10 Years a Freelance Writer

In January 2010, I walked out of my office at the Windstream Communications’ Brownstown PA building for the last time. The other approximately 15 employees and I in the marketing department knew that day was coming for months in advance. When Windstream, a national corporation, acquired the regional company once called D&E Communications, HR reps met with us to tell us our positions were going away. After a transitional period, we would no longer be needed because folks with similar positions in the Arkansas corporate office would be taking on our responsibilities.

As we left the building on our last day, some of my co-workers shed tears as they carried their boxes of personal belongings from the premises. I, on the other hand, had a difficult time holding back smiles and skipping through the hallway.

It’s not that I disliked my job at D&E Communications/Windstream. As a marketing product manager, I was well suited for the position, and it was well suited to me. But after spending a total of 17 years at the company and in the telecommunications industry, I looked forward to a change. 

I had a plan.

In April of 2010, I officially launched my freelance writing business. Ten years later, I’m still at it, working full-time as a freelance writer. I’m blessed, for sure. However, I don’t believe that the grace of God or of some other universal energy has alone made that possible.

Reality Check

A combination of factors have played a role in my ability to launch and sustain a freelance career path:

  • My husband and I weren’t living paycheck to paycheck.
  • I had a generous severance package from my previous employer.
  • My husband was gainfully employed with a salary that could cover a majority of our expenses as I ramped up my revenue in the first two years.
  • We had good health care insurance through my husband’s employer.
  • I had a room in our house that I could immediately use as a dedicated office space.
  • My husband was fully on board with my decision to freelance. 
  • We aren’t suckers for extravagance, and we’ve never made a habit of living beyond our means.
  • Having been in the marketing department in my previous career, I had professional connections that provided me with some freelance opportunities out of the gate.
  • Writing comes naturally to me.
  • Project management comes naturally to me. 
  • I enjoy working independently and can tune out distractions.

Had a few of these things been missing from the equation, I might have ventured down a different professional route. Hanging my shingle as a freelance writer was exciting but also scary. My salary in my previous job was bringing in 60 percent of our family income. Even with a savings account and severance, I would have had to explore other options after year two if my business income didn’t grow and come reasonably close to my past pay.

A Checklist of Factors That Can Make or Break a Freelance Career

To succeed as a full-time freelance writer, you need some writing chops (stating the obvious). But that alone won’t allow you to stay in business. Many other aspects of your personal situation, background, and personality will affect your freelance success potential, too.

  • Current financial situation
  • Living situation
  • Educational and professional background 
  • Professional connections 
  • Work ethic
  • Tolerance for working alone
  • Business sense
  • Common sense
  • Organizational skills
  • Will to learn and adapt
  • Tolerance for constructive (and sometimes non-constructive) criticism

Not all aspiring freelance writers think about whether their current life scenario, personality traits, and mindset are a good fit. If those things aren’t conducive to working as a freelance writer, it will be especially challenging to make a go of it. 

A 10-Question Self-Assessment for Aspiring Freelance Writers

It’s important to carefully assess your circumstances before deciding to rely on freelancing as your one and only income source. Consider your current life situation and personal characteristics. Are you in a position that will allow you to navigate the possible financial and emotional ups and downs while building your business?

Ask yourself:

1. Do I understand how much it will cost me to operate my freelance business?

2. Do I have enough money saved or another source of funds to fall back on if I’m not making enough to cover my personal and business bills?

3. Am I self-motivated enough to meet project deadlines?

4. Am I organized?

5. Do I have professional connections that I can leverage to find new clients?

6. Do I manage my money well?

7. Do I understand what I have to do to run my freelance business legally? 

8. Can I deal with rejection?

9. Do I have an environment where I can work uninterrupted?

10. Am I focused, or will I let trivial personal tasks distract me from my business responsibilities?

If an honest assessment leads to the conclusion that you’re not financially or otherwise in a place that’s suitable for going freelance full time, you may want to dip your toe in the water on a part-time basis. Or you might consider working as a writer for a marketing agency or other company.  I know several writers who transitioned from freelancing to working as content writers for businesses and marketing firms. They’re successful and very, very happy…and they still do some freelance gigs on the side when time allows. 

After 10 years a freelancer, I find it difficult to imagine myself doing anything else. If some aspects of my personal situation were to change, I believe my business is established enough that I could continue. However, I realize there are no guarantees in life or business. 

Your Turn!

What circumstances made it possible for you—or prevented you—to freelance full-time? I’d love to hear about your journey!

4 comments on “10 Years a Freelance Writer
  1. Brad Shorr says:

    Hi Dawn, Great post. All of your insights and recommendations are spot-on. So many people underestimate the importance of having the financial means to sustain a 1-2 year ramp-up. It’s hard to write well and develop a client base when you’re constantly worried about money. One thing that helped me transition to freelance work was specialization. Back in 2005, I decided to specialize in SEO copywriting, which was very much an emerging field at the time. It’s a lot easier to secure clients when you can provide something they can’t get anywhere and everywhere.

    • Dawn says:

      Thank you, Brad! That’s excellent advice! Until you’re able to prove yourself, you have to find a way to stand out from everyone else.

      I hope you’re doing well–I miss collaborating with you!

  2. Holly White says:

    I’m curious how you manage work promised but then not given. Do you always sign a contract with anyone you work with/for? I am of the “toe in the game” freelance variety – purposefully. But even at only a few hours a month, I find that sometimes I’m given a workload, and I sustain it for a few weeks or months, and then the workload either disappears or decreases. As far as I can tell, this is often a known or expected thing, but no one thinks to tell me, the freelancer, about it, so work I had thought was coming in…isn’t. How do you combat that, or is it just the nature of the biz?

    • Dawn says:

      Hi Holly! That’s an excellent question. Typically, I don’t lock clients into giving me a minimum amount of work. That said, I have billed some work on a retainer basis in the past. I.e., they paid me a minimum dollar amount each month for an agreed-upon volume of work or number of hours. That might be a good option for you. To deter clients from promising a one-time project and then pulling the plug, you might consider asking for a 50 percent downpayment upfront and/or putting a kill fee clause in your contracts.

      At this stage of my career, I have a lot of clients that I have been working with for several years. Most consistently have weekly, monthly, or quarterly projects that I can count on. There are a few that work with me on an as-needed basis. I’ve found that somehow things always seem to work out if anyone for any reason must pull back on how much work they send me. It seems like there’s always more work waiting in the wings to fill the void–which is wonderful.

      I hope this helped! You’re welcome to call me some time if you want to “talk shop.” ?

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