You Spent Years Acting Normal Inside a Life That Never Fit | Sari Botton

2026-06-22

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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 d...

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 truest part of yourself while staying open to how life keeps changing you

Sari arrived at the conversation we are having right now by surviving the wrong relationships, the wrong careers, and a deep reluctance to let herself want what she actually wanted. If any of that sounds familiar, this conversation is for you.

You can find Sari at: Website | Instagram | Oldster Substack | Episode Transcript

Next week, I am doing a solo episode on something I have been sitting with for a long time: the hidden resentment you are probably carrying right now, and why it might be one of the most honest things about you. If you think you are not carrying any, that is especially worth your time. Be sure to follow Good Life Project wherever you get your podcasts so you do not miss it.

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