Hello and welcome!

On this episode, I interview the amazing Cheryl Richardson.

Among other things, Cheryl is a New York Times Bestselling Author. She’s written books, often dealing with self-care (which is a big topic for many of our listeners). Her most popular book is probably The Art of Extreme Self-Care. She also co-authored a book called You Can Create An Exceptional Life with Louise Hay of HayHouse.com.

This interview will focus on her newest book called Waking Up in Winter: In Search Of What Really Matters At Midlife. It’s a book about major life transitions.

Cheryl spent ample time on The Oprah Winfrey Show as the team leader for the Lifestyle Makeover Series, and also accompanied Oprah on the “Live Your Best Life” nationwide tour.

She has also appeared on Good Morning America, The Today Show, CBS This Morning, and she’s been in the New York Times, USA Today, Good Housekeeping, and O Magazine.

Here’s my interview with Cheryl Richardson…

Interview with Cheryl Richardson on Waking Up In Winter

Brian: Cheryl, thank you so much for being here. Welcome to the show today.

Cheryl: Thanks Brian. I’m really glad to be here with you.

Question: My first question for you is, after writing six books and cultivating quite a following you decided to take a different approach with your new book Waking Up in Winter, and shift from giving advice to giving readers more of an inside view of who you are through sharing parts of your personal journal. I’m curious, how have your readers responded to this approach?

Cheryl: Well it was pretty scary to do. It was a scary decision, although it’s funny sometimes, the soul calls us to make changes in our life and we have to heed the call, right? We have to respond to the call. And I really did.

 I felt like I had said pretty much all I needed to say in relation to self-care and living a high quality life. I also felt like so many of us are bombarded with a lot of information and ‘how to’ advice (myself included), and I feel like we are hungry for stories and for real life experiences.

So, I made a decision to take a journal that was already written, review it, and publish that as a way of sharing with people a story about what it means to try and live a conscious, evolving life. And what I hoped, Brian, was that when people read it that they would resonate with some of the journey. I mean, obviously they wouldn’t necessarily resonate with the details of my life, but what I hoped is that people would feel less alone, that people would see themselves in some of the internal struggles and questioning that I went through.

For me, it was midlife. That was the transition that I was writing about, and the loss of a dear friend, and a kind of questioning of what really matters in life, and where do I find meaning, and what’s next for me in terms of my own personal and professional world? And I’m happy to say that ninety percent of the people who read the book have that experience. They’ll write to me and say, “Thank you so much for putting to words something that I couldn’t quite articulate but have been experiencing. It’s good to know I’m not alone. It’s comforting to know that there is a purpose to this questioning, the kind of shakeup that happens when we go through a transition in life. I appreciate that so much.”

Every now and then I’ll get an email. I’m sure you’ve had this experience, Brian, with your podcast because they’re so good. I listened to some of them in preparation for this interview, and I’m sure you had the experience of people writing and saying. “Thank you so much, I needed to hear that,” or “It just confirmed for me where I am.”

Then there’s about ten percent of the people who think ‘this is boring’ or ‘I don’t get her’. And, you know, that was it. That’s a risk. It’s always a risk we take when we put our work out into the world. For me it felt like a bigger risk because I was putting out some very personal information in this. I mean, obviously it’s a real journal. It’s not written for a reader, it’s written for me capturing my own experience. So, I knew that if I was going to be faced with negative reviews or criticism it was going to feel a lot closer to the bone. But, you know, that’s the beauty of midlife.

I’m 58 years old at this point. My art has to be more important than other people’s opinions, and I feel like I’m on that journey, in a place in my life. So yeah, it’s been very reassuring and meaningful which is what I wanted at this time.

Brian: Absolutely. And it takes different ways of saying things to reach different types of people, so this style may have resonated very well with certain people.

Question: Speaking of transitions in life, I’m wondering, since this is really the overarching topic of the book, what are the big takeaways for people who find themselves in a period of transition in life?

Cheryl: Well, one of the things I do when I’m all done writing book and I have some space from it is that I go back and look at what was the book trying to teach me. Oftentimes it’s a similar message that it has for readers, and similar lessons. As Americans, we don’t have a lot of space for the ‘hero’s journey’. You know, the last couple of entries really needed to reflect what the journal taught me, and what I realized was I had embarked on a ‘hero’s journey’ without realizing it. I think that’s true for a lot of us, where what used to work in life is no longer working. We start to feel like an unlived life is calling, where we start to question things; everything, our work, our relationships. I questioned my marriage and close friendships. We start to question how we spend our time and energy, the people we’re connected to, what our priorities are, all of that. That begins the descent part of a hero’s journey, where we travel down into nothingness and we start to let go of things that we just don’t have energy for anymore, and we can’t hang onto them. But we have no idea where we’re headed, and that descent brings us into this sort of second stage of the ‘hero’s journey’ which is the mystery.

This is a really important phase where some people will refer to it as being in ‘limbo’, feeling lost, not knowing what’s next. I’ve called this the “zone of in between” for years working with clients where, they were leaving one life behind and they hadn’t yet entered the next life, and there was this “zone of in between”. Often as a coach you sort of host that experience for a client as they go through it, and suddenly I was in it. I write in the journal about conversations I had with my own coach, about feeling like I was just meandering through darkness and not sure of what was going to be next, and what I wanted to experience next in my life, and who I was going to be as a result of that? That’s the mystery phase of the hero’s journey.

I remember a point where my coach said to me something that was so important. She said to me, “Your meandering has purpose,” and it calmed down the CEO part of me that wanted a plan, wanted to know where I was headed and what was at the end of the tunnel. Instead, I decided that the most productive thing I could do was stay in the darkness and meander.

I think that’s an important message of the book, that sometimes we attempt to find light too soon. We attempt we look for answers. We attempt to name goals or to arrive some place way sooner than we might want to because the longer we can sit in limbo, the longer we can linger in limbo, the greater the chances are of our soul revealing to us the important parts of what’s next; the places where we need to grow, who we need to grow into, how we’ll use our gifts and talents in new and different ways, who we need to say “goodbye” to, and who we need to say “hello” to. These are really important questions, explorations,  investigations and experiences that we need to have in life. And I feel like the book is saying to readers who are in that place, whether they are twenty or thirty or fifty or seventy, when you’re in that place of questioning what’s next for you, stay there long enough to let the truth emerge instead of the head or the ego. Don’t just start to make decisions in order to quell anxiety. Does that make sense?

Brian: Yeah. It sounds like a counterintuitive thing to do, so I can understand that it’s probably very tough, but it’s a good message. That’s where we need to spend the time.

Cheryl: It really is. And by the time I get to the end of this journal, what I realize for myself is that some of the things that were so deeply important were right in front of me all along. My life was too crowded to be able to see them. And also, I learned the importance of falling in love with the ambiguity of life, with the unanswered questions, falling in love with confusion and limbo, falling in love with the reality that life isn’t pretty and nothing gets wrapped up in neat little packages and bows.

How do we embrace the inevitable suffering that happens? How do we embrace the questioning of the unknown? Falling in love with the mystery is what brings us to the third stage of the hero’s journey, and that’s the sense that moving up into the light where we realize, “Oh, there is a new me that has been birthed here, and that new me can embrace the unknown in a way that she or he couldn’t early on.” And it’s in the unknown, in that mystery, that we find the depth and the richness of mean