So You’ve Decided To Freelance. Here’s What You Need to Know Before Taking the Plunge

From negotiating pay to doing taxes

56.7 million Americans spend 1 billion hours per week freelancing. Getty Images

Ah, freelancing. Arguably one of the best options for workers seeking autonomy, a flexible schedule and the freedom to wear sweatpants to the office, the field has swallowed a sizable chunk of the American workforce—56.7 million citizens, to be exact, according to a 2018 study commissioned by the freelancing platform Upwork. That adds up to more than 1 billion hours per week spent in the freelance hustle, and that’s only expected to increase as more options in the gig economy open up.

“You know, when people used to say they were freelancing, it was sort of a euphemism for ‘I’m unemployed right now,’” said Caitlin Pearce, the executive director of the Freelancers Union, a nonprofit organization dedicated to advocating for freelancers. “And that’s really changed. Freelancing’s become more mainstream, and more people are realizing that there’s more than one way to work.”

But those positives come with some headaches. You’ll have to hustle—a lot. You’ll have a bit of uncertainty about when that next paycheck is coming in. And you need to get used to an entirely new tax system.

But this installment in Adweek’s annual Grad Guide is here to walk you through how to nab that first freelance assignment, from finding that job to filing those pesky taxes.

Finding gigs

Before you wade into the job-hunting pool, you’ll need to do a bit of self-promotion, according to Pearce. Typically, this means having a website with some kind of a portfolio of your past work, either creative ads, SEO or ad campaigns. Graphic designers and web developers; copy and content writers; and ad managers will all have different examples of what their past work looks like.

“You’re really selling yourself, which means finding the unique value that you offer and your specific niche,” Pearce explained. “That can be a challenge when you’re first getting started, especially if you’re still exploring what talents you have to offer. But your websites, your portfolio, your social media presence should all tell a specific story of the type of work you want to do and the skills you want to bring to a project.”

These same tools could also be used to research the marketplace and figure out what you offer that’s different, said Beth Wiesendanger, senior programs manager for freelancing platform Fiverr, who pointed out that everything from your social media presence to your LinkedIn profile can be used to get a good scope of the competition you’re up against.

“Take a look at other people’s portfolios and see what’s worked well for them,” she advised, adding that you can also look for spots in which they fall short where you can offer your services.

Just like no site and portfolio are created equally, no job hunt and market will be the same, either. Some sites, like Fiverr and Upwork, offer ranges of jobs from small, quick, low-paying jobs to long-term contracts. Folks with more tech-centric chops might fare better on sites like AngelList, while those looking to enter the branding and creative fields might hit up sites like Folyo and 99designs.

Negotiating your pay

Once you’ve found a company that’s agreed to turn your words (or graphics or code) into dollars, it’s time to negotiate what those dollars look like, which means setting your rate high enough that you can cut some sort of profit, but also not so high that potential clients bolt from negotiations.

How much you should charge is a “deeply personal choice,” said Pearce, and one that should take everything from your level of experience to your cost of living to your overhead fees into account. If that math makes your head spin, there are many programs that can help calculate a rough estimate of what you should charge per hour. Some freelancers might choose to charge a flat “project” fee rather than an hourly rate.

“We find freelancers coming down on different places on this,” Pearce added. “But we always advocate people treating themselves like a business and being mindful of letting other people know that this is their profession, and they expect to be paid for their work.”

Once you decide on that rate, there’s one thing that you always should have in your back pocket: a contract. This is the piece of paper that helps solidify, among other things, your rate, the parameters of your project, deadlines and any reimbursement. These are what ensure you get paid for your work. And if you’ve never written one out, there are resources for contracts on websites like LegalZoom and the Freelancers Union to get you started.

Doing taxes

Of course, once you start raking in the cash from your gigs, you have to take care of what’s arguably one of the most daunting parts of being a freelancer: the taxes. Both Pearce and Wiesendanger pointed out that there’s a slew of tech, from apps to websites to e-books dedicated to walking even the least seasoned freelancer through this byzantine task. Services like Bonsai or And Co can help freelancers stay on top of expenses and earnings for the month, which simplifies the process of wrestling with the IRS once tax season comes around.

“In the past five years, we’ve seen an explosion of financial tools—everything to to help from client management to taxes to invoicing and productivity,” said Pearce. “It’s really empowering to see freelancers spending less time tackling those hurdles and more time doing the work that they love.”


@swodinsky shoshana.wodinsky@adweek.com Shoshana Wodinsky is Adweek's platforms reporter, where she covers the financial and societal impacts of major social networks. She was previously a tech reporter for The Verge and NBC News.
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