Episode 18: Living with Conviction
HANNAH: Hello everyone, welcome to another episode of Friends Missing Friends.
Today I talked to Toby Dorr, who is a bestselling author and founder of the Unleashed series, where she inspires women to escape their emotional prisons and find purpose. Her memoir Living with Conviction was released in 2022, and it’s a beautiful testament to the deep and meaningful friendships that she made during her time in prison, including her friend Lisa Montgomery. Lisa was executed by lethal injection on January 13th 2021, and was the first woman to be executed by the Federal government since 1953. Toby and I talked about unexpected sisterhood, deep friendships, and the trauma and grief of losing her friend Lisa.
I got so much out of our conversation, and just loved talking with her. I hope you enjoy.
HANNAH: It's funny because one of the first things I thought of after I read your book was sisterhood. And then I saw that that's actually in your subtitle.
TOBY: Yes. Yes.
HANNAH: Unexpected sisterhood. Yeah, I thought you captured that so well, in your time in prison, just how you connected with the other people and even the little details of like, you put on a talent show and you decorated for Christmas.
TOBY: Yes.
HANNAH: Yeah, yeah. I don't know if you want to speak about that a little bit.
TOBY: Of course, there's my friend Lisa, who was executed and that was just so traumatic. And that's definitely a story of friends missing friends. But you know, also, all the women that I had these deep relationships with in prison, you know, there's one there's two of them that I am in contact with and the rest, I don't even know where they are. So, you know, that's another friend's missing friends thing. There's somewhere out there in the world, but I don't know where they are or how to find them. So, yeah, you know, those friendships that you make in prison is so odd because, I mean, you live together, you sleep together, you shower together, you eat together, you cry together, you're together, together, together, together. It's almost like you're married. It's almost that deep of a relationship with all those women. And so it's a lot deeper than a regular friendship. You know, it's there's something more to it.
HANNAH: Absolutely. And I think you conveyed that really well in your book, and like when you were talking about “my two Lisa's”, so Lisa Montgomery and then your other friend Lisa who you called George. And you said you basically spent all your time together unless you were in your rooms. So what would you end up doing on a daily basis?
TOBY: We would just sit and talk or if we had an opportunity to go to class we go to crafts but there's really nothing to do. So you just sit and talk and you know, there were we might go outside three or four times a week and we would just walk in a circle around this teeny little on this teeny little path, you know, in a little yard that's about the size of somebody's backyard, and we just make a million circles and just talk so I mean, that's all you did is just talk you just, there was no activities to do. But you know, just be together and, and share your lives.
HANNAH: Yeah, it definitely hits me as being very different than the kind of friendship in like, day to day life where you go to work and you live at home. That feels very separated to me. It's very separate. I feel like for the most part I live parallel lives with my friends. And you know, you get coffee you got to schedule it, you know, or but
TOBY: And when you do that, you know when you go have coffee with your friends, you don't nearly get into the depth of where you are in that moment because there isn't time and you're busy and you might have 30 minutes you might have 45 minutes and so you just get through you know, what are the kids doing today and you know, what the weather's like and what I'm working on at my job and you don't really get into the meat of how people really feel, and in prison that's all there was to talk about was how we really felt and how we, what we thought about our lives and what we thought about each other and what we thought about the people in our lives, and all that we had was that stuff that was deep inside of us because there's nothing superficial in prison. You know, you don't talk about getting your hair done or having a coffee. It's there's just none of that happens. So everything just by default becomes so much deeper and more meaningful and more profound.
HANNAH: Yeah it kind of strips it. It strips your life bare to the essentials.
TOBY: Yes, that's exactly right. And I think that's a good description of prison too. You know, prison just strips you bare to just the inner part of who you really are. That's all you have left when you're in prison. And if you're lucky enough, you can focus on that and, and find ways that you think you can bring that forth when you get out of prison because going back to superficial relationships and casual relationships. It just never did work for me after prison because those things are not important. So I have a few people in my life that I have these really deep, deep relationships with. And if you're not a person that I can be deep with then, you know, I just don't take the time because I've learned what you can receive from an investment that's so much deeper and casual friendships just really don't have value to me anymore.
HANNAH: Yeah, I agree and I feel like it can be hard to find those friendship sometimes. Where you really get down to the core.
