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The 5 Faces of Grief with Cheryl Richardson

I’m excited to welcome my friend and bestselling author, Cheryl Richardson, back to Afterlife TV to tell us about her newly released book, Waking Up in Winter. Cheryl talks about the fear and excitement of writing her newest book, which was a big departure from what’s she’s done previously, and how its deeply personal content was a challenge for her to share. She discusses staying connected to what’s true for her and living from a more authentic place. Then Cheryl and I talk about the 5 faces of grief as we face mid-life, the ups and downs of aging and learning how to embrace and accept those changes. This includes changes not only in our bodies but in our careers, our relationships and the inevitable: the death of our loved ones, not just family members and friends but our beloved pets, too.

This episode is jam-packed with insightful lessons and stories you don’t want to miss.

Much love, Bob Olson ~ &

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Afterlife TV is presented by Afterlife Investigator & Psychic Medium Researcher Bob Olson, who is the author of Answers about the Afterlife: A Private Investigator’s 15-Year Research Unlocks the Mysteries of Life after Death.

Check out Bob Olson’s other sites: (a directory of hundreds of psychics & mediums by location with reviews & Instant Readings) & (his personal recommended list of tested psychics and mediums) or visit Bob’s Facebook Page. Bob also has a popular workshop for psychics and mediums at

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Bob: Hi, everybody Bob Olson in here with the Afterlife TV. You can find us at This is where we talk about life after death and answer the meaningful questions you have around that subject. Today, we’re gonna be talking about the Five Faces of Grief, and probably not the only faces of grief but they are certainly five that we are gonna talk about today. Today’s episode is sponsored by Best Psychic Directory, if you’ve been thinking about going to a psychic or a medium. A lot of people are interested in mediums, especially those who are grieving. And so I have personally vetted all the people on Now, today is a very special episode because it is an interview with a very dear friend of mine and Melissa’s that came up with a new book. And we haven’t had an episode in a while, I know you’ll be happy about that. We might not have one for another while after this. So don’t think like I’m back on a roll here, I’m not because I’m still working very diligently on my screenplay for “The Magic Mala.” So, I appreciate your patience with that, but it won’t be long. Today we’re talking about a new book called “Waking Up in Winter: In Search of What Really Matters at Midlife” with Cheryl Richardson. Welcome, Cheryl.

Cheryl: Hey, Bob.

Bob: Hey, listen, I wanna just read the back cover here because it is impressive to me and it also talks a lot about where you’ve come from and where you were when you wrote this book. Cheryl Richardson is the New York Times best-selling author of several books including “Take Time For Your Life,” “Life Makeovers,” “Stand Up For Your Life,” “The Unmistakable Touch Of Grace,” “The Art Of Extreme Self-Care,” and she co-authored “You Can Create An Exceptional Life” with Louise Hay. Her work has been covered widely in the media including on “Good Morning America,” “The Today Show,” and “CBS This Morning.” And in the New York Times, USA Today, Good Housekeeping and oh the Oprah magazine. She was the team leader for the “Lifestyle Makeover” series on “The Oprah Winfrey Show.” And she accompanied Ms Winfrey on the “Live Your Best Life” nationwide tour. Richardson also served as co-executor producer and host of “The Life Makeover Project with Cheryl Richardson” on the Oxygen Network. And as co-executive producer and host of two public television specials “Stand Up For Your Life,” and “Create An Abundant Life.” She lives in Massachusetts. Today we’re talking about a new book called “Waking Up in Winter.” Tell us about this book,

Cheryl: So, it is a journal…So, it’s a memoir in journal form and it was inspired by May Sarton who was a writer. She wrote fiction and nonfiction and poetry and she lived here in New England, New Hampshire, Maine. And, yeah, I found her first journal called “Journal of a Solitude” back in…I think I found it in the mid-80s. I write it in the book. I forget the actual date, but I was at a book fair at a church and I saw it. And it…the subtitle was something like, you know, the year…a year in…the intimate journal of a creative woman or something like that. And she was a writer who had kept this journal and I was not a published writer at the time. But I remember thinking, “Wow, I would love an inside view into a writer’s life” because I imagined that I was going to be publishing at some point. And so I got the book and I read it and it was just that. She was writing about her life, her writing, her writing process, where she wrote, how she dealt with reviews, both positive and negative, how she dealt with dealing with the public, giving talks about her books, going to universities and things like that. And she also had quite an impressive cadre of literary friends and so it was this awesome experience of going behind the scenes of somebody who was doing what I dreamt about doing at some point in my life. And she would go on to publish a series of journals about her life. And it turned out that May Sarton also loved some of the things I loved, flowers, nature, animals. And those were very significant parts of her day that she would write about as well. So you really kind of got to know her, you got to have a sense of who she was and the environment in which she lived and the animals that spent time with her and…So every time she would publish a journal, you know, you felt like you could continue on with her life and I loved it.

And she wrote journals all the way…published journals all the way until ’83 when she died. Her last journal was called “At Eighty-Three” and, yeah. So it was, you know, Michael, my husband, you know Michael, was the one who…when I was sort of trying to figure out what I was gonna write next, he said to me, “Why don’t you just publish a journal?” You know, “You’ve always loved May Sarton but why don’t you give people an inside view into a writer’s life and a teacher’s life in the 21st century?” And I felt both terrified and excited about doing that and I knew, okay, I needed to pay attention to that because any time you feel both of those things together it’s a good indication to at least explore it. And that’s what I did. Ultimately, I ended up publishing a journal.

Bob: Amazing. Now, what terrified you about it?

Cheryl: I mean, really what terrified me about it was questions like, “Who’s gonna wanna read about your life?” Like what we all do, right, when we’re writing. You know, what do you have to say that’s new and different? It’s a complete departure from what I’ve done. I’ve written six self-help books. “Will you really do a disservice to your audience by doing something completely different than what you’ve done before?” And also, I mean, honestly, when you put a book out into the world you really put yourself out into the world. And I knew that it’s one thing to get negative reviews about self-help how to book. It was even more personal and more vulnerable to put my life on the page and it’s really a journal. And it’s not a journal that I wrote knowing that I was going to publish it. This is a journal that existed beforehand and I did that intentionally because I wanted it to be a true journal. I knew I wasn’t mature enough as a journal publisher to be able to write a book without being self-conscious about the reader. So I chose a journal that already existed and, you know, I knew that I was opening myself up to people not only criticizing the book but commenting on my personal life.

Bob: Sure. Sure. Very intimate writings here revealing feelings that you probably didn’t know when you were writing your journal, that you would be sharing these with other people. A lot of people I know already this book just came out in December are really appreciating the fact that you were willing to take that risk. It’s working for the book. It’s working for your, you know, audience and the readers and it was certainly something that I enjoyed. I know you very well and I really enjoyed this book because to me one of the most wonderful things about this book is it gives any reader the opportunity to hear the life story of a self-help author. And recognize that you too are struggling to live and not just speak but live the things that you talk about. Like, you know, “The Extreme Self-Care” book, all those things that you teach you also constantly have to remind yourself of those things that you teach. And ask yourself, “Where am I right now in reference to what I’m preaching to other people?”

