Software Development
Career development / Good Works / Software /

Why technologists spend their time outside the 9-to-5 on side projects

"Every field is evolving, everyone has to play catch up with their areas of work," technologist Rachna Chadha told us. "You can not do that, but you're at the risk of being left behind."

Coding. (Photo by Brian James Kirk)

This editorial article is a part of Software Development Month of's editorial calendar. In Philly, this month’s theme is underwritten by Linode. This story was independently reported and not reviewed by Linode before publication.

It started when Abe and Mindy Massry couldn’t remember which episode they’d last watched of “Game of Thrones.”

It’d been a year or two since the married couple last tuned in, and while combing through episode descriptions online, Abe Massry ended up spoiling some plot points for himself. The pair finally figured out they were ready to start season 3, but Mindy Massry mused: What if there was a website that could help you remember?

So Abe Massry got to work manually browsing the internet for episode descriptions, scraping the info and using things like keywords and natural language processing to build a site that would take a brief description of the last thing you remember and spit out a few episode suggestions. It also offers where to watch it and a short clip.

The site,, started with “Game of Thrones,” but when friends heard of the project, they started suggested things they were watching — “Stranger Things,” “The Office,” “Breaking Bad“or “Mad Men” — and the site grew from there, with Massry using public APIs from streaming services’ descriptions to log nearly 50 shows to date.

The site is not Massry’s first for-fun side project, and it definitely won’t be his last. He’s a full-time software developer, but he’ll usually spend another five to 10 hours a week on projects like the Find Episode website, usually to teach himself a new skill, keep current ones sharp or fix a unique problem in a creative way.

During Software Development Month here at, we checked in with technologists around the region about the concept of side projects — that work-outside-of-work that can seem like an anomaly to those not in the tech world. What we heard: It’s not extra work for work’s sake, but an opportunity to upskill in a fast-changing industry.


“So you don’t like, perform surgery in your free time or do free medical consults on the subway?” a San Francisco-based technologist riffs in a recent TikTok, role playing as if doctors were interviewed for jobs like software engineers. “That’s a bummer, because we were looking for someone who also does their job outside of work.”


side project check! #softwareengineer #softwaredeveloper #techinterview #computerscience #coding #womenintech

♬ original sound – Emily Kager

Massry didn’t use to work full-time in tech. He started building websites for ideas he had and found it enjoyable, realizing it was something he wanted to do full time. Then he started bringing the skills he was learning to his full time job, and has since become a software developer at a Philly tech company.

“I always have tons of ideas, more than I could possibly implement,” he said.

When he has an idea for a side project, he emails it to himself on a thread that’s now many years old. The next time he ships a project and is looking for another one, he refers to this list (which now has about 110 ideas) to find the next best one to implement. It keeps him organized and on track to finish one project, then move on to the next. It’s another idea from his wife, he said.

“Usually I’ll see a demo online of someone using a new language, or see a project on GitHub, that looks very well written to me,” Massry said. “If it looks easy to get started with and usable, I’ll try it out.”

Ben Garvey, senior engineering manager at Betterment, argues that the TikTok is wrong: Sure, surgeons aren’t cutting people open at home on nights and weekends. But maybe they volunteer with a nonprofit or submit research to medical journals.

“We don’t really remember them as side projects, but it could be related to tech. It’s just activities you choose to spend your time doing,” he said. “You could use it as a creative project, where you also learn how to do something.”

The technology turns over so fast, if you were to stay stagnant in your skills, your job prospects will hurt the next cycle around.

Garvey says he too spends hours outside of his full-time work on technical projects. Most technologists who work at a company spend their 40 hours on a certain set of skills or with certain languages. If you work at a tech startup, you might join and start to learn a lot and work new skills, but three years later, it’s unlikely that the company has rewritten to keep up with the latest and greatest, he said. Side projects are likely a way to keep up with the always-changing landscape of tech.

“The technology turns over so fast, if you were to stay stagnant in your skills, your job prospects will hurt the next cycle around,” Garvey said.

Rachna Chadha, architect advisor for technology, architecture and innovation at CVS HealthCare, agrees. She’s been all over the software development field, but recently works and does side projects in the AI space to keep her skills up to date.

“If I look at the books on my shelves from four years ago, they’re not relevant anymore. I can’t find anyone who wants them,” she said.

Chadha has recently worked on some AI projects relating to her Amazon Alexa, teaching the device how to have a conversation with her family members, including identifying them by name. She said it turned out to be a fun project for the whole family, and her daughter, who’s in second grade, is interested in her work and gets to learn alongside Chadha.

Similarly to Garvey, Chadha believes side projects aren’t unique to the tech industry. Friends and family of hers who work in science or other related industries are usually publishing research in their field.

“Every field is evolving, everyone has to play catch up with their areas of work,” she said. “You can not do that, but you’re at the risk of being left behind.”


For some, side projects represent the core interests of the technologist that they don’t get to work on in their full-time job. Garvey currently works in fintech, but his heart is in data projects, he said. One of his favorite side projects is a data expression of his family’s lineage, a colorful, multi-organized data tree with optional music and night mode.

A big consideration of side projects, he said, is IP assignments. By default, any code you write, you own the copyright for. But likely, you’ve signed an agreement saying work you do for your company belongs to them. So, there are different levels of outside work. A small startup might not care so long as you do the work on your private computer. But if the work competes with the work your employer is doing, it’s likely there will be a problem.

These legalities aren’t things most people consider, Garvey said. But maybe it’s not even your company — maybe your company gets acquired and that company has a totally different agreement. It’s important to be aware if your company or a company you’re considering joining has restrictive rules around outside work.

“It should give you pause, and you should decide if you want to sign up with this new group,” Garvey said. “And I’m saying that because there’s lots of examples of peoples’ side projects become revenue-generating, turned out to be leading into new formations of companies or things like that and you want to be sure if your side project becomes your main gig one day, that you think about these issues and probably talk to a lawyer about it.”

All three technologists agreed that side work can be used for upskilling, and that it’s often discussed at meetups and with other technologist friends. Whether the motivation behind producing side projects is to get a new job or to keep up with a new language or program, it usually boils down to a person who likes to analyze problems in a creative way.

“I think a person who does side projects is just a curious person who wants to understand something,” Garvey said. “That’s the motivation for me, anyway. It’s less learning, and more diving into something I find interesting, or finding a way to look at a problem.”

Companies: Linode / GitHub
Series: Software Development Month 2020

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