Guest: Katherine May

[ENCORE] The Sacred Yes to Rest: Katherine May on Retreat, Beauty, and the Healing We Can’t Rush

Three years ago, Katherine May gave us a language for something many of us experience but rarely know how to name: wintering.

Those seasons of life when everything slows down. When grief arrives. When burnout catches up with us. When illness, loss, caregiving, parenting challenges, or unexpected change force us to stop and reconsider how we’re living.

As part of our Sacred Yes: Reclaiming Joy in Midlife series, we’re revisiting this unforgettable conversation because Katherine’s wisdom feels even more relevant today than it did when it first aired.

Together, Jen and Katherine explore what it means to stop treating ourselves like machines and start honoring our humanity. They discuss the value of retreat, the necessity of rest, and why healing cannot be rushed. Katherine challenges the cultural pressure to push through difficult seasons and instead invites us to trust that growth is still happening beneath the surface—even when life appears dormant.

Nestled in this conversation is a gentle reminder that joy isn’t always found by adding more. Sometimes it emerges when we create space. Space for solitude. Space for beauty. Space to notice what’s growing quietly within us.

If you’ve been feeling weary, stretched thin, or ready to step off the hamster wheel for a moment, this episode offers a different path forward—one marked by grace, patience, and the courage to rest before collapse forces it upon us.

In this very gentle and generous conversation, you’ll hear:

  • Why every life includes seasons of “wintering”
  • The difference between retreat and isolation
  • How beauty sustains us during difficult seasons
  • Why sadness isn’t something to fix
  • Practical ways to create restorative space in everyday life
  • What it means to trust the season you’re in

Sometimes the most sacred yes isn’t a leap forward. It’s permission to pause.

The Power of Rest & Retreat in Difficult Times: Katherine May

We’re at the tail end of our For the Love of Calming the Chaos series–and if you’ve gotten a chance to hear the whole series, we hope you’ve been able to take away some actionable items toward further peace in your life. Our last episode in the series is the perfect capper toward extending that ability to calm the chaos during the disruptive times of our lives, but also during the heartbreakingly difficult times. Our guest this week brings us the very comforting message that simply bucking up or trying to cheerlead ourselves into positivity isn’t going to cut it. She gives us permission to actively accept our sadness, and then some tools for how to process it and move it from chaos to a place of peace. Katherine May is an international best-selling author, including the books Enchantment Awakening Wonder in An Anxious Age and Wintering: The Power of Rest and Retreat in Difficult Times. Katherine is going to walk us through not only her own story of a hard winter season she endured, and what she learned, but she’ll show us how we can be gentle with ourselves and believe that we deserve peace, no matter the circumstances. 

Jen and Katherine talk about:

  • When those winter seasons come, just when you think you can’t or will never be happy again and the dark pit feels too overwhelming; that’s typically when the winter begins to cease and recovery begins
  • Giving yourself grace to believe you haven’t done anything wrong if you’re still suffering a week, a month or even six months later – the process of unlearning your old ways of life and relearning new ones can be painful and lengthy
  • Not all the lessons we learn come from happiness, they come from sorrow, and how to accept that 

Chaos doesn’t just emanate from choices that we’ve made or that we’ve onboarded too many things, but sometimes when tragedy or heartache has found its way to our doorstep. Allowing ourselves to rest and retreat at these times is a gift we can all give ourselves.