Beginning a Career as a Freelance Writer

Starting a Freelance Writing Career

Homesteading in Central Appalachia certainly has its benefits, but one of them is NOT its proximity to appealing and well-paying jobs.

In all honesty, when Ian told me he wanted to apply for the position director of Big Laurel, my first thought was “well s***, what am I supposed to do now?”

My job options out here are somewhat limited. I am only eligible to work for AmeriCorps for two years and with Ian’s new job, our commitment here is for at least three. Though it might be possible for me to get a job off the mountain a town or two away, it would probably cause us to get a second car and me spending close to two hours each day driving. Worst of all, a normal job wouldn’t allow me to take springs and summers off to help with the groups and summer camps we host on the mountain.

Working full-time off the mountain would take away much of what I love about living here.

But even so, I can’t easily justify taking a year of work off. Not the least because I’d go crazy. I need to be constantly stimulated or I wig out. Ask my mom how well I did with snow days growing up. I was that kid, the one that cried because she couldn’t go to school. I’m also a planner, so this situation has bothered me for months. I’ve turned inwards, trying to figure out what could be fulfilling for me that someone would be willing to pay me to do.

And then it came to me. Writing.

Of all the new experiences I’ve had since moving to the mountains, this blog has been the biggest surprise. I absolutely love it. I love the writing, the picture-taking, and the increased intentionality that I go through my day with when I know I want to document it later. I love the science of writing online; the constant tweaking of templates and posts to get them to do well on different platforms. The amount I’ve learned is incredible, but there always so much more to experiment with. I can lose myself in my writing for hours, so much so that I forget to eat, sometimes even to sleep.

If I love doing it for free, why not try to find a way to get paid?

So I tentatively began to research freelance writing opportunities. At first the news was pretty glum. 500 word articles were selling for pennies in ‘content mills’ that capitalize on a free market system where low-ball bids from South Asia were monopolizing all the jobs. The better paying opportunities I found were for obscure business-related topics I knew nothing about or for sites where I would have to go through the work of submitting an original 3,000 word article without any obligation from the company to buy it. Writing online seemed like a time sucking dead-end.

But more research revealed that there are people and companies that ARE willing to pay for high quality content. The trick is to find them and get them to appreciate the value you can bring to their business. So I threw myself into research, spending a week signing up for accounts, tweaking profiles and building up portfolios. If I was going to play this game, I wanted to give myself the best shot at success.

I’m relying on two main websites now, Iwriter and Upwork. Both are targeted towards freelancers but they have different strategies and serve different needs.


Upwork is a bidding site. Users are given a certain amount of tokens per month that they can use to ‘bid’ on projects that they feel qualified for. Projects extend far beyond writing: to SEO (search engine optimization), graphic design, software engineering and whatever else can possibly be contracted over the web. Clients get to look at applicants’ cover letters and profiles and choose the applicant they want for the task. Pay rates can range wildly from $2 per 500 words to hundreds of dollars per hour. It all depends on the skills of the applicant and the value of the project. Upwork takes a 10% cut on all contracted work.

Upwork for Freelance Writers
An overview of my profile on upwork

The tricky part of Upwork is getting your first few jobs. The site is over-saturated with writers, and clients are picky about choosing applicants that don’t have any reviews. Most applicants need to drastically undersell their work at first to build up a good reputation. But for those that build a name for themselves and get consistent clients, the pay can be very lucrative.


iwriter for freelance writers
The front page of Iwriter for me

Iwriter is a faster paced game. Instead of bidding, paid writing projects are available immediately after creating an account. Clients post jobs on the site and the writer that clicks on the link first gets the job. Projects range from 150 words to over 3,000 and cover every topic imaginable. Writers have a set amount of time to complete the project, and if they don’t finish it gets returned to the project list for someone else to pick up. Upon completion the client has the opportunity to accept or reject the work. Upon acceptation, the writer gets paid. It’s set up so that you can start earning money in five minutes; the catch is that the beginning rates are very low. $1.50 per page low. 

The key to Iwriter is that there are different levels of writer. Everyone starts out as a ‘Standard’ writer and earns the lowest rates until they move up to the ‘Premium’ level by completing 30 projects and maintaining a high ranking. After Premium comes ‘Elite’ and then ‘Elite Plus”. The price per article goes up exorbitantly as you gain levels, so that a project that would net you $5 as a standard writer is worth $15 in Premium, $30-50 in Elite, and well over $100 in Elite Plus. For the speedy writer this can add up fast.

So How am I Doing?

