CNM 038: Life Transitions & Introspection – with Cheryl Richardson

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

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 meaning that we all longed for.

Brian: That’s quite profound, and it’s incredible that you’re able to articulate it so well. I would have never known where to start in trying to deliver a message like that.

Cheryl: Thank you. You know, that’s what happens when you go through it, Brian. I’m sure you experience that as a coach who goes through your training. In the beginning, you could articulate what you hoped to learn or what you hoped to do, and then you go through and gain experience. That’s what you do during the hero’s journey; you’re finding your way. And as we find our way we find the language and the ability to be able to describe that way for ourselves, primarily, and then ultimately for others.

Brian: Absolutely.

Question: Near the beginning of the book you have a journal entry. You were at a conference in London, and you discussed a twenty-minute period that changed your life. You were recalling a late friend of yours, Debbie Ford, who, during the conference, encouraged the audience to think of a person whose behavior they found hurtful or upsetting. The audience was to explore what made this person hurtful, and then find that quality inside themselves and consider how this part of themselves might actually be a gift in disguise. So I’m wondering, how did this impact you and how do you think this exercise can be helpful to people listening to this?

Cheryl: Well, in that part of the journal I’m talking about when I first met Debbie Ford who was a fellow colleague, a dear friend and a coach. We would coach each other and we travelled often together, spoke at the same events. Debbie passed away in 2013. She wrote a book called The Dark Side Of The Light Chasers which is a really important book. In that book her work was all about young shadow work, embracing all parts of the dark and the light, the good and the bad. I was introduced to her by attending a workshop, a talk of hers at a conference she was speaking many years ago.

She took us through this exercise where she was trying to help people see the gift, the gold in the shadow. She was helping us find the gift that was available to us in this particular situation; in the parts of others that drove us crazy. And so, she led us through this process of identifying somebody in our life that really bothered us, that really pushed our buttons. This was a deep inner process, and it’s important to say that because we live in a culture that tries to find wisdom in quick bursts. Like, ‘I’m going to meditate for ten minutes and figure out why I’m here on the planet’. It doesn’t happen that way. Wisdom comes from presence. It comes from taking time and space consistently. It comes from connecting to our own inner wisdom consistently.

So, it was this exercise where she led us through probably a 45-minute period of getting to what it was about this person that we chose that drove us crazy. I chose somebody whom I felt was very self-centered and narcissistic, who was always insisting on getting his own needs met. Ultimately, she asked us to name a quality that this person had that drove us crazy, and I said “greedy”, and then she had us look for the greedy part of ourselves. I was able to do that and to see how there was the greedy part of me who, as a young girl even, felt like she had to grab things to get her needs met. I can’t do it justice here in a couple of minutes, but I describe this unfolding of the recognition of wisdom in the part of me that judged this man’s greediness. I describe seeing the part of me that needed to be embraced and activated in order to take better care of myself at that time in my life.

Generally, I say this all the time to people – “Any quality that pushes your buttons in someone else is something worth looking up within yourself. So, anytime you feel jealous or envious of someone else, it’s usually an indication that they’re doing something you want to do that you´re not putting energy into.” (Or if somebody is boastful or bold.) “What quality is it in other people that you tend to consistently judge, that may be holding some important information for you, because we are all everything and we only like to acknowledge the good parts.”

Debbie was so beautiful in her ability to help people embrace all of who we are; the light and the dark. So, I think it’s a worthwhile exercise anytime someone pushes your buttons to stop and not react and respond right away, but instead pull back and sit with it. Think about why your buttons just got pushed. What is that teaching you? What does that have to teach you about you?

It’s so easy to point the finger at the other person and to start blaming or focusing on them, Debbie used to always say, “When you point the finger at someone else, there are three fingers pointing back at you. Start with yourself.” So, that’s basically what that exercise was about; the  profound experience I had.

As a result, that really set the stage for me and my life now, doing that very same thing. When I feel my buttons get pushed I stop and say, “Okay, hold on a second girl. What’s going on here for you? What’s the lesson here for you?” And sometimes there’s an old wound. Somebody just stepped on it and that wound needs to be healed. Sometimes, quite frankly Brian, the answer is ‘Wow, that person was really mean-spirited, where’s the mean-spirited part in you?’ Or, ‘Where’s the part that needs to have some of that spirited energy to take care of yourself, or to protect yourself?’ Sometimes that’s the answer, so we need to explore those things.

