Oprah Shares “The Letter from Glennon that Freed Me”
September 21, 2023
Glennon Doyle:
Welcome back pod squad. Today is a big day. Buckle up butter cups because today we have Oprah Winfrey.
Abby Wambach:
Oprah Winfrey baby.
Oprah Winfrey:
Whoah whoah whoah. Here we are.
Abby Wambach:
Yes.
Glennon Doyle:
Here we are.
Oprah Winfrey:
Oh, wow. There is sister.
Amanda Doyle:
Hello, Ms Winfrey.
Oprah Winfrey:
Hey Abs. How you doing?
Abby Wambach:
So good. You’re so wonderful.
Oprah Winfrey:
This is going to be fun. So fun.
Glennon Doyle:
It is. Thank you for spending this time with us.
Oprah Winfrey:
Oh, I wanted to spend this time with you. I’ve missed you so much.
Glennon Doyle:
Oh, I missed you too.
Oprah Winfrey:
I miss you so much. I just remember our first gathering under the oaks at my house, the Super Soul Sunday. Oh my God, that was so fun.
Glennon Doyle:
I know.
Amanda Doyle:
Magical, it was.
Glennon Doyle:
It was. And here we are. And we get to talk about your new book. And I have so many questions. I wanted to start with one of the strategies that you talk about in the book about happiness, happiness strategy that I am now trying to implement in all areas of my life. Can you talk to us about detached attachment and how you discovered this strategy through your experience with experience Beloved, detached attachment?
Oprah Winfrey:
Oh my goodness, Beloved, one of my greatest teachers of all times. What I do know is that everything that is happening to you is there to teach you about yourself. And so even in some of my darkest moments, and recently I had a couple dark moments with bullying online, and I spent so much time going, “Okay, so now tell me why is this happening? What am I supposed to learn from this? And how do I detach myself from the whatever I was attached to?” And I start asking, “What was it I was attached to?” I was attached to the idea of whatever it was. I learned this through Beloved, I learned that this thing that I’d worked on for 10 years and so loved and wanted other people to feel the same kind of joy and understanding of what it means to come through being an enslaved woman and still be able to love.
Oprah Winfrey:
I was attached to the idea of people getting that and getting it in the same way that I was. And I remember after it bombed, it was so hard for me to say the word bomb for a long time, because when people would say, “It bombed.” I’d be like, “Did it really bomb?” Well, it actually did bomb. And I knew that it was bombing, and there’d been so much publicity about it. I was on the cover of Time Magazine and it was our beloved Oprah and all, more press than you’ve seen about anything. And it bombed. And I remember getting the call, it opened on a Friday night, and I remember getting a call Saturday morning saying, “It’s done. It’s over. You’ve been beaten by the Bride of Chucky.”
Glennon Doyle:
Oh, good Lord.
Amanda Doyle:
No.
Oprah Winfrey:
Yes. And I didn’t know what Chucky… I said, “Who’s Chucky?” And I said, “And who’s his bride?”
Glennon Doyle:
“Hopefully his bride is really famous or something.”
Oprah Winfrey:
Yes. And I went into a depression. I asked my chef that morning to make macaroni and cheese for breakfast, and I ate my way through it. And for a long period of time, I was stuck in that wall. And it was a conversation with Gary Zukav who said to me, “Well, what did you really want?” And I said, “Well, I wanted people to feel everything that I was feeling. I wanted the story to live in people’s hearts. We had lived many…” He said, “Well, I felt that.” And I said, “Well, I wanted more than you, actually millions of people to feel that.” And he said, “Well, if you wanted millions of people to feel it, you would’ve done a different movie, because this wasn’t a movie for millions of people. This was a movie for people who could receive it the way you want it to give it and to present it.”
Oprah Winfrey:
And so I learned in that experience that everything else that you ever do in your life is a gift or an offering. You do it with the purest of intention to be a gift in an offering. And if people receive it, they receive it. And if they don’t receive it, that’s okay, because your intention was to offer it as a gift. And so, that is how I learned to detach from my attachments.
Glennon Doyle:
So you’re still attached to the offering, because the complete detachment doesn’t work for me. I have no idea how to be detached from anything.
Oprah Winfrey:
Really?
Glennon Doyle:
Oh, yeah. But I’m learning from this, I’m learning in terms of the pod. All I can do is put everything into each hour with the guest, be in love with what they’re doing, and then let it go completely, walk away from that hour and never check again.
Oprah Winfrey:
That’s right. No expectation. And I’ve had to do this with my girls. Glennon, you’ve been so helpful to me with my daughters and helped me with an intervention with one of my girls who was going through multiple trials. And I now have 887 girls out into the world that I’ve put through school. All of them have my email address and still continue to contact with me with all their stuff, and different levels of people, girls succeeding in the world and managing their lives to the extent that I would want them to.