After a week of research, I have been actively applying for freelance jobs for 3 days now and have made just over $50 total in what I estimate to be about 4 hours of work per day. Not a great takeaway for twelve hours of work, but it’s still beyond my expectations for just starting out.

Much of my time has been spent writing cover letters for Upwork positions. At my experience level they are the key to getting jobs, so I’ve spent over half an hour on each one. At this point I have applied for six positions, heard back from four, and landed two jobs that paid $15 each for a 600 word article. I’m still waiting to complete my interview on the other two, but they are for bigger projects and for significantly more money. The first article was in the healthy food niche, the second for a travel blog. The rate I am comfortable with would be three times what I was paid, but at this stage I want to be flexible and take jobs that give me experience and build up my portfolio.

Iwriter has been a different experience. I’ve written 13 articles and have earned just over $20. Those stats would make me cry except that the articles have been so ridiculous that it’s been a blast. I’ve written articles about cat pee, why men with beards are better, and why weeds always grow near the edges of lawns. These articles take a lot of research on a wide variety of topics, but there isn’t ever a guarantee they will even be accepted by the client. Kind of a raw deal, but hopefully worth it in the long run. Those articles have gotten me 13 reviews closer to qualifying for the Elite level. And that’s where I could start earning $20-$25 per hour of writing.

What are my Goals?

At this point, I’m willing to put in the work to try to make this a success. One year from now I would like to be averaging over $1,000 per month strictly from writing. That sounds ambitious, but I’m surprised how quickly I picked up jobs on Upwork and think at least one has the opportunity of turning into long-term work.

This field of work is incredibly appealing to me. It feeds my competitive streak to write faster, rank better, and get more jobs than everyone else. I want to be able to work completely location independent, so that regardless of where Ian gets hired in two years I will still have my own career. I want to have the flexibility to choose my own hours, my own work assignments, my own work coffee. I want to keep doing the writing that I love and hone my skills in a process of continual improvement. I have the feeling that I’m right on the edge of something big for me, and it’s all I can do to have the patience to see how this all works out.

Finally, a big thank you to you all, my loyal readers. It’s been your appreciation of my writing that has given me the affirmation I needed to take this first step.

One Week Update:

Iwriter is not worth my time. After hours of writing quality articles I have still made less than $25 because seven of my articles have been rejected. A rejected article gets 0 stars, which can destroy your rating quickly. And the rejections seemed arbitrary. I would write three articles for the same person on a similar topic, have two get 5 stars and one get rejected. This is waaaaay too much effort for a miniscule reward, so I will be redirecting my time to applying for better paying jobs with less flighty clients.

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11 thoughts on “Starting a Freelance Writing Career

  1. That’s way better money than novel writing and you can still make up stuff. I may have to look into it. 🙂 Good luck!

  2. I’m so excited for you! If you ever need a quick glance-over editor, I’m particularly free in the summertime 😉 (But seriously, I love reading what you write!)

  3. I came over from Pure Living for Life Facebook post on this article. What a great read and description of your journey!! It is amazing what making a living online can give a person. If you’re a person in a remote area – you can have a job. If you are a person in a heavy population and need extra income. There is a job online. Thank you again for sharing your journey!!

    1. I’m so glad you came over to my site and enjoyed my post Nicholas. I’ve been working with Pure Living for Life for over a month now. Every homesteading journey is unique but they are all worth telling. 🙂

  4. I like your goal of $1000/month strictly from writing. I don’t think its too ambitious because I have achieved this number and so have a few buddies of mine. My advice to you as a writer, is to find the write channels and to stop wasting time on the poorly paid jobs. I started off making $0.02/word for freelance companies and it was terrible. I gained valuable experience and met some great people, but in the end it wasn’t worth it. I still continue my freelance work as of today and I am generating almost $1600 each month just from freelance writing online. It took me a while, but it was well worth it. I do owe a lot of my success to Noah King, a fellow freelance writer who showed me the path to higher paying jobs. He personally connected with me when I asked for help on his website and guided me through the way. You can find his website here:

  5. These are great ideas. I love being able to work from home online! Have you looked into blogging networks? You can work with brands and get paid. I looked at one that accepted non-U.S. residents and I’m sure there are more out there. May be a good option and they tend to pay pretty good 🙂

  6. As a Freelance Writer myself, I can say that these are solid tips, and you give your personal experience. Myself I didn’t do too well with iWriter but they say that upwork is solid. Try Textbroker as well.

    1. Thanks for the tip about Textbroker! I didn’t know about that site and I will definitely be checking it out.

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