Brian: Thank you for that, and I bet there’s a lot going on in all of our lives that we could explore that way.

Question: In the book you also mentioned your love for the Enneagram. I’m aware of what this is but I assume that there are many listeners who might not be aware. Can you share with us what that is and why you love it so much, and why the listeners might want to check it out?

Cheryl: A simple way for me to say it is that the Enneagram is like a personality profile system. A lot of people have heard of the Myers-Briggs or other personality tests. But the Enneagram is really steeped in ancient spiritual wisdom and mysticism. It’s a profiling system that captures the essence of who people are. Russ Hudson, who is one of the world’s leading experts in the Enneagram, wrote a book called The Wisdom of the Enneagram with his Enneagram teaching partner Don Riso who’s since passed away. I love it. Russ says that the Enneagram is the study of everything that keeps us from presence. I love that definition. I was introduced to the Enneagram 35 years ago through the work of Helen Palmer who is another one of the world’s leading experts.

In this personality system, the Enneagram consists of nine different personality types. What I love about Russ’s work is not only do you get a sense of who you are when you determine your type is, but you get a sense of where you came from how your type was formed, your childhood experiences. But Russ and Don also on offer what I would call a ‘path of development’, and that is the type that you are operating at; its highest (balanced) form, mid-level (slightly unbalanced) form, and at the lowest level (unbalanced or unhealthy) form. You get to see a path of development in the areas that you might want to work on given your type.

I was introduced to Helen’s work many years ago. I think I was too young. I didn’t quite get it. I mean, I got it, but I had other things going on. Then, probably twelve or so years ago I was reintroduced to Russ’s work, and that’s where it really grabbed me. The timing was right, and I took the test that was offered in their book and determined my type.

I remember reading The Wisdom of the Enneagram. They have chapters based on each type. I remember reading it and feeling incredibly exposed, incredibly seen and understood both at the same time. I discovered I was the type who was ‘the helper’, no surprise. I also discovered that in my whole body of work, I had been teaching what I most needed to learn. I knew that, and I’ve been a lifelong learner and committed to my own personal growth long before I ever became a coach or wrote books. But this book really captured so much. At that time of my life I thought about what I needed to begin to dismantle and what I needed to begin to express more of in my life. So, I’m a huge fan of the Enneagram.

I’ve since then become friends with Russ. Russ is one of my most important friends and colleagues. He and I are teaching together next month. As a matter of fact we’re teaching a retreat together, and I’m so excited to be able to bring his wisdom to my students and my audience because he’s one of the few wisdom teachers that I find available right now at such an important time on the planet.

I encourage people to check it out. If they go to or they Google “Russ Hudson”, his work is really profound.

Brian: Thanks for explaining what that is. I want people to know about it and understand what it does. I think when people find my platform a lot of them are starting to realize, ‘Well, I might have problems with codependency’. And like you said, they feel both exposed and relieved that somebody understands them. And this could be more of that for them.

Cheryl: Yeah, I think it could be really helpful.

I want to say I’m a student of the Enneagram. I’m not a teacher. And the way I describe it is incredibly simplistic. And, at the same time, if you take a test and discover your type and read about it, especially from the perspective of codependence, it can shine the most comforting light on where you’ve come from and how your tendency toward codependence may in fact be expressed in your lives.

It helps to cultivate a sense of self-awareness that, as you know Brian, self-awareness is half the battle when it comes to healing. It’s just becoming aware of our tendencies and how our codependence expresses itself in life, as well as really trying to realize when we’re behaving in a co-dependent way. I think the Enneagram has a lot to offer in that regard.

Question: Speaking of codependence, in that same chapter you discuss the fact that like many of us, you went through periods of sacrificing your needs in relationships hoping to gain love. You also discussed your propensity for people pleasing and even bullying behavior when you felt unappreciated or resentful. Those sound like textbook “codependent behavior”, so I’m wondering if you could talk a little more about your experience with those tendencies and how you’ve overcome them.

Cheryl: Well, I would say a few things. In that context I’m talking about the Enneagram and how it really did identify me as ‘the helper’, the sort of fundamental underlying grief that I’m only worthy of love if I’m giving. I think that belief ran my life for a number of years. It’s something we always have to watch for. The Enneagram looks at the tendency towards where we go and how do we behave when we’re under stress. I think it’s very common.

