Kate Billing

Wintering: The Power of Rest and Retreat in Difficult Times

"Life meanders like a path through the woods. We have seasons when we flourish and seasons when the leaves fall from us, revealing our bare bones. Given time, they grow again."

As with all things in nature, our human experience has a seasonality to it.

This is something that always comes up in conversation with the women I work with: the seasons of nature and how our human experience is shaped by them, and the seasons of our lives and their impact on our leadership.

Unlike the seasons in nature that, depending on the hemisphere, we all experience at the same time, the seasons of life come to each of us at different times for different reasons.

Right now, I am in a period of wintering. Not just because it’s actually winter here in New Zealand, but in the existential sense as well thanks to a combination of experiences that can be summed up as hitting The Midlife Turning Point.

In her book ‘Wintering:The Power of Rest and Retreat in Difficult Times’, author Katherine May describes the human experience of wintering as follows:

“Wintering is a season in the cold. It is a fallow period in life when you are cut off from the world. Perhaps it results from illness or a life event such as a bereavement or the birth of a child; perhaps it comes from a humiliation or failure. Perhaps you’re in a period of transition and have temporarily fallen between two worlds. Some winterings creep upon us more slowly, accompanying the protracted death of a relationship, the gradual ratcheting up of caring responsibilities as our parents age, the drip-drip-drip of lost confidence. Some are appallingly sudden, like discovering one day that your skills are considered obsolete, the company you work for has gone bankrupt, or your partner is in love with someone new. However it arrives, wintering is usually involuntary, lonely, and deeply painful.”

Anyone in The Midlife Turning Point with me may recognise themselves in the lines above. My current wintering has been building steadily over the past few years. It started with the first whispers of peri-menopause (not that I knew that’s what it was at the time!), then through the whole COVID schmozzle, and on to deep grief for the loss of a loved family member and much of the business my husband and I had worked so hard for.

The sense of ‘falling between two worlds’ that May describes is something especially meaningful within the midlife winter. Its an experience I share with many other Gen Xers who feel ‘no longer young but not yet old’ and on the precipice of a whole new second life in our 50’s and beyond. We’re not who we were, but not yet who we will become, and we’re feeling more than a little lost in the long grass as we try to find our way.

At this point you may be thinking “Bloody hell, Kate! This is all sounding a bit doom and gloomy…” – and you know what, it would be if I didn’t know about wintering and the natural inevitability of it. 

We’re so used to living a life largely without seasons: walking into the supermarket and buying the same food all year round, living in air-conditioned comfort, following the same daily routines all year round supported by technology and artificial light. And these attempts to avoid seasonal change extend into our existential seasons too. We’re encouraged to go around behaving like life is in a state of spring or summer all the time: pursuing happiness, putting on a smile, staying young, keeping up appearances, and never letting others know you’re suffering.

In her book May offers us this “If we don’t allow ourselves the fundamental honesty of our own sadness, then we miss a cue to adapt. We seem to be living in an age when we’re bombarded with entreaties to be happy, but we’re suffering from an avalanche of depression. We’re urged to stop sweating the small stuff, yet we’re chronically anxious. I often wonder if these are just normal feelings that become monstrous when they’re denied.”

If we have seasons as a lens through which to view our lived experience, we can watch for them, prepare for them, and embrace them when they arrive, for all that they offer rather than deny or attempt to escape them.

Here are FOUR practices I’m using to help create the capacity I need to make most the most of this particular winter, the division of the year and my midlife experience:

  1. CREATE SPACE: I’m retreating from the world a little – deliberately doing less, saying no to more, turning off technology, turning off the lights, and making my needs for rest and reflection a priority. This creates the capacity to process all that winter offers, including its role as a time of transformation and preparation for new growth.
  2. DIVE IN: I’m diving headlong into grief for everyone one and everything (including aspects of myself) that are being left behind, giving myself permission and time to experience ALL OF IT rather than resist or try to move through the experience too quickly in an effort to leave the pain and sadness behind and get on with life. I’ve learned the hard way, that doesn’t work.
  3. SLEEP MORE: I’m adjusting my sleep/wake rhythms, heading to bed earlier and allowing myself to sleep until I wake up without an alarm. Part of the natural seasonal shifts in our circadian cycles, driven by changes in bright light and length of day, is that we need to sleep more in the winter so I’m rolling with it.
  4. EMBRACE SILENCE: There is a stillness, a glorious quiet, a silence that whispers beautiful questions in winter – especially in the mornings. I’m embracing it with silent walks to let my mind wander as dawn breaks and stars still fill the sky. I’m sitting on the couch with a hot cup of tea, journal in hand, looking out at the lake as the sun slowly rises and quiet amazement fills my heart about the healing and regenerative power of winter.


We live in a time when it seems that acknowledging winter and allowing yourself to experience it as an act of self-care, growth and healing is a radical act! All too often we think it would be selfish to do the things I’ve outlined above. That we must put others’ needs before our own.

But our lives are cyclical, not linear. Better that we see them for what they are, prepare for the seasons that will inevitably come, embrace winter when it arrives, in midlife or any other time, and use it as the crucible for change that it is: creating the conditions for the spring and summer that always follow.


Be safe and well.

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