Cheryl: Yeah. I mean, one of the pieces of feedback that I get…I mean, my writing has been pretty self-disclosing. It’s just, you know, I teach from my own experience. It’s kind of like I’m very clear and have been clear for a number of years that part of my purpose here is to really…well, let me say it this way. My number one priority is my own growth and evolution and then I just share what I learn as I go along. This is a different way of sharing that, right? And, yeah, I love it when people say to me, “Oh my god. You’re not perfect. You don’t have it all together. You haven’t figured it all out,” or, “I was really surprised when I read your book that you struggle with things, you still struggle with stuff.” It’s like, “Yeah. It’s called being a human being on planet earth.” And life happens, hard things happen. We have grief, you know, we have losses. We have major changes in our life, both internal and external changes.

And I’m always searching for how do I really stay connected to what’s true for me, my own authentic truth, my own authentic voice? How do I need to grow so that I can stay true to that voice and then how do I express it in all that I do, whether it’s my personal relationships or my writing or my teaching? You know, I want everything to be an expression of just what’s true for me. And so in order to do that, I’ve got to be willing to constantly cultivate a sense of self-awareness that lets me know, “Okay, wait a second here.” You know, I guess, I would say that from…I’ve known from a very, very young age that on some level I came to the planet this time to do a lot of personal work. Like, I’ve just known that for a long time and anytime I’ve had astrology readings, astrologists will say to me, “Okay, girl. You better buckle up because this life is a lot about learning lessons and growing and evolving.” So I’ve always known that. I will naturally share that journey with readers because it’s something I’m always engaged in. Like, am I being honest with myself, therefore, am I being honest with others?

Bob: You know, one of the things that I noticed about you before I read the book, for instance, let me give this example. When you read a self-help book yourself written by somebody else, I have read the same book, we’re talking about it together. And then you’re talking about the exercises that you do and I’m thinking, “Exercises? What exercises? I didn’t do the exercises.” You know, you always do the exercises. You always fall through with what the author suggests that you do. And, of course, that falls right in line with especially your first books because you gave a lot of sort of homework to people in every chapter and it helps people to learn and grow from that. And what was really interesting is your authentic self is to not just put these exercises in your book and expect people just to not do them and move on to the next chapter because you too actually when you read other people’s books, follow through with those exercises.

Cheryl: Well, in some ways, it’s the coach in me that knows that the only way our lives change is by taking action, right? You can gather all the information you want, all the wisdom you want from other people, but if you don’t put it into action in some way, then things aren’t gonna change. And so even when I think about this book, you know, “Waking Up in Winter” and the fact that it’s a journal, part of the reason I wanted to publish this one was I wanted to show people how I take action on a regular…Like, what I do to grow and evolve and to question my life and to question myself. And, you know, this particular journal, this particular period really was about…it was a hero’s journey. So it was a period in my life where I started to really rethink everything and there were…those things that I did. I went to see a therapist and I write about, you know, what happened during therapy sessions. And I was doing dream work and I include dreams and what I learned about myself. And, you know, I talk about past life regression which was really scary for me to do that. I mean, it happens to be a form of therapy. I’m a huge fan of and have been for over 20 years. I mean, my first regression work was done probably 25 years ago and had a profound impact on my life. And so I couldn’t…I mean, it was part of that journal and I thought…I went back and forth, “Do I wanna leave that in?” It’s like, “Well, yeah,” because this is what I did and it was really significant during this period that is covered in the journal. It really played a huge role in my life. So, these are the things I do and so, yeah, if I’m reading a book, well, I think about “The Magic Mala.”

When I read “The Magic Mala,” right, I was like, “Oh, my gosh. This is such a reminder that crafting, consistent thoughts, like, just paying attention in some systematic practical way to how we’re thinking on a regular basis has a profound impact on your life.” And that’s why, you know, it’s funny this morning as I was getting ready to come up here, I have this jewelry case that I opened up. And I have all these mala things because I’ve been collecting them. I mean, I’ve collected them over the years, but I was looking at them thinking, you know, “They’re just so important to me.” And now, you know, I read that book. I take it out. I have a set of mala beads next to my bed. I do my gratitude list or, you know, if I’m focusing on something, I mean, yeah, I know that the only way things will get better for all of us is if we do something different. We don’t just think about it or talk about it. You put it into action.

Bob: Yeah, that’s right. One other Amazon reviews someone said, “What the book did for me was deliver so much relief that what I am going through is most likely much more common than I thought. And it just made me feel so much less broken.” I think that’s one of the things. People are able to relate to, look, you bathe in this stuff. You think about this midlife. You think about midlife, but you, you know, before that it was whatever that stage was you were going through. You think about these things very deeply on a regular basis. Some of these people are just very, very busy. They’ve got kids, they’ve got jobs, they’re, you know, got all kinds of things going on. And they might not have the time to do that sort of thing. And so someone else who’s going through midlife might, like this woman, you know, might think, “There’s something wrong with me,” you know. And then they read about you and here you are the self-help author, very successful, who also is going through the same things. I think that’s one of the great benefits of “Waking Up in Winter.”

Cheryl: Well, you know, that kind of a review really touches my heart because, you know, it’s funny, this time when I published this book unlike all my other books I didn’t have a publishing contract, I had no deadline and no promise to anybody. And I did that because I swear to you up till the day that I pressed send, so even after I had a contract when I made a decision, you know, to publish with HarperOne up till the day I press send I was still debating on whether or not to publish this book. And what I hoped most of all is that women in particular would read this book, women in transition, especially midlife women, would read this book and feel a sense of comfort in knowing that they’re not alone because I, I mean, I can go back. I bet you can too, Bob. I can go all the way back to the beginning reading Louise Hay, Shakti Gawain, I mean, so many, you know, a lot of the early Emmet Fox memoirs of early self-help teachers. And being just…I can just remember feeling so comforted reading their books. Like, “Oh my God.” You know, I’m not alone here. There is a path and I’m not broken. I mean, I love that she said I’m not broken. I mean, we’re not broken. We’re just trying to find our way home, you know.

Bob: Yeah. And none of us are perfect, you know, and anybody who’s pretending to be is not doing…And one of the things you talk about that I love so much in this book is basically living from a more authentic place. If you’re just joining us, we’re talking about “Waking Up in Winter.” The new book “Waking Up in Winter: In Search of What Really Matters at Midlife” by Cheryl Richardson. Cheryl is joining me here and we’re actually gonna talk about something that I call the Five Faces of Grief. Something that we can focus on today but let’s see one, two, three, four. At least four of them are directly pulled from your book. Your book is not a book about grief, but you could certainly say in some ways there is a…there’s a theme of loss within there.

Cheryl: Yes, absolutely. Absolutely.

Bob: And let’s start with the first because when you’re talking about midlife and you’re talking about the struggles that some people go through midlife, my first face of grief here I just called youth, one of the things that we’re losing or, you know, we’re passing by is our youth. What can you say about that?

