“What do you do for a living?” is basically a standard greeting in the United States, so being American, almost 30, and not having a straight answer to that question can be daunting.
When I first started telling people about my new career path, the response was mostly uncomfortable reactions and blank stares. That’s crazy. That’s irresponsible. That’s impossible.
After over two years of making it work, I now often get the opposite reaction: “You’re living the life! What a dream job!”
The reality of the job, of course, is that it’s a little bit of both.
In short, I’m a freelance writer, and I have no home.
Costa Rica is my home base, but I go where impulse leads. I spent last summer backpacking around Europe and the summer before living in New York City. I spent a winter traveling from Mexico City down to the Yucatan, lived on a vineyard in Tuscany for a month, and have bussed up and down Central America more times than I can count, all while making a living from my laptop. And, I get to do something I have loved obsessively since I was old enough to put pen to paper.
Behind the scenes, the answer is longer and messier. I’d like to pull back the curtain a bit for you all and explain what it’s really like, so I’ll give you this: 1) how I got here, 2) why it’s crazy and irresponsible, 3) why it’s my dream job, for now. If you’re still interested by the end of all that, I’ll link you to some helpful resources. Because one thing you should know right now is that if you’re thinking about self-employment of any kind, no one’s going to hold your hand.
Deciding To Be A Freelance Writer
After burning out in my previous job, I saved up so that I could move and find a new job. Except, on impulse, I decided to quit and fly off to Costa Rica to do a Spanish immersion program. After that, I traveled around Central America for a few months on my savings. I was enamored with the freedom of my newfound lifestyle, the rewards of constant learning (a new language, a new form of dance, a new type of cooking, a new bus system), and most of all, with the “sweet waist of America,” as Pablo Neruda called it. I was nowhere near ready to leave Central America or give up travel for a desk job – but after 6 months, my bank account balance disagreed.
As they say, necessity is the mother of invention. As much as I had always loved writing, it wasn’t until I looked at my nearly empty bank account and pictured going back “home” that I finally quit daydreaming about being a published, paid writer and started taking action. I read everything I could about freelance writing and dove in head first, finding clients in every corner and crevice of the internet I could.
My First Year Freelancing
The first year of freelancing, unless you’re coming into it with an extensive and relevant professional background, is rough. A friend of mine once asked me what I think the biggest reason I’ve made it as a freelancer is, and honestly, it’s that I stuck around. Between constant rejection, clients that don’t pay, and very unstable and low pay, most people give up a few months in.
Anyone who tells you that you can quit your job right now and make it as a freelancer, a blogger, a digital nomad no matter who you are is lying. Among other privileges, you need to either have a lot of money sitting around in your savings, a ballin’ sugar daddy, or lots of friends and family with couches. I had the third.
As soon as I decided that I wanted to continue traveling and figure out a way to make money online, I spent a good portion of my remaining funds on a flight back to my hometown, where I hadn’t lived since I was 18. I stayed in my Mom’s basement for the first 6 months of my freelance writing career. When I needed to get out, I visited friends and slept on their couches. There is absolutely no other way I could have afforded to pay rent when I started out.
After those first 6 months, I had saved up a little money and built up a humble client base. I felt ready to finally leave again, but I wasn’t quite ready to start paying U.S. rent prices. I spent the second 6 months of my freelance career living rent free by offering my writing and digital marketing services in exchange for room and board. I’ve found that having even minimal skills in things like blogging, WordPress, and digital marketing will instantly land you a “volunteer” or work exchange gig on a website like workaway.info with even the most booked up, popular hosts.
I spent three months living in NYC rent-free, helping a woman edit a test prep book she was publishing and market her petsitting company in exchange for a free room in Manhattan and a $40/week food stipend. I then spent another three months living in a $300/night beachfront yoga retreat and spa in Costa Rica, blogging for them in exchange for a room and three farm-to-table meals/day, plus free yoga. I worked about 15-20 hours per week in both cases, so I was still able to do my regular work on the side and save up money.
Finally, at the end of my first year, I felt stable enough to commit to paying rent. I got a cute little house in Costa Rica for $300/month and was still able to save a good amount of my earnings while living there to start going on trips again.
Step One: Join Freelancer Websites
I started out by making a profile on PeoplePerHour.com, a notorious freelancer website similar to Upwork. While you basically have to underbid hundreds of other freelancers to get a mediocre gig that pays half a rupee on these websites, they are a good place to start out if you have zero published work and no portfolio or experience.
In order to show some level of experience on my profile, I may have beefed up my experience a bit. My previous job was working in university admissions recruiting students. Of course I’ve written press releases! (These were actually just flyers I handed out to students at my presentations about upcoming admissions events, but I spruced them up and made them look official). I definitely have experience writing email marketing campaigns! (These were actually just mass emails I sent out to high school students encouraging them to apply to the university). When you got your degree in the most impractical thing possible (philosophy), you at least learn how to bullshit well.
Step Two: Land Paying Gigs
The easiest way to explain what getting started looks like is for me to tell you my first five gigs and how much they paid.
- Proofreading the content on a UK nursery’s website.