TOBY: It is really hard, especially you know, today in the world, so many of us care about where we live and what our zip code is and what car we drive and what we wear and where our kids who go to school and how our hair looks and how others perceive us. And so when those things are important to you, you can't really get deep down into who you really are and let that come forth because the people you're with, that's not what they're into.
HANNAH: Yeah. Yeah, absolutely. I was wondering if I could read a short portion?
TOBY: Sure.
HANNAH: The other Lisa turned out to be the infamously Lisa Montgomery mentioned by my guard during suicide watch. I studied Lisa carefully. I saw nothing frightening. Both indicted, Lisa and I showed up on the evening news on a regular basis. And that drew me to her. We were members of the high-profile criminals that the media loves the sensationalize club.”
So that strikes me that's such a specific situation to be in where the media is just like hounding you.
TOBY: Yeah, and you know, everything you do so the media couldn't talk to me when I was in prison, but they can show up on my court appearance and they go, you know, today Toby looks sad. Today. Her eyes were downcast. Oh, and I think she might have a new pair of glasses, you know, and it's like, oh my gosh, really? That's not news. But you were so scrutinized, and Lisa Montgomery, even more so than I, I mean, the media loved to put these photos of her in the news that made her look like this heinous animal, you know, that had no redeeming qualities at all. And I think that that picture was taken the night she was arrested.
And, of course, you know, she's in a stressful situation. And there were so many other photos of Lisa, but the media never use those because they made her look like a real human being. And that's not what they wanted to portray. And, you know, so Lisa and I would both watch the news in our prison day room. After one of our media appearances, and it would be so funny because we would be like the leading story on the news. Oh, Toby Young went to court again today. And it's like, that's not news. But to them it was and you know, and you were the headlines in the newspaper and everything was scrutinized. And at one point I fell and broke my leg and you know, when I walked into the courtroom, and I was on crutches, and you could just hear the gasp in the courtroom, and you know, I know they probably thought I got in some big prison fight or something, but I just slipped and fell.
HANNAH: Yeah. You mentioned that it drew you to her that must have been like a catalyst to really grow closer to have that in common right away.
TOBY: Yes. Because, you know, the other women that we were in prison with, they never made the news. Their cases weren't these big cases that were on the news all the time. And so really, it does draw you closer together because you can commiserate with each other and you know what it's like to be this headline sensation over and over and over again, and how you just never feel like you have any peace and so that really did draw us together. And I believe that the Lisa Montgomery that I knew is the Lisa Montgomery that could have been if the world would have done what they needed to do and watch out for her as a child, as an adult after she had suffered the horrific abuse that she'd suffered as a child still as an adult.
If someone would have noticed that she was so broken and made it possible for her to go to counseling or to get on the kind of psychotropic drugs she needed to be on or psychiatric drugs, I should say psychiatric drugs that she needed to be on. I think she would have been the woman that I knew and loved. And inside prison, you know, it was such a structured environment. And I think Lisa's life was pretty much disarray you know, her whole life, disarray and chaos and pain. And inside prison it was so structured and regimented and she didn't have to make a single decision. She didn't have to decide how she was going to what she was going to cook for dinner or how she was going to pay the electric bill. There were no decisions for her to make. And, and she was under psychiatric care and on some different psych drugs that dealt with the issues that she had. And so I believe the world could have loved the Lisa that I knew, but they never got a chance to know her because she was not offered those things, you know in the world outside.
HANNAH: That's absolutely heartbreaking.
TOBY: It is you know, and Lisa's crime was horrific. There's no justifying it. There's no excusing it. There's no making it better. But I don't think that the world is a better place because the government killed my friend Lisa. It's the same place it was when she was in jail. You know, it's not a better place. It didn't make the world better. And now, Lisa had four children and 12 grandchildren, and those children and grandchildren, it's been a year and a half since she was executed and they have suffered so much. I mean, it has been traumatic for them.
And so what we did to try to right a wrong was to create another tragedy for another set of families, and we can't undo the tragedy that the first family went through or felt, but now we've added tragedy for many more people. So we've just exponentially made this crime bigger, instead of remedying it and it just breaks my heart. I don't think the death penalty makes us a better country, or makes us a better society. I think it makes us a society that needs help and needs love. Because Killing is killing. Whether you do it in the name of the government or you do it in the name of a crime, it's still killing someone. And leading up to that when the day when her execution date was set. I couldn't breathe you know I read it in the newspaper, the headlines, and it was just I never thought that day would come. I mean, Lisa was the first woman they'd executed in 70 years and the government had not done any executions for like 17 years. And now all of a sudden they're coming back and they did like eight executions in two months.