Cheryl: Well, right in the beginning of the book I talk about the day I turned 50. And let me just say that I’ve always been somebody who’s celebrated my birthday. One of the real benefits of being somebody who does this work on a regular basis is life just feels like it gets better and better. It doesn’t mean that everything is like hunky-dory, fine, no problems. No. It just feels like…I feel like I’m able to handle life better. I’m able to be more present to life, to accept what happens, to work through the challenges that I get faced with. And so I’ve always been someone who looks forward to birthdays. I don’t dread them, just like I don’t dread the beginning of the year. A lot of people do when they’re not living life authentically. When they’re not living life the way, you know, the way that they want to or that they imagine they could. But the day I turned 50, it was really interesting. Literally, that day, my birthday, I was on an exercise machine in my home and I thought, “Wow, 50.” You know, chances are I’ve got more years behind me than ahead of me.” And I started to think about things like, you know, “I wonder how long I’ll be here. I wonder who will die first, me or Michael.” You know, “I wonder if I do die first who’s gonna like, you know, look through my journals?” Like, “What am I gonna do with my journals?” Although I will say in my estate planning, I wanna be cremated and the journals come with me. We all get cremated together. That was the decision. It was scary to think about it and yet I knew, you know, what the hell. I mean, it’s the truth. Like, let’s just dive into it and I really began to explore things like what would I regret not doing, who would I regret not becoming?

And what does it mean to get older and to say goodbye to certain things that my physical body won’t do anymore? I mean, I’m a huge believer in the fact that if we keep telling ourselves, you know, we have to pay attention to what we say to ourselves, right? Oh, I’m getting older, oh, I’m at midlife, oh, it’s all downhill from here, I mean, that’s crazy things that I hear people say. Like, I mean, you know, I spent enough time with Louise Hay to know, don’t do that. But the reality is that there is a stage we enter at midlife where we don’t have the same energy for things that we used to. So if you don’t wanna call it physical energy, then let’s just call it psychic energy or energy in general because life is energy. And I do have more wrinkles and I do have sagginess in my body in places I didn’t before. And my skin feels different and I can’t, you know, I’m strong. I mean, one of the things I did do after turning 50 was made a decision to invest even more seriously in my strength, in my muscle strength because I figured for as long as I’m gonna be here I wanna be in good shape so I can really enjoy it.

But there are certain things that you do lose and we’re not a culture that is interested in having that conversation. Instead, we glorify youth and we want to just pretend that we’re gonna live forever. And I think that just does a real disservice to ourselves, to each other, our relationships and to the kind of life that we lead. So, yeah, we lose. There’s a lot of things. You know, there’s…I have arthritis in my fingers and it comes from years of typing. And, you know, when I first started to see…and believe me, I’ve had like a million people tell me, “Well, if you change your diet,” and I get. I know about all that stuff and while I absolutely change my diet and it’s, you know, low inflammatory, you know, anti-inflammatory diet and all of that, the reality is these hands have been working for a long time and they have lost something. And what does that mean and how do we integrate the real losses that come with aging into our lives? I think that’s an important question to explore.

Bob: Yeah, it is. And, you know, one example that comes to me, you know, I exercise, and I don’t recover like I used to, you know. So I actually have to pace myself and think about how hard am I gonna exercise because I may feel this for the next few days. I remember, and this is probably a decade ago, someone asked me to help them move. And I actually thought about, “Geez, if I help them move, like, I’m gonna be sore, you know, for days after that,” because I’m using parts of my body that I’m not used to using. And that was the beginning of my midlife, you know, experience of recognizing my body is not what it used to be. But then you’ve got, you know, you get your mind, you’ve got your looks, whatever. You got all kinds of things that go along with growing older. Again, these are things that we grieve, and we get to see in “Waking Up in Winter” what your process was for dealing with the grief of youth in this particular case.

Cheryl: Yeah.

Bob: Now, the second one I wanna talk about was career because that was a big one for you as well. At the age of 54, things are changing for you, you are very candid about how your career was changing and much of it consciously, some of it, you know, also unconsciously. It was just happening the way it was happening, but you were also recognizing, you know, new voices coming up. And I loved how candid you were about that.

Cheryl: Yeah, you’re being very sweet about it. I mean, I write about the fact that, you know, there were a couple of experiences I had. I remember them distinctly where I was watching…in one case, I was watching a colleague who is much younger than I am and is really just a beautiful teacher, this young woman. Another case I had received a blog from another colleague of mine who is younger than I am. Both of them just really very successful, really hip, really speaking to lots of people, I mean, you know, helping lots of people. And I write very candidly about how, you know, one day I woke up and read the blog. And started thinking, “Oh my gosh. I’m not relevant anymore. I’m the elder. I’m not that young hip person.” You know, and, again, you know, we talk about youth, you know, probably I’ll never fit into that size dress ever again and nor do I want to. I mean, it’s just where I’m…like, that’s not a priority. I’d have to do a lot of work to get there. I could get there but I’d have to do a lot of work. I wanna use my energy in other places. And so, yeah, I just decided…again, it was a journal. So it was honest, just exploring instead of pushing it under the rug and ignoring it. Just really looking at, “Okay, what does it mean to be…to become an elder in my work, you know, to be somebody who has been around for a while?” And then I thought about some of the elders that I had the privilege of having. Louise Hay was one of them. Marion Woodman who is a young analyst, who was a very important mentor and teacher of mine early on, who was an elder, you know, these people had a profound impact on my life and still do.

I mean, I’m still talking about them today and there are things that I do every day of my life that were inspired by these people. And so I began to just really start to both own what was no longer gonna be because let me also just say that from a career standpoint because we’re talking about the loss of career, you know, at some point. And this was a big theme in this book, this kind of CEO woman, make it all happen, push, push, push, drive, you know, write the 75,000 blogs. And get on media, you know, just everything you need to do to be a well-known teacher that I had done all my life, you know, for my career, at some point it’s like enough already. You know, when I started to look at the amount of time I was spending in a car driving to the airport, sitting in the airport, sitting on a plane, back in a car to the hotel, in a hotel room by myself, all of that to get on stage for 90 minutes to speak in front of 3000 people, which I loved. But that was a lot of time before and after that I suddenly recognized was very valuable time. And all of that work as examples or same thing with television, you know, getting on a plane, going to the…you know, all the producing work you do before him, it’s a lot of work. And so I had to deal with…and it’s a lot of very heady, toxic work. I mean, not toxic. That’s not what I mean. What do I wanna say? It’s interesting that that word came out.

Bob: Taxing.

Cheryl: No. It’s like seductive, which is probably why I said toxic, but it’s…because, you know, it can be really…it just can be so seductive to do things like be on television or to have lots of people writing to you. Or to have a bestselling book, to have a number one New York Times…I mean, on one hand, I’m so blessed and grateful. I’ve had an amazing career and what I’m most grateful for is the way that my work has helped people, and I know that it has. There’s a certain…And we all go through this in different ways in our careers. There’s a certain way in which we have to face the music that the highlight of our career may be over and it may be time to just go about doing your work in a different way. And I think that’s what started to get unraveled in this journal.