Oprah Winfrey:
And I learned, the sophomore year, one of my daughter girls who’d come here and was going to Wellesley and was having multiple mental illness issues and was miserable. And I remember saying to her, well, do you want to go back to South Africa? And she said, “No, I’ll just slug it out until my senior year.” And I said, “Slugging is not going to be good for either of us, because at the end when you graduate, there is no joy in the slug. There’s no joy in the slug. So I want you to be as happy as you can be now.” Anyway, she ended up slugging it out, and I learned in that experience that I wanted to go to Wellesley. I had wanted to be in the white dresses and the graduation and the whole thing. And so I convinced her to go to that school instead of staying in South Africa. And that was my desire, not her desire. And it turned out to be a miserable experience for her.
Oprah Winfrey:
And I learned from that experience, because there’s nothing that’s ever happened to me that I’m like, “Okay, what am I supposed to get for this?” To release all of my expectations about what anybody else, particularly the girls, would turn out to be, would do with the education, I offered the school, I did the school as an offering for girls to grow their own wings and to soar. And some grow, some don’t, some take harder to grow than others, some take longer to actually leave the nest and fly. Can I be okay with just the offering of the school? Can I just accept that, Abby? You see what I’m saying, right?
Abby Wambach:
Yeah.
Glennon Doyle:
Everybody who’s raising a teenager, a young adult knows exactly what you’re saying. Can we be okay with just the offering?
Oprah Winfrey:
Can you just offer it and whatever, and however they choose to receive it, be okay with that? Be okay with that and have no judgment about it. I would have to say that even now, not being attached to the outcome of anything that I do, I realize that I started the People’s Fund of Maui, because I was so interested for myself in finding out what is the best thing that could help people in this moment in time? The fires came you all, and in Maui, I was home that day and had been told that we were going to have to evacuate ourselves. And it was a scary time because how do you get all the animals out? I have horses and dogs, so which way are we going to go? Which direction we’re going to take? I’d gotten in the Jeep and gone down the road myself, because I didn’t trust all the reports to actually look at the fires myself to see where they were. And they looked really pretty contained.
Oprah Winfrey:
So I felt better about it after getting on the road and looking at them myself and say, “There’s one there and there’s one there and there’s one.” And they were saying to me, security was saying, “Well, there’s one six miles from us, there’s one eight miles from us.” I got in the car myself and went and looked and I felt better, and then decided to go take a hike, literally. And as I was coming down from the hike, I hiked up about two miles on the mountain, and then I was coming down, I started to notice it getting dark, but it was the middle of the day, it shouldn’t have been getting dark. And I was like, “What’s going on? What kind of cloud is that coming in?” And it turned out to be a wall of smoke on the other side that was Lahaina burning in the middle of the afternoon because the winds had changed and the fire came.
Oprah Winfrey:
During that time, we were still trying to figure out for ourselves, “Are we going to have to evacuate? What is going on? What is going on?” And when we realized the devastation that had occurred across the way from us on the other side of Maui in Lahaina, we were all just in the moment trying to figure out how I was, how to best serve, where are the shelters? Where are the people? Wherever. And so those first couple of days, I was literally going around to the shelters asking people, “Tell me what you need? Tell me what you need?” And at first it was just people needed underwear, people needed towels, people, they needed shampoo and being able to keep themselves.
Oprah Winfrey:
And then people started to call me, text me asking, “Where can we send money?” Well, I didn’t know. I said, “Well, I’m here on the ground. I don’t know where to send. Other than the Red Cross and the Humane Society, which I’d gone out and bought 300 pounds of dog food and taken by the Humane Society, other than that, I don’t know what to tell anybody.” So I said, “I will do some research myself.” I started researching. There were some people on the ground doing things, but nobody was getting money directly to the people. Dwayne The Rock had called saying, “I’m so sorry for what’s happening. Is there anything we could do?” We started talking about having a fundraiser, a telethon, a concert, and in those discussions realized, it’s going to take too long to do that, I said, “That’s going to take too long and that’s going to take too much money in order to have a good concert and do it in Honolulu because you can’t do it here.” I said, “That’s going to take millions and millions of dollars. Better to take that money and give it directly to the people.”
Oprah Winfrey:
In the meantime, my godson, Gayle’s son, Will sent me this article on Dolly Parton. Dolly Parton when this happened in her hometown, Gatlinburg had had a concert, and in that concert raised 12.5 million, she called it My People’s Fund. I called Dolly, I sat down with Dolly’s people, Dolly’s team, the head of her foundation, Jeff. I said, “Jeff, tell me how you all did this.”
Oprah Winfrey:
I was so excited, I went, “Oh my God. Okay, they were able to do that.” I thought, “Okay, what could we do if we built a team?” Put together The Rock and his team, my team, we decided we’re going to have to get somebody to manage the money on the ground. We called this firm EIF, we talked to them, we researched them, we negotiated the fee down, so that all the money other than what we were needing to pay people to actually be on the ground, was going to go directly to the people. I was so excited, makes me want to cry right now. I was so excited for the announcement.
