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Off Brand

An Apple iOS feature proves that sometimes even the most well-intentioned nudge could use a rethink

We all appreciate a friendly nudge, don’t we? That’s probably what Apple figured when it introduced a feature in iOS 13 that nudged users to adjust their privacy settings.

Since lots of us claim to be concerned about how technology spies on us and thwarts our privacy, and the privacy settings for apps can be difficult to navigate and keep track of, Apple’s nudge — a pop-up message inviting users to adjust settings on certain apps — seems like a helpful design solution to a genuine problem. …

Off Brand

Instead of intentionally hiding the ‘unsubscribe’ button, let customers leave gracefully. They might just come back.

No one loves a quitter. I don’t (just) mean that in the sense of a high school coach shaming anyone who walks away from the team. I’m referring to the moment a consumer quits a subscription-based business or service — one of the hottest business models of the moment, from giants like Spotify to box-merchant startups like Stitch Fix, to yes, us (as in, Medium).

Such enterprises, particularly newer ones, naturally focus on signups, easy onboarding, and racking up impressive numbers of new customers on a monthly or quarterly basis.

To the extent such companies think about offboarding, the strategy…

Create strong culture, stay laser-focused on problems, and set wildly ambitious goals

In 2012, shortly after Airbnb acquired our startup, I overheard co-founder Joe Gebbia giving guidance to a designer tasked with redesigning the homepage. He said, “Build something the internet has never seen before.” I vividly remember thinking, What does that even mean? And is this the bar for everything around here? Looking back, I’ve come to recognize that this mindset has been one of the key ingredients in Airbnb’s historic growth.

I first joined Airbnb as an engineer, then became one of the first members of the budding PM team. Back then, there were a couple dozen engineers, a few…

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