Listening in With … Cheryl Richardson

Judith Orloff

Cheryl Richardson, a best-selling author and public speaker, is considered one of the founders of the life-coaching industry. She’s known as an advocate for what she calls “extreme self-care,” nurturing ourselves in an empowering way that naturally enables us to better nurture others. Her latest book, Waking up in Winter (HarperOne, 2017), chronicles the start of the inward journey she took at midlife to discover what really matters most to her. Here, she talks with Unity Magazine editor Katy Koontz about how taking such a hero’s journey changes your life and why the effort is worth it.

Katy Koontz: Does midlife require more courage than any other phase of life?

Cheryl Richardson: It certainly requires a different kind of courage. I think of it as the hero’s journey, which has three stages: the descent, being in the mystery, and then the ascent. You emerge into a new life based on who you’ve become after facing the descent and the mystery.

The more I have the courage to sit with not knowing and not to try to make things happen, the richer, deeper, and more satisfying my life becomes. To take this hero’s journey, we need to be willing to reassess our lives and ask ourselves, What’s working and what isn’t? Have I stayed in a job I can’t stand for longer than I want to? Have I stayed too long in a relationship I know I need to leave? Have I taken care of myself financially, or do I feel at the mercy of outside forces? If we’re brave enough to begin that reevaluation process and then sit with the not knowing, then the life that emerges is always far greater than the life we could’ve created for ourselves.


KK: It sounds like trust is a big part of this.

CR: Yes, and this is where the spiritual part comes in. For me during this reevaluation, everything was up for grabs. It’s a life-altering, foundation-shaking experience to be reevaluating your connection to everything, including the Divine. So yes, it requires a lot of trust, but there will be a period where you don’t trust anything. You don’t know what to trust, and that’s really scary.


KK: We often ask for the courage to take action, but you’re talking about the courage to surrender and allow. It’s the opposite side of that coin.

CR: That’s a beautiful way of saying it. You’re right. It’s not the courage to push through. It truly is the courage of surrendering to and building a relationship with the unknown.

My process wasn’t a self-help adventure where I sat down with a list of questions. It was more like being thrown down a rabbit hole, not knowing where I was going to land and bumping into things along the way—including dissatisfaction, confusion, and also joyful experiences. For example, I realized how much more I love being outside in nature than I was aware of before. The journey is about looking at what do I love and what don’t I love, what works and what doesn’t work, what is feeding me and what is starving me?


KK: Was there anything you could hold on to during this?

CR: Once I realized I wasn’t supposed to know what’s next, I saw it as an exciting spiritual adventure. I kept journaling, dug deep, and got to know myself better—and I paid attention to what gave me energy and what didn’t. That really became the way I measured things. Did an activity or a relationship energize me or leave me feeling drained? Did I look forward to doing certain things, or was I dreading them? These are the kinds of daily mini-evaluations I began to make as part of my purposeful meandering period.


KK: And then you just followed that, using it as a litmus test?

CR: Exactly. So for example, I explored my interest in angel investing—helping to fund companies that are doing great things in the world. I was invited to attend a meeting of a group of angel investors and I left feeling incredibly excited and energized. I thought, Okay, I have no idea where this is going, and I’m not going to make it mean anything. I’m just going to take the next step because this is giving me energy.

I slowly began to make the shift from being a gladiator to being more of a chalice. Instead of grabbing ahold of a business idea or setting a new goal, I decided I was going to allow myself to gently surrender to life and see what fed me. And if something did, I would take the next step. I wouldn’t make a global decision to get myself into anything deep. I still don’t do that. I just tiptoe through my life because I want to be available to what the universe is bringing me in the moment. Being honest about what feels aligned with the most authentic parts of who we are can prepare us for a really kick-ass second half of life.


KK: I love that rather than seeing yourself as a stroke victim, you say you’re a “stroke triumphant,” capable of seeing the gifts in that experience.

CR: When people look at those who are disabled or recovering from anything, they look at what they lost instead of what they’ve gained. If your cells are no longer performing what’s normally defined as the regular job of the brain, consider what those cells might actually have been inhibiting before. That is now the gift that becomes available.


KK: There’s a great metaphor about unity and oneness in that.

CR: Exactly. As humanity, we are one animal. We all play different roles, but how well do we support each other? The body’s cells cooperate; humanity does not. That’s why we’re in the situation we’re in today.


KK: That’s not a decision that comes to us naturally in our youth. It’s best done with a little more perspective.

CR: You need a lot of experience under your belt, yes. Midlife is really about self-care and pulling inward. Women have menopause. Men have andropause. Some people will take sabbaticals during this time, and others will downshift into a less stressful job that requires less of them for a while so they can actually be present to this stage.


KK: Is more courage needed now because of the crazy state the world is in?

CR: I’ve read books from the 1800s that talk about the dire circumstances of the day. The details are always different, but the human experience feels challenging every step of the way. I think the greatest amount of courage that’s needed right now is to support the demise of the patriarchal system, which clearly doesn’t work. We’re experiencing the breakdown of that system now. Commitment to our inner life is crucial, as is having the courage to not be seen by the external world for a while as we turn our vision inward. When you care more about yourself as a soul than you do your career, your social media status, or your reputation, you can’t then help but care more about the state of the world and the state of humanity.


KK: What sort of advanced spiritual tools or practices do you rely on to accomplish that?

CR: Sometimes the most advanced tools are the simplest—like meditating. Go sit someplace where you will be uninterrupted and set an alarm for 10 minutes; train yourself to be the master of your own mind. Don’t let yourself get up. If you do this every day for two weeks, it will radically change your experience of the world and that will dramatically change your life.