Oprah Winfrey:
So I said to The Rock, “Listen, how much do you want to put in?” I said, “I think $10 million would be great to start.” Because anytime you go to a charity, somebody is raising money. If somebody donates $10 million, that’s a great start. And I have, on many occasions given $10 million, and people are always excited with that 10 figure. So I said, “Let’s start with $10 million and invite other people to join us.” I got up in the middle of the night in Hawaii after it was being announced. It was being announced at eight o’clock here, so it’s two o’clock in the morning, I was so excited. And I was hit with all of this vitriol, when I was hit with, “Why aren’t you paying for the whole thing yourself? And how dare you ask other people? And what’s wrong with you? And what didn’t your house burn down?” And all of the…
Oprah Winfrey:
Everything from I had a blue light and a laser, and I set the fires to, I set the fires because I was trying to… People were saying that I was deliberately doing this, because I was trying to get other people’s land. It was awful. And it made me so sad. It made me sad. But not just, it didn’t make me sad for myself, because it was like when I was on trial years ago for saying something bad about a burger.
Amanda Doyle:
Texas will do that to you.
Oprah Winfrey:
Texas will do that to you. And the defense attorney was yelling at me and saying, “You did this. This woman is a liar. And she did this to deliberately destroy my clients.” Well, a calmness came over me and I felt like, “Well, he is not talking about me. I know that that is not who I am.” The trolling didn’t affect my spirit, because I know that’s not who I am. I know that’s not who I am, so I don’t know who you’re talking about, but that’s not who I am. But it did make me very, very sad.
Glennon Doyle:
Of course.
Oprah Winfrey:
Because I thought, “Wow, this is what we’ve become? This is who we are?” You live in a country now, where you can say, “Let’s do a world of good for people,” and then you are attacked for that. And you know what I immediately start thinking? What is this supposed to teach me? And I thought of every kid, every time I’ve ever said the word cyber bullying, but didn’t understand really what that meant. I thought of, “Oh, this is what happens if you don’t know who you are, and the dark side comes for you.” The dark triad, as Arthur Brooks says. If the dark triad is coming for you and you don’t know who you are, you will get lost in it, you will get lost in the darkness.
Oprah Winfrey:
It made me so sad because I thought, “Wow, we live in a world where this can now happen.” But I was able to separate myself from it. And the thing that I’m most proud about myself is that I had prayer and then I sat and I did my gratitude journal, I normally just do five things a day. I think I did 27 that day, sitting on the porch, I cried a little bit and I wrote a little bit, and then I got up and I went to visit my neighbors who’d lost their homes up the hill and asked them, “What can I do to help you?”
Glennon Doyle:
So what were you attached to?
Oprah Winfrey:
I think I was attached to the idea. I was actually thinking this morning, Glennon, because I’m still going over it in my head like, “How did this happen? What was I thinking before?” I remember saying a prayer the night before, like, “Oh, G, let this work. Let this work. Hope this really works.” The difference between what Dolly was doing and what we were doing is that we have 10 times the amount of people. I remember thinking”, “Let this work.And I was thinking, “Okay, so I was attached to the idea of it being successful?I don’t know.” I still am trying to figure this one out. I still am trying to figure it out. Because on the ground where the people are actually receiving the help, the people are grateful, the people are thankful that there is a People’s Fund that’s saying, “We’re going to put money directly into your account. We’re not even going to make you stand in line and wait for a check.”
Oprah Winfrey:
Because we were told by the elders, Dwayne and I sat and met with the elders before and they said, “That’s not going to work in Maui. Hawaiians are too proud. They will not want to come any place and stand in line and look like they’re asking for money. But if you can find a way to just drop it in their accounts, they’ll take it.” So I don’t know. I’m still figuring it out, which is a good thing because I know it shall be revealed. And in the meantime, I just keep going forward.
Glennon Doyle:
You keep doing the work.
Oprah Winfrey:
Keep doing the work.
Amanda Doyle:
When you said, “I know that’s not who I am,” when in your life did you know who you were? If you look at the timeline of your life and if that triad came for you at any point, can you pinpoint when you would say, “You’re not even talking about me.”? Because I think that confusion comes when you’re not real sure, maybe they are talking about you.
Oprah Winfrey:
Well, actually, I’ll have to say, sister, I can call you sister, right?
Amanda Doyle:
Oh, I wish you would call me nothing else for the rest of my life.
Oprah Winfrey:
I have to say that, the epiphanal moment was on trial in 1998 for saying something bad about a burger. Because up until that point, you all, I was dragged every week by the tabloids, so the tabloids was my social media before. Stedman and I were dragged for everything. And the usual thing was, “Why won’t he marry her?” And, “Why is she so fat?” I have been, I think more than anybody else in this country, made fun of, ostracized. It was a normal thing for all the comedians to make jokes about me on their nightly shows. I didn’t go on David Letterman for three or four years, because he had done nothing but make these Ms. Butterworth jokes about me, “Ms. Butterworth, Ms. Butterworth.” Yes. And so I was a very different woman before that trial. That trial grew me up.
Oprah Winfrey:
And before that trial, I was always calling Maya Angelou crying about something that somebody said. And I remember one time I called her and I was in the bathroom crying, I don’t even remember what the thing was. And I was in the bathroom, door closed because people were in the house and I didn’t want them to hear me crying. And I was sitting on the toilet seat crying on the phone with her, and she said, “Stop right now and say thank you.” And I said, “Maya, but you not hearing what I’m saying.” And she said, “No, say thank you right now.” “Why am I saying thank you?” She said, “I said, say thank you.” And I said, “Thank you.” She goes, “I want to hear it, thank you.” ‘Thank you.” She says, “You say thank you, because God’s put a rainbow in the clouds. You just can’t see it. And when you get to the other side, you’ll be able to see that the rainbow was always there. So say thank you because you’re going to come out on the other side of it and you’re going to be better.”
