
Sari Botton shares her journey of midlife reinvention and the challenges of living authentically.
Gotta love a good midlife reinvention story, and today we’ve got a great one! Sari Botton built her career editing some of the most celebrated voices in American literary nonfiction. Then, in her mid-50s, she watched doors close in her face, turned down for jobs she was overqualified for, told by interviewers in their 30s that she had "done enough." Out of that experience, she launched Oldster Magazine on Substack, a publication dedicated to aging honestly, at every age. It became a global phenomenon, and led to a book deal. She turned 60 and called it the best moment of her career. In this conversation, Jonathan and Sari explore: Why the most painful thing about midlife is not getting older but realizing how long you spent performing a version of yourself that never quite fit What it costs to live at the intersection of "should" and "whatever," and what becomes possible when you stop The Gen X inheritance: latchkey-kid freedom, zero parenting bandwidth, and a generation that had to figure out what normal even meant Why the best memoir illuminates the mundane, and why women claiming that territory is a quietly radical act What it means to be "found-ish": knowing the…
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