I look at my early life and attribute a lot of my healing, by the way, to the twelve step programs. They saved my life. Al-Anon saved my life early on and really helped me to understand my own codependent nature I would say. I’ve come a long way because I’ve done a lot of work, a lot of therapy, a lot of twelve step meetings over the years, a lot of personal work around recognizing that I’m worthy first and foremost of my own love, my own attention, my own care, and the meeting of my own needs.

So much of my work is around those topics; identifying that you even have needs, and then going about the business of getting them met – identifying that we are lovable and worthy of attention, love, care and comfort, then soothing and all of those things. So much of Waking Up in Winter takes the reader on a journey through what it means to pay attention to oneself; to pay attention to what feels good and what doesn’t, what comes up, what’s longing to be explored more deeply even when it’s not pretty.

So, I think the antidote to codependence is really turning our attention inward, turning our attention away from others to ourselves, and not in a Narcissistic way. I often joke that very few narcissists show up at my workshops or at the talks that I give. It’s usually people who have been victims of narcissism and really need to develop a healthy sense of self and a healthy sense of attention towards oneself.

Journaling in and of itself is a wonderful way to pay attention to what’s going on in your life; what are you thinking? How are you feeling? Instinctually, what’s going on? What do you feel? What’s going on in your gut? What’s going on intuitively? Paying attention to what’s going on inside instead of what’s going on in the outside. That’s a lesson for us all, right Brian? Whether you’re codependent or not (I’m not sure who isn’t a codependent, really) that whole notion of paying attention to ourselves, paying attention to our own truth is what allows us to be in relationship to others in a healthier and more authentic way.

Question: Thank you for elaborating on that. What is your favorite part of your book Waking Up in Winter and why?

Cheryl: I would say the end. (Laughs)

It was such a scary book to publish. I had to go through and edit it, of course, for grammar and punctuation because it was just a raw journal. And I kept most of the rawness there. I really wanted it to be a true journal. Every now and then I had to give context. For example, when I talked about the Enneagram I knew people wouldn’t know anything about it, so I had to add that piece in. It was really scary for me.

I thought, ‘Do I really want to put a journal out into the world?’ And, ‘What are people really going to be interested in? Isn’t it kind of pretentious?’ or, ‘Who´s going to Identify with my life?’ I was living a life a lot of people say they’d like to live as a writer and a traveling teacher and all of that, and I’m at a point in that journal where I’m really questioning whether or not I want to continue that work that a lot of people see as a reason to be incredibly grateful. Of course, I was grateful. But I also wasn’t happy. So, by the time I got to the end, I was just glad I did it.

I made the decision to go with Harper One because the editors there really got what I was trying to do. I got the advance for the book. I put it in the bank and I never touched it. I told myself, “I probably won’t publish this. I’ll just work on it, and if I don’t publish it I can always give the money back.” I knew I could do that. I had a contract. So, it wasn’t until the day that I finished editing the last entry and pressed ‘send’ that I thought, ‘Oh, thank God that’s over with’, because it was just so anxiety-provoking all the way through.

Now I just see myself as an artist. My words are my paints and my pastels and I thought, ‘No, this is what the artist wanted to put out into the world, and I need to honor the artist within me.’ I feel like when I get to the last journal entry that I get to a piece of what it was I was searching for when I began that experience. And what I get to discover about what really matters, not only at midlife, but I think at any point in our lives, is the truth. And that’s the part that makes me happy – is the truth.

Question: And what is that truth?

Cheryl: I don’t want to give away the end of the book. (Laughs)

Brian: Fair enough.

Cheryl: It’s funny, when I’m speaking or being asked to read excerpts I always want to read that part, but I cant. One time, I remember when I was launching the book I started to read the last entry and somebody in the audience yelled, “No, don’t give up the ending!”

And I thought, ‘Okay, I can’t do that. In some ways when you publish a journal it feels more like you’re reading a novel than a self-help book. It really is a memoir In journal form. And so, I discovered after giving talks about the book over and over again, that telling the ending of it really does give away something important that the reader works towards. So I’ll just hold that secret I guess.

Brian: We’ll leave the audience in suspense. You have to pick up the book if you want to know. (Laughs)

Question: Speaking of the end of the book, you also leave readers with about seventeen questions (I counted them) to ask themselves that support midlife introspection. What do you think is the most important question someone should be asking herself or himself to prepare for a new season of life?