Bob: Well, right. I think so, too. The other thing that I took away from it was that…and because we are talking about loss. When you talk about grief, you’re talking a loss, but really once you read this book you recognize, yes, there is a loss. There is always a loss when things change, right? But there’s things to be gained and so it’s really about career change, you know, whereas youth, okay, you’re never gonna be young again, right, at least not in this lifetime. But with career, it’s not necessarily that you’re losing something and then there’s like a void or an emptiness. It can change, and it can become something different.

Cheryl: Yeah. I mean, I think that that’s an important point. You said it really beautifully when you said, “Well, there are some things that you lose. There’s also some things that you gain.” So those losses are tempered by what you gain, more time with loved ones, more time for me, more time in nature, more time with, you know, my dear little animal who was a soulmate, more time just to myself, more time to write, more time to create art. I mean, more time to have deeper conversations with people to develop and offer programs that are closer to home. And allow me to really delve deep with people instead of delivering a keynote on stage but you know what? It’s awesome to get on stage in front of 3000 people and to feel this amazing connection with the audience. That’s a loss that I’m still, you know, it doesn’t mean I’ll never do it again. I probably will at some point but not like I did before and there’s a certain magic that happens that you do lose. But there’s a new magic that happens. Like, sitting on the back deck at sunset and suddenly a hummingbird shows up in front of my face and, you know, flutters there for 30 seconds. And I’m like breathless because I’m so just joy-filled at what I just experienced and that makes up for it.

Bob: That’s right. The other thing is though we don’t know what we don’t know as far as about the future.

Cheryl: Well, that’s, I mean, look at Louise Hay, right?

Bob: That’s what I was gonna say.

Cheryl: I know.

Bob: So Louise Hay. How old was she?

Cheryl: Sixty years old when she started Hay House.

Bob: Okay.

Cheryl: Yeah.

Bob: So, you’re not even there yet and that’s where she started her career.

Cheryl: Well, and you know what? She had somebody like Reid Tracy who stepped in very early on and did all the heavy lifting so that she could just do. And that, I mean, you’re making, I mean, thank you, Bob, because I know what you’re doing which is…it’s not like I’m rolling over and dying people. It’s just that I am bringing my work to the world in a different way. And I am also really gratefully surrounding myself with wonderful people who are supporting me so that I can just be focused on the kind of helping work that I know I’m here to do, and that I get so fed by that I wanna do.

Bob: You know, it’s interesting, this is gonna be a little different because I had this thought recently about midlife, you know, because I was reading your book. But also, I recognize that some people might look at me and think, ”Oh, Bob’s going through a midlife crisis.” And I don’t see it that way and then they’re…

Cheryl: Why? What are you doing?

Bob: Well, it’s a for instance. So, you know, I got a motorcycle. I got one of those three-wheel motorcycles. It’s a Spyder.

Cheryl: It’s awesome.

Bob: Shawn and I we’ve been out on it.

Cheryl: Oh, my gosh. Can I just tell you? It’s like a highlight of my summer last year. It’s so much fun.

Bob: It’s a lot of fun. And I’m thinking about getting a sportscar and same thing. That will just convince some people who he really is going. But it’s interesting because my perspective on it is I’m not doing these things to get back my youth. I’m doing these things because I now have the means to do what I always wanted to do. I always wanted to be able to own a Spyder or, you know, I always wanted to be able to own a sportscar. Before I just couldn’t afford it and also, you know, we have…now I have, you know, just the means. That can mean time, that can be abundance, that can mean…

Cheryl: I was gonna say you have the time also to be able to enjoy and that’s just it. In this stage of our lives, you know, when you come out of the household or stage where you’ve just been working your butt off. And, you know, you and I both know that mean we’ve worked really, really hard, more than a fulltime job for sure unlike parents who I don’t know how they do it, you know, because neither one of us have children where people live, you know, who are raising kids or working like five full-time jobs and one life one day. But we’ve worked hard for a very long time and now part of the beauty of midlife is deciding, you know what? I’m gonna create some space in my life and all of the things that I’ve wanted to do, now I’m gonna really assess those. And say, “Okay. I mean, for you it’s not about the Spyder or the sportscar because I know you. It’s about being out in nature surrounded by beauty.” I mean, when I think about the day you and I did the Spyder ride, I mean, you know, we’re out in all the elements, we’re driving by the ocean, the sun is out, the waves across, I mean, I know. Look at you. I can just see it.

Bob: Yeah. Can’t wait to get back out there.

Cheryl: I can’t wait either. It wasn’t about the things. It was about the fact that we were now giving ourselves…We were exposing ourselves to the elements that are so important to our soul, you know.

Bob: That’s right. It’s about the experience of…

Cheryl: That’s exactly right.

Bob: You know, and the same, it’s funny because Michael and I were just having this conversation the other night. You know, for me, the sportscar…if I could have invisible…an invisible sportscar so nobody would see me in it, that would be even better for me. I don’t care to be seen in it. It’s not about that. It’s about the experience of driving the sportscar.

Cheryl: Yeah. He’s the same way. Well, you know, and let me just say this about men. You know, I’m married to an artist who has loved cars since he was a little boy. That’s really his only thing. Like, he doesn’t spend a lot of money except on cars or designing like, you know, designing our home, let’s say. But for him, cars are like art on wheels and so every day when he walks out to the garage and he sees his sportscar, it’s beauty that speaks to his soul. And I think that’s true for a lot of men when it comes to cars to tell you, “Yeah. There were some of us who were trying to reclaim our youth.” But I think it’s more than that and I think we do men a disservice by just, you know, “Oh, you’re going through a midlife crisis.” I find that kind of demeaning and…

Bob: Well, it is, but I think it’s also just a misunderstanding as well. You know, I saw an episode of some show and there was like five guys staring at like a vintage Corvette. And one of the guy’s wives come out and she goes, “I’ll just never understand it.” You know, they’re just standing there staring at me.

Cheryl: Yeah. Yeah. I can tell you, I totally understand that now being married to Michael. I do.

Bob: So, we talked about youth, number one. Number two, career. These are faces, what I call faces of grief. Different ways that as we age, as we get older there’s loss involved and because of it, we grieve that loss. The third one I wanted to talk about was tribes. Now, you used the word tribes in your book “Waking Up in Winter” and I liked that word. I know a lot of people use it where…other ways to describe tribes. How would you describe it?

