DiscoverThe Generalist AdvantageE39: Breaking Social Norms with Samantha Stilwell.
E39: Breaking Social Norms with Samantha Stilwell.

E39: Breaking Social Norms with Samantha Stilwell.

Update: 2025-07-31
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Why Listen: 
You’re craving work that aligns with your values.

Episode Description: 

Samantha Stilwell is a cultural anthropologist, consultant, flight attendant, and community builder—sometimes all at once. In this wide-ranging conversation, she opens up about discovering the concept of a “portfolio career” and how it validated the winding, multi-threaded path she’s chosen. We explore what it means to live intentionally without conforming to social norms, how to choose projects that align with a deeper mission, and why success doesn’t always look like scale. Whether she's decoding workplace dynamics in Kenya, building community with women founders, or flying across northern Quebec, Samantha shares how generalists can find purpose by following their own internal compass. 

Key Highlights:  

  • Portfolio Career: Samantha shares her discovery of the term and how it reframed her diverse experiences with intention and pride. 
  • Redefining Success: She describes how success has shifted from titles and outcomes to living fully and building human connection. 
  • Breaking Social Norms: From wedding planning to work structure, Samantha challenges expectations in favor of alignment and sustainability. 
  • Slow-Build Projects: She explains how to embrace longer timelines and lower visibility in order to maintain high quality and joy. 
  • Power of Small Moments: The episode emphasizes that micro-interactions, not just grand milestones, are where generalists often shine. 


About Samantha: 

Samantha Stilwell  is a cultural anthropologist by profession—meaning she’s a story-listener and a story-sharer. But the one story she’s still writing is her own career path. Flight attendant, consultant, keynote speaker, community builder, author—Samantha wears many hats (sometimes all at once), but her throughline is always the same: a deep curiosity about people and the cultures we create. Whether she's 35,000 feet in the air or speaking on a global stage, she brings an anthropologist’s lens to everything she does—helping others understand themselves, each other, and the world a little better. 

  Find Samantha 


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    E39: Breaking Social Norms with Samantha Stilwell.

    E39: Breaking Social Norms with Samantha Stilwell.

    Julie Lavergne