Wintering: A Conversation With Author Katherine May Author of 'Wintering: The Power of Rest and Retreat in Difficult Times'

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Life is made up of seasons. While we would love to live in the metaphorical spring and summer of our lives when everything is beautiful and in full bloom, it is inevitable that as we continue to live and evolve as human beings, we will inevitably encounter autumn and winter when life changes. We might have lost our health, a job, a relationship, a dream or feel like we have lost all ‘control’ and we are forced to surrender and pick up the pieces. The silver lining in those moments is that we can be greeted with clarity and wisdom that we wouldn’t have gained otherwise.

Today I am thrilled to be talking with New York Times best-selling author Katherine May about her timely new book, Wintering: The Power of Rest and Retreat in Difficult Times (Riverhead Books). I had such an uplifting conversation with the UK-based author about her own wintering period and what can be learned universally through those hard moments. We also talked about empathy, resilience and how we can heal.

Landscape Photography and Interview by Alison Engstrom

I love how at the beginning of the book you address a deep-rooted belief that I had for decades, this idea that we are only to live in the metaphorical spring and summer seasons. After years of reflecting, I think that created a lot of suffering.  Yet as you say, the leaves will fall and we can be left to pick up the pieces, life can take a turn with our health, career, relationships, things can end. You say, “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.” 

For me, I have been through that cycle so many times and I know how painful it is. It’s an absolute truth that we should not stop telling stories about wintering. At the same time, those times we lie dormant for a while and when we are pared back to our absolute essentials—that’s often financial, social, or in terms of our health—that’s when everything collapses. There is something about those times, as vile as they are, that you can look back on and always see this spark that happened somewhere within. I think that is connected to hitting rock bottom in a lot of ways. You find your survival instinct in them; you find that thing that propels you forward. You also find the kind of courage to admit to the things that you can no longer do or that no longer serves you. All of those changes that you don’t really want to make can only come when you are broken a bit. Does that ring true for you?



Absolutely. We think this shouldn’t be happening to me and that creates so much resistance to anything we are experiencing in life. That can make it even so much more difficult. It’s not like you play the victim but you think that life should be easy, a mentality that caused despair, depression and anxiety. 

We get that from all sorts of places and can repeat it over and over again. In a way, it sells to say that, it’s almost commercial to say, here’s the solution or here are ten easy steps to get you out of it. The hardest thing to say is, I cannot do anything right now, sorry. I am not useful in the sense that you want me to be. I think it’s almost taboo to say that. 



I am not sure if this is an American perception versus Brit, but I think so often we are told to just be happy but I think being able to accept when life deals you a blow can make it easier, just saying that can make you take a deep breath.

I don’t think we have the same culture of having to be happy but I don’t think we are allowed to acknowledge suffering either. We are supposed to have a stiff upper lip and to not react—definitely not feel sad, definitely not feel hopeless, definitely not drop out—just keep calm and carry on and that’s really harmful to so many of us. It’s horrifically ableist when you start digging into that.



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I think when you don’t address something it just festers and it could even turn into a health issue.

We are accepting stress as normal more than ever; that really bothers me. Our whole culture seems to be pointing us and advising each other how to endure more stress rather than cutting it off at the source. That’s just loads of health problems like yours and mine. 

Author Katherine May; Image Courtesy of Author

Author Katherine May; Image Courtesy of Author




I think 2020 was the year we all had to sit with ourselves and we had to acknowledge if we are unhappy or if something wasn’t working maybe with ourselves, our relationships or our professional life. Your book came into the world when the world really needed it. 

The book came out first in the UK about two weeks before it really hit here. I had a couple of weeks when people were not thinking the book was about the pandemic. It’s a book about my life, in a lot of ways, and it felt very specific to me. When were having early conversations about it, we were thinking how we would clearly need to say why it was relevant to people and I haven’t had to do that work (laughs). I think in truth, I might not have done that work anyway because even before the pandemic, people were saying, you wrote that for me, you wrote about my life. I think we have always underestimated how many people are actually suffering at any given time. 





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The book offers many life lessons learned through observing nature and the creatures who adapt from the honeybees, grasshoppers, and ants to dormouse. Can you talk more about what inspired you to write the book—I know you and your husband had a health set back and your son was having some trouble in school?

