November 26, 2017

Pride, Work and Necessity of Side Projects: Product Designer and Manager Caylee Betts’ Entrepreneurial Outlets in Realizing Swipies, Meetup group Moonlighters and More



What are you working on—on the side?

I have a couple! For the last two years, I’ve manufactured and sold a reusable paper called Swipies. I sell them publicly online, but I also do custom-branded projects with customers like Airbnb, General Assembly and Moz. It’s a great side project because it’s a real business, but it doesn’t require my attention constantly. I need to ship orders a couple times a week, but other than that, I can improve and grow the business at my own pace. It’s also cool that it’s a physical product since my job is entirely digital. It’s really nice to get hands-on.

My second project is a memoir about my experience with anxiety, including a reusable guidebook (printed on Swipies!) for working through a panic attack or high anxiety situation. This is a huge project because of the amount of research and interviews I need to conduct. Once I have the content in order, I need to work with legal and medical professionals to review the book. And I have yet to even look into working with an agent, publisher and printer. One step at a time!

Lastly, I recently started a Meetup group called Moonlighters, and I am planning to run a couple side-project-accountability-and-support groups in 2018. I have lots of ideas I like to pursue outside work, so I felt that surrounding myself with others who do the same would benefit all of us and all of our projects. I’m really excited about it!

How do you manage to work
on your side project(s)?

I try to avoid putting too much pressure on myself with side projects. So instead of creating specific timelines or deadlines for my side projects, I keep a long list of things I want to pursue and I pick them off as motivation or inspiration strikes. So, on a day when I am more in the mood for a mindless task that I can complete while catching up on TV, I’ll inspect the quality of a couple thousand sheets from a new Swipies shipment or I’ll edit a bunch of photos from a recent custom-branded project. On other days, I am feeling really creative and want to dig into branding or coding or creating something new, so I focus on that. I also let myself go through ruts. There are times I won’t work on a side project for a couple weeks at a time. And that’s ok. This isn’t a great format for running a business, but it’s a healthy way to run a side project, in my opinion.

Why have a side project?

Personally, I can’t not. I grew up in an entrepreneurial family, and I have that fire in me. I ran my own business for 5 years, and have helped other small businesses get off the ground as well. Since I am no longer doing my own thing full-time, I love having an entrepreneurial outlet. I love that I can flex tons of different muscles with side projects, and I can do something different than what I do at work. I also learn a ton in a practical way. I’ve taught myself a good chunk of my coding knowledge through side projects. If you’re interested in professional self-improvement, I highly recommend taking on a side project!

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Diptych courtesy of Caylee Betts.

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Read more about the joy of side projects.


This series, devoted to side projects, is delivered in association with Chicago creative agency 50,000feet—dedicated to helping brands and businesses soar.


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