Cheryl: Well, I think early on in the book when I talked about self-care I think I was doing an interview with a young woman in Germany who was really feeling like self-care what meant that, you know, you were telling people to be arrogant and selfish and inappropriate and all of that. That was, I think, the first time when I talked about tribes meaning that tribes are the systems that we grow up in. Well, I’ll say one my…one of my definitions for tribes particularly in this book is the systems that we grow up in. Whether it’s a family system, the educational system, the religious system, the political system, whatever it might be, really have such a powerful influence on us especially early on, right, because we know from the study of brain science that from in utero to five, six years old, so much of what a child takes in gets, you know, filed in the subconscious. And then begins running their lives as adults. So these systems are really powerful and the closer the system, the stronger the engagement with the system the more powerful they are. So our family of origin. We grow up with certain rules and certain guidelines and certain beliefs. And as we get older if we’re awake enough and we’re doing this work, we start to really question those beliefs and rules. And at midlife, I think, one of the real gifts of midlife at least for me and for a lot of women that I’ve spoken to is that your suck it up muscles go slack. And suddenly, you know, you start to realize, ” Wait a minute, I don’t want to get up at 7:00 in the morning.” This is a very common one for human beings, interestingly enough.

I don’t wanna get up early and I’m not gonna judge myself for getting up early. If I sleep until 8:00 or 9:00, I’m gonna decide that my body wants to go to bed later and get up later. And who made up this rule that said, you know, “The early bird catches the warm, and, you know, if you sleep late you’re lazy or you’re irresponsible or whatever?” I hear a lot of people talk about that. So I talk about challenging…paying attention to the rules that were created by the tribes we grew up in and/or high schools have tribes. When you think about the cliques in high school, colleges. Sorties have tribes. Our workplaces become tribes and what are the messages? How are we not living authentically? We go back to that and with that, another theme in the book is how our relationships change. The loss of friendships, the loss of certain connections maybe to family members, how our relationships change as we grow and evolve because they will. Some of them will change. Some marriages will end. I talk about a very close friendship for many years that ended and needing to end it consciously together as a partnership. And I talk about revisiting my marriage and really looking at my relationship with Michael and some of the things that we were doing that were influenced by the tribes we grew up in that needed to change. And I think that’s a big topic that comes up at midlife that causes us to face one of the most difficult losses we face. And that’s saying goodbye to people we’ve loved and been in relationships with while they’re still alive and we just know the relation has to end.

Bob: Yeah. I know a married couple who ended up getting divorced and what was interesting…So they had children pretty young, early 20s. And then when their kids went off to college, suddenly there was nobody in the house but bam and it’s been a long time. And all of a sudden, they recognize they had nothing in common anymore. They wanted different things from life and they hadn’t had the opportunity. They didn’t have the time or the space to talk about those things. In fact, the guy I know didn’t even really wanna think about those things and she had been thinking about those things. Finally, she had the opportunity to try to talk to him about it and she realized they wanted very different things from life. So they realized they weren’t compatible anymore and they loved one another and in some ways, it was a loss. It was even a loss to me because, “Oh, here’s my friends. They’re not together anymore and, you know, we’re never gonna get together as a group, you know, with them.” In other ways, I was very happy for…especially her because she knew what she wanted. He just wanted the same. So I was very happy for her that she got to do the things that she wants to do that he would have held her back from. But then I also felt bad for him because he wanted things to stay the same. And because she didn’t want that anymore, he was having a loss that he was really out of control of. He could have changed to be what she wanted but that wouldn’t have been right either. So it’s very interesting that we see these things but we…not only do we lose friends and lose groups of friends. And these tribes that you talk about, but we see our lives change because they’re splitting up or, you know.

Cheryl: Yeah. That’s a really good point. I mean, and that happens a lot. I mean, I hear from so many women who say, you know, “I’m reading these books. I’m doing this work. I’m becoming more awake and aware. And how do I get my husband or my partner on board?” Because it’s sad. You know, sometimes we outgrow people and sometimes every soul has their own spiritual path. That’s what I always tell people. You know, we’re souls. We’re not human beings. We’re souls, we’re in a physical body. It’s my belief anyway and we all have our own spiritual paths. And, honestly, for some people, their spiritual path is to stay the same. Like, they chose to come here for that reason and we need to respect that. And so sometimes it does mean friendships and/or relationships. And that’s a great point that I didn’t even think of which is, how it then influences us because suddenly you don’t have the couple to hang out with anymore in the same way. And I think we see that happening more and more as we get older into midlife.

Bob: Yeah, that’s right. All right. So we’re talking about youth, career, tribes, the forth one. So now we’re gonna get into things that certainly the Afterlife TV audience is a little more familiar with and we’re talking about loved ones who pass. We’re talking about loved ones where we have losses, like we were just talking about. In this particular case, it would be loved ones who pass. You talk a lot about a good friend of yours, Debbie Ford, and you talk about that in the book. And you talk about her life because she comes up where it keeps reminding you of what an impact she had on you. But not just her life but also her passing had on you. So, what do you wanna say about loved ones?

Cheryl: Yeah. I mean, so losing Debbie was…Debbie was a real catalyst for this particular period of my life, this hero’s journey that I go on, that I didn’t realize till I got to the end and went back to edit this journal. It was like, “Oh, for crying out loud. This has been a hero’s journey.” And, yeah, when Debbie died, it was a very…it was a surreal experience for me because we were close, we were colleagues, we were fellow writers and teachers. We had done teaching together and workshops together and television. We were both on Oprah together and so that when she died I saw her a couple of days. The last time I saw her was two days before she died and she, you know, she said to me along with, “Take more vacations.” You know, she said something really powerful. She said listen, you know, “Right now it doesn’t matter how many bestselling books I’ve had. It doesn’t matter how many fans I have on Facebook or followers on Twitter. All that matters is my son and what’s gonna happen to him, you know, my loved ones that I’m leaving and where I’m going from here.” And that was really potent because I felt like I was at my own deathbed. You know, we had lived such similar lives and then she also said, “Stop doing things that bore you,” which was really bizarre, like, just out of the blue. And we talked about that and it stayed with me and I realized…I remember thinking when I got in the car to driving back to a friend’s house that I was staying. I remember thinking, “Well, this, you know, I’m entering that stage in my life where I’m gonna start to lose people.” You know, I’ve since then lost my father and lost my cat and lost some other friendships.

And so, yeah, it’s part of that. We are invited, I guess, sometimes forced, but invited to build a relationship with the loss of the physical presence of people. And, you know, thank God for your work, Bob. I mean, really, I can’t tell you…first of all, I keep a stack of “Afterlife”…answers about the “Afterlife” in my library because I’m always giving that book out. I think it’s such a beautiful gift for people who are grieving and your video on suicide. I mean, I just posted that yesterday on Facebook because somebody was really struggling, and I went and found it. And, I mean, it’s just enormously, we don’t talk about these things enough and people really struggle and they suffer in silence in the most horrible ways. And so your work has been so helpful to me. You know, when I lost my dad, I mean, I just…I knew he wasn’t really…his physical body was gone, but that his consciousness and his spirit was around me. And I think that we are invited to build a relationship to…we’re invited to enter into a relationship with loss in a different way. And for me with Debbie, you know, that was…it was an important part of this particular journal because it really, you know, not only did it…was it instrumental in me rethinking how I was working and how I was living. But also, it was instrumental…It was teaching me how to survive the loss of a love, somebody you really deeply cared about that you can’t pick up the phone and call them. You know, and it’s like just so weird. I mean, sometimes I still, I think, “Oh my God. I wish Debbie was here,” because we used to coach each other and, “Wouldn’t I love her wisdom about such and such right now,” you know.

