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TLP486: Unruly: Deconstruct the Rules, Defy the Norms, and Define Your Success

The Leadership Podcast

Release Date: 11/19/2025

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Lauren Wittenberg Weiner is a speaker, business therapist, and bestselling author of Unruly: Deconstruct the Rules, Defy the Norms, and Define Your Success.

In this episode, Lauren shares the pivotal moment that crystallized her unruly philosophy. When told she couldn't do something, she learned to transform that doubt into motivation rather than letting it paralyze her. She explains how reframing negative feedback as challenge fuel drives her leadership. 

Lauren explains the difference between gatekeepers who clone themselves and gateways who open doors. She tackles the transactional trap and why building an unconditionally supportive village matters more than networking scores. 

Lauren discusses managing multiple demanding roles through ruthless curation of priorities. She emphasizes that priorities must be constantly reassessed as circumstances change.

Listen to this episode to learn how breaking free from conventional expectations can lead to more authentic success and fulfillment in both leadership and life.

 

You can find episode 486 on YouTube, or wherever you get your podcasts!

Watch this Episode on YouTube | Lauren Wittenberg Weiner on Unruly: Deconstruct the Rules, Defy the Norms, and Define Your Success

 

https://bit.ly/TLP-486

 

Key Takeaways

[02:36] Lauren reveals she almost joined the circus as a dancer between college and graduate school after a friend who was a trapeze artist convinced her.

[04:09] Lauren explains the philosophy of "unruly" crystallized over many years, starting when she was a "good girl" who did everything expected of her.

[09:12] Lauren discusses her "prove me wrong" attitude, explaining she reframes negative feedback as a challenge rather than trying to forget it, using research about not thinking about a white bear.

[13:09] Lauren outlines her three-step framework: know the rules, find the space between them, and change them when needed.

[15:42] Lauren clarifies she's "not a big believer in breaking the rules" but rather in knowing what rules say, finding space within them, and changing them consciously and thoughtfully when they don't work.

[22:16] Lauren describes the shift from leaders being "gatekeepers" who pick people who look and think like them to being "gateways" that allow different people to prove they're qualified.

[25:28] Lauren discusses transactional versus non-transactional relationships, and emphasizes the importance of having an "unconditionally supportive village" of people who pick you up when you're down and cheer for you unconditionally when you succeed.

[29:23] Lauren explains how redefining luck as preparation influenced their breakthrough when winning a $200 million SOCOM contract, saying "we didn't get lucky, we were prepared."

[33:48] Lauren discusses "ruthless curation" of priorities as an iterative process, using the example of her kids being a priority but their spirit week costumes not being her priority.

[37:54] Lauren advises her 35-year-old self to "stop worrying about what anyone else thinks, figure out what you want" and own your decisions without feeling guilty.

[40:25] And remember…“Never assume you can't do something. Push yourself to redefine the boundaries.” - Brian Chesky

 

Quotable Quotes

"Just because you can do something doesn't mean you have to." 

"You can't hack your own psychology. You can't stop doing what your brain is going to make you do, but you can move around it and understand it and use it to your own advantage."

"It's not about bringing people in that aren't qualified. It's about allowing people to show that they're qualified, even if they don't look or think or have gone on the exact same trajectory that everyone who came before did."

"Transactional begets transactional and non transactional begets non transactional."

"You've gotta have the same people who will pick you up when you're down and who will cheer for you unconditionally when you make it."

"Stop worrying about what anyone else thinks, figure out what you want."

"Nobody else gets to define for you what makes sense for you, but then own your decisions."

 

These are the books mentioned in this episode

Resources Mentioned