Karen Sawrey - Hustling for Fun and Profit as a Technical Writer: A Freelancing Starter Kit

Catherine Heath | October 13, 2021

This is a summary of a talk given at Write the Docs Prague 2021.

Karen is a rock musician, a cat parent, and generally a person with diverse interests and hobbies. She’s a technical writer, copywriter, copy editor and translator. 

Her colleagues often ask her how to start freelancing, and that’s exactly what this talk is all about. Hustling is a means to end, and she was very intentional about picking this word for the title of the talk. 


Hustling means that you set some kind of goal, to develop a skill, or to work with some kind of technology. It’s more experience, and allows you to battle-test your skills. It also results in additional income, so you get the best of both worlds of having a job and freelancing on the side. 

She loves working in data security but she found a freelance gig working for a company that manufactures digital guitars, combining her work with a love of music. Everything’s possible if you dedicate enough time to find the right gig. 

It’s important to avoid burnout and not to hustle too hard. She had a point where she was working too much and too hard, and then became a bass player. It was a pretty dark place and she doesn’t recommend it. 

Hustling is hard but rewarding, and the opportunities are endless. Hustling is optional if you pick your battles carefully. 

Getting started

You have to get permission to hustle. Read your working contract carefully to make sure the non-compete clause doesn’t prevent you working anywhere else in tech. 

You might be allowed to do some consulting work and not writing work, or vice versa. 

You might also have signed a non-disclosure agreement, so make sure you follow the rules. You can’t talk about your work to anyone. 

To be able to pay taxes you need to register your work as a freelance entity. You can be a registered solopreneur, private entrepreneur, company (LLC) or digital residency. You can hire people like a tax lawyer, accountant, or a personal banker. 

Read what you’re signing and negotiate for better conditions. 

Finding work

You can visit freelance websites such as Upwork and Freelancer, but she found these sites to be less than optimal. Instead:  

  • Network on twitter, and Slack and Telegram communities. 

  • There is a jobs channel in Write the Docs, and it’s possible to find part-time freelance opportunities there. 

  • Consider digital nomad communities and virtual job fairs such as Write the Docs conference. 

  • Maintain your own swipe file of companies you want to work for to inspire you. 

  • Build your portfolio by linking to public knowledge bases that you have worked for, and consider screenshotting your docs. 

Process and pitfalls

You need to have your own machine to work on. It might be illegal in your country to use your computer provided by your full-time employer and the documents on it belong to the company that gave it to you. 

Keep your accounts separate. Make sure not to leak information between your accounts and keep your client’s work private. 

People will find out about your hustle one way or another. Do not work for clients who you consider to be evil or doing things that you don’t like. Consider creating your own NDA. 

Freelancing is your freedom to make bold decisions. 

Getting paid

Never undercharge yourself. When you’re approached by someone asking you to freelance, you should ask them what their budget is. They are now compelled to tell you how much they can afford to spend. You need to be paid for the value you bring. 

Here are some tips: 

  • Translate your contract agreement into whatever language your client uses for their legal paperwork. 

  • Provide an invoice in both the language of your client and the language of where you live. Include every tiny detail in your invoice. 

  • Choose a bank that is supportive of you as a freelance entity. Shop around for benefits and extra services. 

Final remarks

Karen encourages technical writers to start freelancing. It’s important to avoid burnout and negotiate everything. Follow these tips to kickstart your freelance career!

Listen to the full talk here. 

About the author
Catherine Heath
Catherine Heath

Catherine is the Community Builder for KnowledgeOwl. She is also a freelance writer based in Manchester. She writes blogs, social media, copy, and designs owl-based images. 

You can find out more about Catherine on her personal websites Away With Words and Catherine Heath Studios.

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