5 Burning Questions You Have About Going Freelance But Were Afraid to Ask

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Looking to quit your day job and strike out on your own? You’re hardly alone. Nearly 54 million Americans are now freelancing, according to the Freelancers Union, and more people each year are making the leap by choice (rather than defaulting to freelance after, say, losing a job). But successfully turning your side hustle into your main gig requires more than just ginning up work and doing it well. We asked Johanna Turner, a certified financial planner and certified public accountant with Milestones Financial Planning, to walk us through the biggest “what now?” money questions that new freelancers face.


Sole proprietor, limited liability corporation, corporation—oh my! When it comes to freelancing, you’ve got plenty of options about how to structure your business and there really is no one-size-fits-all answer. But think about how much you’d stand to lose if your business went belly up and collectors tried to sue you. “Let’s say you’re in your thirties, with no credit card debt or student loans and some home equity built up,” says Turner. “That net worth means you’ve got something at risk if something happens. But if you’re just starting out and have more debts than assets, you don’t really have anything to lose.”

Establishing an LLC or an S corp creates a wall between your personal and professional finances. But these also require money and paperwork. With an LLC, for instance, regulations vary by state and many business experts recommend having a lawyer review your articles of organization and operating agreement before you file anything. With an S corp, you might skirt some self-employment taxes, but you’ll also have to file payroll taxes and pay unemployment (weird but true). “You’re most likely going to have to hire someone to set that up and manage it,” says Turner, “So the savings you initially expect may be overblown.”


Whether you’re a graphic designer or a dog walker, get ready to pay estimated taxes four times a year (generally April, June, September, and January). The IRS—which offers a worksheet with Form 1040-ES to calculate tax estimates—expects you to tally your estimated income for the entire year and mail taxes in four equal installments. And if you pay Uncle Sam too late or too little, plan to get hit with penalties and interest charges.

“Quarterly estimates aren’t that difficult once you understand how they work and you’ve been freelancing for a while,” says Turner. “But in the beginning, a lot of businesses aren’t making money or don’t have a good sense of how much they might make this year.”

Here’s where shelling out for some time with a professional can save you time, stress, and potential penalty fees down the line. Even if you’re determined to go it alone when it comes to filing taxes, many CPAs will let you pay for a short consultation to review your plans. “When people first come in, they almost always bring shame with them—I don’t know what I’m doing, I probably messed this up, whatever. It’s OK," says Turner. "The important thing is to realize that to grow your business, you probably want to spend time on your business, not on learning tax codes.”


Cash flow can slay even a profitable business, because how much you’re invoicing doesn’t matter much if you don’t have the cash on hand right now to buy needed supplies or pay the rent. So how do you master the financial ebb and flow of freelancing?

Start by tracking your business expenses diligently (check out software like QuickBooks or Xero to spare yourself from Excel spreadsheet hell), then factor in any annual slow periods. If you know that work will dry up in the summer, say, because you mainly work for universities, you’ll need to make enough the rest of the year to cover those lean months. Then put yourself on a set paycheck—and resist the urge to splurge when you have a flush month. “Some advisors say you should have three or six months socked away, but I’d prefer you have a year of expenses saved up,” says Turner. Don’t think about taking more out of the business until you’ve met that high mark.


First, congrats on taking coverage seriously: The Affordable Care Act requires that everyone have health insurance (save for a small number of exemptions that you must apply and be approved for). If you used to have insurance through an employer, odds are you’ll be able to continue that same coverage through COBRA for up to 18 months. Your employer will no longer pay part of the premium, though, so prepare to pay more—sometimes a lot more—for the luxury of not making a switch.

Another option that can be more cost-effective is to check out your state’s health insurance marketplace. (Do an Internet search for your state and the words “health exchange” and make sure the site you’re on ends in .gov.) All of these exchanges have a defined open enrollment period, but don’t be put off by that: Losing or leaving your job is considered a special event that gives you a defined period of time to opt in to coverage.


First, the bad news: Freelancing means you won’t get the employer match that many corporations offer on retirement plans, essentially doubling the amount of money being saved for retirement. And, as a freelancer, socking away funds is going to require more effort than merely signing some form from HR. But the good news is that it won’t require much more effort, and picking a plan now doesn’t mean you can’t switch to a different type of plan as your business grows. “A financial planner or CPA can walk you through the different plans and help you pick one that matches your needs,” says Turner. Here are the three most common types of retirement plans for freelancers:

A simplified employee pension (SEP) IRA is available at most banks and brokerages, requires just one page of paperwork to get started, and can be funded with up to 25 percent of your net self-employment income, up to $53,000.

A one-participant 401(k), also known as a solo or individual 401(k), can be funded either pretax or post-tax, and you can access the funds before retirement under certain scenarios, like needing a loan or a hardship distribution. You can contribute up to $18,000 in deferred income, plus a portion of your net earnings up to $53,000 total.

A savings incentive match plan for employees (SIMPLE) IRA is a favored choice for small business owners who have (or plan to hire) employees. It allows you and those workers to contribute up to $12,500 annually and elect either a 2 percent fixed contribution or a 3 percent matching contribution (more on that here).

So how much should you be squirreling away? Twenty percent of your income, says Turner. But if that figure feels overwhelming, take a breath. “So many people can’t do 20 percent, so delay saving at all,” she says. “But every year that you put off is another year that you’ve missed the ability to max out that plan and earn that compound interest. Start as soon as possible—even if it’s only 1 percent—so you’ll get in the habit of saving early.” Your gray-haired future self will thank you.