Christopher Cashdollar

Design Leader & Strategist / UX and UI Designer

Writing & Speaking

Most Recent Writing
Where I Am Supposed To Be

Where I Am Supposed To Be—The Parenting vs Entrepreneurship Struggle

“A glance at the sticky note that compiles my to-do list for the day elicits an audible sigh that feels like defeat. Too many tasks now have to be bumped to tomorrow.”

Most Recent Speaking
DesignBrew Philadelphia

Design Thinking

Adopting a Design Thinking methodology is critical to modern product design. Or so you’ve been told. Yet, a Design Thinking process doesn’t guarantee a transformation of your design culture, nor does it mean you’ll end up with a better product.

All Articles & Essays:
All Speaking Engagements:


DesignEdu Today

DesignEdu Today, Episode 59: The Differences Between Agency and Freelance Life and Design Fundamentals (2018)

“In this episode Chris Cashdollar, Principal of Cashdollar Design, joins Gary Rozanc to discuss a wide array of topics. The conversation starts off with a discussion on ways to better prepare students for careers as freelance designers such as working with popular CMS templates, the ubiquitous need for writing skills to persuasively promote your work, and the need for internships to augment classroom learning.”

Designers Drink Podcast

Designers Drink Podcast (2016)

“Even though he’s been VP of Design at Happy Cog and done work for Ben & Jerry’s, Harvard, Viacom, the United States Holocaust Memorial Museum and, this guy is down-to-earth. Chris and I talked for almost three hours, so I’m releasing this in two parts. In Part One, we make martinis and talk about the downfalls of responsive design, core values and how to create values for our own companies, and the best way to kickoff projects.”

HOW Magazine “Designing to Remember: USHMM Website Redesign” (2014)

“Chris Cashdollar has many claims to designer fame. He’s worked on high profile brands such as Ford Motor Company, Verizon, Zappos and more. Among all of his success, his most recent project has proven especially meaningful.”

The Shakes

The Shakes, Episode 46: Veep (2014)

“Do two letters in front of your job title change that much about you? Happy Cog’s VP of Design, Chris Cashdollar, discusses that transition from working creative director to VP and what, if anything, changes. Chris also educates the gang on the Ramen Rennaisance, puts his two cents in on what happens when meetings go horribly wrong and steals Joy’s heart somewhere along the way.”

The Big Web Show

The Big Web Show, Episode 69 (2012)

“In Episode No. 69 of The Big Web Show, Happy Cog creative director Chris Cashdollar (@ccashdollar) and Jeffrey Zeldman (@zeldman) discuss the joys and challenges of redesigning typography mega-site; nimble versus waterfall; process versus inspiration; running a creative department that is interactive in every sense of the word; the two sides of a design education (learning and teaching); fostering collaboration; and the transition from doodling eight-year-old to graphic design student to interactive creative director.”

© 2021 Christopher Cashdollar

Yes, Cashdollar is my real name.