Everything You Need to Know Before You Become a Freelance Writer

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

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Thinking of making the jump and becoming a freelance writer? Or maybe you simply find yourself asking: What is a freelancer?

In this post, I am going to explain everything you need to know about freelancing. I quit my day job and started freelancing full time about two years ago, and I am currently making more than I made as an employee while also working quite a bit less than I did then. Plus, I cut out nearly two hours worth of commuting out of each day…and I get to work in my pajamas.

So, what is a freelancer? Well, the all-knowing Wikipedia defines it as “a person who is self-employed and is not necessarily committed to a particular employer long-term.” That pretty much sums it up. I do work for other people either piecemeal or as contract labor. I’m not an employee. And I work 100% remotely. (Note: you can be a freelancer and not work remotely, and you can work remotely and not be a freelancer.)

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

Is freelancing right for you?

Truthfully, only you know the answer to that question. I’m sure that working from the comfort of your couch with a cup of coffee in hand, snuggled under a cozy blanket sounds good to a lot of people. However, the actual day to day life of working for yourself may not be a good fit for everyone.

The first thing you may want to consider is your own personality. If the thought of not having a steady paycheck or health insurance makes you start to feel a touch panicky, freelancing may not be the best idea for you. There is a lot of uncertainty, especially in the beginning.

Another thing to consider is your work ethic. Do you have a hard time completing tasks without some sort of manager breathing down your neck? Are you able to hit deadlines with ease? Can you hold yourself accountable? If you need the authority of an employer to keep you working then being a freelancer will likely be a disaster for you. You gotta be able to hold yourself accountable and keep track of all the upcoming deadlines. All. By. Yourself.

One thing that many people forget to consider is the fact that freelancing is often a little bit lonely. Working from home in an empty house day after day can be difficult for some people to take without going a little bit crazy.

Since I am always at home by myself all day long, my filter for what is acceptable when around other people has slipped a little bit. For instance, I have a habit of singing to myself, not real songs, but sort of sing-songing whatever I happen to be doing:

🎶Pouring the juice. I’m pouring the juice. 🎶

Do that shiz in Target, and people will 100% look at you like you are crazy. All I’m saying is just make sure you can handle the solitude.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

If the majority of what you do is type away into a laptop, you could work from a coffee shop, library, or co-working space to keep you from feeling too lonely. Just remember that doing so will add the commuting time back into your day, and you may end up spending a fortune on lattes.

To be a freelance writer (or any other kind of freelancer), you are also going to need thick skin and be able to deal with rejection. There will likely be a lot of it—even if you are a rockstar at whatever you do. Be prepared for projects you don’t land and pitches that fall flat. You just gotta roll with the punches.

In addition to freelancing for my bread, I also dabble in acting. Auditioning for roles definitely toughened me up because you hear no pretty much constantly as an actor. Yet…it still stings when you don’t land something you really, really wanted. Make sure you can shake that off.

Finally, and maybe the most important thing of all is making sure that you can afford to tighten the belt when things get lean. Because they will. In my experience, freelancing comes with a lot of feast or famine. The first year was mostly famine for me with constant hustling to find the next bit of paid work. The second-year has been much better, and I am finally coming into my stride. Currently, I am bringing in more than I did as an employee while putting in fewer hours, and I’m even setting some ambitious income goals for 2020.

All that said, the only thing that really made this whole freelancing thing possible for me is my husband. His steady income picked up the slack when invoices were paid late or a client suddenly didn’t require my services any longer. I’m not saying a single person can’t be a freelancer, but I would definitely make sure that I had a cushion of savings in place that could keep things afloat when needed before doing freelancing full time.

The other option is to wade in instead of cannonballing into the freelancing pool. A lot of people start the journey in their spare time before quitting their day job. That is also a solid plan for those that don’t have any backup cash coming in.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

How to start freelancing for beginners

Where and how you start will likely depend on what avenue you are taking as a freelancer. The majority of my work comes from writing. So, this section will be skewed in that direction…because, well, it is what I know.

I recommend starting a blog as a jumping-off point. That is basically how I started freelancing, although I had my blog for over a year before I even considered leaving my 9-5 (err more like 8-6ish). To get clients, you will need some sort of portfolio or proof of your work and a blog provides that. Of course, if you are already employed in the industry you want to start freelancing in, then you already have a resume that will back you up.

I was an ophthalmic tech before freelancing which means I worked for an eye doctor. I wrote in a lot of charts…but that line of writing wasn’t really going to get me any clients. My blog, on the other hand, helped me land a few.

Starting a blog isn’t as hard as you might think. Not only that, but you can also turn your blog into a source of income with affiliate marketing and sponsored posts if you want to put in some extra effort.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

Medium can be a good way to start as well, and it won’t cost you anything if you don’t want it to. I would have jumped on the Medium train a lot sooner if I had known about it when I first started my journey as a freelance writer.