Cheryl: I included those questions because I am a teacher at heart and when I got to the end of the journal I thought, ‘You know, I want people to talk about their own journey, their own experience, where they are at this time in their life, whether it’s midlife or another transition point.’ I thought about the questions I had been considering for myself and with my own clients back when I was coaching. So, those questions really are meant for people to think more deeply about their lives.

My spontaneous answer to that is something I ask myself pretty regularly and that is, “If today were the last day of your life, would you be happy with how you spent it?” If you were to look at a calendar over the next week or the next month, would you be happy calling that the last week or the last month?

Now, I know if I look at my calendar right now there are things that are not necessarily pleasurable. But are there more things that are pleasurable, that are meaningful, that are so silly or satisfying or important. Are there more things in your day, in your week, or in your month that really reflect what’s important to your soul?

That journal begins with what happened when I turned fifty, and the questions I started asking myself like, “What did I really regret?” (and I don’t mean that I didn’t jump out of an airplane or I didn’t go to Machu Pichu). To me, it was more “Who didn’t I become?” “What didn’t I express?” “What parts of me are longing to be expressive that just keep getting ignored?”

One of the ways we get to those answers is by just looking at, “Am I happy with how I’m spending my time?” It keeps us locked in the present and it keeps us locked into the reality that we have a finite amount of time here. Use it well.

Question: You worked closely with some very well-known people like Louise Hay and Oprah. Would you care to share any funny, special, or otherwise significant memories from working with any of these people?

Cheryl: Both Louise and Oprah are very funny. People always ask me what it was like to work with Oprah. We spent a lot of time together on the show for a couple of seasons, and we also traveled together when she was launching the magazine.

Oprah’s funny on stage and in her shows, but she’s really really funny (in person). She´s got a great sense of humor as does Louise. I was teaching a workshop that I teach once a year called Speak, Write, Promote: How to Become a Mover and Shaker. When I first developed that workshop, I invited Reid Tracy who’s the publicist. He was and still is Louise’s right-hand-man even though she’s passed. I invited him to teach it with me, and Louise would come and sit at every workshop right in the front row in the beginning. She must have come to three or four of them. She would just sit there like a student in the most adorable way and take notes, and at lunch time she would tell me what she learned. She would just repeat things that were important to her.

Both of them really taught me the importance of having a sense of humor. Louise especially had this childlike way about her. I remember one time we were sitting in a restaurant eating and somebody had ordered a decadent dessert that had all this sauce. When she was done, Louise said, “Give me that plate!” We’re in this fancy restaurant, and she’s licking the raspberry sauce off this plate. I remember her saying to me, “You have to lick up every last bit of joy in life, Cheryl.” She really did that all the way to the end. She made her ninetieth birthday and she really soaked up every bit of joy in life that she could. I feel really blessed to have been able to spend time with both of them, to learn from them, and to travel with them. It’s pretty wild when you think about it. I never put that on a dream board (laughs). I never expected that. But what a gift.

Brian: Absolutely.

Question: What’s your biggest piece of advice for a codependent person?

Cheryl: Well, my biggest piece of advice is going to be something Louise said to me one day when we were traveling. She said, “Cheryl, you will be with you longer than anyone else on the planet. Why not make it a good relationship?”

Brian: Fantastic.

Cheryl: Yeah. And I think that is a really important statement that I say to myself a lot. Cheryl, you’re going to be with you longer than anyone else on the planet. What can you do right now to make it a good relationship?’ I think that’s a very wise perspective and question for a codependent person to be asking. ‘How can you serve yourself right now?’

Question: Well said. And is there anything else that you’d like to share before we wrap up the show for good?

Cheryl: I think that’s it. It has been wonderful talking to you, Brian. And thank you for what you’re doing. It’s such an important service, and you bring really great experts. I loved some of the people that I listened to. I appreciate so much that you take your precious time and energy and put it out to the world in this way. I have no doubt that you’re serving a lot of people in really powerful ways that you probably don’t even know.

Brian: I appreciate you saying that. The reason I do it is because I do get a response from it, and I know that it’s helping. That’s what keeps me going, so thank you for saying that.

Cheryl: You’re very welcome. Thanks for having me.

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  1. Great episode! Put Cheryl’s book on my TBR list. I’m so glad you are back.