Retrospective: Three Years as a Freelance Tech Writer

Gimli: Whatever luck you live by… let’s hope it lasts the night.
Legolas: Your friends are with you, Aragorn.
Gimli: Let’s hope they last the night…
Lord of the Rings: The Two Towers

The end of the year is usually a good time to look back on the world’s previous solar orbit. For me, the end of 2016 also represents the end of three years paying my bills as a freelance technical writer. It has been a learning process, to be certain. It has also been a tale of unearned luck, which I fully acknowledge. I’ll try to make this narrative worth your time.


The first freelance job

I interviewed with a large aerospace contractor on a job-scouting trip in December 2013. The interview seemed to go well, and I found myself in an ideal position early in the year, doing internal communications for 15-20 hours a week, giving me time to pursue other opportunities, should they present themselves.

While I was in the unenviable position of spending a couple months living with my father and bonus mom at the age of 45, I quickly found other options. Some friends of my father’s were going to be out of town and in need of someone to watch their home in a rather nifty neighborhood in southwest Orlando. That would cover me for another two months. Surely I could find a steady gig by then, right?

Meanwhile, I was socking away money from the aerospace job, which was a good thing, because I knew my “rainy day” fund wouldn’t last forever. And then I started noticing things. My customer was consistently unhappy with my perfectly decent prose. Rewrites were becoming a way of life, with subsequent discussions often producing no better results in the customer’s mind. No one talked to me. I worked in a cavernous, cheerless warehouse-like structure with no windows. I was happy to be working…BUT…the efforts were going for naught.

One day the customer made up their mind that I was no longer acceptable, and nothing I did was going to convince them otherwise. I was sent home for good, received my last paycheck, and that was that. The subcontractor I worked for would not return my calls, and there I was: unemployed, my stuff in storage, and living in someone else’s house. A nice house, to be sure, but not my own.

Living by my luck

Lucky Break #2 for 2014 came when another friend of my father’s needed a home (condo) sitter down the street from where I was holding down the fort previously. This temporary housing arrangement would last until November. Surely I could find steady work by then, right?

Lucky Break #3 arrived in the form of a phone call from a space-focused consulting group in Washington, DC, who needed a technical writer to help prepare reports for NASA. I didn’t have any recent space work by that point, but when they wanted references, I could refer them to two or three people I had worked with at NASA who were already in NASA Headquarters, where the company was situated. I gave the interview their names and, within a day, I had an employment contract in my inbox. I have never, to this day, talked with anyone at the company face to face. [Lesson Learned: your reputation matters.]

Lucky Break #4 came in the form of a former coworker and mentor needing a technical writer for instructional design work. It was not my usual line of work, but I had done similar work 13 years before that. So I set to work learning about the mysteries of obesity management as I wrote scripts for Florida Hospital. I even learned some things to improve my own not-so-healthy body mass.

However, I severely underestimated how many hours it would take me to do the work. My friend was gracious enough to pay me for the hours I worked, but she didn’t have to, and I had expected her not to after I reached my self-declared limit. [Lesson Learned: have a clear idea of what you’re signing up to do.]

Anyhow, with that work being done, I’d stashed away enough money to take a leap of faith and rent an apartment of my own. I figured, “I can find another job by the time I run out of money, right?” It was a close-run thing, even so.

Talking to a coach

While I was treading water at Someone Else’s Home #2, my friend Kate was starting a professional coaching business of her own. She needed someone to practice on, and honestly I needed the advice. So far, I had been taking–if not charity, at least whatever job came my way. If I wanted to earn a steady living, I realized that I needed to identify a niche, an actual space in the market that I could identify and say, “If you want X written, I’m the guy you need to call.”

The problem was, I wasn’t certain what my niche was. This is where Kate was able to help. Through a series of one-hour phone calls and some homework I did in-between, I managed to get my priorities straight. For example, I had visions of repeating the work I did at my last permanent job: proposal and marketing writing for a small engineering firm. However, I was discovering that the folks willing to hire me part-time didn’t pay enough for me to keep my rent paid. Also, the small entrepreneurs I was marketing to were not always open to my professional communication advice.

