It’s the plunge when every freelance writer must stand on the edge of the board and consider at some point: “Do I dive into the freelance life, or do I continue to tread water as a moonlighter?” The transition from full-time employment at a magazine, website, publishing house or media company to standing on your own two legs — er, 10 fingers — isn’t merely about having contacts and assignments, but having confidence in your ability to manage finances, your attention span, taxes, and the list rattles on.

Though plenty of journalists are able to reap success without being confined to a single publication or job title, understanding what’s waiting for you in the deep end can help you know if you’re fully prepared to jump. As a professional writer who has been freelancing for a decade and consulting full-time for about a year, I knew I was ready when I had a steady workflow that allowed me to survive, save, and travel — without worrying too much about the specifics.

Even so, like many of these freelancers, I built my freelance trajectory through trial-and-error and through developing systems to keep me honest and accountable. As the trite saying goes (but hey, it’s true): It hasn’t always been easy, but it’s definitely been worth the risk.

Here, well-known and talented writers share their perspective for transitioning into #thatfreelancelife as seamlessly as possible:

Knowing if you’re ready to freelance full-time

Much like becoming a parent, chopping to the runway-inspired bob or agreeing to make it Facebook-official with a new mate, it’s tough to ever know if you’re 100 percent ready to tackle a new chapter. That being said, being proactive goes a long way in setting you up for success as a freelancer. For freelance lifestyle reporter Wendy Rose Gould, her first gig out of college at a small newspaper quickly taught her the on-staff life wasn’t for her. Unhappy and dissatisfied, she decided to take the route of teaching English abroad in Seoul, where taking on spec assignments felt like a natural side-hustle. By reaching out to former internships, she was able to land a column, and eventually once she was back stateside, test freelance writing as her only employment. “I hustled hard — worked for pennies sometimes — but really built up an arsenal of clips. It’s been 10 years since then, and I’m doing better than I ever have before,” she shared.

For Amy Gorin, MS, RDN, a freelance writer and owner of Amy Gorin Nutrition, the transition was a tad more complicated. While working as a magazine editor for eight years, she spent seven of those attending night school to become a registered dietitian nutritionist. As she pursued her passion for health, she knew she had to combine her editorial expertise to build a fulfilling career. That’s when she stepped into freelance writing, eventually prompting her to let go of the harbor of the masthead — and ahem, the 401K —to really test her skills. Years later, she’s built a name, blog and business for herself. Those eight years though? Needed to help her navigate the ropes.

Without a set “ready Freddy” rule for going freelance full-time, the most important question to ask yourself is if you’re prepared to take the chance, without knowing the final income. It also helps, according to many writers, to have some savings to rely on as you begin to build your client base.

How to financially prepare for the shift

As the media industry continues to pivot, so do the opportunities for talented writers — meaning if you scour hard enough and craft your skills, you can find plenty of lucrative opportunities. While they might not always be traditional journalism assignments, content marketing, ghostwriting and SEO gigs continue to sprout. While additional income is always welcomed, no matter who you are, when you’re supporting yourself completely, your taxes, savings account, your retirement plan and your spending money all become your sole responsibility.

Truth be told? It’s a lot, but not an impossible feat with careful planning. Before I decided to quit my full-time gig, I ensured I had at least six months’ worth of expenses covered, so in the rare circumstance that all my clients decided they weren’t assigning anymore, I would still be able to pay the bills. Luckily, that didn’t happen, but it provided a cushion big enough to give me the guts to go for it.

For Gould, stowing away money wasn’t as much about creating a financial umbrella for rainy days, but accepting the inevitable ebb-and-flow of freelancing. It’s not only unpredictable both in assignment and payments, but it’s continuously up and down. Like me, Gould suggests having at least three months in the bank, and then working your way up to at least eight months. Once she achieved this milestone? She opened up an IRA.

“At first, I wasn’t able to max it out, but I always made sure to put something in the account, even if it was only $50 for that month. I’ve been fortunate enough to be able to max out my IRA over the past several years, and am in the process of opening a Solo 401K,” she explains. It’s not only for the post-50 (and 60) days either, Gould also has a travel fund where she can prioritize what matters most to her, including jetsetting. While your lifestyle will change as a full-time freelancer, she notes it’s important to still carve out the funds to continue many of the activities you enjoyed while on a salary.

It’s also important to note that all of the dollars in those checks don’t fully belong to you—a big chunk goes straight into the pocket of Uncle Sam, which requires you to tuck away a percentage for tax season. Speaking of which—taxes aren’t just an annual pain for freelancers, but a topic that should always be top of mind. See how the new tax law might affect you.

How to set yourself up for taxable success

guide for freelancing full time

While it’d be a sunshiny day for every freelancer if taxes were suddenly voided from their plethora of direct deposits, one of the greatest shifts when becoming a solo-preneur is understanding your tax picture, bracket and requirements. Freelance writer and editor Aly Walansky has a steadfast rule for herself and recommendation to fellow consultants: Always pay quarterly taxes. These can be set up by your tax accountant (oh yeah, get one of those too!), and help make your payment lower in mid-April. While you’ll pay the ultimately the same, it can be less overwhelming to pay gradually then to shell out a lump sum at once. And once you’ve made above a certain threshold, it can also lower your risk of being taxed mid-year for not giving the government their due quick enough.