Time: 5 hours, Pay: $35
- Fake book reviews for a book blogger (fake because I’d never read the books).
Time: 1.5 hours, Pay: $18 each
- Ten property descriptions for a real estate agent.
Time: 6 hours, Pay: $200 total
- Guest posts for a garage door repair company in Ohio published on sketchy third-party websites for SEO purposes.
Time: 2 hours, Pay: $50 each
- Career overviews of various job titles for a career resource and advice website.
Time: 2 hours, Pay: $15 each
So, the work was not thrilling, and the cash wasn’t pouring in. At the time, I was just excited that someone wanted to pay me to do things online.
But eventually I needed to start paying bills. I moved onto looking for freelance work on job boards like ProBlogger, where gigs are more interesting, look better on a resume, and pay higher. They also tended to be regular weekly or monthly work instead of one-off jobs.
Step Three: Stabilizing My Income
It took me an entire year to start getting gigs that paid well. I then spent my entire second year as a freelancer just trying to reach a point of stability and sustainability in terms of my workload and income, which mostly came from building up a larger client list and a reputation, so that people come to me offering me jobs. I no longer have to send out 100 applications and hustle to get new clients on top of getting my work done.
To give you an idea of my progress over 2 years, here are a few of my current gigs and their pay:
- Comprehensive camping guides to major tourist attractions in the U.S. for an RV rental website.
Time: 4-5 hours each, Quantity: 1-3/week, Pay: $240 each, $240-$720/week
- Articles on personal finance (how to improve your credit, how to pay back your student loans, etc) for a personal finance website.
Time: 45 minutes, Quantity: 2/month, Pay: $100 each, $200/month
- I write food and beverage guides to NYC for an apartment rental database.
Time: 45 minutes, Quantity: 1-2/month, Pay: $120 each, $120-$240/month
- I write guides to the best online degree programs for various disciplines for an online education database.
Time: 3-4 hours, Quantity: 4-10/month, Pay: $150 each, $600-$1,500/month
- I do WordPress updates and website changes for a tour company in Costa Rica and send them comprehensive monthly SEO reports. The WordPress edits take me an hour or two, and the SEO report takes about 2 hours.
Time: 3-4 hours, Pay: $150-$300/month
- I write in-depth cover stories and conduct interviews for a music and arts magazine.
Time: 2-3 days, Pay: $200 each, $200/month
Then, I got cocky and decided to go on a 3 months backpacking trip through Europe, during high season, on my new freelancer salary…
Why Being a Freelance Writer is an Irresponsible, Insane Thing to Do
A couple months into my second year as a freelancer, I got cocky. I’d been working on a long-term project, receiving a decent, stable income, and saving up money. So, I decided I was ready to backpack through Europe for 3 months.
I landed in London ready to make the most of my new backpacking-with-income lifestyle. Within 3 days I was going to afternoon tea, casually charging $150 to my credit card for a glass of champagne and some mini sandwiches. Within 4 weeks, I was landing in Venice, one of the most expensive cities in Europe, with -.17 cents in my bank account.
Say Goodbye to Your Regular Paycheck
Here’s the thing: when you’re self-employed, your income is never completely stable. Around the same time I arrived in Europe, I finished a long-term project with a client that was making up about 75% of my income. I thought he would have more work for me, but it turned out he wouldn’t be ready to start the next project for another four months. Meanwhile, I was not making enough money on my remaining gigs to sustain travel in Europe during peak season. Back to the job boards, and back to the work exchange websites.
When I landed in Venice and realized I was out of money only 1 month into my 3 month trip, I scoured workaway.info for a work exchange gig I could do in Italy so that I’d have room and board covered for a while while I looked for new gigs. Luckily for me, my writing and digital marketing experience came through, and a host family in Tuscany with some of the best ratings on the website wanted me to come live with them as soon as possible.
I spent a month living in a small medieval Italian town, helping the woman, a sommelier in the world’s most revered wine region, build up a website and blog for a new wine club she was launching. I filled up on homemade pasta made by her husband, swam with their daughters in their natural pool overlooking the Tuscan hills, learned how to properly pour and taste wine, and discovered that some wines truly are life changing. I also got some great experience for my freelance career. And, during my last week there, a company I had applied to almost a year ago emailed me out of the blue and asked if I would still be interested in writing for them. They’d pay me $720/week for three articles…DEAL!
That was far from the only time I’ve panicked about money after losing a client. Once I was back in Costa Rica, only 4 months after I had landed the $720/week gig, I woke up to a single email from them that cut my income in half. The company was in a slow period and needed to cut my workload down to 1 article per week for $240. Such is the life of a freelancer.
Sure, you can get fired at any job, but companies hold far less stock in random part-time freelancers than they do in full-time employees. Plus, while a good writer can be very valuable to a company’s bottom line, it’s also one of the first things to go when budget cuts are needed.
There are two other big reasons that being a freelancer is an irresponsible, insane thing to do, and they’re facts of the job that no one ever wants to be real about: taxes and health care. This is especially true if you’re American, but I know it’s a huge pain point for all freelancers.
