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Pickle Me This

October 12, 2022

“Learning and Growing Through Our Entire Lives”: A Conversation with Ann Douglas

In 2013, when the anthology The M Word: Conversations About Motherhood was published, I was so thrilled to receive a blurb from parenting writer Ann Douglas, and so it felt like things had come full circle when I was able to provide an endorsement for her latest book, Navigating the Messy Middle, a book that marks a shift in Douglas’s own professional journey. “The best thing about Ann Douglas’s perspective, as always,” I wrote, “is her understanding that one-size-fits-all advice fits no one. Instead, in Navigating the Messy Middle, readers will discover an empowering guide to finding one’s own way through the ups and downs of midlife, a time when seeking strength in connection, embracing the changeability of the physical self, and focusing on one’s real values and priorities can create a powerful moment of (finally!) becoming.”

Thank you to Ann Douglas for agreeing to answer some of my questions about her book, which I enjoyed so much, and which you can pick up right now from your favourite bookseller.

What more can we ask of ourselves but that we remain open to the opportunity to learn and grow as humans, both individually and together?

Ann Douglas

Kerry: This book was born out of a midlife shift for you after years of writing about parenting. How did it feel to make this pivot (scary? exciting?), how did you decide on where to land, and in what ways did your experience tie into themes and ideas explored in the book?

Ann Douglas: I had been feeling, for the past couple of years, that I was aging out of the parenting books category. (It’s hard not to feel this way when your youngest child is 25!) Now don’t get me wrong. I will always care passionately about parents and kids, and I will continue to advocate on issues affecting them. But in terms of being immersed in the really hands-on years of parenting? I am well past that stage, and so it seems like the right time to pass the baton to the up-and-coming generation of parenting writers. And there are a lot of them doing really amazing work.

In terms of deciding what would come next for me as a writer and a person, that was more exciting than scary. I’ve always been the kind of person who has a million ideas for creative projects, so it was simply a matter of seizing the opportunity to write about something else. In terms of landing on which “something else” that might be, there was a bit of serendipity involved. I’d had a rollercoaster ride of a journey through midlife, so midlife growth development was very much top of mind for me. And then, out of the blue, I received an email from my literary agent, telling me that she was dying to talk to me because she knew what my next book needed to be about. She needed a book about midlife and she needed that book to be written by me! We started brainstorming the possibilities and developing a book proposal. That casual conversation (in September 2019) resulted in a book deal (in February 2020, right as we were heading into the pandemic).

I guess the common thread in terms of my career as an author is my life-long fascination with human development: how we continue to learn and grow throughout our entire lives. Midlife has been a deeply challenging time for me, but also an opportunity for tremendous learning and growth. In fact, I can honestly say that it has been my favourite life stage so far.

I guess the common thread in terms of my career as an author is my life-long fascination with human development: how we continue to learn and grow throughout our entire lives.

Ann Douglas

I wanted to capture that sense of possibility in this book, while also endeavouring to keep it real. Because no one wants to read a faux positive guide to anything in 2022—not after everything we’ve been through over the past two-and-a-half-years. That’s what I tried to do in this book: to be both “fiercely honest and wildly encouraging,” as the subtitle of Navigating The Messy Middle indicates.

Kerry: Fercely honest AND wildly encouraging? IN THIS ECONOMY, ANN??? How is that possible? 

Ann: If there’s one thing I’ve figured out at this point in my life it’s that you don’t have to settle for a single emotion. It’s possible to feel anxious, hopeful, discouraged, grateful, and frustrated all at the same time. Heaven knows I feel all those things simultaneously myself—and I do so on a regular basis.

So honest and encouraging? It’s definitely possible to have both those things at the same time. In fact, I feel like I’ve been focused on those two experiences for my entire career as an author: trying to write with honesty while at the same time offering encouragement. (Over the years, countless readers have told me that they really trust me and I think that’s why: that blend of honesty and encouragement.)

If there’s one thing I’ve figured out at this point in my life it’s that you don’t have to settle for a single emotion. It’s possible to feel anxious, hopeful, discouraged, grateful, and frustrated all at the same time.

Ann Douglas

Kerry: As the shape of the book emerged, what parts surprised you the most? 

Ann: This book ended up being much more political than the book I had intended to write—and that my book publisher had intended to acquire. As I note in the opening pages of my book, “My agent negotiated the deal for this book in February 2020, just as the pandemic was beginning to be felt here in North America. The days and months that followed ended up changing everything, including me. I found myself launched into an eighteen-month journey into rethinking pretty much everything about my life. And judging by the depth of the conversations I was having with other women, I know I’m not the only one who was profoundly affected by this multi-layered experience of pause—the pandemic pause layered on top of the self-reflective pause that is so characteristic of midlife.” So that was definitely the biggest surprise for me: the approach I ended up taking in writing about midlife—that mix of personal and political. I have to give my publisher a lot of credit, for allowing me to write the book that demanded to be written (as opposed to the one I had planned to write). So, kudos to Douglas & McIntyre.

Kerry: Almost every argument I have about anything these days (with myself or others!) comes back to the fact that the answer or reality lies not in anything definitive or black or white, but instead somewhere in a grey area in between. The middle, as your book shows on a variety of levels, is a magical place rich with wisdom and opportunity, but yes, it’s going to be messy. How do you try to reconcile that and be comfortable in that uncertain and variable space? 

Ann: I feel like the pandemic has been a masterclass in learning to live with uncertainty. It’s become pretty clear that nothing is entirely predictable and that there’s no simple solution to anything right now. Life is messy. Life is complicated. And yet, as humans, we have brains that are capable of sorting through that that messiness in a way that allows us to spot patterns and land on solutions. Maybe not perfect solutions. (Is any solution ever perfect?) But the kinds of solutions that allows you to steer clear of endless second-guessing, and regrets. The kind where you can say to yourself, “I made the best decision I could with the information I had at the time—and I reserve the right to rethink this decision next week. Or maybe even tomorrow?” What more can we ask of ourselves but that we remain open to the opportunity to learn and grow as humans, both individually and together?

It’s become pretty clear that nothing is entirely predictable and that there’s no simple solution to anything right now. Life is messy. Life is complicated. And yet, as humans, we have brains that are capable of sorting through that that messiness in a way that allows us to spot patterns and land on solutions.

Ann Douglas

About Navigating the Messy Middle:

Roughly 68 million North American women currently grapple with the challenges of midlife, faced with a culture that tells them their “best-before date” has long passed. In Navigating the Messy Middle, Ann Douglas pushes back against this toxic narrative, providing a fierce and unapologetic book for and about midlife women.

In this deeply validating and encouraging book, Douglas interviews well over one hundred women of different backgrounds and identities, sharing their diverse conversations about the complex and intertwined issues that women must grapple with at midlife: from family responsibilities to career pivots, health concerns to building community. Readers will find a book that offers practical, evidence-based strategies for thriving at midlife, coupled with compelling first-person stories.

Offering purpose and meaning in a life stage that can otherwise feel out of control, Douglas pushes back against the message that women at midlife are no longer relevant and needed, highlighting the far-reaching economic, political and social impacts of these messages and providing a refreshing counter-narrative that maps out a path forward for women at midlife.

Both a midlife love letter and a lament, Navigating the Messy Middle both celebrates the beauty and rages at the many injustices of this life stage and provides readers with the tools to chart their own course.

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