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.

creative nonfiction writing

New essay published in Tenderly

Last month, I was happy to have my second publication in Tenderly, a vegan-focused Medium site. The essay is called “I Don’t Feel Comfortable as a Vegan Activist Because of My Evangelical Upbringing.”

This publication felt special to me because it bridges my past and current writing selves. Until May, I thought of myself as a creative writer and primarily focused on writing and submitting creative nonfiction and fiction. In May, I became a full-time freelance writer. Personal essays in mainstream publications (by which I mean not literary magazines) are a way for me to connect these two writerly identities.

For those who didn’t see my first Tenderly publication that came out last July, check out “Should Vegans Eat Honey?


New articles in Tenderly and SYFY

Oops, I moved across the country and almost forgot I had a blog. Well, I’ve been publishing a lot lately because I’m now a full-time freelance writer. You might’ve noticed I revamped my website to reflect this career shift. Most of what I write is content for businesses, but I’ve also been getting into more journalistic writing. Check out my two latest pieces:

“Should Vegans Eat Honey?” is an article I wrote for Tenderly in July. Tenderly is a new online magazine dedicated to all things vegan and I absolutely love it. I conducted several interviews for this article, which was fun and interesting. I was excited for the opportunity to challenge myself as a writer.

“Geek Road Trip: Have a Close Encounter at South Carolina’s UFO Welcome Center” is an article I wrote for, the website counterpart to the SYFY channel. When I drove from Florida to the Midwest with an SUV full of my dog and belongings, I came upon something wonderful called the UFO Welcome Center. Please read about it.

I hope everyone is well! :) I realize most people who read this blog still likely follow me from years past, when I lived in a different place, had a different job, and even a different name. I thank you all.


New poetry publication!

poetry south cover

Okay, so my poetry publication isn’t that new, but I’m excited to announce I have a poem in the 2018 issue of Poetry South! The issue came out at the end of last year, and I’m so happy to have work in it.

I’ve noticed something funny. Because I feel confident about my prose, I sometimes become frustrated that I don’t get more or better publications. But because I’m still insecure about my poetry writing ability, each poetry acceptance feels like a shock. A pleasant shock, but still a shock.

poetry south poem

I am beginning to write more poetry. The experience feels odd. Poetry was my favorite form of creative writing in middle school, high school, and college. Somewhere along the way I realized the poetry I was writing was “bad,” and then for years I associated poetry (or at least mine) with adolescence and immaturity.

I’m returning to poetry because I enjoy it as a creative outlet. There’s a feeling I can’t quite pinpoint that I have when I write poetry that I do not have when I write prose. BUT, a nasty editorial voice saying “what you’re writing is no good” keeps popping into mind as I write poetry, much more often and much more loudly than when I write prose.

That voice is just going to have to deal with it. I’m still gonna write poems. :)

creative nonfiction fibromyalgia health writing

New article on Inside Higher Ed

I have a new article on the Inside Higher Ed site. It’s called “Navigating Graduate School While Managing a Chronic Illness.”

This publication excites me for three reasons: 1) I got paid for writing it, 2) it has to do with health/illness, which is an area I want to write and speak more about, and 3) it draws on my recent experiences and I’m trying to find more ways to meld my non-creative career experiences with my writing.

I’d be honored if you gave it a read, and positively pleased if you shared the link with someone who you think might be interested in it.


Did you know I write an email newsletter?

Well, sort of. I don’t know if I’d call it a “newsletter.” I used to call it a “weekly email,” but then writing every week became too difficult, so it’s an “occasional email.”

But, I wanted you, dear blog readers, to know that I’m sort of blogging in this email form, so you may sign up if you’re interested. It’s the email list for Chronically Lit, but the emails themselves are in a casual, conversational style that I usually use when blogging, and although Chronically Lit focuses on chronic illness, most of these emails would appeal to a more general audience.

Today I wrote about gratitude and I thought hey, that’d be a good blog post, too! But instead of blogging the whole thing, I’d rather encourage you to read the email I sent today and sign up for future emails.

creative nonfiction writing

New short essay up on Brevity blog

Brevity is known as the go-to site for flash creative non-fiction. I haven’t been published there (yet!), but they also have a blog that’s pretty awesome, and I’m happy to announce my writing was published on it a few days ago.

