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The Challenge of Defining Success as a Freelancer
What does it mean to do well in your career when you can’t be promoted?
Around the end of last year, freelance writers started showing up on Twitter to sing a song of themselves. In long threads, they posted links to the articles that had made them proud, netted them a lot of cash, or simply been published somewhere important. For some, it was a way to tout their best stories and attract editor attention. For others, it was about comparing prices and commiserating over diminishing rates.
Many offered a reality check, proclaiming themselves lucky to have found work in a slowly deteriorating media landscape. A few were refreshingly honest about the invisible forces that worked to their benefit, like generous parents, wealthy spouses, or no student loans. Functionally, all were doing the same thing: giving themselves a year-end review when they don’t have a job, office, or boss to do it for them.
I’m a freelancer, too, and while I didn’t tweet out a list of my own, I took note. Collectively, the threads struck me as an interesting thought experiment, offering valuable insight into the work culture of a group of people who have no work culture.
Learning to recognize and celebrate success can be tough as a freelancer. That’s not just because we can struggle with time management, a shrinking pool of opportunities, professional envy, and irregular cash flow. It’s also because, when you’re a freelancer, you’re rarely venturing down a well-trodden path. What does it even mean to be successful when you can’t be promoted, get a raise, or give yourself a title that makes sense to the rest of the world?
According to the most recent edition of Freelancing in America, an annual joint study by Upwork and the Freelancer’s Union, American freelancers racked up more than 1 billion work hours last year. Between 2014 and 2018, their ranks swelled by 7%, to 56.7 million people — in part, according to the study, because of the entrance of younger workers into the labor force (compared to other generations, members of Generation Z are most likely to pursue freelance work) and the fact that it’s becoming increasingly easier to find freelance work online. What’s more, the percentage of self-proclaimed freelancers by…
