freelance writing

How I Became a Full-Time Freelance Writer

I recently wrote a twitter thread about how I transitioned from being a college writing instructor to a full-time freelance writer. I received positive feedback and thought a blog post on the topic might be useful.

First, I want to say I’m still learning. I’ve been freelancing as a primary source of income since May–for 8 months–and still feel like a beginner. Although my hourly rate is now good ($50-100), I took a major financial hit during the transition that I haven’t quite recovered from yet.

In 2019, I drained my savings, used credit cards, and borrowed $2,000 from my parents after staying with them for two months. Ouch. (I should also note that a major part of this financial strain came from a cross-country move and can’t be pinned on my work transition.)

As I recently told a friend, I have a nice place to live, health insurance, and enough money to pay all my bills on time, but I’m going to owe the IRS money when I do taxes because I haven’t set enough aside and I’m not currently contributing to a retirement fund. So, I haven’t quite reached financial stability as a freelance writer yet.

Still, I’ve made enough progress as a freelancer to feel optimistic about my future in this career path. The last 8 months have been rocky, but I’ve learned so much.

Establishing an Online Presence

Early on, I retooled this website to present myself as a freelance writer rather than an educator and creative writer. I also updated my LinkedIn account and created a Contently portfolio.

I have no idea how much any of those things helped. I do know that many clients google writers prior to hiring them and having anything online that builds your credibility is helpful.

Learning to Write Content

I wrote content years ago, so I was already familiar with its principles. I had also been teaching professional writing, which is a similar writing style. Still, I needed to freshen up my content writing skills to successfully switch career paths.

HubSpot Academy

Content writing is generally done by businesses as part of an inbound marketing strategy. Since I’d been out of the private sector world for 5 years, I took some HubSpot Academy courses to refresh my inbound marketing knowledge.

I only fully finished one HubSpot certification track–Inbound Marketing. That series didn’t get into the nitty-gritty of content writing, but it did freshen up my familiarity with the purpose of content writing and help me know how to phrase my client proposals.

This year, I plan on taking more HubSpot Academy courses.

Learning on the Job

As far as actually writing content, I (re)learned a lot by, well, writing content. Editor feedback has been crucial to my development as a content writer. Content writing differs from academic writing in many ways. Even though I already knew that, old habits die hard.

Here are some content writing style choices that didn’t feel natural to me initially, but now come more easily:

  • Using contractions frequently
  • Writing short sentences
  • Writing short paragraphs (usually 5 lines maximum)
  • Using headers regularly
  • Integrating bulleted and numbered lists whenever possible
  • Using “you” frequently
  • Bolding and italicizing text for emphasis

As a new freelancer, I was also grateful for clients who provided style guides. I learned quickly that I need to read every word of these because different clients view different styles as “normal.” It’s not like the academic world in which everyone in a discipline adheres to a standardized writing style.

Also, if a client shows any dissatisfaction with your writing choices, it’s a big help if you can point to the style guide as the reason you made those choices.


For months, I didn’t think I needed any help with my grammar, punctuation, etc. I mean, I used to teach this stuff! But when you have to write 3,000 words in a single day and have to proofread it while you’re experiencing brain fog, typographical errors happen.

I just recently added the Grammarly extension to Google Chrome after having a editor note that I’d written “lended” instead of “lent” and misspelled both “bankruptcy” and “collateral” in an article about business loans. Those are embarrassing, easily-preventable mistakes. They made it look like I hadn’t proofread even though I had. I was just tired and missed the errors.

Of course, Google Docs and Microsoft Word have their own built-in grammar and spellcheckers. uses an online editor that doesn’t have a built-in check system. I think Grammarly goes above and beyond the Google Doc’s checking system, but I ended up turning it off for Google Docs because it was slowing that application down majorly. I haven’t noticed it creating much of a lag for other sites, however.

After a few days of using Grammarly, I can say I like it so far. Grammarly isn’t a replacement for actual grammar knowledge, but it can help you catch little mistakes that you might’ve missed if you were tired or in a rush.

