Cynthia Closkey, Partner and Owner at Shift Collaborative, has a knack for making complicated things make sense. Her background in technical writing, software, and web design, brings a problem-solving mindset to everything from untangling communications challenges to improving user experiences.
Cynthia joined Shift in 2015 when she merged her website firm with the company. More than a decade later, she’s finding new things to build, improve, and explore. We caught up with Cynthia to talk about her approach to problem-solving, and her passions and hobbies.
Tell us about your background.
I started my career as a technical writer, combining my geeky tech side with my affinity for clear communication. In many ways, that’s still what I do: translating complex concepts to fit the audience and using technology to build great user experiences.
I worked at software companies large and small, including Oracle and NeXT Computer. After a few years in the tech world, I went back to school for a graduate degree in management. Eventually, I started my own web design firm, which I merged with Shift in 2015.

What part of your work energizes you the most?
Solving problems. It could be overcoming a communications challenge, finding a clear and manageable information architecture, or helping someone find the right process or tool to get around a sticking point.
What are you passionate about outside of work?
I care about our environment and keeping it healthy. We can each contribute, even in small ways, to making things better.
Over the last few years, I’ve been creating a pollinator habitat in my backyard, complete with a natural frog pond, swamp milkweed, and other native plants. I was thrilled this year to find so many Monarch caterpillars munching on the milkweed and to see butterflies using the flowers to build up energy for their migration.
I also keep backyard chickens. They are so interesting and get along fine with the suburban wildlife. They adore scratching around to forage for bugs, and they wait impatiently for me to bring them treats after work. My two are Lady Elaine Fairchicken and Henrietta (you’ll note the Mr. Rogers’ Neighborhood references).




Do you have a creative hobby or side project?
I started woodworking last year. I used to watch The New Yankee Workshop on PBS decades ago and have always been drawn to furniture design.
I’ve made only a few things so far, but gaining confidence with the tools and techniques has had the lovely side benefit of helping with home repairs. I’m working up to adding built-in seating to my living room.
What’s one book or podcast you think everyone should check out?
The Anthropocene Reviewed by John Green, both the book and the podcast. The podcast came first, and the book adds a few topics. They’re short essays about things in our world, each assigned a rating from one to five stars. Thoughtful, funny, and informative.
I give it four and a half stars. (It would have gotten five if there were a sequel to the book.)
Tell us something people might not know about you.
I’m a compulsive optimizer. When I run errands, I plan them like a UPS driver (all right turns, no lefts). I strongly dislike running an errand for a single item and instead aim to make every trip include multiple stops — maximize tasks completed.
I also know how to play blackjack and count cards. Some former housemates were part of a blackjack team and used their winnings to fund their software startup.
And my favorite vegetable is spinach.
The Lightning Round…
Coffee or tea?
Coffee, please
Beach or Mountains
Mountains
Cats or Dogs?
Cats
Salty or Sweet?
Salty
Early Bird or Night Owl?
Night Owl
All the Right Turns
At Shift, we’re all about finding innovative ways to problem-solve. Cynthia brings that mindset to everything she does, from helping clients communicate more clearly to plotting the most efficient route for a post office, Lowe’s, and garden store. (Remember: maximize!) We’re glad she’s part of what makes Shift happen for our team and our clients.