There are writers that consistently make $10k a month on the platform (I am not one of them…yet!) You will need a membership if you want to make any money though, but it is only $5 per month or $50 for the year. It is well worth the investment in my opinion. Feel free to check out some of my Medium musings to get a feel for the site.

Those looking for other types of freelance job ideas may want to try their luck on Fiverr. There are plenty of graphic designers, video editors, etc, etc that make a good living on Fiverr. I can’t personally give advice on making money there, but this post explains a lot of the ins and outs.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

Places to find freelance writing work

Once you have built up a little bit of writing proof to show to potential clients, you can start looking for freelancing jobs in earnest. I recommend the following resources:

ProBlogger: When you first make the jump to freelance writing, you will be busy looking for jobs to keep the paychecks coming. ProBlogger’s job board has led to several short and long-term writing assignments for me. You can find work in just about every possible niche you can imagine.

Pitchwhiz: If you are looking to pitch publications both big and small, signing up at Pitchwhiz is a good move. (it’s free, yo!) You will find a dashboard with lots of opportunities, and you can also sign up for email alerts. The interface makes it quite easy to send over your story ideas to various editors.

This Post: Goats on the Road is a travel blog that I follow because they crank out some amazing content with glorious photography. This post, in particular, is a good one for finding places that need writers. The majority of these publications will be more relevant if you want to write about travel, but there are a few with a broader range of topics to try out as well.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

Upwork: I would be amiss if I didn’t mention Upwork because it is a great way to get started in the freelancing world. The fees are kinda steep, but you have to pay to play more often than not so you might as well take advantage of the tons and tons of jobs you will find here. I actually got a job from Upwork that led to a recommendation that led to an introduction that led to a pretty substantial gig off of Upwork. So, it doesn’t always hurt to pay a few fees. This site also offers lots of different types of work—not just freelance writing.

Facebook Groups: I actually found my first two freelancing positions in a local facebook group, and I found another one on the jobs section of the Facebook marketplace. All of these jobs were from local businesses that needed help, two were VA positions and the third was a writing gig.

Local Networking Events: If you live in or near an urban center, you can likely find networking events to attend. I haven’t actually landed any jobs from networking events, yet, but I have made some good connections that have been helpful. Also, I should mention that I’m really bad at face to face networking because it always makes me feel awkward and pretentious. However, the last event I attended was with two of my acting buddies (it was actually put on by Netflix!) One of them was amazing at networking, and I probably got better at it just by watching her. So, now I’m feeling more confident about networking at these types of events. It’s all about growth, right?

Pitch to Local Publications: While I was still working my 8-6ish, I pitched a local website using my blog as my resume, and they said yes! It was one of my very first pitches, so I was super stoked. Plus, I still write for them once or twice a month. Don’t overlook those local sites, someone is writing all of that content you see there, might as well be you.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!


Making money until writing (or your main gig) kicks off

There will be times when you don’t have enough clients or you just aren’t getting the volume of assignments that you need to stay busy or earn the money you require to make ends meet. When that happens, it is good to have a few extra moneymakers up your sleeve that can add a little green to your bank account.

Fancy Hands: I did a substantial amount of work for this site when I first made the jump to freelancing to fill in the cracks in my paychecks. Most of the work is simple and can be completed rather quickly. Basically, each task is supposed to take no more than 15 minutes and comes with a price tag attached ranging from $2 to $9, depending on complexity. You choose tasks that you want to work on so you have complete control of how much time you spend. The types of tasks will vary a lot—I once got paid $2 to call a restaurant and ask if they sold gift cards.

Amazon Flex: I actually signed up to do this when they first announced it was available in Charlotte, but I never took on any hours. Basically, you sign up to work a shift delivering packages for Amazon. They pay was advertised at $18 an hour, and you drive around delivering boxes in your own vehicle. Here is some testimony from people who actually did some work with Amazon Flex since I can’t speak on it personally.

(Speaking of driving…you could also sign up to be an Uber or Lyft driver. Plus, there are other driving options if you have a car that is good on gas like Doordash or Postmates.)

Utilize Other Skills: Throughout my life, I’ve worked a lot of different jobs. Like most people, I did some time as a bartender and a server. I actually loved bartending when I was in my early 20s, so when I saw a woman on Facebook looking for someone to bartend at her wedding, I thought “why not?” That little gig led to my name being put on the list of vendors at the wedding venue, and I ended up booking a second wedding. I made $450 working that second wedding due to a few incredible tippers. Not bad for a single Saturday night’s worth of work, right?

Become a Trivia Host: If you are outgoing, you can try your hand at trivia or music bingo hosting. I did both of those for short times the first year I was freelancing. I actually had a lot of fun hosting, but since I am also an actress (on occasion) it didn’t bother me to hang out on the mic all evening. If you are very introverted, this gig may be a tough sell for you. (I am also on the Charlotte Dinner Detectives cast. There are shows in cities all across the U.S. which hold auditions regularly. It is a paid gig that is a ton of fun.)

