The Hard Financial Lessons I Learned as a New Freelancer

At the beginning of March, I started work as a freelancer, excited to embark on this new career as a writer and podcaster. I set about making spreadsheets and lining up assignments. Every social-media ‘heart’ and ’like’ seemed like an extra vote of confidence in favor of me betting on myself. I even threw a party to celebrate. Then, one month later, I hit a low. I overdrafted my checking account for the first time in years. I felt embarrassed, of course, but mostly, I felt a little panicked. I thought I’d researched all I needed to know about freelancing. I thought I had the spreadsheets! Turns out, spreadsheets can get you only so far as a freelancer, contractor or gig worker. More young people are taking this type of work, as a full-time freelancer or as a way to augment their 9-to-5. And in a world where you’re often doing the marketing, the money managing and—oh yeah—the actual work of your own freelance business, there are always going to be some lessons you learn the hard way. ‘It’s all an experiment,’ says a founder of a financial firm for creatives and other freelance workers. ‘You have a hypothesis: ‘Can I do this and make a living?’ Get some data and what you do with that data, you make adjustments to the hypothesis. If you look at entrepreneurship from that perspective, then you’ll realize it’s all an experiment.’