The Complexity of Simplicity with Jill Winger

This is a salty conversation and it’s also the kind of conversation that cracks you wide open. I sit down with Jill Winger - not to discuss her incredible work with Old-Fashioned on Purpose, her courses, her planner, or her book which are all amazing - but to talk about her life philosophies, our shared hot takes, and to lean into our complexity as humans. We explore the complexities of modern communication, the importance of intentional living, and the challenges of building community in a polarized society. We talk about being reflexive contrarians and sometimes needing to go to an extreme to bounce back to some nuance. We discuss the value of discomfort in personal growth as much as we talk about when and how to choose ease, the balance between generalism and specialization, and the necessity of real human connection in an increasingly digital world. We explore choosing when we need to choose discomfort (often!) but also when we need to choose ease. All around, about holding the tension between modern and old-fashioned ways of living, and just holding the tension between so many paradoxical qualities of ourselves and our lives. 

Find Jill: 

Instagram: @jill.winger

Website

Youtube

2025 Old Fashioned On Purpose Planner

Meal Craft

Old-Fashioned on Purpose: Cultivating a Slower, More Joyful Life

Resources Mentioned: 

Reclaiming Conversation: The Power of Talk in a Digital Age by Sherry Turkle 

Essentialism by Greg McKeown

Molecule of More by Daniel Lieberman, MD and Michael E. Long

10x is Easier Than 2x by Dan Sullivan

Hope for Cynics by Jamil Zaki

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