I Quit Freelance Writing for a 9 to 5. Here’s Why It Didn’t Work for Me

I Quit Freelance Writing for a 9 to 5. Here’s Why It Didn’t Work for Me

Two years ago, shortly after graduating college, I started freelance writing part-time.

While I was focused on working a full-time job in media, I still contributed personal essays and listicles to a series of publications. This was a smart move because I accepted a job offer working at a real estate content marketing company, rather than a more traditional news outlet, after graduating college.

Part-time freelancing kept me creative as I worked a desk job by day. However, it was mostly about the writing in the beginning.

I enjoyed the art of writing, and I treated freelancing like a hobby, but I soon recognized how easily I could make writing my full-time gig.

Going full-time freelance for the first time

A year ago, I realized I made more income freelancing than my actual desk job.

That’s when I decided to go full-time freelance for the first time ever and begin treating my writing as if it were a business.

It was an excellent transition. I earned twice as much per month than I did at my marketing job. I also could make my own schedule, so I didn’t have to commute to work at 7 a.m. anymore.

However, the decision to freelance full-time wasn’t just about the money. I was living in Omaha, Nebraska, but I was considering a big move back to the East Coast.

Freelancing gave me the freedom and liberty to work remotely from anywhere in the world, as long as I had a reliable internet connection. When I left my desk job, I wasn’t tied to working in the Great Plains anymore.

Earlier this year, I moved to Philadelphia, Pennsylvania because when you’re a freelancer, you can live anywhere. However, I failed to realize how many of my freelance journalism  connections tied me to Nebraska.

Editors loved the stories I covered in the Midwest because most writers were from major coastal cities. When I moved to Philadelphia, I entered a much more competitive media market.

Plus, the cost of living — and income taxes — were higher in Philadelphia compared to Omaha.

My income wasn’t meeting my expectations, so I decided to apply to desk jobs.

freelance writing

Returning to the 9-to-5 again

I accepted a full-time job working in corporate communications a few months after moving to Philadelphia in one of the largest buildings in Center City.

I enjoyed the structure of my schedule. When you’re self-employed, it’s difficult to adhere to such a strict schedule. After coming home from work, I continued to freelance part-time, clocking in hours at night and on the weekends.

However, after two months, working two jobs became exhausting. As you’d expect, when I came home from my full-time job, all I wanted to do was crash, eat dinner and fall right to sleep.

The last thing I wanted to do was write. Freelancing became a chore. I started turning down assignments.

I also wasn’t producing the work that required more time, such as reported stories. I stuck to mostly web copy. Although both are sustainable sources of income, they don’t reflect my passion for writing.

Fortunately, I was saving half of my paychecks the entire time, so I quickly considered returning to full-time freelancing.

Going full-time freelance for the second time

I ended up leaving that job.

I missed being self-employed. I hated waking up early to commute to work. I hated wearing business formal. I hated being cooped up in a cubicle for eight hours a day with the exception of a half-hour lunch break.

Most of all, I hated being managed by someone else. I’m a self-starter, which is why being self-employed fits my professional style.

By this time, I’d been living in Philadelphia for seven months. I had the opportunity to network with local editors and other types of writing clients. Again, editors were coming to me for stories, so now I could finally start saying yes to accepting the work.

Goals I’d wish I’d adopted the first time around

The second time around, I have two different goals for myself, that would’ve benefitted me the first time I went full-time freelance.

1. I’m focusing on anchor gigs

According to Funds for Writers, anchor gigs are “businesses or individuals with whom you have an ongoing relationship and a steady flow of projects and income.” In other words, these are recurring people you can count on for work.

Don’t just secure one anchor client, but secure many.

When I started freelancing, I had one consistent client that paid extremely well. This worked to my advantage starting out, but when I relocated to Philadelphia, the freelance budget had been cut significantly.

Now, I work with four different anchor clients. Together, these four clients go towards paying the bills. Two are publications, the others are small marketing agencies. That way, if one client has their budget cut, I have three others to rely on.

2. I’m consistently building a pipeline

This means I’m always networking with new potential clients and marketing my services across the board, no matter how much work I already have scheduled out.

The reality is, I’ll eventually need new work, and you never know who that next client will be.

You need to be proactive with how you sell yourself to those you come across in professional spaces.

Whether you’re currently freelancing full-time, or are working towards one day making that transition, it’s important to figure out where your income is coming from. It’s also incredibly important to constantly curate an editorial calendar, so you’re never going without work for a long period of time.

Although it requires much more effort than working a traditional 9-to-5 desk job, writing full-time for myself is far more rewarding in the long run.

What do you wish you would’ve known the first time you first transitioned to full-time freelancing?

Filed Under: Freelancing


  • Fan Seats says:

    Thanks for sharing with us your experiences and doubts you had when beginning. I started creating content as a freelancer several years ago and only now starting to get a system in place where I can make this a full time lifestyle.

  • Great article, thanks for sharing! I work as a freelance editor, and do some writing on the side as well. It really helps having a few ‘anchor gig’ publishers sending me manuscripts on an on-going basis, and then of course it’s all about finding new clients to add to the list. 🙂

  • What a useful list to send us. I will try to approach many of them. Thanks, Jera Brown!

  • Sandy says:

    This was the story of my life. The only difference is when I went to a 9-to-5, it was on a commission basis and just ruined me financially. Thank goodness I had freelancing as a backup and now, almost two years down the line I’m finally starting to see the light at the end of the tunnel. It was fun reading this piece and yes, relying on a single client is a dangerous game.

  • Tracy Line says:

    Great article. I freelanced for years and then quit to do a 9 to 5 and it did not agree with me. As a mom, I love the flexibility of freelancing and being able to be in charge of my schedule.

  • O'Dell Isaac II says:

    I have always loved writing, and I am very interested in freelancing. Content mills, even at the height of their popularity, have never paid much. How do I get a foot in the door?

    • Sandy says:

      Hey there, this is something that stumped me for about two years until I got unceremoniously dumped by one content mill ( the one with the largest chunk of income). I went onto job boards and *cringe* Craigslist and now have a steady stream of clients. Just be careful and make sure your potential new customer is legit and actually exists. Where possible, ask for a deposit or upfront fee. A few great agencies also advertise through CL.

  • Love this article. Hits right St home with me. Answered my dyeing question 9-5 or not. That is the battle.

  • Never really thought about the anchor possibility until recently, but thanks again for highlighting this. It shows me that I’m on the right track with that way of thinking. I also agree with your mention of continuously building a pipeline. I’d be interested to know how you market your services and through which channels. Until then, thanks for the great article and all the best as you continue your freelancing journey!

  • Neha Srivastava says:

    Totally agree with the article. Having an anchor client as well as constant networking and marketing of your services is key to a fruitful freelance career.

  • JB says:


    This was inspiring as I am considering the same. However, could you be more specific as to how you found/connected with anchor clients once you moved?

  • Stacy says:

    This article has a LOT of great content for the 9-to-5’er debating the merits of going freelance full-time. However, the single most valuable sentence in it may be this one: “It’s also incredibly important to constantly curate an editorial calendar, so you’re never going without work for a long period of time.” There can never be too many reminders to treat your freelancing as a business and plan ahead for success!

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