Oprah Winfrey:
The answer to that question is, before this, I was thrown by everything everybody said, listen, somebody made a negative comment, I would try to track them down. I could get a thousand great comments and then one negative comment and I’d be calling them up, “Why did you say that?” And trying to convince them, “You shouldn’t have said that.” And then it was six weeks of being on trial, six weeks of having your truth tested. And we all know that that’s what trial is all about. And then I realized sitting there on the witness stand, “Oh, I have a really big life, so therefore I get the real trial.” But everybody has trials. People have trials of divorce, they have trials of job, failure, not succeeding, children, not raising children the way you wanted, they have trials in their life. And all trial stands outside of you to force you to be able to answer, “Who am I really?”
Oprah Winfrey:
It’s what we talk about in Build the Life You Want, that metacognition of being able to separate yourself from the feeling or the circumstance or the trial or the challenge or the difficult. That’s out here. This past week, going through all this online craziness stuff, I was like, “Oh, well, that’s out there.” Literally, I’m sitting on my porch listening to the birds singing, and that’s out there.
Glennon Doyle:
Yeah.
Oprah Winfrey:
That’s out there. How can I be detached from that?
Glennon Doyle:
It’s that scripture… I’m just thinking for the first time that this is what blessed are you when you’re persecuted is.
Oprah Winfrey:
Yes.
Glennon Doyle:
It’s because we’ve got these voices inside of ourselves that are always telling us we’re crap or we’re little… But then when it comes from the outside, when it really, really comes from the outside and you listen to it long enough, there’s a part of you that stands up for yourself.
Oprah Winfrey:
Yes. Because you know it’s not true.
Glennon Doyle:
You know it’s not true.
Oprah Winfrey:
The epiphanal moment, as you were saying, Amanda, sister Amanda, as you were saying, that moment when he’s literally holding up Time magazine and he’s saying, “You are influential, aren’t you? That’s what it says here in Time Magazine. So you deliberately used your influence.” And I’m thinking, “I wasn’t thinking about influence. Everything you’re saying is not true. It is not true.” And when I came down from the witness stand, I literally said to my producer, “Oh my God, you’re going to love it. I was on the witness stand for two days straight.” I said, “You’re going to love it up there.” She goes, “I don’t think so.” I said, “Oh yeah, because you’re going to get to figure out who you really are. You’re going to get to figure out who you really are.” And that was sweet. I say that was a big test to come to that realization, but I came away from that with a knowingness about myself that I did not have before the trial. That’s what the trial taught me, “This is who you are.”
Glennon Doyle:
This is who you are. So would you say now, when it comes, like it came this past week, are you able to recover faster? Because I think-
Oprah Winfrey:
Oh, absolutely.
Glennon Doyle:
It’s beautiful to hear that you still… When people say, “Just develop a tough skin and it will never affect you.” That’s not real, is it? It does hurt at first, right? Would you say it?
Oprah Winfrey:
Yes. It hurts at first. I was stunned, but I was more stunned, disappointed and saddened that this is where we are in our country, that this could happen. There isn’t anybody who’s lived a straighter, more deliberately trying to be good life raised as a good girl, that whole good girl syndrome, all that stuff, there’s nobody who is paid more taxes, don’t have the offshore funds, not trying to get away with anything, literally just doing the right thing. And I was like, “How could this be?” It did not compute for me, so trying to understand that.
Glennon Doyle:
Is that what you’re attached to? Good? “I’m good.”?
Oprah Winfrey:
Yeah. That’s good therapy right here. That’s good therapy, right here in the middle of the podcast. This is fantastic.
Glennon Doyle:
One time when I was having a good girl breakdown because somebody said I was bad, I was talking to Liz Gilbert on the phone crying to her, and I said, “It’s like that Steinbeck thing.” I said, “Now that we don’t have to be perfect, we can be good.” And she said, “No, no, no. Now, that we don’t have to be good, we can be free.”
Oprah Winfrey:
Woo, fantastic, Liz. That’s great.
Glennon Doyle:
The good thing gets me.
Oprah Winfrey:
That’s what we’re all striving for, is the freedom, is the liberation. And what I’ve found is, you know what? Love liberates. And when you’re able to offer it and able to receive it, that’s when the deepest sense of freedom comes is when you can give and receive it openly with no attachment.
Glennon Doyle:
With no attachments. With no attachments. Speaking of love and freedom, I want to talk about your parents for a moment, if that’s all right. You lost your mother Vernita Lee in 2018 and your father Vernon Winfrey last year. You told me that after her parents died, Gayle said she felt unmoored, like she’d lost her anchor to the earth. And I have a friend who told me recently that her relationship with her parents was so complicated that her grief after their passing was tinged with a newfound lightness, like a first time freedom for her.