It’s funny, I was already planning to write the book before that all happened. My sincere intention was to write about a wintering period looking back on my life from the upland (laughs). It all started hitting when I was writing it, it got in the way of me writing the book, as well. First, I thought this was so inconvenient then I thought, no, I need to write along with this and obviously it became a different book. I think it helped me articulate wintering because I was given a blow by blow account of it. It was an interesting type of wintering because it pushed all of my different buttons. My husband suddenly fell so ill and it brought home this idea, what if I lost him. I had already chosen to leave my job because I knew my stress levels were not sustainable. My health just collapsed before I could even get out of the door. That was like being slapped in the face by a lesson that I was ready to learn already (laughs). Then the issue of my son’s happiness, which is very fundamental, really hit my self-esteem, too. It was a perfect storm, but luckily, nothing terrible as it turned out happened. Maybe that’s hindsight that lets me say that.

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The concept of wintering is beautiful, it’s visual and metaphorical. Can you explain where this ‘aha moment’ came to you and what it means?

It really was an ‘aha moment’; the title was borrowed from Syliva Plath because we studied Ariel in school. That poem has always been an enigma to me; it seems like there is an unraveling happening in it, so I guess that was in the back of my mind. It came to me when I was trying to talk to a friend about her own wintering period—she was talking about her career ending, getting older, how everything was decomposing around her, that she was losing out and she couldn't recover. I turned to her and said, you are just wintering, you are in your darkest period and it will come back. It literally hit me, ah! It works as a word; there is a thing of beauty implied as well, a stillness. I felt like I needed to capture that. 




Going back to nature, I recently moved from New York to an area outside where there are a ton of trees. I once read a stat that said Americans, and Brits too, spend at least 90% of their time indoors. I think we are very disconnected from nature and we can learn a lot of lessons as you talk about in the book. I love how you write, and i am paraphrasing, how things might look dead, but there is life happening around you—maybe not palm trees—you just can’t see it. 

It’s a funny idea that nature is only beautiful when it’s sunny. It’s about appreciating what’s at your doorstep because that is what you got. It’s all very well to dream about that Caribbean island and move there, if that’s what you need, but actually in the meantime, there is always something you can find. I increasingly think there is more to it than that. It’s like having a conversation with your own landscape. There is something about the fluidity of you and nature and that exchange of being when you get to love and trust a landscape. It’s about finding value in that. 

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I think approaching life as different seasons can help you through and surrendering to what is. Each can be beautiful with its own silver lining. I love how you talked about being diagnosed with Aspergers in the February chapter and you said, “I had to adapt. I had to surrender. The only thing breaking me was pretending to be like everyone else.” That gives me the chills.

You know it gives me the chills hearing it back. It’s a simple lesson; that’s the lesson of my entire life and it took me forty years to learn that. I was trying to live someone else’s life and it hurt me. All I needed to do was live my life. It’s of equal value; it’s not of lesser life, it’s just different. The problem for girls like me is that we didn’t get given a pattern on which to live because it wasn’t available for us. I don’t think people realize the profundity of that. If you are not taught how to live, you make it up for yourselves. If you get it wrong, you are harming yourself. I had to learn how to listen and that was tough, too. 




You talk about embracing uncertainty and that unhappiness is not always being a bad thing and that it indicates that something isn’t right.

Yes, it’s instructive. All of these dark emotions that we feel are really instructive and yet we are taught to flinch away from them, so we don’t learn simple lessons to help us see what is going wrong. How did we get there? 



I think some of the clarity I have received in life has been through those darker moments. 

Yes, those moments when you cut through the fog of depression and you have those sharp moments of clarity. They are like guides, aren’t they? 


One of the things you have said is that readers have responded with this idea that you have given them permission to share their own wintering stories. 

When I wrote the proposal for the book, I wanted to put words into people’s mouths for them to use the next time this happened to them. It’s really fantastic to see that happening. People write me letters saying they are wintering at the moment or that they have just come out of a wintering period. I just think yes! (laughs). There is a toolkit that we don’t have and that we deserve to have. We think we are doing everyone a favor by making that forbidden knowledge and like all forbidden knowledge it is toxic. When you can just open up a conversation that says to me, hey, this is the stuff I have been through, I get it. We immediately make a connection. I don’t know your life but I have a taste of what you have been through and that matters to me and I can express authentic care to you immediately. To me, that is a wonderful thing. 

