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April 3, 2025 42 mins

AMY WILSON is a writer, podcaster, and performer. She is the author of the memoir When Did I Get Like This? and her latest book Happy to Help. Amy is also the co-host of the Webby-honored parenting podcast What Fresh Hell: Laughing in the Face of Motherhood. She and co-host Margaret Ables have racked up over 11 million lifetime downloads and 800 episodes since the podcast's launch in 2016, and regularly perform live shows for audiences around the country.

As an actor, Amy appeared on Broadway as "Sunny Freitag" in the Tony Award-winning play The Last Night of Ballyhoo. She was a series regular on the sitcoms Norm (ABC) and Daddio (NBC). Other TV guest appearances include Veep, Felicity, Blue Bloods, Unforgettable, Ed, Law and Order: CI, and Deadline. She wrote and performed sketch comedy for NBC's Live on Tape, which filed in Saturday Night Live's famed Studio 8H. Amy is also the creator of Mother Load, a one-woman show which she toured to 16 cities after its hit off-Broadway run. Amy's writing has also appeared in The New York Times, Redbook, CNN.com, NPR Books, Parenting, Parents, Baby Talk and Big Apple Parent. Amy graduated from Yale University with a dual degree in English and Theater Studies. She lives with her family in New York City.

In this episode:

  • The way Estelle and Amy first connected through Listen to Your Mother [1:32]

  • How Amy’s book Happy to Help: Adventures of a People Pleaser manifested [6:43]

  • The formative experience in Catholic school that shaped Amy’s overachiever mindset [9:19]

  • The way Amy used adage to structure her book, and how that happened [10:57]

  • Why Amy included research in her essays and how she seamlessly weaved it into narrative [13:33]

  • The real reason many women take on too much, and why that’s not a personal flaw [17:03]

  • How perfectionism and people-pleasing show up differently at home vs. in the workplace [24:46]

  • Her creative process, perfectionism, and letting go of “doing it all” [31:55]

  • The early impact of magazines on Amy — and women [33:10]

  • Advice for women feeling overwhelmed: It’s not you—it’s the system. [38:07]

  • Sitting in the silence of not knowing [39:54]



Connect with Amy Wilson:

 

Website: https://amywilson.com

 

Podcast https://whatfreshhellpodcast.com

 

TikTok https://tiktok.com/@amywilsonauthor 

 

Buy Happy to Help on Estelle’s Bookshop: https://bookshop.org/p/books/happy-to-help-adventures-of-a-people-pleaser-amy-wilson/cd2aa83f8af88dfc?ean=9781958506783&next=t&aid=98827&listref=authors-who-have-appeared-on-freelance-writing-direct

Estelle’s Listen to Your Mother episode (Amy

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