Oprah Winfrey:
And also freedom, yeah. I didn’t feel that. But can I just say this? That the email that you sent me after my mother passed was the most freeing offering, was the most freeing, was the most visionary, and was the most profound thing I’d ever experienced in terms of dealing with that passing. Because you said that she would now be able to finally see me, and that freed me.
Glennon Doyle:
I had this vision, Oprah, when I heard about your mom’s passing, and it was just like… And I had a vision of your mom being in a different place wherever people go, and her being able to look back on the earth, this is crazy, but true, Abby knows. And just seeing the whole planet lit up, just lit up, lights everywhere all over the planet, all lives that you had touched. And then I felt her seeing that for the first time, her impact, and then I felt, “Oh my God, then she will understand for the first time that she was part of that, that she’s going to be so freaking proud.”
Oprah Winfrey:
Well, you being able to put that in an email to me was the best eulogy, was the best sermon, was the best offering I received, period, full stop. I don’t know how that came to you. You said you were just sitting out somewhere and you just decided you were going to write that to me, and it changed me. It changed me, and I think it opened me to receive the spirit of my mother in a way that I had not thought I would. In Maya’s passing, still feel Maya, felt her presence, felt her with me, I felt her biding in me. I feel more Maya like now, and I hear myself saying things and moving through the world, and it’s my Maya-ness coming through. And I always felt that because I lacked a connection with my mother here on earth, that that would not happen, that wherever the spirits are, that she would not be a part of me and I of her, even though she had given birth to me.
Oprah Winfrey:
But what you wrote to me in that email opened the channel for me to receive her in a way that I would not. And so when I wrote to you and told you how you blessed me with that email, you blessed me, or meager words do not measure up to what you really did, was you opened a channel for me to be able to receive the spirit of her in a way that I would not have.
Abby Wambach:
Good job, Glennon.
Oprah Winfrey:
Good job, Glennon.
Abby Wambach:
Good job.
Oprah Winfrey:
Yeah. Did you know you did that?
Glennon Doyle:
No Oprah, I did not know that.
Oprah Winfrey:
I tried to tell you in the email, but-
Glennon Doyle:
Well, thank you.
Oprah Winfrey:
That’s what you did for me.
Glennon Doyle:
When was the last time, Oprah, that you had a sidesplitting laugh?
Oprah Winfrey:
Oh, I’ll tell you that Gayle and I have sidesplitting laugh, not sidesplitting, we’re rarely sidesplitting on the phone, but when we get together, there’s sidesplitting. I’ll tell you who, I have one of my daughter girls is a budding actress, and she, Thando cracks me up all the time. And she had just had a big skin breakout and had used some products by some famous person whose name I won’t mention. And she was just recently in the CVS store and sent me a text of all of this person’s products on display and she said, “Oh, there they go again, spreading zits throughout the universe.” “There they go again.” But she just… She is so funny that I just say her name and I start to laugh because she’s got… Because every time I text or call her, she’s like, “Mama, mama.” She doesn’t call me mama, it’s “Mama, mama.” So no, it’s with Thando.
Glennon Doyle:
So wonderful. Okay, there’s a part in your book where you talk about envy. Is there anybody, Oprah that you’re still envious of?
Oprah Winfrey:
No. It doesn’t exist for me.
Glennon Doyle:
Wow.
Amanda Doyle:
So good.
Oprah Winfrey:
Doesn’t exist for me.
Amanda Doyle:
Do you ever envy a version of yourself that you’re not yet?
Oprah Winfrey:
Doesn’t exist for me.
Amanda Doyle:
She’s a real varsity over here people.
Oprah Winfrey:
No, doesn’t exist for me. I feel like if I was envious of anybody, the way the law works of, coming back to you, I think I just would get slapped in the face immediately. Because guys, is there anybody who has a more awesome, incredible life?
Glennon Doyle:
No.
Oprah Winfrey:
When you think about… I hike a lot now and I’m always not focusing on where I’m trying to get to, but I consciously stop and take breaths and turn around and look at how far I’ve come.
Abby Wambach:
Damn.
Oprah Winfrey:
Yeah. That’s how I get myself to the top, not by focusing on the top, but looking back at how far I’ve come and say, “Whoa, you didn’t think you could make it to that point, you didn’t think you could get to the tree. We have a big tree out there in the center of halfway up, we call it the Hope Tree, “You didn’t think… Look at how you got there in 40 minutes. And it used to take you 55 and on the first day you did it, it was an hour and 38.” And so I look back at how far I’ve come and think, “Wow, I’ve already been farther than I thought I was going to make it today. I now think I can go a little further.”
Oprah Winfrey:
And the way I do it is I don’t focus on where I got to get to, I just focus on one step after the next step, after the next step. And I let that become the rhythm of my entire body. Just, “What is the next step? What is the next step? What is the next step?” And that turns out to be a great metaphor for living? Nobody, would I envy. Nobody.
Glennon Doyle:
And talk about just the next step. You say Stedman will have an outcome, plan, plan, plan, but for you-
Oprah Winfrey:
Oh, Lord.