Let’s talk about Online Surveys…  A lot of posts about freelancing that I see recommend doing surveys. I tried that method in the beginning, but I could never make enough to justify the time. My retired father-in-law does them for fun and has been getting gift cards on the regular. So, maybe I’m just slow? But, for this reason, I don’t recommend doing surveys as a way to make money to pay your bills.

Tools to help you on your freelancing journey

Just like any other profession, you need a few tools of the trade when freelancing. Here are my suggestions:

Wave App: Once all that freelance money starts pouring in, you may need a way to track your finances. I rely on the Wave app to keeps track of my dollars. Wave is pretty robust, and I only use a fraction of what it can do, BUT it is free. So there’s that.

Contently: Speaking of portfolios…If you don’t have a writer’s website or blog to showcase your stuff, then you can easily create a simple portfolio like mine using Contently. This is another free tool, and as a freelancer, free is always good stuff, right? If you are completely new to the freelancing world and want to get your name on a post somewhere, feel free to reach out. While I am not in a position to pay for guest posts at this time, I am happy to give you a space to flex your writing muscles if you have a post idea about travel or Charlotte, NC that you would like to pitch.

Liberty Healthshare: Unless you have a spouse that you can bum insurance off of, you will need some coverage as a freelancer. Self-insured plans are pretty darn expensive, but you can get a more affordable option with Liberty Healthshare. I used this service for two years with zero complaints (now I am bumming from my husband.) This may not be the way to go for everyone, but if you are in good health with no chronic conditions it could be a very good fit.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!

Trello: I keep myself organized 100% using Trello! I love this free tool, and I use it to keep track of my blogging tasks, freelance writing tasks, and even my chores around the house. It is a great tool that can be used for all the things you need to keep track of—if you need help figuring Trello out, you can check out my post on creating an editorial calendar using Trello. If you find you still need more instruction, I have a course on using Trello to smash all of your blogging goals which can easily be applied to freelance writing as well.

Grammarly: If you aren’t already using Grammarly to check your typos, then what are you waiting for? When your bread and butter comes from your writing, you want to make sure that it is always looking good. While Grammarly won’t catch every single mistake (and sometimes it flags things you definitely meant to type), it is still a very useful tool.

Spreadsheets: I’ve found that the best way to keep track of the money flowing in is through spreadsheets. I used them to tally up my monthly income, keep track of who has been invoiced when, and to track my work-related miles. If you don’t feel like making your own spreadsheets, you can find plenty of templates for sale on Etsy. You may even be able to find some free ones if you dig around on Pinterest for a while.

Ready to make the leap and become a freelance writer?

Now that you’ve read through all my tips on freelancing, are you ready to make the leap? Heading off the beaten path into unknown territory is definitely scary stuff, but I am happy to share my limited knowledge if it helps. Ask your freelancing questions below, and I will do my best to give you a high-quality answer.

Think you may want to become a freelance writer? Here is everything you need to know before you make the leap--all my freelancing tips!


Making Sense of Affiliate Marketing



  • Reply Kimberley Marquis January 9, 2020 at 10:12 am

    Such great tips! I’ve always wanted to get into freelance writing, but with a blog, never really have the time! Great read! xx

    • Reply darabre@gmail.com January 9, 2020 at 4:35 pm

      Thanks! Blogging can take up a lot of time, that’s for sure.

  • Reply Julene January 9, 2020 at 10:15 am

    I had no idea there were so many websites that offered freelancing gigs. I’m looking for some side income, and you gave me some really great options! I also thought I was the only one that sang mundane tasks to myself. 🤣

    • Reply darabre@gmail.com January 9, 2020 at 4:35 pm

      Hopefully, you snag some work! And I’m always singing 😀

  • Reply Amarachi Ogbonnaya January 9, 2020 at 11:00 am

    I have been freelancing for a while now, I’ll say its cool

    • Reply darabre@gmail.com January 9, 2020 at 4:35 pm

      I agree!

  • Reply Jennifer Gainer January 10, 2020 at 10:31 am

    Wow there are a lot of opportunities out there honestly I had not heard of many of these, but they are good to know about if I decided to go this route in the future. Thanks.

    • Reply darabre@gmail.com January 10, 2020 at 11:40 am

      I hope you get to make the jump if that’s your goal. 🙂

  • Reply The handy journal January 10, 2020 at 10:49 am

    Thanks for this post ! I was considering becoming a freelance writer as a side hustle , and this post was very helpful ! I think the start is the hardest part! thanks for sharing !

    • Reply darabre@gmail.com January 10, 2020 at 11:40 am

      The start is definitely the hardest (and scariest) part.

  • Reply Janay January 10, 2020 at 7:45 pm

    O wow this was very informative and interesting! Everyone considering being a freelance writer should read this!

    • Reply darabre@gmail.com January 11, 2020 at 11:03 am

      Thanks! I hope it helps a few people on their journey.

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