Grammarly also has an interesting feature where it analyzes the tone of your writing in emails. Although I don’t think this feature is 100% accurate, I can see it being useful.

Finding Freelance Writing Gigs

When I first looked into freelancing, I looked everywhere. I wanted (and still want) journalistic writing to be a big part of my income, but I knew I had to be realistic and seek out content writing gigs, too.

Opportunities of the Week

To find freelance writing opportunities, I subscribed to Opportunities of the Week. I cannot praise this newsletter enough. It’s worth the money (and also available for free to those who can’t afford to pay).

Most of the opportunities posted there are one-off journalistic publications, but I landed an ongoing health-focused journalistic writing gig that I’ve been doing for 10 months after finding out about it through that newsletter.

Freelance Job Boards

While preparing to become a full-time freelancer, I also bookmarked and regularly checked the following job boards:

At first I also regularly checked Indeed, Craigslist, and LinkedIn, but they didn’t really have anything that worked for me. (I’ve recently learned that LinkedIn has a freelance network, but I haven’t yet applied for it, so I can’t say how good it is.)

Unfortunately, I didn’t track where I found which gigs. Often, I’d see the same gig listed on multiple boards. The two ongoing content writing gigs that currently make up the bulk of my income came from job board ads.

While surfing job boards, I quickly realized that I could make more money content writing than journalistic writing, at least at this stage. There were many remote online media writing jobs I’m qualified for but decided against applying for because they only paid $15 – $25/hour.


In addition to applying for gigs listed on job boards, I used Upwork to find work. Even though I’d heard bad things about it, Upwork turned out to work well for me. Yes, they take 20% of all the money you make, but you can deduct those fees at tax time so it’s not that big of a deal.

As a new freelancer, Upwork felt a little safer and easier than gaining work through job boards. I knew I would be paid and I knew I wouldn’t be scammed. Upwork provides a communication interface and takes care of employment details, so writers don’t have to fill out separate 1099s or share their personal info with each new employer.

Through Upwork, I found a doctor team looking for a writer to ghostwrite health-focused content about lifestyle, nutrition, and other issues related to thyroid health. Although I now realize I was underpaid, this opportunity worked well for me. It helped me practice being a freelancer in the sense that I was writing, working on a deadline, researching, and regularly communicating with a client about their needs.

The other ongoing opportunity I received through Upwork was for a website called Damodara. This was a good opportunity for me because the posts are mostly about nutrition, and two of my content niches are food and health. Also, these articles are published under my name so I can share them freely. For example, check out “10 Iron-Rich Vegetarian Foods.”

I’m not currently doing any work through Upwork, but that’s primarily because I haven’t had time to apply for more work. I plan on adding a video to Upwork soon, freshening up my profile, and using the site to apply for more health- and food-focused gigs. Time will tell if I can find gigs that pay my current rate through Upwork.

Writer Networks

There are dozens of writer networks out there, and so far I’ve found one that works well for me: The work they’ve offered me has varied. The assignments have all been ghostwriting, so I can’t name the clients. All assignments have paid $.10-.12/word. My favorite gigs have been about wine. My least favorite have been about the financial sector.

I applied to a few other writer networks with mixed results. One accepted me, but then the pay they offered was so low I turned it down. One rejected me after months of silence. Another accepted me, but then never offered me any gigs. Another never acknowledged my application.

I haven’t applied to more writer networks yet because it takes a lot of time and in my experience, doesn’t always pay off. You have to set up a profile and sometimes take a quiz or write a new, unpaid writing sample. I have a list of writer networks I’d like to apply to: Scripted, Writer Access, Envato Studios, Quietly…and the list goes on.

Moving Forward

Switching to full-time freelance writing has been a trip. I’m glad I took the leap, and I look forward to my future as a freelancer. I plan on sitting down with a cup of tea and plotting out my next work year (knowing, of course, that I’ll need to be flexible and a lot of what I think will happen will not happen). Once I have an idea of my 2020 freelance goals, I’ll write a post about them here.