Glennon Doyle:
You stay in the moment and let intuition guide you. I tend to over prepare, get nervous, freak myself out. Do you not prepare for things? Or you just, you bring your full self and you trust that you will know what to say, what to ask?
Oprah Winfrey:
For some things, I think you need preparation. For instance, I’m speaking at an event tonight, and for weeks I was thinking about, “What am I going to say?” I always know that by the time I get there, something’s going to show up for me to say. And so last night I started organizing that in a way that I could be concise, because for a graduation or something like that, you don’t want to be up there rambling. You want to make these points, these points, these points and get off. But I just have the confidence to know that I’ve lived long enough, I know enough things, I know how to talk, and if I have a central point to talk about, I know I’m going to be able to share that as an offering in a way that it will resonate and land with people. I feel confident about that. You should too, Ms. Glennon, because you are damn good.
Abby Wambach:
I keep telling her.
Oprah Winfrey:
You are so damn good.
Glennon Doyle:
Really?
Oprah Winfrey:
Just so darn good at that. So darn good at it. So you angst about it?
Glennon Doyle:
Oh, yeah.
Abby Wambach:
You’re doing better.
Glennon Doyle:
I’m playing with the idea that I can just be me. I’m not sure about it. I went into a meeting Oprah and I said, “What am I supposed to do?” And the person with me said, “Just be yourself.” And I said, listen, “I don’t know how much longer I can keep that up.”
Oprah Winfrey:
This is the funniest thing, because that’s really all there is. Listen, I made a career out of it. I made an entire career out of it. And the most comfortable space I’ve ever been in is sitting on that Oprah show for 25 years. I just was never more myself than with that audience every day. I felt like millions of people felt familial to me in a way, because I’ve reached a point where I felt comfortable sharing myself in a way that I would not be judged by people. And even if I was, I’d track you down and see why. But I know that there is no other answer. It’s a favorite jokey line of ours, whenever I’m going off someplace or going to be speaking or something big is happening, somebody in the family will say, “Just be yourself.” But I love you saying, “I don’t know how much longer that can work for me.”
Glennon Doyle:
Whatever the hell that means.
Oprah Winfrey:
It’s going to take you to the end, Glenn, it’s going to take you to the end, sister Glennon.
Glennon Doyle:
All right. I already asked you if I could ask this.
Oprah Winfrey:
What?
Glennon Doyle:
I want to ask you about a part in the book that made me raise my eyebrows.
Oprah Winfrey:
Yeah.
Glennon Doyle:
Okay. Made me raise my and I just want to read it to you and get your thoughts about it. It’s a part that Arthur Brooks wrote, not you. Okay.
Oprah Winfrey:
Okay.
Glennon Doyle:
So he’s talking about friends conflict and how to handle it. And he says quote, “Maybe your friends are religiously opposed to something about the way you live and you conclude that they are quote, ‘Denying your humanity.'” Okay, that’s in quotes, “Denying your humanity.” And he says, “We’re not talking about abuse here, just difference in beliefs.”
Oprah Winfrey:
Yeah.
Glennon Doyle:
He goes on to say, “This is completely self-defeating, because it leads to your loneliness and isolation. The solution in this case is humility.” Oprah, I got to tell you, had to put this book down-
Oprah Winfrey:
Doesn’t work for you?
Glennon Doyle:
I had to circle my room walking, Abby knows, circling the room, walking. What? Okay, my thoughts about this are, I think first of all, my queer self was triggered because I felt like the words religiously opposed, and then putting, denying your humanity in quotes made me feel like he was suggesting that denying your humanity was like a overstated, right?
Oprah Winfrey:
I don’t think he intended that, but go ahead.
Glennon Doyle:
Okay.
Oprah Winfrey:
I want to know what it is about that triggered you? What is it about that that didn’t sit well with you that made you feel somehow confronted?
Glennon Doyle:
Yes, something I was attached to.
Oprah Winfrey:
I was going to say, yeah. How about that?
Glennon Doyle:
Okay. I felt like it was written from a person’s point of view whose humanity had never been questioned. Because I felt like anybody who puts denying your humanity in quotes as if it’s not a real thing, is someone who has never felt what it feels like to have someone else’s religious views doubt your very divinity or your very-
Oprah Winfrey:
Reason to exist.
Glennon Doyle:
Reason to exist. And I thought, “Isn’t it interesting for a person whose humanity has clearly never been threatened in a way that makes him relate to that, suggests humility for the other person?” Because to me it feels like…
Oprah Winfrey:
Person who’s trying to deny your humanity should have some humility.
Glennon Doyle:
Should be humble about it. It was just an example of why sometimes reading a white man’s perspective gets tricky, because he’s suggesting humility for the very people I think, who should not be choosing humility. Because to me, he suggests that, if we do not be humble in that moment, if we confront the other person or we draw a boundary, then we will end up lonely and isolated. But the times I felt lonely and isolated are when I don’t confront the person, when I just say, “Okay, your difference of opinion or your belief I guess, is okay. It’s not a deal breaker between us.”