KK: Do you do a particular type of meditation?

CR: Nothing fancy. Ten minutes focused on a word, and often I don’t even use a word anymore. I’ve been practicing consistently for the past three years, and now I use this practice whenever I’m feeling overwhelmed or irritable. I sit down and set an alarm for 10 minutes. It works every single time.


KK: So the overwhelm and the irritability is just your soul’s way of getting your attention?

CR: There you go. I like that. I also use journaling as a spiritual tool. Many people are intimidated by journaling, but it can be as simple as making lists of what matters, or taking photographs. I spent one whole year on journaling about pleasure. Every night before I went to bed, I wrote down five things that brought me pleasure that day, like staring at a beautiful rose in full bloom, watching a tree sway in the wind, taking a hot bath with essential oils, using a new face moisturizer that smells awesome, holding hands with my husband while walking to dinner, playing with my cat—whatever it might be. That became my spiritual practice, really capturing those moments of pleasure and seeing them as food for the soul. The soul loves pleasure! The soul is here to experience life fully and deeply, not to conquer it.

Every night, I journal on Instagram (my username is CoachOnCall). I post a picture and I list five things I’m grateful for. I invite my followers to post their gratitude lists too. It’s beautiful. Not only am I fed by what I’m grateful for, but I am also fed by what other people are grateful for. I do that sometimes on Facebook as well.


KK: I love that practice!

CR: You could keep any kind of list— the five ways I was patient today or five signs of beauty I noticed. I like to think of myself as a curator of beauty. Every now and then, I’ll post something beautiful on Instagram, which brings me to another fun spiritual tool: taking photographs of things that touch your soul.

I took the most amazing picture of a hummingbird drinking from a flower in my garden, and that nourished me all through winter. Right now, I’m looking at the way the sunlight is coming through the window and lighting up an amethyst crystal in my office, and I want to take a picture of that. Taking pictures is a way for me to combine presence with beauty.


KK: I love the idea that journaling doesn’t have to be complicated.

CR: Louise Hay used to say this all the time: “I’m a very simple woman, and simple practices dramatically change my life.” She was right. Everything that I’m mentioning is about making you more present and connecting you to your inner world so that you learn about what matters most to your soul. Those are the advanced spiritual tools we most need to be paying attention to.


KK: Are courage and faith intertwined?

CR: Yes, particularly when you’re on a hero’s journey and you are in transition. It requires faith—putting your trust in something that you can’t really see. As I went through that mystery period, I also reevaluated my relationship with God. I put my faith in things like nature—for example, the full moon rising and casting the most extraordinary light. That’s divine energy that connects us all. I think we need to give ourselves permission to let our faith change, to let it grow and evolve. I think that takes great courage because you have to question the platform you may have been standing on for a long time.


KK: After all, even Mother Teresa questioned her faith.

CR: All of the great saints had crises of faith. As our spiritual selves evolve, our relationship to the greater oneness evolves as well, as does our relationship to God, to the Creator, to the Universe—however you define it.


KK: You’ve often talked about passing up good for great, but in this example, you’re not talking about achieving more but connecting more.

CR: As we get older, connecting with ourselves, with each other, and with something greater than ourselves becomes more and more important. I don’t have a lot of patience for cocktail-level conversations. It’s rare that you find me in a party where I need to make small talk. I find it a waste of energy and time. I want deeper conversations.


KK: Go deep or go home.

CR: Exactly. Everybody I talk to says they want that.


KK: Are we all called to take the hero’s journey at some point?

CR: I think we’re all invited to take it, but we don’t all accept it. The question is how present you are for your life. That’s why the hero’s journey starts with the recognition that life as you’ve been living it is no longer working. You’re dissatisfied. And then sometimes the hero’s journey is thrust upon us. I see this all the time. People say, “I lost my apartment, my job, and my marriage all in the same month,” and what that tells me is chances are there were signs along the way that the person ignored.

I’ll ask if they were happy in the job they lost, and they answer, “God, no! I’ve been miserable for years.” Then I’ll ask if they did anything about it. They say, “Well, I couldn’t afford to leave my job.” That’s never a valid excuse. You can’t confuse tough choices with having no choice at all. We all have choices, and sometimes making those choices is difficult. But if you don’t pay attention to the stirrings of your soul that are telling you something isn’t working anymore, then you run the risk of things collapsing around you. Then you get what I call a cosmic rug-pulling, where suddenly the rug gets pulled out from under several areas of your life.


KK: But even then, there’s still hope.

CR: The universe always responds when we pay attention to the soul. I wrote about this in The Unmistakable Touch of Grace. There is this divine power ready to support your efforts. You don’t have to be worthy enough to receive it or do anything to deserve it. Grace is your birthright. The minute you start looking inside and paying attention to your inner life, this divine force begins to rally behind you.

You see signs that you’re not alone and that the more you trust this divine energy, the more you are cocreating with it all the time. This divine energy has only your best interest at heart. You’ll develop such a strong connection to your inner life that you will feel you’re living from the inside out. Most people, in contrast, are living from the outside in, feeling yanked around by the nose.

By the way, I still feel that way multiple times a week. This is called being in human form on earth. We just have to be aware of it and keep pulling ourselves back from the ego and back to the soul that really, truly wants to experience life in the most glorious way.


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CHERYL RICHARDSON is the New York Times best-selling author of seven books, the most recent being Waking up in Winter, published by HarperOne in December. Richardson was the team leader for the Lifestyle Makeover Series on The Oprah Winfrey Show as well as the first president of the International Coach Federation.