The No-Win Design Problem (with Desiree Garcia, Automattic)


January 3, 2020
"I don't think we have figured out how to evaluate people for what might make a good manager or leader — down the line — because we're still looking at: 'Are you shipping?'"


Desiree Garcia is a senior designer at Automattic, the company behind and most recently, Tumblr. Their goal is to democratize publishing so that anyone with a story can tell it, regardless of income, gender, politics, language, or where they live in the world. She's also an editor at A List Apart, a webzine that explores the design, development, and meaning of web content, with a special focus on web standards and best practices.

In this episode, we discuss:

  • How a psychology degree can influence design and teamwork
  • What we miss about the old web
  • Star Trek's Kobayashi Maru and how it applies to design
  • How to respond to situations that can't be won
  • The challenges of talking about your work
  • Designing things that "aren't real"