Oprah Winfrey:
Well, I think it depends upon what you are willing to sacrifice to get along with the other person. In my own relationships, I have perhaps sometimes chosen humility with my family. And in other times I’ve chosen divorce, I’ve chosen, “I no longer want to be a part of this relationship and I humbly take myself out of it. I humbly remove myself from being in contact with someone who feels that demeaning me or diminishing me or doesn’t see me for who I really am.” I think my interpretation of it is, you must sacrifice that if you really want the relationship with the person. And my experiences, I’ve chosen that I’d rather not have the relationship.
Glennon Doyle:
Yeah.
Oprah Winfrey:
Sayonara.
Glennon Doyle:
Same. I love that. I humbly will never see you again.
Oprah Winfrey:
I will humbly never see you again. Peace out. And I do mean peace, peace out. And that was a real hard one for me, because when I first started making money and my salary was published in the newspapers, I don’t even know how they got the salary, because I was like, “Really? I’m making that much money?” And I went to my accountant and go, “Is this true?” So you can no longer say to your family or all the people coming to you for money, “I don’t have it.” And I realized that when I first started making money, that I had been taking care of my family since. And everybody who’s listening to us right now, if you’re the one or certainly the first one in your family to succeed, you’re looking at Abby, you’re the first one in your family to succeed, you become the First National Bank.
Abby Wambach:
Yes.
Oprah Winfrey:
And this is the thing that I teach my girls starting in eighth grade, that if you choose to be successful in life, number one thing you’re going to have to manage is all your family and all the people who feel like that success is owed to them. And so for me, in the beginning, I did not know how to handle it because saying I didn’t have it when I was making 22, 25, $50,000 a year, I didn’t have enough to service everybody in the family. I distinctly remember that when I was in Baltimore, that everybody always only needed $500, my family members, they would need five, that was a number, $500. The day, and I do mean the day I moved to Chicago and there was a picnic at my mother’s house in Milwaukee, everybody needed 5,000.
Glennon Doyle:
Wow.
Amanda Doyle:
Cost of living in Milwaukee.
Oprah Winfrey:
Nobody asked me for 500, everybody needed $5,000. My half sister asked me, my aunt asked me, two cousins asked me, everybody $5,000. So I had to learn how to manage that in such a way that, wow, I felt so put upon so unseen for myself, the thing we’re talking about, so denied, my humanity denied by multiple family members who just thought I was their bank. And if you don’t do it, then something’s wrong with you because, “We’re family, we’re blood.” That whole blood thing, I don’t even remember… “Hey, Oprah remember me? I’m your cousin.”
Glennon Doyle:
“We’re blood.”
Oprah Winfrey:
“Hey, Oprah, remember me? Blood.” I actually had a fourth cousin, not third, fourth cousin say to me, “I was in the house the night you was born, now that’s got to be worth at least 25,000.”
Abby Wambach:
No way.
Amanda Doyle:
It’s like a monopoly set for all those who are there in the house, 25 for you.
Oprah Winfrey:
25. “That’s got to be worth at least 25,000.” Yeah, she did say that to me. She did.
Abby Wambach:
So how did you humbly remove yourself?
Glennon Doyle:
The time, dinner of a lifetime.
Oprah Winfrey:
I had the dinner of a lifetime, where I had all the family and all the friends and all the people. Because I got so tired of people seeing me as a bank. So I had a dinner of a lifetime where I brought the attorneys in and I did the contracts for people and I set up trust funds and I said, “This is what you’re getting and this is what you’re getting and this is what you’re getting and please don’t come to me anymore.” And then the people who came afterwards, I humbly removed myself from their lives. That’s what I did.
Glennon Doyle:
“Humble restraining orders for all of you.”
Oprah Winfrey:
“I humbly now remove myself.”
Amanda Doyle:
It’s all fun and games, but you said from ’86 to ’98 you had no family relationships, because you couldn’t actually be in a real relationship based on people because people were just coming to you all the time.
Oprah Winfrey:
All the time.
Glennon Doyle:
Which is sad.
Oprah Winfrey:
Yeah. Kind of sad. I did the thing guys where I wanted to have, one time when I first, I bought a farm in Indiana and I had this Currier and Ives idea of the Christmas and the trees and the sleighs and the dogs and the whole thing and I brought all my family together. It was the worst experience. Don’t, never do that again. That was the first and last time that ever happened. There was no… Nothing. Oh, no. Everybody was mad at every-
Glennon Doyle:
How quickly did you know?
Oprah Winfrey:
I knew as people were arriving, I could feel it. I could feel the tension. You know what I was feeling? I was feeling, “What am I going to get? What am I going to get? What am I going to get?”
Amanda Doyle:
Looking under the tree kicking the presents.
Oprah Winfrey:
“What did she get? And then she got more and she should have had more and…”
Glennon Doyle:
They hoped it was an Oprah’s Favorite Things’ Episode.
Oprah Winfrey:
Oh my gosh, it was interesting. But anyway, I think I’ve reached a point now where I feel a great sense of contentment in my life. Even when I was going through all this stuff last week, I was thinking, “Wow, I feel so good that I’ve reached the point of my mental spiritual evolvement, that even in the midst of crisis, I still know that I’m okay and I’m going to be okay.” That’s a wonderful thing. And that’s not gleeful happiness, but I am able to, in the midst of any trial, make myself happier.
