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As many industries struggle to recover in the ninth month of the COVID-19 pandemic, people are wondering, perhaps even more so than usual: Should I start freelancing?
Traditionally, this choice is often spurred by people’s desire for freedom, creativity, and projects that speak to their interests. For many people at this particular moment in time, though, it’s less of a choice than an obligation: Some workers have been forced into freelancing by the economic disaster that is COVID-19, during which people have increasingly taken contract work where they can find it. (Freelancers are also eligible for unemployment assistance via the CARES Act until at least March; per the new stimulus package, they may also be eligible for an extra $100 per week along with the $300 added to typical weekly unemployment benefits.)
VICE spoke to eight people about what it’s like transitioning to freelancing full time. Everyone’s experiences with going solo are different, but one thing is certain: Doing taxes when you’re self-employed sucks.
Interviews have been edited for length and clarity.
Case Erins, 30, Kansas City, MO, performer
Photo courtesy of Case Erins
I worked as an office manager in a chiropractor’s office for a little over five years until I made a very dramatic move from health care to entertainment and writing in 2018.
At my old job, my boss and I butted heads over the routine nature of the role. I’ve always been miserable in office jobs, but it came to a head after half a decade of doing the same thing every day. In my free time, I was doing some performance work acting in murder mysteries and princess parties in my free time. As the company I performed with grew, acting started to look like something I could actually make money doing, so I took the leap.
There are certainly shortcomings to freelancing. We’re not as secure in terms of worker protections. I do a lot of my gigs as an independent contractor, which means I don’t get sick leave, family leave, etc. There are unions like SAG/AFTRA to take care of big-time actors, but most performers just have to cross our fingers for good working conditions.
Insurance is also a challenge. Most employers don’t offer it, and applying through the Marketplace can be difficult because it’s not really set up to deal with the inconsistent pay that I tend to make. Even when I could make mostly-correct calculations, I couldn’t afford the premium anyway. I’m fortunate to be married to a fantastic woman who actually likes office work, so I get my insurance through her job. Self-employment taxes are a challenge. They’re SO much more complicated and it can be quite overwhelming, but I’m starting to get the hang of it. Plus, I make enough money to pay my bills and still get takeout every now and again, so that’s good enough for me!
Even so, being able to make my own schedule and only do jobs that I actually enjoy makes a huge difference. I’m a lot happier now.
Whether freelancing is viable in the long run definitely depends person-to-person. If you’re highly independent and can learn to schedule leisure time for yourself, you can avoid overcommitment, but if you’re not good at saying no to gigs, your work/life balance will probably suffer. COVID has made entertainment freelancing in particular even more precarious. However, I’ve seen lots of new job opportunities pop up that didn’t exist before because of it: I’m currently doing murder mysteries on Zoom from the comfort of my own home, and I think that’s pretty cool!
To make full-time freelancing viable in the long-term, you have to be extremely flexible. The hardest thing for me to learn was to allow for time off. When I first started freelancing, I wasn’t sure if I would have enough money to pay all my expenses, so I said yes to every gig, no matter what. This led to working way too many hours, and the constant fear that I might be double-booking myself. After it started to become apparent that I would be able to stay afloat, I started being pickier about the gigs I accepted and gave myself consistent blackout times. I strongly recommend that every freelancer give themselves time off as part of their week-to-week schedule.
Erica Burgess, 24, East Hollywood, CA, producer and videographer
I was working close to 45 hours a week as a manager at an arcade and laser tag arena. Eventually, I realized that even if you are the most loyal, hardworking, and trustworthy employee, you can always be replaced with zero hesitation by someone who will work for cheaper or the owner of the company’s nephew. I became a music festival videographer and was doing that until COVID destroyed our industry. Since then, I’ve used my experience in video (from freelancing only—I’m entirely self-taught) to learn how to produce livestreams for electronic artists. I also started moonlighting as a VJ and I’m hoping to grow that into a new career one day.
I wish I’d known that working freelance means that you’re constantly pursuing leads on gigs, and it never stops. I’m always looking for gig postings online and talking to clients about future projects. Despite this, it’s perfect for me. It gives me the freedom in my schedule to travel and take on more work because I don’t have to conform to a 9–5 schedule. I’d estimate I work anywhere from 50–90 hours per week; you don’t really count when you’re enjoying the task. I typically rotate between four or five different projects at any given time.
I don’t really have a work/life balance. I’m on call 24/7, and I work on projects in the middle of the night if inspiration strikes me. I can’t imagine restricting myself to only working specific hours of the day—I enjoy the freedom of working when I naturally want to. In the long-term it’s exponentially more difficult than clocking and doing tasks you are told to do, but I can’t imagine going back now knowing I can live without it.
