Using Bold Characters to Find Permission

Aline Brosh McKenna is the brilliant writer behind some of the most iconic films and TV of our time: The Devil Wears Prada, 27 Dresses, Morning Glory and Crazy Ex-Girlfriend. Now, she’s back with The Devil Wears Prada 2.

Before Hollywood, Aline studied literature at Harvard and worked as a freelance magazine writer in New York. She was 38 when everything changed with the release of The Devil Wears Prada - and she’s been creating sharp, funny, deeply relatable stories ever since.

In this episode, we talk about writing for Meryl Streep (no biggie) the acting and magazine career that never happened and what life as an award-winning screenwriter *really* looks like. Plus: the motivating advice every single woman needs to hear.

✨ IN THIS EPISODE:

00:00 Introduction

03:15 27 Dresses and People Pleasing

04:24 Learning Not to Smallify

07:09 Writing Bold Characters

08:11 Devil Wears Prada Two Return

12:35 ‘Failed’ Acting Dreams

17:31 Working With Great Actors

23:20 Writing Meryl’s Big Speech

25:35 Scrappy Creativity Mindset

26:34 ‘Failed’ Magazine Career

29:00 Screenwriting Doors Open

32:07 Comedy Cred And Awards

35:23 Nine Pilots No Series

41:57 Ask For What You Want

💬 QUOTES TO REMEMBER:

I wasn't taught to “smallify” myself by my mother, and that's maybe one of her greatest gifts.

If it becomes necessary to apologise to get what you want, I think that’s okay. As long as you're aware that you're doing it... as a tactic or a strategy.

Learning to withstand and be amused by failure is so key and so critical.

🔗 LINKS + MENTIONS:

Devil Wears Prada 2 is in cinemas now!

Join the How To Fail community: www.howtofail.supportingcast.fm/#content

Elizabeth’s Substack: www.theelizabethday.substack.com

📚 WANT MORE?

Stanley Tucci - A DWP cast member no less! The iconic Nigel…sorry, Stanley came on HTF and talked about dealing with the loss of his late wife, surviving cancer, finding love again and…failing to swim: swap.fm/l/WCW054IGNZnSnTzEXPTN

Dawn French - Another genius comedy writer who talks about heartbreak, humour, adoption and meeting Jennifer Saunders: swap.fm/l/NJDrzxLKhyi6icOrxmHT

💌 LOVE THIS EPISODE?

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Website: www.elizabethday.org

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Elizabeth and Aline answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content

Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com

Production & Post Production Coordinator: Eric Ryan

Engineer: Matias Torres

Assistant Producer: Shania Manderson

Senior Producer: Hannah Talbot

Executive Producer: Alex Lawless

How to Fail is an Elizabeth Day and Sony Music Entertainment Production.

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