This essay is based on a transcript of a conversation with Ben Chipman, who works in commercial partnerships at NBCUniversal, about his experiences working as a freelancer. It has been edited for length and clarity.
I got into freelancing by chance when I was in college, enrolled at Duke University in 2019, and helped launch the Creator Economy program there.
I was already active as a content creator on LinkedIn and TikTok, so I understood the creator space. I hosted an event at Duke University with influencer and alumna Serena Kerrigan. During the event, I became friends with her creative strategist and followed her work in 2021. She taught me how to create content that aligns with digital trends and build an audience.
I started reaching out to creatives on LinkedIn, offering social media management and content management, and gained some freelance clients while I studied.
My graduate school job offer was rescinded
I was already working as a freelancer, but I had intended to get a corporate job after college: Duke’s culture was focused on becoming a lawyer, doctor, or consultant, and I internalized those expectations.
I interned at LinkedIn in the summer of 2022, between my junior and senior years of college. I learned so much. At the end of 2022, LinkedIn offered me a job for graduates of their Business Leadership program. I didn’t apply for other jobs because I spent my last year thinking I would have a job lined up when I graduated.
I graduated in May 2023. That same month, I was informed by LinkedIn that my job offer had been rescinded because the program had ended. The tech industry hiring downturn left me and many of my classmates in a state of shock. It felt like the rug had been pulled out from under our feet.
Instead, I’ve been forced to work full-time as a freelancer since August.
Freelancing was difficult at first
My “fun money” in college came from freelance work, and it was a shock when it became my only income. I thought I’d move to San Francisco for the LinkedIn job. Instead I moved back to my home outside Boston, and it wasn’t an easy change.
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I was grateful that LinkedIn had at least informed me that my job offer had been rescinded. It helped me focus on figuring out what to do next. Many of my colleagues were holding off on job offers. I knew I had to bet on myself and figure out how to gain more experience.
It wasn’t hard to find customers.
I reached out to some of the creatives I worked with in college, and Kerrigan’s creative strategist introduced me to a few people. I asked them if I could pitch them projects or help them develop a strategy. To get a foothold, I offered to take a small percentage of any brand deals as compensation.
I reached out to some of my old mentors on LinkedIn and people I respected in the creative economy and told them I was available to work with them in any capacity.
My first freelance clients were influencers, and the market was booming for freelancers as fewer companies were hiring full-time employees and investment in the creator economy was booming.
Contract work was in high demand and I had no trouble finding clients.
I liked the flexibility and versatility
The majority of my work has been with startups, including the creator app Canopy. I worked on a variety of projects for them: I led their influencer marketing campaigns, ran their newsletters, and helped launch their podcast.
I liked the flexibility – I like to get up early at 6:30am, work for a few hours, have a leisurely lunch, take a yoga class, and then go back to work. I spent three months traveling, staying with friends in Lima, Peru, and working remotely from Madrid.
Financial worries were stressful
There were some things about freelancing that I didn’t like.
I felt anxious when one contract ended and I didn’t know when the next one would come. Within two weeks, an email for another job would usually arrive in my inbox.
The biggest reason I quit freelancing was financial insecurity. It was hard to deal with. I was so stressed about money for the first 6 months. I didn’t want to live at home, but with the rising cost of living and rent, I couldn’t afford to move.
I also wanted the opportunity to learn something new. Freelancers are hired for their expertise and problem-solving. Learning new skills can be difficult for some clients. Companies have more budgets to support the continuing education of their employees.
I also wanted to see for myself the quality of work that you would expect from a Fortune 500 company. When you work for a startup, there’s a lot of work to do and you don’t necessarily go through the same processes as you would at a large company.
I got a job at a company
I first found out about my current job, Commerce Partnerships at NBCUniversal, in January. I met my current manager while I was freelancing for a startup during college. We would meet a few times a year to catch up and talk about my career goals. They encouraged me to look for a role on their team.
I applied in February and interviewed remotely from Madrid, heard I was accepted in April, and started in May, a year after graduating, when I moved to New York and began working in the office three days a week.
As a freelancer, I loved taking lunchtime yoga classes, but working set hours suited me well and it was nice to have colleagues to chat to around the water cooler or over coffee.
When I was a freelancer, I used ChatGPT as a manager. I would give them instructions like, “Act as a senior content strategist for company X” and ask them questions. It’s refreshing to have a real human being as a manager and be able to ask questions. It’s good to have a personal perspective.
But in a larger organization, people’s roles and jobs are more clearly defined. As a freelancer, I felt more ownership in seeing a project through from the initial idea to the final product.
I learned a lot from freelancing but I wouldn’t recommend it to graduates
I would like to go back to freelancing in the future. Since my first job offer was rescinded, I’ve been thinking I have no choice but to bet on myself. But first I want to expand my skills so that I can charge more for my clients.
Working as a freelancer has taught me more than I would have learned in an entry-level role. Knowing how to manage my workload and come up with ideas for a company has helped me in that role. Still, I wouldn’t recommend going freelance right out of college.
Wages are not keeping up with the rising cost of living, leading more Gen Zers to choose portfolio careers – careers where they freelance on the side to earn extra money to support themselves.
Nowadays, people work as freelancers out of necessity.
