The Gen X Comeback in the 3rd Chapter of Life (Issue 659)

The Gen X Comeback in the 3rd Chapter of Life (Issue 659)

December 10, 2025 · 59 min

About this episode

Larry Cornett and Jonathan Small discuss the challenges and reinventions faced by Generation X in their careers and identities.

Thank you to everyone who tuned in live today! In this livestream conversation, I sat down with Substack writer and podcaster Jonathan Small to talk about what it really means to navigate work, identity, reinvention, and retirement as members of Generation X . Jon and I traveled different career paths. He moved from magazine publishing to digital media, podcasting, and entrepreneurship. Check out his current Substack publication, Small Talk . I shifted from a big-tech career (e.g., Apple, IBM, eBay, Yahoo) into independent coaching as a solopreneur. But we’ve both lived through the same constant pattern: industries rise, industries fall, and Gen X is constantly forced to reinvent itself. We talked about how traditional career expectations failed our generation. The idea of a stable, decades-long job with a pension evaporated. Entire fields collapsed (e.g., print magazines, early tech companies), and many people clung to the past too long, only to find themselves shut out of the future. What has kept the survivors afloat is adaptability . As I shared in the conversation, I’ve learned to watch the “ canaries in the coal mine ” and pivot before a company or industry fails. Jon had…

People in this episode

Host: Larry Cornett

Guest: Jonathan Small

Topics covered

Keywords

Mentioned in this episode

Organizations: Substack, Apple, IBM, eBay, Yahoo

Books & works: Small Talk

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