Bob: Yeah. I mean, since writing this particular journal you lost Debbie, you lost your father, but probably friends along the way. One of your early losses was your friend Lucy, right?

Cheryl: Yeah. I mean, she was the first one. First time I was up close and personal to death in ’91 and it was such a gift because I actually got to be with her when she died. She didn’t have any family and up until that point I’d been terrified of death, let alone being with a dead body and she gave me such a gift. You know, it really…it was a sacred experience to actually be with someone when they took their last breath. And she was in her 80s and she had lived a full life just like Louise. I mean, I also, you know, we lost Louise this year.

Bob: That’s right.

Cheryl: But Louise was, you know, also lived an incredibly full life and was ready to go as was Lucy. So that was different, and it was an interesting experience, a really lovely experience because the both of them were willing to talk about dying, and the dying process. And most people who get older, again, the older generations don’t. We don’t talk about death and we do people such a disservice because if we were to talk about it and prepare for it, it could just be a very sacred experience. And there’s a lot to be said, you know, about that topic. We should do another whole podcast sometime about how do you prepare for…how do you be with people when they’re dying, you know.

Bob: Yeah. I mean, a lot of people tell me they gave a copy of answers about the “Afterlife” to their friends who was terminally ill and they knew they were soon to pass. And that their friend was very fearful of death, but they didn’t know how to talk to them about it. So they gave him the book and said, “Read it if you want. Don’t if you don’t.” And that usually led to conversations afterward.

Cheryl: Which is such a gift and what’s wonderful about that book is I love the format, the Q&A format because you can give it to somebody who maybe would be like, “No. No. No. I don’t wanna talk about death.” But you just leave it with them and they can open it up and, like, choose where they wanna, you know, what they wanna read about.

Bob: Yeah. That’s right.

Cheryl: It’s a great resource in that way.

Bob: I think it’s a great conversation that anybody can have with their friends and family members. You know, for many people, it would be very odd and strange but if you can get over the discomfort of starting that conversation with somebody maybe just ask them. You and I and Mellissa and Michael have had this conversation about, you know, how do we want to die. What do we want to happen after our deaths? Those kinds of questions that a lot of people don’t know when somebody dies. They don’t know what it is that they want. Do they wanna be cremated, buried? Do they want a stone? Do they, you know, what do they want?

Cheryl: Who do you want coming into your house? Like, you know, I remember our lawyer, our state lawyer saying to us, “Okay, you’ve just died. The both of you have just died, who’s gonna have the key to your house to come in to see everything that’s in there?” And that was like a big wake up call. Like, Holy mackerel, who do we want? Like, who’s, you know, if the both of us were to go and if one of us were to go, who are we gonna call upon to be there for the other? Because I know, you know, I mean, I know we’re gonna talk about pet loss, having lost my Poupon, my cat just a couple months ago, you know, it really just put death in a very different perspective. Like, you know, the grieving of that was incredibly painful and I needed support. And, you know, just thinking about who you’re gonna turn to for support should you lose a loved one. Just the other day I was having a conversation with a very close friend, someone I’ve known for over 30 years. And she said to me, “I’m so afraid of my husband dying. He’s so important to me.” She said, “But I know that if he died, I’d be on a plane and I’d be at your house.” Because I know that’s where I’d wanna be and I just was so touched by that. I thought, “And I would want you here,” you know.

Bob: That was really nice. You know, it’s sweet awful. We’re talking about the Five Faces of Grief. This is just five things that I came up with that four of them really came out of Cheryl’s new book “Waking Up in Winter: In Search of What Really Matters at Midlife.” That is not a book about grief but certainly, within her journal talking about her own life, these are things that, obviously, stood out to me. And then the fifth one was very interesting because just as your book was coming out, you lost your pet, Poupon. And Poupon is a cat that you had for 10 years and he obviously had a big presence in this book.

Cheryl: Yes, he did.

Bob: And so anybody who reads it will recognize how important he was in your life. In fact, you were making decisions about your career and the changes partly because you wanted to be able to spend more time with Poupon.

Cheryl: Mm-hmm. Yeah.

Bob: And this is true for a lot of people. A lot of people feel this way about their pets and we recognize that our pets don’t live a long time when you think about it. So tell us about what you have to say about this fifth face of grief when we’re talking about the loss of pets.

Cheryl: Well, yeah. I mean, like May Sarton who wrote about her dogs and her cats in her journals over the years and the loss of them, I did not expect to be, you know, at ten and a half years, Poupon was ten and a half years old, I didn’t expect to lose him. It came on very suddenly, like, it often does for animals who instinctively hide when, you know, they hide their illness when there’s something wrong because in the wild they need to protect themselves. And then we don’t find out until it’s really advanced and we found out that he had a tumor in the middle of his chest. And within, you know, really within two weeks, that was it. We needed to put him to rest so that he wouldn’t suffer, and I had no idea. And he died just about a year after my father died. So I had just completed the year of firsts, you know, on the anniversary of my dad. And a week later Poupon died and animals are interesting beings. I mean, I think some animals are true soulmates who come into our lives very intentionally to teach us a lot about life ourselves. And who also come into our lives because there’s something they’re gonna get. You know, I think Poupon was…he was born outside, found outside. I think he was born from…I think he was feral, he had a feral mother, was very frightened when we got him, took him. He was very, very young, came out of foster care. That’s how young he was and, I think, I was a mother to this little being that really taught him how to trust and how to feel safe. And he taught me a lot about being a mother. I don’t have children. He gave me that experience, some experience of joy that you have in nurturing this little being. He taught me a lot about boundaries, a lot about stopping and playing and resting and having fun. And I had no idea how hard the grief would be when I lost him, and I know you lost Libby.

Bob: It will be on February 1st. So that anniversary is coming up.

Cheryl: Yes. So that anniversary is coming up and you had a similar relationship, wouldn’t you say? I mean, he was like…she was a soulmate to you, right?

Bob: Oh, my goodness, yeah. I mean, you know, Libby was, you know, with the exception of Melissa, Libby was, you know, the biggest thing in my life. And those two ladies made up most of my day. I would think about them all the time and spend most of my time with them. Now, Libby wanted things…the great things that she brought to me was having at least two walks a day. And, you know, at the beginning and for many years, you know, a good decade, we’re talking about, you know, 45 minutes or 60-minute walks twice a day and they weren’t quite as long as she was getting old. She died a year ago when she was thirteen and a half and our walks were shorter, but we would still have them. And that got me out into nature and help me…she balanced me not just through that but just like by being around. A big hugger. I would hug her, kiss her all the time and it’s interesting that these are the things that I recognized I really missed. And I’ve talked about this before in the show but as you touched upon, I had no idea how much that was going to shake me, that passing. And I think part of the reason that it does is because all of us and so many people who listen to the show or like this, our pets are family members and they’re in our lives all day long. I’ll just give an example. When my father passed, I didn’t live with him anymore. So he wasn’t part of my everyday life and, obviously, a big part of my life but when he passed it was just…I wasn’t used to him just being there all the time. When Libby passed, “Oh, my goodness.” You know, everything changes and as you know, you know, you’re constantly…when you have a pet. And especially you spend a lot of time with them, you’re always thinking about them. What their needs are.