And you want to do something, you know, and I tried, I talked to the media a couple different times and I tried to let people know that this was not, just, it was not kind there was not an answer to a problem. It was just a bigger problem. And you know, I think some people listened but not enough and not the right people and then you know, and then her attorneys got COVID so they put her execution on the you know, on hold. And we were so happy because we thought you know, that would give us time that we could try to reach somebody who could stop this. But it didn't stop it and then you know that her attorneys filed all these stays because Lisa was so horrifically abused as a child, and that was never brought out in her trial.
And I don't know why her attorneys didn’t bring it out, but I believe if they had she wouldn't have gotten the death penalty. People would have seen how broken she was. And you know, it just it was just so heartbreaking and so her attorneys filed all these appeals, you know, trying to bring up this horrid abuse that she suffered at the hands of her stepfather and all of his friends and her mother, and there was dozens of appeals, you know, and then one would be overturned and we go oh, okay, well, that one's overturned, but there's still these other five and then one would get overturned and we go oh, okay, but you know, it's only four days away, and we've still got four of those appeals in place.
And then the next one would get overturned and then the next one would get overturned and then the day of her execution, there were still two appeals that had not been overturned, and she was supposed to be executed at six o'clock in the evening. And the courts worked all night to try to get those last two Appeals overturned. And at about 10 o'clock at night, one of them was overturned. And that left just one appeal still in place. And, oh, we were just you know, it's already four hours after she was supposed to be executed. And we prayed and prayed and hoped that they'd leave that last appeal in place and that when the sun came up the next day, my friend Lisa would still be here. But just after midnight, they overturned that last appeal and at 1:31am on January 13, you know, Lisa was executed.
I've lost children, and I've lost both of my parents and those were hard. But this losing Lisa was something in a totally different family because someone's going to kill her and there's a date and a time set and the watch that date and time count down and count down and count down. And you and then there's appeals and you get your hopes up and then they're overturned. And then there's another one and it was just this roller coaster for two months. Just this huge roller coaster and you know, my Lisa would not allow any of her friends or family to be there and I wanted to be there so bad. And back when we were together in prison I always promised her that I would be, but she wouldn't allow it because she didn't want any of us to suffer by watching, because Lisa was still my beautiful friend Lisa at the end and caring about other people.
And so I wasn't there, and her children were there but they weren't inside they were outside the prison picketing and you know holding signs to try to save them off. And so I wasn't there. And I don't know exactly how it all happened because there were no cameras in there and I didn't see but she was executed seven and a half hours after her scheduled time. And I wondered, you know, was she laying on that table that whole time just waiting? Was she, did they bring her in and take her out and bring her back and take her out? I mean what was it she was going through those last seven hours? And I'll never know, but she's a peace now I think and so maybe it'll all be okay someday.
TOBY: But it's still just feels like such a loss for so many people and it's just hard. It's still hard. And George and I are very close and I see George I saw George every week for quite a while and now I moved out of town and I haven't seen her for a while but George and I would just get together we would just cry you know for those whole two months because we felt so helpless and there was nothing we could do. And you know, I wrote to Lisa and some of my letters got returned one time because I used a blue envelope and you know they're not allowed to have colored envelopes. You know, there's just so stupid. You can't have a colored envelope and you're going to be dying in a week you know?
So, you know, we just we just tried to be together and hope that she could feel us loving her from a distance but it was a terrible thing. And I think I think we need to end the death penalty because what the family feels there's no excuse for putting the family through that on purpose. And there's been innocent people who've been executed and we know that and just executing one innocent person should negate the death penalty forever. Because you can't undo executing you know it just so that's something that I feel very strongly about the death penalty and I hope that in talking about Lisa that I can maybe present to people aside of the death penalty that they never thought about that what it's like for the people who love the person that's being executed.
HANNAH: And I mean and just from what listening to you talk and also reading your book, I mean, I really felt her. Her spirit.
TOBY: Yeah, so that's what I wanted. I'm so glad to hear that. And, you know, I had some book reviewers on a on the Instagram book tour, who have been reviewing my book and one of them she pointed that out and she said Toby talks about her friend Lisa Montgomery who did this horrible crime and I felt like I knew Lisa and I can understand loving Lisa and I thought that was just beautiful that she wrote that in her book review because that's really what I wanted people to feel. I didn't want to preach at them about Lisa I just wanted them to show the Lisa that I knew.