Paying Your Taxes
First, taxes. We all pay income taxes, and freelancers are not excluded from this, even if they live abroad. But on top of income taxes, we also pay a 15% “self-employment tax,” regardless of how little money we make. So, if you make $10,000 your first year (which is a plausible first year income for a fresh-out-the-womb freelancer writer), you are exempt from income tax, but you still have to pay 15% self-employment tax. You’ve got to give up $1,500 of your income even though you’re already living below the federal poverty level.
Once you get your income up, you’re adding income tax on top of that. If you make $35,000/year, you owe 15% in income taxes and another 15% in self-employment taxes, for a total of 30%, which is about what someone who makes $300,000/year through traditional employment is taxed. With a $35,000/year income, your tax bill comes out to about $10k! Of course, you can write a lot off if you’re self-employed, but it’s still rough. And taxes don’t get taken out from your income, so you have to save up the money and do it all yourself or pay an accountant.
Healthcare and Benefits
Then there’s healthcare. You don’t get benefits at all as a freelancer – no pension, no 401k matching, and no healthcare. In the U.S., unless you qualify for Medicaid (which you may during your first year), you’ll be paying a pretty penny for health insurance from the marketplace. On top of that, travelers need travel insurance. And that only covers emergencies – more extensive coverage can only be had with a pricey international healthcare plan.
Realistically, it’s hard enough to afford one of those things, let alone all three. For my first year, I had Medicaid and travel insurance. For my second year, I no longer qualified for Medicaid, so I only had travel insurance (and I may or may not have to pay the penalty for not having ACA compliant health insurance in the U.S., even though I don’t live there).
So, two years in, and I still struggle with taxes and health insurance, although I’m finally starting to get it squared away. After that, it’ll be time to think about how I’m going to save for retirement. That being said, many Americans with a 9-5 don’t have these things either.
Why Freelance Writing is a Dream Job
They say that freelance writing is “feast or famine”, and it’s largely true. If it’s stability and consistency you need, stay away. But if you’re here in this life for a wild ride, if you, like me, find yourself attracted to extremes, have a thirst for change, and an inability to tolerate monotony, freelancing is incredibly rewarding. It may be unstable and trying at first, but I’d rather live my life the way I want than give up my dreams for the promise of a stable future that, let’s be real, isn’t all that promising in modern America.
Plus, once we have experience and an impressive portfolio, freelancers are able to build the costs of things like healthcare, taxes, a home office, and unpaid hours answering emails and finding new clients into their rates. Talented freelancers are often able to charge $75-$100/hour (especially in web development, but yes, even writers). Right now, I’m averaging about $50/hour between my various clients and am confident that I’ll be able to get to at least $75 by the end of my third year. While $75/hour as a freelancer does not equal $75/hour as a full-time employee with benefits – to be safe, most freelancers calculate that about 50% of their income is lost to the costs I mentioned above.
Freelancing is also a fantastic way to break into a new industry. Sure, I could have tried to get my foot in the door as a staff writer somewhere, but without major connections, it wouldn’t have happened for years, if ever. Instead of wasting years as a low-paid, coffee fetching intern or waiting for a company to give me a chance to get some experience, self-employment allowed me to go out there and grab it myself. After two years, I know more about digital marketing and growing a new business than people I’ve met who have spent twice that long working full-time jobs for big name marketing and PR agencies, because there’s so much bureaucracy there that they’re rarely allowed to take on any real responsibility.
It can take years to achieve true stability as an entrepreneur or freelancer, but once you do, the sky is the limit. You create your own career, and you can pivot, alter, revamp, quit, slow down, or accelerate whenever you want. You can create anything you want from it. And you get to learn new skills and subjects on a daily basis.
It was always the uncertainty, the constant change and growth, and the infinite potential that kept me going. I knew I would never be bored. But more than that, it was the autonomy and agency that freelancing gave me over my own career, and ultimately, my own life. It only took a few years of working for a company that sold workaholism and lack of sleep as glamorous and placed devotion to one’s company above devotion to one’s family (and self!) for me to know that I needed to feel like I was in control of my career and not the other way around. Freelancing may be a roller coaster, but you are always in the driver’s seat.
Of course, being location independent is a huge blessing. While it’s not always the jet-setting, bucketlist busting, poolside relaxing lifestyle it’s shown as (you do actually have to work if you want to make money), it is pretty amazing that I can pick up and go anywhere I want whenever I want. I can meet my friend in Mexico City at the drop of the hat just because flights are cheap, I can go visit my family for a month at a time, and I can live in just about any country in the world.
I may not do this forever, but I’m certainly going to take advantage of it for now. I have so many ideas rattling around in my head for where I want to take this career in 2018, and the fact that it’s totally up to me is the best part. In fact, two of my big goals are passion projects that offer no income. A big plus of freelancing to me is the flexibility it gives me to work on projects because I think they’re important, without the influence of money affecting them.
Where my office jobs always felt like they were closing in on me, the possibilities of self-employment feel endless. I hate talking about this career as if it’s the “dream job” that bloggers and life coaches and entrepreneurship gurus try to market so they can sell their e-courses, because the difficulties are very, very real. But the advantages are truly priceless.