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How to Make “I’m Thinking About Freelancing” Happen

Photo-Illustration: by The Cut; Photos: Getty Images

Amid all the turmoil and upheaval of the past couple of years, you’ve probably pondered a future outside of the hamster wheel of a corporate job – or had no choice but to quit your job. steady. According to a study by freelance platform Upwork, 36% of the US workforce held freelance jobs in 2021, an increase of 2 million people from the previous year. Of those who haven’t dipped their toes into the self-employed pool, the study found that 56% said they were likely to become self-employed in the future. For some it is a choice; others have been forced out of a company due to layoffs, lack of childcare and babysitting duties. But no matter what, becoming independent means you’re on your own.

Below, five self-starter freelancers over the past two years offer help, with advice on how best to build your new business on your own terms, recruit clients, stay organized and keep your workflow – and your income – reliable.

When the pandemic hit, I was working as a senior news producer for Patriot Act with Hasan Minhaj. After the season ended in June, I returned to Wisconsin to spend time with my parents, sister, and extended family. In September, we learned that the show was not renewed. I was at a point in my life where being close to my family seemed more important than striving for another impressive line on my resume. I just lost the disk.

I keep a list of people I’ve worked with in the past to check in with every six months or so. I set calendar reminders to send a quick note saying, “Hey, I remember we had a great experience working together, I’m available.” This dramatically increased the amount of work I was getting. There are people who think reaching out is mercenary, but if you’re genuine, people don’t treat it like someone asking you for a favor.

When my grandmothers died, they left me some money. One grandmother left each of the grandchildren $5,000, and my other grandmother had money in investment accounts. It was around $50,000. I agree that’s a pretty large sum of money, but it’s my retirement fund. I’ve dived into it when I’ve had really slow times or when I’ve been unemployed but I’ve tried to treat it like something that doesn’t exist because I want it to be something I can put to good use later.

I was laid off from my job as a content strategist and social media manager just before the pandemic hit, so finding a new job in marketing was nearly impossible. Eventually, I took up freelance projects and established relationships that led to referrals and regular freelance work that actually provided me with an income. I certainly make enough money, but the perks of a full-time position are really attractive, like employer-provided health insurance, paid time off, and a 401(k). So I’m still looking for a full time position that could provide that.

The simplest yet most effective thing you can do is start creating a spreadsheet for everything. It doesn’t have to be pretty or perfect, but you should document all your plans, bills, and finances – both money coming in and money going out – as soon as possible. I also use Google Calendar and Todoist to manage all my deadlines, working hours, projects and tasks and Wave to manage my invoices.

I feed on feedback and want in-depth, specific feedback on a project. The best way I’ve managed to overcome this is to take the initiative to work on more projects with a client. This way I automatically set new goals and push myself to do more so I can grow instead of feeling too comfortable. I always explicitly ask for feedback at the end of each project to better understand what the client wants in the future.

I went to law school, but ended up working in business development for a record company instead of being a lawyer. I didn’t look back on the legal stuff until the pandemic. I realized that if I ever had to change careers and do what I was in school for, now is the time to do it. I quit my job in early 2021, read the books, passed the bar exam, and completely turned to this new freelance career in music law.

Not only does the bar exam take months of in-depth study, but it still takes a few months to get your results. As soon as I knew I was successful, I formed an LLC and then had to open a specific attorney trust account to hold client fees and money. There are only a few banks that offer this so I had to do some research. I also joined a coworking space because as a lawyer people have very sensitive topics to discuss so they want an in-person meeting rather than just talking about it on Zoom.

I was lucky to find a good community of other lawyers – some music lawyers and people in other practice areas – who were there to answer my questions. Many people go headlong into what they think is right and don’t take the time to research and make sure what they are doing is the right way to do it.

When the pandemic started, I was working at a large design agency as a senior designer. There was definitely a glass ceiling in my field, especially for black women. In the summer of 2020, my fellow black employees and I, of whom there were few, wrote a collective action letter to my employer, which elicited a broad response from the company to bring new elements of diversity and inclusion that surprisingly had never been a part of the business. These changes happened very slowly. The straw that broke the camel’s back was that they were spoiling a bereavement for a COVID death. At the beginning of 2021, they gave me a day of mourning, then they tried to revoke it. I sent a very scathing letter to management and left.

I’ve always had high self-esteem, but I was naive about how a workplace can make you question yourself. It took me six months to regain my self-confidence. When I resigned in February 2021, clients started coming to see me. These clients really respected what I had to say. They embraced the work I did. They recommended me to other people. I started to remember why I loved being a designer and art director in the first place.

As someone who can worry about a myriad of things, I had to say to myself, What little thing did you obsess over for days six months ago? I have to tell myself every day: you don’t remember. It’ll sort itself out. The most ambitious and talented people think their job is the worst, and so they work harder. You might think there’s a reward for this self-flagellation, but it takes a long time to realize that you can be critical of yourself, and it’s worth having a critical eye on your own work, but you should also take advantage of it.

I worked as a broadcast assistant for an Irish national radio station for four years. About a year into the pandemic, an opportunity arose to start editing a podcast for an American client. This snowballed into other opportunities until I realized I had enough freelance work to start doing it full time.

I was back home in Wexford with my parents when the pandemic hit, so luckily I had no rent or bills to pay at the time. I had saved some money, which helped me through the quiet early weeks when I wasn’t as busy as I am now. I also make sure to budget for things like tax bills and expenses. Finding a good accountant is so important. Be sure to keep accurate records of receipts, invoices. Things can get overwhelming and it will make life easier for you and your accountant if everything is in order.

When you’re just starting out in the freelance world, it can be very tempting to say yes to every offer, especially if the money is good, but there’s also a risk that you’re taking on too much. I’ve been in a few of these situations and realized the importance of sticking it out, being clear about your expectations and how you will and won’t work. I make sure not to respond to work-related emails and messages outside normal working hours – 6pm is usually my cut-off time – and I don’t normally work weekends unless I’ve given my agreement at the beginning of a project. I have also set a minimum daily rate, which ensures that I will not be underpaid. I recently decided to write a document detailing what I expect from clients and what they can expect from me. I now send it to every new client I work with to avoid any potential issues later. That way we can both be sure it’s a good fit.

Interviews have been edited and condensed for clarity.

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