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I feel like there are so many layers to the book. What do you hope that readers walk away when they finish the book?

I hope it’s about compassion for other people as well as self-compassion, which is so important. But also the next time we come across someone who is suffering, something that we haven’t suffered, we don’t reach for those terrible assumptions that they have got it wrong. I can remember hearing that from my youngest years when you would see someone in trouble. I hope we can learn and acknowledge that wintering is an inevitable thing that will happen to all of us and that we can see other people’s suffering with much more compassion. Acknowledge it for what it is, suffering. It’s not our business to judge it. We are all human and we all screw up anyway (laughs). 





Empathy is something that can go a really long way.

A massive way and it’s tiny. It doesn’t cost any money. I think there is some type of fear that if we empathize with someone we have to pay for them somehow. I think that empathy is a tiny gesture that makes huge waves for people; it’s transformative. 

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Wintering is also about exploring the resiliency of ourselves, something you said about swimming in the ice-cold ocean and said, “By doing a resilient thing, we felt more resilient.”

That’s so circular and you have to break into that circle in the first place to get it. There is a pain barrier that you break when you enter into ice-cold water. It still makes me fearful. You come out and you think, I just did this thing and I have crossed this crazy boundary. This has been a year when there has been very little opportunity for very exuberant expressions of joy and excitement.


I think our society does a disservice by the busy syndrome and that rest isn’t something that should be respected. Personally, I have a certain sense of guilt inside of me when I rest that I am trying to work on.

Resting is part of your work as a human being. I am the same, being autistic, if I don’t take time out, I go into complete collapse and the level of exhaustion I get is not normal compared to the general population. I think everyone needs that trigger point that says, stop, this is enough. Again, this is a recent idea that we never, ever, ever rest. It’s not historical. We used to run out of things to do and now we never run out of things to do because we have the internet and it tells us more things to do (laughs). 


There is a whole culture of self-help people  who advocate: Do more! Motivate! Get it done! I used to subscribe to that until I realized, no, this is hurting me. 

I think about this a lot, I read a few books a couple of years ago on why we should cut off social media and all of them were about how it would make you more productive. I had to think about that, okay, I spend far too much time on Twitter and I realized that’s because I go on there to be aimless. That’s when I realized that I should stay on social media because, for me, it gives me social contact when I am too exhausted for other social contact. It connects me with other people who have a similar background to me. I am not being productive when I am on Twitter and that is awesome! (laughs).



They always say that every generation does better than the ones before. I really loved how you talked about teaching our children that wintering is a skill to be learned and to approach their obstacles with a sense of gentleness not pushing them. Something you helped your son with as he was facing his own obstacles as a young child. What would you say that advice looks like? 

It’s about genuinely listening to them and taking what they tell you at face value. You will be surprised when children tell you they are tired. They have often signaled well before then that they were or that they were upset. It’s really hard to listen to children for some reason. Children are actually really good at self-regulating, if you allow them to do that. You are trusting them with their ability to self-regulate but we don’t. We constantly push them into things and we force them to do loads of activities that we think are actually improving them. We tell them from a young age that they will need this to get into college or whatever the stage is in your mind. You can listen when they are telling you that they are sad or afraid and you stop problem-solving with them. I am not the most perfect parent to give out parenting advice but on a basic level that was what I was trying to do for him. He regained his trust in me when I started to listen and engage in what he was telling me. He’s back at school happily. That’s important for me too, it wasn’t a one-way journey. 



Would you say the antidote for wintering is self-love?

I think it’s three things, the first is watching for it coming and performing rest and retreat before it has to force you because you will be forced into it, if you don’t voluntarily do it. You can catch it early and soften the blow if you can listen, which is very hard. The second is to surrender; you cannot bypass winter, you cannot make it go faster. The third is genuinely finding self-compassion and not the kind of self-compassion that comes in a Facebook meme, like I love myself, I am perfect, which to me isn’t self-compassion at all, it doesn’t acknowledge the truth of yourself. You have to see the dirty bits of yourself, that is where compassion lies. Compassion is an act of humility; I am no better than anyone else. I love myself anyway.  



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