Through my discussions with Kate, I came to realize that I really did work better with larger organizations–small businesses rather than sole proprietors–that knew what technical writers were supposed to do, respected that role, and were willing to pay for a known service. This mindset helped keep me focused on where I wanted to go, not just who might give me money. [Lesson Learned: a good professional coach is a worthwhile investment, especially if you don’t know where you want to go.] So, okay: once the Florida Hospital gig ended, I had a plan in mind: I would focus on a particular market, in a particular size category, with a particular operational culture. It was a great theory.


When things get ugly

I’m not going to lie: as long as money is coming in, I’m not a very aggressive self-marketer. Part of this is because I’m content as long as my basic needs (rent, utilities, Disney Annual Pass, occasional social outings, personal savings) are met. And while I was socking away money into the rainy-day fund, I knew that the DC space work and the Florida Hospital gig would end, which they did. I was doing some work for my former employers here and there, and then some side jobs with my solo-entrepreneur customers, but I was also painfully aware that the rainy-day fund was dwindling.

This was a time of great stress, no lie. If I hadn’t started eating better and exercising [Lesson Learned from the content of my day job], I probably would’ve become that typical American wreck: under-exercising, under-sleeping, overeating, and overstressed. Medical bills were piling up, too. Not fun, but at least I had a cool pad to condo-sit.

The luck you live by

I was about two weeks away from running out of work to do and liquid cash (i.e., money that wouldn’t carry a penalty if I withdrew it) to spend when I got a call from another friend from Disney who was in need of an instructional design technical writer. The content? Sales, service, and finance training for Nissan representatives talking to dealerships.

Did I know anything about this line of work? Not really. Was I willing to put myself into a room with subject matter experts and learn what they had to say so I could translate that stuff into a classroom script? You bet. The pay was right, too. I was able to get out from under some debts that were crushing me, and I could pay my bills without stress. What does stress look like? That’s when you spend your last two free dollars tipping a taxi driver.  [Lesson Learned: Work your network, don’t throw away anyone’s phone number.] That job is still paying the bulk of my bills today.


The Nissan job continued while work from most other sources dried up. However, toward the end of 2015 I was also starting to develop a local professional network through a friend’s coworking space, which I had been sorely lacking when I first got here. So I’ve had somewhere to go, and people to talk to on occasion when sitting around the apartment gets to be too much quiet. [Lesson Learned: Freelancing has its ups and downs, and it’s worthwhile to acknowledge them and take steps to mitigate the downsides.]

After attending a couple space launches and talking with space people I knew and missed, I realized that I needed to stay in touch with the business I love. In August, I signed up to do reporting for a buddy’s space news site. This did a couple things: first, it kept me in touch with the industry I loved (space) and second, it kept my name out there. [Lesson Learned: Find ways to do work you’re passionate about.]

Lessons learned after three years of winging it

What will 2017 bring? I am not entirely certain. I am still on call for Nissan and Spaceflight Insider. Random new jobs appear, and I continue to pay the bills. Oh yes, and I still have a number of volunteer activities that I engage in because I care about the work enough to spare a little of my time to do it. In any case, the things I’ve learned over the past three years have served me well enough to keep the bills paid:

  • Your reputation matters.
  • Have a clear idea of what you’re signing up to do.
  • A good professional coach is a worthwhile investment, especially if you don’t know where you want to go.
  • The content of your day job can have applications beyond simply doing the work.
  • Freelancing has its ups and downs, and it’s worthwhile to acknowledge them and take steps to mitigate the downsides.
  • Find ways to do work you’re passionate about.


About Bart Leahy

Freelance Technical Writer, Science Cheerleader Event & Membership Director, and an all-around nice guy. Here to help.
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