What It’s Like to Go Freelance

by Alanna Greco

Abandoning the 9-to-5 life sounds incredibly exciting to some, and incredibly terrifying to others. With more and more people opting to live gig to gig, it’s probably something that you’ve thought about. But besides waking up knowing that you can theoretically wear sweatpants all day, what does going freelance really entail?

We spoke with five freelancers — Alanna Bass, a web designer; Amanda Lyon, an event manager; Ali Fenwick, a writer; Jane Meng, a makeup artist, and Adriana Picker, an illustrator — and asked them to share what it’s actually like to go freelance.

Everybody has a different reason for doing it.

Jane went freelance because she wanted to prioritize spending time with her family after her 5-year-old cousin confronted her about missing his birthday party (it was because of a blackout period at Jane’s retail job and yes, she felt horrible). Amanda decided to take a year as a freelancer in order to learn more about the different opportunities in her industry, and Ali left corporate life after feeling burned by legacy media.

But of course, you don’t need a reason to go freelance beyond the simple fact that you want to. “In the beginning it definitely wasn’t a sound business decision,” says Adriana, “but I had to go on gut and the fact that this is the life I wanted to lead.” Plus, if you make the leap and absolutely hate it, there’s nothing stopping you from going back to a full time job.

Do some prep work before making the switch.

Alanna, Ali, and Jane all started freelancing as a side hustle before quitting their full time jobs, which is a great way to build up a client base before going out on your own. But if that’s not an option, or freelancing takes you by surprise (hello, layoffs!), it’s helpful to do some research. Look at other people who freelance in your field, and don’t be shy about asking someone for an informational meeting.

Additionally, it’s a good idea to hone in on what exactly you’re going to be offering to clients. Freelancing is a great way to try new things and audition jobs, but when you’re starting out “you should have a very clear, concise example of what you do,” says Alanna. “Otherwise if you go out the gate saying that you can do it all, people aren’t going to trust you.”

Yes, not having a steady paycheck is scary.

Every freelancer has a different way of dealing with the inconsistent paychecks. If you can build a nest egg that’s fantastic, but if you’re living more paycheck to paycheck, Alanna suggests keeping a close eye on your expenses. “I know how much money I need each month — rent, power bill, etc — so I game out the type of jobs I take on. I’ll make sure that I have number of jobs with a larger payday, and I figure out when it will cover me until so that I know when I can afford to do smaller and maybe more exciting jobs.”

It’s also important to have a sense of your industry’s ebbs and flows so that you know what to expect financially. And pro tip from Jane: you might qualify for quarterly taxes, which can save you a ton. She manages her money by using multiple bank accounts. “I have one for business, one for personal, and my boyfriend and I also have a separate account for bills and rent, and once I put money in there I don’t touch it, which really helps,” she says.

No, you can’t just stay in bed all day.

When you have days that you don’t have to be anywhere, there’s a massive temptation to stay in PJs and work from your bed. But really, you can only do so much of that before it starts to get lonely, and less-than-healthy. (During her first year freelancing, Ali remembers having conversations with her dog, who she says “was a great sounding board but didn’t give much feedback.”)

“I have to be really strict with myself because working from bed is lovely sometimes, but it’s not good for your mental health,” says Adriana. “It’s important to get out into the outside world.” Join a co-working space, have work dates with friends, or even just put some real clothes on and work at your desk to get into a professional mindset.  

You’ll constantly be thinking about your choices.

Taking charge of your career is a huge responsibility, and without any managers setting expectations, it’s easy to become stagnant. That means it’s a smart idea to be self-critical. “I’m in a constant state of evaluating,” says Amanda. “After every gig I’ll ask myself, ‘Am I enjoying this?’ ‘Is freelance still the right move for me?’”

And there might come a time when you decide that freelance is no longer right for you, and there’s nothing wrong with that. “I love freelancing, but I’m considering going back to full-time work,” says Alanna. “It’s to the point now where I want to be able to go on trips and do nice things rather than worry about if I can pay my rent.”

A lot of being freelance is about knowing what you want and need.

When you’re on your own, you have to negotiate your own rates, set your own boundaries, find the jobs that you want, and defend your choices every single time you get a new gig. But that’s not necessarily a bad thing. “The number one thing that I like about freelancing is knowing myself and feeling empowered to make my own decisions,” says Amanda. “It’s been an eye-opening thing to understand what I want out of my day — and in a larger way, out of my life — and then deciding to make it happen for myself rather than putting it on a company.” Ali feels the same. “The biggest lesson I’ve learned is that it’s you. You’re out there and it’s up to you, and at the end of day that’s all you’ve got. That can be scary but it’s also empowering in a way.”

And that’s one of the best things about freelance: it’s an opportunity to think about what you want and to go for it. When you have full control over your career, your time, and your money you’re forced to consider what you’re working towards. Freelancing brings up some big and sometimes scary questions (like “What the F am I doing with my life?!”) that can be easy to avoid in a full time job. That’s not to say that freelancing will find you all the answers — but at least you’ll be thinking about the questions.