Glennon Doyle:
I think that’s my favorite part of the book, is what’s really stayed with me too is the idea that happiness is not dependent on not having unhappiness.
Oprah Winfrey:
Correct. That you need it to balance. It’s the yin and the yang and it’s the cloudy days that make the sunny ones so great. I’m the opposite, I love cloudy days. So I think, “Oh yeah, you got to get some sunny days in there in order to get the clouds to come back.”
Glennon Doyle:
Yeah. Sunny days are bossy.
Oprah Winfrey:
Sunny days create too many expectations.
Glennon Doyle:
Yeah. They’re bossy.
Amanda Doyle:
Amen. The tyranny of the sun. Tyranny.
Glennon Doyle:
The sun is like, “Come out. You got to come out or you’re depressed. Come out.”
Oprah Winfrey:
That’s right. Or you got to do something, you got to have activities, you got to enjoy it.
Glennon Doyle:
The sun is like the epitome of toxic positivity, it’s like, “Settle down.”
Oprah Winfrey:
Exactly. But a cloudy day, a rainy day, wow, it’s liberation for me, no expectations.
Glennon Doyle:
Oprah, we love you. You are just… You’re my North Star and I am grateful for every single offering you make to the world.
Oprah Winfrey:
Can you get me my phone? Because I want to just see if I can find Glennon’s email. I have it. Where is it? I want to just read that to the people if I can see it. I had it for so long. I printed it out and I have it in my drawer, so that Glennon, I always in times of trial, can go back to it. See if it’s going to come up. I don’t know in this moment. It’s not.
Glennon Doyle:
It’s okay.
Oprah Winfrey:
Wasn’t meant to be. I want it to so much. So I thank you all for having me on here.
Abby Wambach:
You’re the freaking most best in the whole wide world.
Glennon Doyle:
She’s the most best. That’s what Oprah is.
Oprah Winfrey:
Got it.
Glennon Doyle:
Oh, okay.
Oprah Winfrey:
This is written 11-26-18 and the subject is on mothering love. “Hello my friend, my sister, my example, I’m sitting on a balcony on Cayman Island and right at this moment writing an essay about the word mother, what that word really means, how it’s less to me a fixed identity we can be or not be and more an energy we can offer or not offer. The essay is about how some of us who can check the box mother never really learn how to offer mothering love and how others of us who don’t check the box, harness it and offer it widely and wildly. The essay is about how much better off the world would be if we gathered up mothering love and used it like a floodlight instead of a pointed laser aimed only at the few we’ve been assigned.
Oprah Winfrey:
As I’m writing this essay on the balcony, my sister just sent me a text that says, ‘G, Oprah’s mother died. She was 83. I wanted you to know.’ I just got that text a minute ago. I would never presume to guess what your relationship was like, how complex it was and is to be your mother’s daughter, what your feelings are this week, what your feelings have been or will be. I just wanted to say, that you are my example of how to gather up mothering love and use it as a floodlight to illuminate and warm the world. You are my and the world’s best example of grace, which means that we can somehow give what we’ve never even received. I don’t know much, but from everything you bravely say and kindly don’t say, I’ve gathered that you didn’t get the mothering love you deserved and needed as a little girl and a grown girl.
Oprah Winfrey:
To me, that is what makes you a miracle. It is a miracle that somehow you took the broken pieces that she put in your hands, all of them and you spun them into gold and opened your hands wide and offered that gold back to the world. Which is not just a gift to the world, it is a gift directly back to your mother, because you worked with what she gave you, ensured that her legacy through you is gold. With your help, your mother’s legacy is gold. What a gift. If there is a Heaven, she can see that now. She can see that her miraculous daughter somehow, somehow turned her offerings to gold. God, bet she’s amazed and grateful. Well done, good faithful, miraculous, badass, servant. In your corner forever.” My friends, that is my letter from Glennon that freed me and I thank you.
Glennon Doyle:
I love you.
Oprah Winfrey:
Thank you. Love you.
Abby Wambach:
We love you very much Oprah. Thank you for coming on.
Oprah Winfrey:
Thank you.
Glennon Doyle:
Bye.
Oprah Winfrey:
Bye.
Glennon Doyle:
Okay, pod squad, we’ll see you next time.
Glennon Doyle:
If this podcast means something to you, it would mean so much to us if you’d be willing to take 30 seconds to do each or all of these three things. First, can you please follow or subscribe to, We Can Do Hard Things? Following the pod helps you because you’ll never miss an episode and it helps us because you’ll never miss an episode. To do this, just go to the We Can Do Hard Things show page on Apple Podcasts, Spotify, Audacy or wherever you listen to podcasts and then just tap the plus sign in the upper right-hand corner or click on follow. This is the most important thing for the pod. While you’re there, if you’d be willing to give us a five star rating and review and share an episode you loved with a friend, we would be so grateful. We appreciate you very much. We Can Do Hard Things is produced in partnership with Cadence13 Studios. I give you Tish Melton and Brandi Carlile.