I started working as a freelance writer in the summer of 2011 when I first became hired by Yahoo. I had just graduated college and I was contemplating either heading to graduate school or heading into the corporate world, neither of which sounded very exciting. I knew I wanted to travel but that required a lot of flexibility and money. I heard about the opportunity with Yahoo! through a friend or maybe through an online job ad, I’m not really sure. Either way, I wasn’t sure how much money I could really make being a freelancer so I kept my job as a music editor with a magazine I was working for.
A couple months after being hired as a featured contributor with Yahoo! for their travel and entertainment sections I was making decent money, enough to pay my bills and even save some, so I decided to quit my job with the magazine. It was so strange to not be working a structured schedule and it was even stranger to not be working full time. I could work anytime I wanted and in the comfort of my pajamas if I felt like it. I could say yes to any plans my friends offered and rearrange my schedule accordingly and STILL get paid. Seemed like a dream, right? A year and a half later I still work for Yahoo! and several other places now as a travel writer and I’ve learned a few things about what it’s really like to be a freelance writer.
You HAVE to be self-motivated
Sure, it’s awesome to be able to wake up at noon, grab a laptop, and declare your bed (or if you’re traveling, the beach) as your office for the day. It can also be really, really hard to motivate yourself to work with no one bossing you around, no office to have to get up and go to, no scheduled time to work. After a few months of freelancing I took note on times I was the most productive (early in the morning, turns out) and also what I needed to do for myself to ‘get in the mood’ to write. Sometimes it can be difficult for me to balance my freelance writing with my creative writing. It seems like I am writing all day, every day, for someone or something.
When I write all day for different publications it can be hard to sit down and work on my book or a short story I’m working on. So now I get up in the morning, make a pot of coffee, take a shower, put on clothes (I feel like a slob if I don’t), and basically get ready as if I were getting ready to go to an office. If I’m traveling I head to the nearest coffeeshop in the morning or work from my hostel before going out and doing any sightseeing for the day. Adding structure to my day helps me stay motivated.
You learn how to say NO
Your best friend wants to go to the movies or head to the wine bar for $4 glasses of wine. Your significant other wants attention. Your cat is meowing at you insistently to pet him/her. There are always opportunities to get distracted and to do something, anything else than write. You just have to learn how to say no.
Sometimes if I’m hanging with a friend I’ll say, “okay, I need to be back home by this time to work” and they get annoyed. You just have to write an article, what’s the big deal? Can’t you go do XYZ with me and write later? NO. This can be really hard for me as I’m a huge people pleaser but I’ve learned how to put my foot down. I typically go to a coffeeshop when I need a few hours of complete alone time to work. There’s no boyfriend begging for cuddle time or a friend knocking on the door to hang out.
People think you’re just on your computer
I think this is one of the most difficult aspects of being a freelancer for me. People see you on your laptop and they think you’re doing nothing. They think you’re just browsing Buzzfeed for the millionth time or Facebooking or doing something else completely irrelevant. I stayed with my mom and step-dad last December for a month in Houston and I always felt bad because I would stay holed up in my room all night working. (At the time, working at night was what worked best for me). Didn’t I want to watch “The Voice” with them? Why was I being anti-social?
Finally, after a couple weeks of this I had to sit down with them. “Look, I’m not trying to be anti-social. I’m working on my computer. Writing is my job. I’m not just sitting on my computer doing nothing. I have deadlines everyday and if I don’t meet them I won’t be paid. Just like you go into your office everyday and sit at a computer I have to do the same thing, except I don’t have to go anywhere.”
I’ve had to have this talk with a few different people. What’s the difference if I go into an office for 12 hours a day and work on a computer or work on my computer at home or in a coffeeshop for 12 hours a day? Work is work regardless of where you go.
You’re considered unstable
Most people don’t get what freelancing is all about. In America you’re supposed to get a 9-5 job after college complete with a 401K, benefits, a savings plan, the whole shebang. I mean, that’s what everyone DOES and if you don’t follow suit you’re looked at like you’re lazy, unreliable, and broke. When I told my boyfriend’s mom I freelanced she instantly questioned me about how much money I made because she said to her, freelancing sounded like it wasn’t a steady job.
Sure, I don’t have benefits and sometimes I am broke, but I’d much rather have flexibility in my career while doing something I absolutely love than take a mediocre job just to please the people around me who would feel better themselves if I did the standard 9-5. One time my mom asked me, “don’t you just want to get a REAL job?” I have a real job, thank you very much.
You have the world at your hands
I realize at this point on this post I’ve listed some negative things about freelance writing so now it’s time to talk about why it’s freaking awesome. As a travel writer I get opportunities all the time to write pieces on really, really cool topics. Earlier this year I was offered the opportunity to spend 10 days off the coast of Belize on someone’s private island to cover a research project being conducted by Cornell University about the Big Blue Hole. 10 days free food and accommodations while staying in paradise!
Other times I’ve been able to research and write about serious social issues taking place in Africa or Papua New Guinea. This is the kind of thing that I live and breath for. Learning about new cultures, other worlds, strange cuisine, interesting people, etc is what fills up my heart with happiness. As a freelance writer I have the ability to constantly seek out new opportunities all around the world.
You can live anywhere you want
Recently I found a few different apartments in Costa Rica for $300 a month including all utilities, fully furnished, right on the beach. I have the freedom to take up an opportunity like that anytime I want to. And believe me, I am extremely tempted considering how cold it is in Michigan right now. I know freelance writers who have made homes for 3-6 months at a time in Thailand, South America, Ireland, etc. Why? Because they can. They have a quench for culture and adventure that can’t be fulfilled living back in the States. As a freelance writer you can make a home anywhere in the world as long as you have good wifi.
With all of this said, I love my job. It might not be right for some people but for me it’s exactly what I’m looking for. If you’re thinking of becoming a freelance writer there are tons of opportunities out there but understand it takes a lot of hard work, it’s not always easy, and there are a lot of people who are going to tell you to give up and get a “real” job.



Always nice to read your articles… everytime something of yours is posted on Matador, I seem to follow it to your website haha. Costa Rica apartment is my vote! Maybe one day I’ll figure out something to be as flexible as you.
Thanks for the read,
Danny
Thanks for being a regular reader, Danny.
My vote is Costa Rica, too!
Agreed, people really don’t understand the freelance lifestyle and can make some pretty silly assumptions.
Thankyou for the heads up! Ive always loved writing and yes my family do the same saying I need a real job. A real job doesnt have to be boring, it can be fun! It can be what your passionate about and what you excel at! So I say continue on doing what you love, the people around you ae jealous thats why they tear you down. I got my first offer to write a article on travel to a magazine just by blogging. I have no job, not much money, but this is the opportunity ive been waiting for all my life! It only takes creativity, determination and a love for what you do.
Kelly – Congrats on your travel writing opportunity!! I agree, a “real job” doesn’t equate “a boring, mundane job.” A job can actually be something people enjoy…a concept many people have a hard time understanding.
Always interesting to read your posts! I work overnight (three 12hr shifts a week) and people have an extremely hard time understanding my work schedule! “Can’t you get up early before you go to work so we can have lunch?” They don’t realize this would be like asking them to get up at midnight after working 12hrs and then having to go back to work the next morning. Every job has its perks and its disadvantages!
Good point. I agree.