324: Design Despair

How Overcast has managed feedback channels and its presence on social networks, and the results (so far) of creating an official Reddit community.

Successes and struggles with taking breaks from work.

As David celebrates five years of Widgetsmith, we discuss choices we make to keep our businesses scalable without giving up the working styles we prefer.

With our iOS 26 updates submitted, we reflect on the summer, customer reactions to the redesigns, and what we're looking forward to doing next.

Laying groundwork for future analytics, insights, and utility needs.

A pragmatic and productive path through the final weeks of the iOS 26 beta season.

Fighting through the motivational challenges and choosing a direction when the system design isn't an easy, universal win.

Should we adopt Liquid Glass or stick with our existing designs? And if we do adopt it, how much should we redesign and rethink along the way? (tl;dr: yes; much.)

Tradeoffs for requiring iOS 26 this fall, and a clever strategy to manage compatibility with iOS 18.

Initial impressions of WWDC 2025 and what we're going to be doing this summer.