The finances are the hardest part for me. I started freelancing when I was 22, so my parents set me up with a mutual friend accountant to handle the taxes and expenses, who I still use to this day. I’m still young enough to be under my parents’ health care, so I have a bit of time to figure that part out.
Sharifa Khan, 27, Queens, NY, photographer
Photo courtesy of Sharifa Khan
After graduating from college, I began a full-time position in finance as a HR manager and marketing associate. Outside of my professional life, I always saw myself as creative, but I didn’t come from a cultural background that provided space for that part of me to thrive. In 2017, I did some photography jobs on the side, and it was clear to see how much of my heart was in that over anything else I had ever done, so I took the plunge.
Freelancing can be incredibly stressful when I have multiple projects going with different clients, but if I’m able to create a stream of income that is viable for the long run, I don’t think I would trade freelancing for a full time position ever again. I have a long-term plan to build a business from freelancing, but I wouldn’t consider it a stable source of income quite yet.
Budgeting personal and business costs is the only way I’ve been able to manage finances. I have to ensure I have enough saved up at all times to cover surprise expenses, like ordering in when you’re on deadline or replacing broken tech, since a regular, consecutive income isn’t guaranteed. I shift 30 percent of any income to my savings to cover taxes and other expenses. Even today, I sometimes struggle with taxes. I look forward to having an accountant just tell me what to do someday. I also wish I had a better understanding of rates and tips on how to ask for the correct amount. I think a lot of us get screwed over that way in the beginning.
My advice: Saving will give you the freedom to explore projects you really like. Save a decent amount of money before you commit to freelancing full time, if possible—I’d say $10,000 if you don’t have an established clientele, and $5,000 if you do. These numbers really depend on the person’s position and how much expenses they are going to be responsible for, such as rent and car insurance.
I also suggest finding a mentor or peers, especially to support you in the emotional parts. People sometimes don’t think about before they go full-time freelance is the loss of co-worker relationships, which can be vital for motivation. It might be helpful to find someone who can make you feel like you still have that while you’re finding your way.
Ursula Wren, 27, Asheville, NC, software developer
I actually never decided to become a freelancer. Prior to learning to code, I’d worked in screenprinting since I was a sophomore in high school. My family was always pressuring me to go to college, so I convinced them to help me pay for a coding bootcamp instead.
I knew I wanted to work remotely, but I was hoping to find a full-time position at a remote tech company. I’ve now been writing code for three years and have yet to be offered a full-time position. I’ve worked for three different companies, all of which started by promising me a full-time job at the end of a “trial period” as a contract worker (meaning, I was self-employed), but none of those offers ever materialized. I’ve actually heard many people in tech complain about these kinds of “permatractor” positions. Tech companies expect us to behave like full-time employees without any of the benefits that come with that.
Before beginning to freelance, I didn’t realize how much I’d have to pay in taxes. I was also blown away by how expensive health insurance is. To be perfectly honest, my finances are a disaster. I don’t have health insurance. I have a ton of debt. The capitalist game of finances makes me want to scream.
If I could find a relatively secure income in another field outside of tech while still freelancing remotely, I’d swap to that. That being said, I’ve given up looking for a full-time tech position. I don’t even want it anymore. I’ve grown really attached to the flexibility of being my own entity. I don’t think I would ever willingly go back to working under someone’s thumb in an office or being managed full-time.
Ivy Vernalis, 22, Brooklyn, NY, sex worker
I graduated from college in the middle of the pandemic with a double degree in creative writing and art history, but the job market is so tough right now that I haven’t even tried looking for a full time job in my field. I also worry I wouldn’t be able to get a job because I’ve been doing sex work, which is something I really enjoy and luckily have been able to create income from.
I’m 22 and still on my parents’ health care, which is a privilege that has definitely allowed me to take care of myself at little personal cost. I’m starting an LLC this year, but I dove right into this and definitely didn’t work out the finer points of financials in advance. I’m enjoying my work a lot, but I think, long-term, I may need to gravitate towards something that provides more job security and a concrete schedule.
I wish I had thought more about scheduling and a work/life balance before diving into freelancing full-time—especially due to the fact that I work a lot on social media. Because my work is always at my fingertips, I could pick up work at any time, which—thanks, capitalist hellscape—I feel compelled to do. I work all the time—probably 40–50 hours a week on my phone for technical matters, plus shoots, which are anywhere from two to six hours. I shoot around three to five times a week depending on my schedule. It’s nice to be able to lean away if I need to with a flexible schedule, but I need to work on creating more space for taking care of myself. I work myself physically more than my body can take, sometimes doing four shoots in a row and then ending up in bed for two days. Freelancers should know that setting a manageable schedule is very hard, and very important.
