks largely to strategies I gleaned from those conversations—I’ve developed a roster of copywriting clients, published in major news outlets, and begun a book-length personal writing project. Still, I have so much to learn.

The aim of this newsletter is to have conversations with writers I admire about art, creativity, inspiration—and money—and make those available to you, whoever and wherever you are. I may also include some of my own musings about freelancing, creative work, and reading recommendations.

If you made it this far, I hope you’ll subscribe and follow along. More soon!

Olivia

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