My post is titled, “#ShareYourRejection: I Received 330 Writing Rejections in One Year, and I’m So Happy About It,” and I’d be honored if you read it. I found out the Brevity blog has 45,000 email subscribers, so this is probably my most widely-read piece of writing so far.

I don’t think I’ll consider myself a “successful” writer until I have a book published, but I’ve made a lot of progress in my writing career in recent years, and I wrote this post to help encourage people who are interested in a similar path. It still feels surreal to call myself a “writer” or to talk about my “writing career” at all–I’ve spent more years of life viewing a writing career as a pipe dream unavailable to me in any real sense than I have pursuing it in earnest.

lit mags updates writing

Introducing Chronically Lit

chronically lit jay summer

Today is the official launch of a major project I founded and have been working on for hours a day–Chronically Lit. You can support the project by following it on twitter or instagram, and by signing up for the weekly email list (I’ll be sending out the first email today).

I’ve been doing so much writing for the site, I think I’ll just let it speak for itself rather than explain here. Consider checking out the following:

  • In an “In Conversation,” I and the site’s other editor discuss our vision for the site
  • For the past three weeks, I’ve written “Link Roundups” on Friday, which are collections of links related to chronic illness in literature and culture
  • Today, my first “official” piece of writing went live, the first part of a multi-part book review of Sonya Huber’s Pain Woman Takes Your Keys and Other Essays from a Nervous System

I’ve also been working with several writers on essay edits, and those essays will go live over the next two weeks. Exciting stuff!

fear lit mags personal growth weirderary writing

Goodbye, weirderary

Yesterday, I wrote a goodbye post for weirderary, the online literary magazine I began with friends and classmates back in 2015. (I’ve blogged about it a few times before.)

Creating weirderary was fun, and I’m glad we did it. First-hand experience is an excellent teacher, and I learned so much reading the thousands (yes, thousands!) of submissions we received, editing those we selected, conducting interviews, and writing book reviews. I’m grateful I gained that experience and also proud of myself for pushing forward and starting a lit mag in the first place–something I’d wanted to do since high school but hadn’t, for various reasons, but mostly fear.

After us three weirderary editors graduated from the MFA program we were in and began seeing each other much less often, I could feel the energy and excitement around weirderary fizzling. Instead of the thrilling endeavor it felt like before, it became, to me at least, unpaid labor. A pile of tasks. And they weren’t horrible tasks, sometimes they felt rewarding, but when I looked at my overarching career, I knew they weren’t the best tasks I could do with my limited free time in order to move the direction I want to move.

When I was trying to decide if I should let weirderary go or not, I tried to envision the future best case scenario. It involved a lot of work on my end, with a disproportionately small reward. It also involved missed opportunities.

Being an independent lit mag editor is a labor of love, and I now understand why so many small lit mags don’t have staying power. I’m writing about all of this openly here because I think the burnout and at times even resentment editors can feel are things people don’t often talk about with transparency. (Hmm, should I write an essay about that?) I loved weirderary when we began it, and I love it still, now, but I think if I’d stuck with it another year or two, that love would’ve soured.

Thanks to anyone who read it. Stay tuned…I’ll soon announce my newest endeavors.

creative nonfiction fibromyalgia health ibs migraine pots writing

New publication in MTV Fit

New publication: Staying Fit with Chronic Illness Required Me to Redefine “Exercise”

A friend shared a link to a (secret?) Google doc containing a compilation of tweets from editors looking for pitches. When I saw an editor at MTV Fit (a fitness vertical on MTV’s UK site) was looking for health- and fitness-related essays, I spontaneously pitched her one on exercising with chronic illness in that moment. She said yes!

This was exciting for me. I’ve only pitched a couple of times (that’s how I had the Marie Claire article published), and because my background is in creative writing, not journalism, I still feel like I’m sort of faking it when I send a pitch.

I’ve been submitting to lit mags for a while now and I feel like I have the hang of submitting. It’s relatively easy and mostly repetitive. You submit whatever you’ve written, in full, along with a short cover letter that is more or less copied and pasted aside from a personalized sentence or two.

Pitching, however, is a whole different ball game. The cover letter isn’t a formality–it’s the entire thing. Lit mag editors often purposely avoid reading cover letters accompanying submissions until after they’ve made a decision. Mainstream editors reading pitches generally make their decision based on the cover letter–the pitch–alone.

Lately I’ve been writing more personal essay than fiction, so I see a lot of pitching in my future.