HANNAH: Yeah, I thought you did a beautiful job of that.
TOBY: Thank you. Thank you.
HANNAH: I one thing I was wondering is, there's so much in the book about time that you spent with Lisa. But if you were just to think off the top of your head if you have any particular memories--
TOBY: Yeah, you know, this one day we were all feeling kind of down because it had been winter and we had been able to go outside and at the prison we wrapped together we went outside rarely so when we got to go outside it was such a great joy and such a relief to be able to go outside. And so we went outside on this one particular spring day. And it was just a beautiful day. And we, the clover was blooming and so we made crowns of clover. You know how you tie the clover together and make a crown when you were a kid and we all made crowns of clover and we put them on our heads. And we wore them when we were walking around the track. And you know I even wrote a poem about those crowns of clover and we were holding hands and walking around the track and we're in our crowns of clover and we saw a bird some birds building a nest in a tree and it just felt like we were part of the world again. And that day was just like a breath of fresh air.
HANNAH: It's such a beautiful image of you wearing the crowns and holding hands.
TOBY: Yeah, it was almost like we were little girls again. And we didn't have to worry about what society thought of us because here we were sheltered in this prison yard and we could just be free we could just put on our crowns a clover and just skip around the track and hold hands and that's exactly what we did.
in prison, I wrote in a journal all the time, I filled about 25 journals while I was in prison. And I wrote a lot of poems and I wrote a lot of stories about, you know, the women I was in prison with and, and, you know, just my life and, you know, I think writing there's something about writing and it's different if you type something into the computer is totally different than taking a pen and writing on paper. So I always recommend to women, if you're struggling with something, pick up a pen and a piece of paper and just write and don't care about what you write, just write what comes out because sometimes I think things I think your hands connected to your heart, and your keyboard’s connected to your head. So when you're typing something that comes from your head, but when you're writing it comes from your hand. And you can write some of the most healing things without even realizing that they're inside of you. And so you know, when you're feeling really down or you're really sad, just grab a pen and a piece of paper and just write whatever comes out. And you might be surprised at where it takes you for me it took me to writin’ a book.
HANNAH: And you also created journals for women in prison, right?
TOBY: I did. Yes. I have a set of workbooks, three workbooks. It's called the unleashed series. And they help women rebuild their lives and go through you know, personal development and then becoming a part of a healthy community and then finding your gift and taking it out into the world. And I'm also writing a leadership series of workbooks too for women who really want to, you know, start their own movements and become a leader and, and really make a change in the world. So those will be coming out within the next year.
HANNAH: Oh, that's amazing. Wow. That's beautiful. And that's, I mean, the impact you're having, it's gonna be like a ripple effect that you might not even realize or ever really, truly know. But I know it's going to change people’s lives.
TOBY: Well thank you. That is my purpose. And I hope that you know, long after I'm gone that this book will still people will still be picking it up and learning something. That's my dream.
HANNAH: Absolutely. And, and you also are sharing Lisa's spirit and her personality and her soul with the world.
TOBY: I'm letting people see a side of Lisa that they never would have known. And, you know, I'm working on a second book and I'm not quite sure what form it's going to take but Lisa is going to be a big part of that second book, whatever form it takes.
HANNAH: Yeah, is there anything on your mind that you haven't had a chance to say yet, or?
TOBY: If there is someone in your life who has made a mistake and they are in prison or jail, write to them, just at least write to them. You don't have to commit to go visit them. But receiving a letter when you're locked up is a game changer. It's means the world to people and a letter takes just a few minutes of your time. Even if you just send a card and sign your name. Do something don't just let people sit in prison in jail and forget about them because they deserve more than that. They I think people are redeemable and that none of us are our worst mistake. And I also think that all of us have prisons. I had a prison before I ever went to prison. I just didn't know it. And so you know, really my message is that we need to escape our prisons. And if it's a spiritual prison or an emotional prison, then change your something in your physical life that will make a difference in how you feel. And what you know how you believe. And if you're in a physical prison, then the only thing you can do is to change the way you think and feel and then that way you can find your freedom because you can't, you know, get out of prison, but you can find freedom behind bars and that's what I did.