3 simple secrets of side writing hustles

Will Kelly
3 min readAug 27, 2022


Photo by Sincerely Media on Unsplash

Side hustles are all the rage because of the economy and the extra hours each day that working from home affords us. I’ve had more than a few during my professional career, such as technical reviewing computer books to technical writing to writing articles for publication.

Here are my three secrets:

1. Side writing projects should be fun

It took me years to admit to myself, but side projects should be fun. For example, freelancing for TechTarget brought to be a lot of joy. The writing assignments were always interesting. I was writing for them taught me how to think about the industry and technology adoption challenges in new ways. It was a very formative experience for me as a writer. All of this made it easy to come home from the gym after a day of work and sit down at the keyboard again to write some more.

Over the years, I’ve had some side projects that weren’t so much fun. It was hard to dedicate an evening or weekend time to these projects. While I’m constantly refining how I pitch new projects, even now, when I’m not freelancing, there

2. The best color for side projects is evergreen

When you work side writing hustles, I’ve discovered that the best projects were often the so-called evergreen content projects. For example, for as many publications and websites that I wrote over the years, I never wrote about breaking news. It required a turnaround time that wasn’t always possible with a day job.

3. Never factor the money you make into your budget

My father always worked extra jobs and shifts when I was growing up. One thing my parents never did was factor any of the money my dad made from those additional jobs into the family budget. In some ways, I guess I was predestined to have side hustles.

Pre-pandemic, the money I made from writing articles went to luxuries like my summer vacations. It also went to build up my “war chest” and gave me a cushion during layoffs.

During the pandemic, I did lose out on some side hustle money for circumstances outside my control, most often budget cuts. While the losses stung a bit, the lost dollars didn’t hurt my monthly budget.

Final thoughts

I’m far from the type to romance hustle culture or constantly having to be on when it comes to working. Writing side hustles have helped me learn new areas of technology I wouldn’t have had the chance to touch in my day job. Writing side hustles have been a cushion for me during layoffs.

Will Kelly is a product marketer and writer focused on DevOps and the cloud. His technology interests include enterprise mobility, collaboration tools, and remote work. He has written for TechTarget, Opensource.com, InfoQ, and others. Follow him on Twitter: @willkelly.

Originally published at http://willkelly.blog on August 27, 2022.



Will Kelly

Writer and product marketer | Learn more about me at http://t.co/KbdzVFuD.