Well, you know, all I have to do this. I have to take her out. I have to feed her. I have, you know, you have these rituals that sometimes they create, right? So part of the void…we always experience the void when someone passes. Part of the void is just that they make up so much of your day and now it’s not there anymore and you have to fill that with something.

Cheryl: Yeah. Well, and their love is pure. You know, I remember I was talking to, I think, my therapist after Poupon had died and I was just really in so much pain. And I said to him, you know, “There wasn’t a day that went by that this being didn’t bring me joy. Like, we didn’t fight.

Bob: Yeah. That’s right.

Cheryl: We didn’t, you know, I projected a lot on to him like I think we do with our pets, of course, but the love is pure. And the relationship is just…it’s the closest we get to unconditional love, which is a powerful experience for us humans. And then like you said, they are woven into the fabric of our lives and so everything I do every day I catch myself even now and it hasn’t really been that long. But, you know, I’ll be doing anything. You know, I’ll be getting in the car and I’ll think about how I used to think about Poupon. And like, you know, when I was gonna get back and how I don’t have to think about that anymore. I’ll make tea in the morning and I’ll go to take out the almond milk. And he would always come running and urting. He didn’t meow. He urted and he wanted his own almond milk, or I would take a bath. And, you know, he would always sit on the windowsill next to the bathtub. And I remember also, Bob, and I think you brought up a really important point. I remember thinking, “This is so much harder than when I lost my dad.” And then feeling so guilty about that. Oh, my God, but the reality is this was a soulmate. He was like our child and he was somebody that I cared deeply about and thought about every day, all the time, whether I was home or not. And suddenly when they’re gone, it feels like there’s just like all the air has been sucked out of the house and there’s this presence that’s no longer there. And, I mean, I do wanna say to people listening, “It does get better. It absolutely gets better.” And because in the beginning, it feels like, “Oh, my God, this is gonna take me down.” But it absolutely gets better and slowly over time we begin to appreciate the lessons that we brought to each other. And as you know and I’m not there yet, but I count on you, you know, their spirit lives on and is present with us. I just think part of the grieving process for me is still…I’m just still grieving his physical presence and…

Bob: And companionship.

Cheryl: And companionship, exact…I mean, I catch myself so many times during the day, I’ll just start to cry and I’ll think, “You were my little companion and you’re not here. And I can’t believe I’ll never see you again in physical form,” you know.

Bob: Now, there’s another side to this face of grief that I’m not sure I’ve ever heard anybody talk about. I know you and I both felt it and I remember, you know, I remember feeling it. I’ve gone through it. You know, 10 or 11 months later, Poupon passed and I remember you feeling it and then feeling guilty and you do. This is what happens. You feel this thing and then you feel guilty instantly, which is when our pets pass. And this is true for human beings, especially if you’re a caretaker of something. There is also…for lack of a better word, there’s also a certain freedom that comes from their passing. And if you’re a caretaker, well, we’re all caretakers of our pets. So then all of a sudden you’re able to do things and this is what I mean by freedom, that you weren’t able to do before. One example, you know, you and Michael come up and we hang out and the typical thing was, “Oh, It’s such and such a time. I need to get back to Poupon.” That was just, yeah.

Cheryl: Yeah. I got to feed him. I got, you know, just don’t wanna leave him there for too long. Yeah.

Bob: And then all of a sudden, you know, you’re here and you go, “Oh, you know, we don’t have to do that anymore.”

Cheryl: Or we took a trip together.

Bob: Yeah. We went away.

Cheryl: I mean, imagine what it was like when, you know, when our animals were here there was always…not only did we have to prepare for them to be well taken care of, which we did. But then we were thinking about them while we were gone and we were missing them. And feeling bad and hoping that they were okay. And all of a sudden there is a relief that you get, a relief that I felt of, “Oh, I can stop worrying.” And then I feel guilty for the relief.

Bob: For the relief.

Cheryl: Exactly.

Bob: I mean, even things like you can have flowers in your house. Before you had to be very choosy about which flowers because if there are poisonous Poupon might have eaten them or chewed them. So many of those things.

Cheryl: Yeah.

Bob: Also, there’s that side to it, too. I bring it up because I want people to recognize that they’re not the only ones who might think these things. They’re natural feelings. Also, nothing to be guilt…feel guilty about. I don’t think we could take that guilt away but…

Cheryl: But I will say this about that guilt because I was reading. There’s a wonderful book called “The Grief Recovery Handbook for Pet Loss.” There’s also “The Grief Recovery Handbook.” But for pet loss, in particular, I remember when I was reading that book where the author said something like, you know, “When the guilt comes up and it will, just ask yourself, was there any malicious intent behind whatever it is you’re feeling guilty about?” And when the answer is, “No,” you know guilt isn’t the appropriate response. It’s something else and it’s probably grief. And I just really remember that because there is relief. Poupon was a handful. He was a soulmate. He wasn’t an animal. This cat got into everything and was a hunter and he wanted to live the way he wanted to live. And we were gonna basically bend ourselves around him. And so there’s been a huge weight off of my shoulders not having to worry about him but, of course, I would give all of that up to have him back.

Bob: That’s the point there. Yeah, exactly. So that’s another side to pet loss that I think is important to talk about. So those are the Five Faces of Grief that I came up with: youth, career, tribes, loved ones, pets. A couple of other things. If we just take a couple more minutes because actually, we’re doing pretty good on time. I just wanted to ask, do you talk about, in the book, leaning into your purpose? It’s a big part of your book, of course, because you keep asking yourself about this particular question. And it had a lot to do with the career aspect, what we’re talking about. What did you mean by leaning into your purpose?

Cheryl: It’s a good question. I forget where I said that in that book. When I started to really pay attention to Debbie’s question after I had sort of gotten into the grief part, when I started to pay attention to, “Stop doing things that bore you,” I had to really look at what aspects of my work in particular no longer really fed me or challenged me or stimulated me in some way. And I remember there was somebody and it might have even been you, Bob, I remember having a conversation with someone and I know it was a man who said to me…I was talking, for example, about, you know, the loss of being on stage in front of thousands of people and, you know, doing keynotes because there is some magic in that, the connection with the audience that I would love. But that, you know, there were just certain things I didn’t wanna do anymore. And somebody had said to me, “Listen, the reality is when you master something, when you’ve done it a lot and you really know what you’re doing, after a while anything great gets boring. And in order for us to grow, we need to be stimulated and we need to engage in new activities.” And so in paying attention to what bored me, what I realized was by starting to let go of some relationships, some activities, some elements of my work that were no longer feeding me. For example, there’s a big difference between giving a 90-minute keynote, which is really supposed to be more inspirational and motivational even though I never liked those terms.

