Paper Napkin Wisdom · Leadership & Entrepreneurship Insights for Founders and Executives · 2026-09-06 · 16 min
There are six years of my life that I have occasionally looked at as missing. Around 2018 and 2019, things at home changed. My family needed more of me than I had been giving, and not in some abstract work-life-balance sense. They needed my attention. They needed my presence. They needed me to be there in a way that made continuing to push at the same pace impossible. So I stepped back. At the time, Paper Napkin Wisdom was doing extremely well. The podcast was frequently appearing in top charts around the world. The audience was growing, the conversations were growing, and there was real momentum around what I was building. Then I stopped pressing on the accelerator. Over the next six years, a lot happened in podcasting. The medium exploded. People whose shows had been behind mine went on to become some of the biggest names in the industry. Entire businesses and media companies were built around podcasts in ways that were difficult to imagine when many of us started. Every once in a while, I would look at one of those people and wonder. Where would I be if I had never stepped away? The Strange Mathematics of Regret The mind is very good at creating an alternate version of history.
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