Hayley McMahon, 25, Washington, D.C., social media contractor
Photo courtesy of Hayley McMahon
I worked in non-profit communications before I started freelancing as a social media contractor. I left a really toxic job at the end of 2019 and I was afraid to jump back into a full-time 9 to 5 and potentially put myself in a similar situation.
I originally intended for freelancing to be a fairly short-term thing. I hoped it would help me maintain some financial stability and control my own working environment as I took time to find a full-time job that I knew I would really be happy in. Then COVID-19 hit and many non-profits lost a lot of their income sources. I started taking on more long-term contracts and found a couple of clients that I really loved working with.
I’m not planning to freelance forever. There are days where I really, really miss the stability of being a full-time employee. I used to know that I was getting paid every other Friday, and now checks just come… when they come. It takes a long time for some organizations or clients to process invoices, and that can delay payment. Sometimes I feel like half of the work of freelancing is just trying to track down unpaid invoices. Freelancing is precarious—you don’t know when you’re going to find your next contract, and you don’t know when you’re going to get paid for your last one.
The finances are the hardest part. There’s A LOT of administrative work behind freelancing. The taxes… oh my god, the taxes. Taxes for freelancers are way more complicated than they are at a regular W-2 job where most things are done for you—and they’re WAY more expensive! I think most people, including people who hire freelancers don’t realize that we pay an additional self-employment tax of 15.3 percent on top of federal, state, and local income taxes. That’s fine when you’re consistently making good money, but if you’re a freelancer who makes $2,000 or $3,000 a month and you only get to keep 65 percent of what you earn after taxes, it can be really hard to make ends meet. I keep a detailed spreadsheet of every single invoice and check that comes in or goes out. It’s the only way I’ve found that I can keep up with it all.
I’m very lucky to get health care coverage through my husband; I really don’t know how I would do it if I didn’t have that option. I really expected the work/life balance to be better than it was with a full-time job because I work a lot fewer hours, but it’s actually much less of a balance now. As an employee, you tend to have a set schedule, and when you have to work overtime, you generally are given a heads-up. When you’re a freelancer, client needs can come up at any time, and it often means I have to rearrange my work plan for the day to make things happen on time.
Chaya Milchtein, 25, Milwaukee, WI, automotive educator
Photo courtesy of Chaya Milchtein
I’d worked in the automotive industry for nearly seven years when I was laid off in April. I launched Mechanic Shop Femme three and a half years ago, while still working full time. When I got laid off, I took some time to grieve, and then jumped headfirst into scaling my small business as an automotive writer and educator.
Honestly, I’m loving it! I wish I’d started sooner, but I worried about not looking for a more secure full-time position instead of taking on work that felt a whole lot less secure. I reframed freelancing as self-employment and focused on having a range of revenue streams. If you don’t put all of your eggs in one basket, once things dry up or slow down in one revenue stream, you have another that you can focus on to make up the lost funds. I was surprised at how many opportunities were out there, and found that a lot of working for yourself is following up and juggling a bunch of balls, all at the same time.
If I can offer one piece of advice, it would be to get an accountant. An accountant will be able to advise you on taxes, the best way to buy insurance, and other financial parts of freelancing. This will help you avoid taking advice from people that aren’t dialed in to your very specific business. You can’t know everything, and you should leave accounting to a professional if you don’t specialize in it. Make a plan for your finances and work it. The money you invest in support will come back to you multifold.
Jessy Molina, 43, Baltimore, MD
Photo courtesy of Jessy Molina
I was the director of diversity, equity, and social justice at a local independent school. I decided to move into full-time consulting work because I wanted to support more organizations and institutions to make long-term, sustainable change around equity and justice. I also had an interest in doing more conflict mediation and healing work with people and communities.
This is the best professional decision I have ever made. I am thrilled that I get to support people in healing from racial trauma every day, and in doing so, continue my own healing journey. Our bodies are carrying the weight of racial stress, anxiety, and trauma, and I’m grateful to support people to find more freedom and joy. We have to learn how to talk about race and racism in this country, and to make systemic changes with big impact. I am grateful to be part of that.
I’m also so thankful that I get to work at home with my children. It’s a joy to help them with their homework, sneak in a favorite episode, or make cookies after lunch. It’s certainly difficult to balance on some days , but overall, I am loving the extra time we have together.
The most important part for me was connecting to my purpose. Who am I and what I am here to do? Serving as a mediator, facilitator, and trainer helps me get closer to my purpose of building connection and community among people and supporting people to live full, free, and whole lives.
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