But that’s really…you can’t go deep with people, I decided that what wasn’t…well, what fed me more was doing smaller retreats for like 50 people where we could spend a weekend together and really talk about important issues and really help people. And so by looking at that, I began to get clear and clear about what my purpose is here. I mean, first and foremost, my purpose is to grow and evolve as a spiritual being. That’s my definition of my purpose and I think it’s a useful one for most people. In addition to that from my work perspective, I’m here much like Louise Hay. Louise Hay said, “I’m here to help the people.” And that’s what I’m good at and I like helping people. I feel fed by that and whether someone is struggling with a relationship or career, or their health, or their business, now, I’ve got a big business background. I work a lot with CEOs, you know, helping them to grow their companies while they’re growing themselves. I love that work and my purpose I sort of…I naturally began to lean into more of my reason for being here as I started to let go of things that just weren’t top priorities anymore.

Bob: Yeah. And I saw when you started to get into that, that work or going to CEOs, I mean, it just fed you. Oh, my God. You start talking about, you light right up, you know, where’s the other stuff? You’ve been there, done that. You ever done it.

Cheryl: Yeah. And I do wanna say this because I think this is important. Every time I write a book, I don’t know if you do this, but every time I finish a book, at some point I ask myself, “What did that book have to teach me? What did the writing of it and the book itself have to teach me?” The big lesson of “Waking Up in Winter” is the importance of learning to wait, to sit in limbo, to dismantle one’s life, to release the things that maybe no longer feed us and just wait with the space. And I think this is a midlife conversation, wait with the space and allow what’s next to come to us. And if we’re clear about who we are and what’s important to us and if we’re clear that we wanna feel alive, we don’t have to figure out how to do it, but that we want more aliveness and that’s really ultimately what this book is about, wanting more aliveness. Then it’s like, you know, a power greater than us lines up to support us and brings to us opportunities. And one of the opportunities I write about was being introduced to angel investing, which, you know, was something you’re right. I mean, I suddenly joined this group of professional angel investors and started investing in companies, and started working with some of the CEOs to support them and working with other members to choose the companies that we would invest in. And every time I would go to a meeting or have lunch with a colleague, I would leave feeling invigorated and energized and excited. And that’s what became my guiding force, was what’s giving me energy, what’s making me feel alive, what’s stimulating me intellectually. What calls to me energetically and says, “Do more of this.” And I think that’s a really good thing to pay attention to in midlife.

Bob: Now, I think so, too, and you were learning. You know, when you started to go with that group to sort of hang out, you were learning so much from them. And it’s one of the reasons, it’s a good…it’s just a good introduction for me to say this, it’s one of the reasons that I don’t feel bad. I know there’s a lot of people who love this show and I know there a lot of people love who love what I do and I haven’t stopped. I’ve just taken a break, but I’ve taken a break for the same exact reason. I’m learning a new craft which is screenwriting.

Cheryl: And you have so much energy. Like, you light up, too. Like, you started to talk about that, I’m like, “Whoop, there you go.”

Bob: Yeah.

Cheryl: You paid attention. This opportunity came to you and you grabbed ahold of it and it’s been…seems like it’s really been feeding you.

Bob: It feeds me in so many ways, obviously. You know, I love writing, but this is a whole new way of writing and I’ve had so much to learn. And, you know, I’ve been working with a mentor once a week and I’ve learned so much not just as a writer or a screenwriter but as a storyteller. And I see myself…I know you see yourself as a writer. I see myself as a storyteller more than anything. So, anyway, and the reason that I brought that question up, leaning into your purpose, you gave the exact answer that I expected you to give. It’s perfect but it’s also, I think, what led you into writing this book. Putting out as a memoir, as a journal. Well, I liked what you did with it. I think in the rewrite of your journals was you wrote it so that it sounded like you were talking to me or, you know, talking to the reader.

Cheryl: Mm-hmm. Well, because a lot of times, I mean, in a journal I’m talking to myself.

Bob: That’s what…Yeah.

Cheryl: Yeah. So it sounds like I’m talking to you because that’s what journal writing is and you’re right. You know, when…the energy I felt when Michael said, “Why don’t you just publish a journal,” is the energy I still feel and, you know, will probably I have the next journal. I mean, there is a journal after this one that continues on and I’ll probably edit that and put that out at some point, too, because I have the energy for it.

Bob: I know a lot of people in reading your reviews are inspired to either start or get back to journal writing as a result of reading, which is a really nice thing as well. I’m glad you wrote it. You know, I think it seems more natural that a woman would really relate to it, but I know that I’m not the only guy who really enjoys…not only enjoyed but got a lot out of this book. And maybe partially because of the career that you’ve had. You’ve had a career that any man and I’m saying that because we know the gender inequality that exists, you’ve had a career that any man would have been like thrilled to be able to have. And so when you have a career like yours, you’re…when you’re speaking, when you’re writing, you’re speaking to both genders, really. You know how it feels, too.

Cheryl: I think, yeah. I mean, I think if you’re a guy who is really at midlife, too, and is really questioning the direction that you’re headed in and feeling like some things aren’t working and you’re not sure what will, I think, I mean, some of the emails I’ve received from men have been actually some of the most beautiful emails. So, I think, it does speak. You know, it is, my audience is primarily women, a high percentage of them, but I think it does speak to men. It speaks to us as human beings who are looking for something just deeper and more authentic in life, really.

Bob: That’s right. So people can get this book anywhere?

Cheryl: Mm-hmm.

Bob: Certainly, it’s on Amazon. You can get it at bookstores which is, you know, that’s not always possible anymore but you certainly are. HarperOne is the publisher?

Cheryl: They’re the publisher, yeah.

Bob: Great. You enjoy working with them.

Cheryl: Yeah. They’ve been great. They’ve been wonderful. They’re really wonderful. Yeah, my editor is terrific and the team there has been really great.

Bob: And they were perfect for this kind of book, I think, really is well suited for…to put out a book like this.

Cheryl: Yeah. Yeah. I mean, I’ve been published by Hay House, of course, and, you know, I’m still part of that family. It’s an important family to me. This particular book was different than what they typically published and so I just felt like it really needed a different publisher this time around.

Bob: Well, thank you, Cheryl, very much for being here today.

Cheryl: Thank you. Thank you, Bob. I always love talking to you.

Bob: Everybody, thank you so much for listening. Again, you’re listening to the Afterlife TV. You can find us at and I’ll be seeing you soon, okay? I hope you’re doing well, too. Thanks. Bye-bye.

Afterlife TV is presented by Afterlife Investigator & Psychic Medium Researcher Bob Olson, who is the author of Answers about the Afterlife: A Private Investigator’s 15-Year Research Unlocks the Mysteries of Life after Death.

Check out Bob Olson’s other sites: (a directory of hundreds of psychics & mediums by location with reviews & Instant Readings) & (his personal recommended list of tested psychics and mediums) or visit Bob’s Facebook Page. Bob also has a popular workshop for psychics and mediums at

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