Episode 13: Radical Generosity with Maggie Gentry


Today’s episode is with Maggie Gentry, founder of Own Your Why. She is a thought partner and business coach that helps creatives who are deeply craving support and space to make the pivotal transitions that will sustain their soul work. Her journey from a marketing background to owning her own business is really interesting, and she tells us about the spiritual shifts she’s made toward trusting her intuition and going through an intensive meditation training. The most exciting change that Maggie has made in her work has been turning her Own Your Why community into a pay-what-you-can offering, and how that embracing radical generosity has affected her. Her generous spirit really radiates through in this wonderful conversation!



  • How traditional goal setting can be too arbitrary to allow us to adjust to new information

  • What it’s been like to crave structure yet wanting to rebel against it in favor of flexibility

  • Busy-ness as consumption, and how digital consumption can parallel the consumption of food

  • The difficulties of uncertainty in business, which contrasts with how we often see it portrayed

  • Establishing boundaries between life and work

  • Our complicated relationships with money as business owners, supplementary income, and stress tolerance

  • Trying out taking a full time job and how that didn’t align

  • How the Being Boss podcast connected all 3 of us, and the origin story of this podcast

  • Maggie’s long and leisurely morning routine - slow mornings are her most important self care

  • Meditation training and noble silence

  • Maggie’s self-care must haves - self-care that doesn’t just “check the box”

  • Maggie’s astrological chart and how it relates to her business, communication, and more

  • How the philosophy behind Simon Sinek’s Own Your Why inspired Maggie to try a totally  new pricing model - pay as you’re able

  • Radical generosity

  • The importance of trust (Maggie’s word for 2018) and inner work in her life lately

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Rebecca Hass

Pianist and composer