Gould also suggests using the resources available to the freelance community to manage taxes. While she personally uses Intuit’s Quickbooks to keep track of her expenses and miles, there are countless other resources that could be potentially helpful. If you’re also still figuring out how to motivate yourself to save, knowing you’ll have a bill to federal and state might be a useful trigger. But don’t just do it once a year, according to creative director and writer Makasha Dorsey. Instead, try to reconcile your income, your expenses, your budget, your write-offs as often as you can. She suggests if not weekly, combing through monthly will save you time, energy and stress.

If it all feels like a bit too much to manage on your own, that’s because it could be, according to Gorin. That’s why it might be beneficial to take it off your plate and give it to someone else. “One of the first things I did when going out on my own was seeking out other professionals to help me. My taxes are too complicated now for me to feel comfortable doing them on my own, especially since I’m an LLC. So I have an accountant who advises me quarterly on tax preparation,” she adds.

While learning to delegate — and where to invest your hard-earned cash to make your jobs easier — is an integral part of working for yourself, there’s another soft skill that’s indispensable as a freelancer: self-motivation.

How to keep yourself accountable and on-task

Since no one will scold you for missing a deadline, you have to create your own processes to ensure you never lose a client. Or at least, try not to. The tricky part of determining what will be impactful for you is that it’s unique to your working style. While some can manage with a spreadsheet, others need more robust programs or apps to keep them focused. But what’s more important than whatever you choose, according to Walansky, is your mindset: “Never ever stall. You may think you have a ton of time, but you have no idea if a windfall of work will come in the interim. I start working on assignments the second I get them, even if I have a month to work on it,” she explains.

For Gorin, time management has proven to be an important talent to hone to keep herself accountable. To ensure she doesn’t overwork herself or agree to work when she doesn’t have the time, she says she lives by her Google calendar. “If I’m unsure of whether I should take on a new project with a tight deadline, I block out how many hours I think my other projects are going to take for the week to see if I’ll have time,” she explains.

I log around 60 articles a month, which averages out to about 15 a week, give or take. Considering my publications bleed into the dozens, I pull on my old editor hat and self-impose deadlines. Before a month starts, I look at my workload and assign myself days to complete stories, usually a few days before their actual due date. And each Sunday, I check in on the progress for that week’s worth of content to make sure I’m never in a bind: Is my research finished? Are my interviews completed?

Though I’ve had some weeks with unpredictable mishaps, I’ve mostly been able to live by this system, keep clients and take on new ones… with never working a single Friday in the process. I do, however, work from wherever I am — whether it’s a bus driving between Casablanca and Marrakech, an 8-hour flight from Malaysia to Sydney, or a two-hour ferry between cities in Croatia — to ensure I can maintain my digital nomadic writing life. It’s a compromise for sure, yet one I’m willing to make to travel.

But while some freelancers thrive at home, I’ve learned I’ll never meet those deadlines if I hang out in my pajamas. Instead, I’m much more productive in a public setting. After I’ve showered, had my coffee and turned myself into a sweatpants-free human, I find co-working spaces and coffee shops much more up my alley. I also try to wake up at the same time and finish work around the same time, with a shift in time zones being the only exception. Having a place to “go” to makes this much more likely to happen, and creates the much-needed schedule I need to remain in the zone. After all, it’s not only about how you work, but where you’re the most productive, at home or out of town.

Though Walansky and Gould agree there’s no place quite like their couch or desk to zip through articles, a change of scenery, even in your own home, can help inspire your work. Since Gorin gets restless easily working from home, she finds ways to break up the hours: “I have a home office. So I’ll usually spend a few hours in there each day, move over to the dining room table and maybe later in the day pop into the coffee shop down the street,” she explains. “I also schedule my recipe development and food photography in small bursts, usually in the morning to take advantage of natural lighting, to break up my week.”

To determine what keeps you the most focused and on task, test out different areas in your town, taking note of how quickly and effectively you work, sans distractions. And if your budget allows, invest in whatever method works from you —from membership dues at a communal working space and renting office space to constructing your concentration-perfect at-home office.

The move to freelance isn’t a simple one, but with the right prep — and plenty of pep talks — you can build a career for yourself. Perhaps the best advice of all? Not keeping quiet about your worries, frustrations and pitfalls. Continue to invest in your network, chat with other freelancers, and of course, read our blog to inspire your leap. If plenty of professionals have made it happen before you, there’s no doubt you can wrangle in the bylines, too. The first step of course, is taking one.


Disclaimer: This article is meant as a guide for informational purposes only. It does not constitute a solicitation or provision of legal or financial advice, nor does it establish a client-attorney relationship. Please consult a professional in making any decisions for your business