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An Interview with Good Words CEO Caity Cronkhite

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An Interview with Good Words CEO Caity Cronkhite

September 28, 2021

This past March, Jerrard Dorran of The Not Boring Tech Writer Podcast sat down for an interview with Good Words CEO, Caity Cronkhite, about her (definitely not boring!) career path from full-time technical writer to CEO of Good Words LLC. “I never could have imagined that freelancing in my living room, doing my own projects for fun, would ever turn into something this big or something this impactful.” 

On “Existential Googling” and Technical Writing 

Among the insights Jerrard gathered from Caity was how she was able to put together her interests in science and writing. As a student at Carnegie Mellon University, she says, “I knew I was interested in the sciences and […] in literature and writing[.] But, as I went through my academic career, I hit the end of my junior year and […] realized that I wasn’t sure what I wanted to do with my life or how I wanted to […] marry those two skill sets.” 

So she did what any person would have done at the time and went to the source of all knowledge: the Internet. “I did some existential Googling, if you will, [to see] if there were any good career options for people with two seemingly very different skill sets in writing, [with] a background in technology. And that’s how I found tech writing.” 

Luckily for her, Carnegie Mellon offered a program in technical writing, and she was able to graduate with that degree. A week after graduating, she was San-Francisco-bound, driving a U-haul across the country to her first job. Caity began her career as an in-house technical writer for Salesforce, then as a lone technical writer at various startups. After gaining more experience in the field, she took on the challenges of being a freelance writer. Through her interview with Jerrard, she offered advice on each of these career paths.

On Being an In-House Technical Writer in a Large Team

“[T]he biggest thing I learned in that experience,” states Caity, “was how to create documentation and communication materials, in a large complex system, that [are] scalable and [work] for customers, but also [work] for a huge number of writers who are contributing to that content. I learned a lot of really great skills about how to create good, scalable, consistent documentation, even in an extremely complex environment like that.”

On Being a Lone Technical Writer

Caity remembers that, “I learned just as much in those roles as well: […] how to start documentation from scratch, how to implement documentation systems, how to take an environment that has no documentation and no communications protocols and build those […] in ways that were going to be scalable as the company grew.”

On Being a Freelance Technical Writer

Freelancing became quite the surprise for Caity. “I found it to be quite liberating. And I know […] some of the liberating elements of it can also be a little intimidating for people who are just getting into freelancing or thinking about trying it out.” 

Caity’s first freelance role came as a part-time technical writer for an aerospace project. “[I]t was a sort of profound change for me, where I suddenly got to pursue all these really interesting projects in multiple industries. I worked on really interesting teams who were developing really cool new technologies. [I]t was the beginning of a beautiful phase of my career. […] I suddenly had control over my schedule and over the projects that I was working on, and the clients that I would work with, in ways that I had never had in my career prior to that point,” she recalls. 

Writing Her Way to CEO

Eventually, Caity’s love for freelance work turned into something bigger than herself. “I never had an ambition to be an entrepreneur or to own my own business. […] But as my freelancing career grew, I started to bring in new clients, […] and all of a sudden I found myself having more work, more opportunities for projects, than I could take on and handle myself.” 

Instead of walking away from the projects and clients, Caity once again took a leap into the unknown by hiring her first employees. In 2017, she incorporated Good Words LLC into its own business, and in 2018, she hired her first consultants to help her out with her projects. Just four years later, Good Words LLC employs over 20 writers and content producers. 

“It’s been really exciting to see my freelancing career, which I was so passionate about, grow and scale into something that is now much bigger than just me.”

Caity uses her own experience as a technical writer to make Good Words a great workplace for remote freelancers. “At Good Words we like to say [that] we’re a soft place for freelancers to land. So we like to give our staff members these really excellent opportunities and the flexibility that comes with freelancing, but also [remove] some of the barriers that exist for a lot of people who are just getting started. [… I]t’s been a real privilege to me to be able to share that [opportunity] with other people.”

Career Advice for Technical Writers

To finalize the podcast, Jerrard asked Caity what her advice is for listeners who want to follow a career path similar to hers. Here’s a summary of Caity’s advice:

  • Know what your interests are, what you enjoy doing, and what you like. “That’s a big piece of advice,” she says. “It applies to any career path,” not just technical writing.
  • After you know that, don’t be afraid to look for interesting opportunities—and follow them. “Getting into freelancing was sort of a scary jump, but I’m so glad that I did it! […] I’m so glad that I tried it out and took that risk because it really opened the door for me for many things.”
  • Always make room for networking. “Networking has been huge in my own career. […] In growing my business or in finding new projects or looking for new opportunities, I still talk to people from my network that I met a decade or more ago. I often come across really cool opportunities and projects for my staff, just through happenstance [and] conversations with people.”
  • Stay tuned to the technical writing community. “[T]echnical writing is kind of a small universe. [A] lot of us are the only technical writers in our companies or the only technical writers on our teams. I’ve met a lot of tech writers who don’t even realize that there’s a whole tech writing industry.” Among the communities Jerrard and Caity mention are the Society for Technical Communication, Write the Docs, and I’d Rather Be Writing.  

Listen to the entire podcast to hear more insights from Caity and Jerrard’s conversation.



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