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The Roundup: Designing for a future that doesn’t exist yet

What five designers taught us about working at the edge of the known

Eli Woolery's avatar
Eli Woolery
Aug 22, 2026
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Yesterday I went to a design leaders happy hour in SF, hosted by Kai Hailey (who led the Sprint Leadership Academy at Google when I first met her in 2018), and Peter Merholz (co-author of Org Design for Design Orgs).

It was fun to see them, and catch up with a few other folks I know from the design & tech world. One of those people happened to be Nick Foster, former head of design for Google X, who we coincidentally had on the podcast almost exactly a year ago.

Recently Nick had been doing some consulting with companies like Anthropic, and it got me thinking, when the present is changing so quickly, how do you even go about designing for the future?


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None of us know where this is going

The first step in designing for the future is admitting that none of us know where this is all headed. But as designers, it’s a space we can shape, and those who do it best have made peace with not knowing what they’ll find there.

Most of us, as Nick Foster said in his episode, are “comfortable in the world of known problems.” We talk to users, gather insights, iterate on feedback. That loop works when the problem is visible. But what do you do when you’re designing for people who haven’t been born yet, or for technology that won’t arrive for a decade? What do you do when the problem itself is still forming?

Nick Foster: Could, Should, Might, Don't—a new way to think about designing for the future

Aarron Walter and Eli Woolery
·
August 20, 2025
Nick Foster: Could, Should, Might, Don't—a new way to think about designing for the future

Most designers are comfortable in the world of known problems—we talk to users, gather insights, iterate based on feedback. But what happens when you're designing for a future that doesn't exist yet? When you're creating products for people who haven't been born, or technologies that might not emerge for years?

Listen now

That question ran through several of our most provocative conversations this year. One trait kept surfacing in the designers doing the best future-facing work: they’ve learned to be genuinely comfortable not knowing.

Comfort with ambiguity

Nick spent years at Google X on more than 200 moonshots, from flying machines to nuclear fusion. His book, Could, Should, Might, Don’t, argues that most futures thinking collapses into comfortable, predictable patterns that shrink our imagination. He’s blunt about what it takes to resist that:

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