S17 BONUS EPISODE: Rachel Cargle on reimagining the life we want to live.

28:23And it really was a gift. Do you think you were brave? Is that a word that you would attach to your decision? Yeah, I think it was brave. I would certainly call myself brave because of the fact that I didn't have any resources of my own. I knew that I was coming out of a situation that was very safe and very financially secure. I had no degree. I had no money saved. I hadn't necessarily been working. His mother had a daycare. I'd work there sometimes. And I had never paid a bill before. You know, I went straight from college to getting married, living with my husband. I had no real world experience.

28:58So I think I was a bit brave in assuming that I could figure it out. So the end of your marriage prompted the first phase of your self-exploration, what did that consist of for you? It was a lot of curiosity, a lot of reading, a lot of studying. I think one of the first steps to understanding ourselves is to study others who we find value in or who move us. And so I took a lot of time studying other women in particular who reflected to me how I wanted to live in the world, whether it was because of what they were able to do or who they were, the personalities that they had, the characteristics that they took on, their personal style, how they related to their communities.

29:43The first leg of my deep self-exploration really started in studying and looking at clues from other women on how could I exist in the world? What options did I have? What was possible? And I think that's what definitely led me to be a feminist because I was just so incredibly moved by all of the powerful women I was reading about and learning from. I think what is so interesting and helpful about that first failure that you've chosen is that I imagine there will be people listening to this who do feel stuck in a marriage or relationship, but they don't feel that their own instinct about it is enough of a reason to leave or dismantle it.

30:25And I really value you saying that actually that seed, that sort of knocking seed is very much worth paying attention to. Because to go back to your previous point, there's a kindness to it. To know yourself is also to be able to show up for others and to enable others to live their most authentic lives. Absolutely. And I mean, the truest truth, if you think about it, is that he wasn't right for me, then I'm not right for him. And it's unfair to keep him in a space where it's very clear that we're not right for each other. And it's kind to release people to go and find what's true for them. Because if I really had the feeling that he is not right for me, then it wouldn't make sense that I would be right for him.

31:09And I told him in the moment that I told him that I would be leaving the marriage, I said, you deserve someone who feels sure of you. and I am excited for you to experience that type of love because it just can't pour out of me because it's not true for me. And so I would like to also feel that way towards someone and it's only fair that we release each other to go find that and have the opportunity to have something more true and deeper.

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32:16If Hayley Bieber's doing it, I want it too. With Shopify's built-in AI tools, marketing and beautiful templates, you can reach customers wherever they scroll. In 2026, stop waiting and start selling with Shopify. Sign up for your£1 per month trial and start selling today at shopify.co.uk slash fail. Go to shopify.co.uk slash fail. Hear your first This New Year with Shopify by your side. This week on Lipstick on the Rim, we sat down with the one and only Rachel Zoe and wow, this episode is a ride. We talked about everything. Motherhood, divorce, finding herself again, joining Real Housewives literally overnight.

33:02And then she said this. Can I tell you a true story? In COVID, in the darkness of COVID, I had a cat eye every single day where nobody saw me, not one soul. And when I had COVID, not even my ex-husband saw me or my children. And you know what I did? I went in to my bathroom. I did a black liquid liner, put on lashes. black liner in the water line, a full lip, did my hair and sat in my bed. And that is what I did. And I looked at myself and I said, you are not a well person. I said, are you fucking okay? You have 104 fever. You are like, you are like contagion right now. If you love fashion, beauty, or Bravo, this Rachel Zoe episode is a must.

33:58It's out now.

34:04so you mentioned your curiosity there and the amount of autodidactic education that you were doing your second failure is dropping out of columbia which is one of the most prestigious higher education institutions in america if not the world tell us first the story of how you got into columbia i was working as a nanny in new york city and the little girl who i would care for would go to her Girl Scout troop meetings at the church right across the street from the campus. And me, you know, a poor Black girl growing up in the Midwest of the United States, I had never heard of Columbia. I wasn't aware of it.

34:42I didn't understand the prestige of it. And what really pulled me in when I, you know, recognized it and kind of looked into it was that the prolific Black woman anthropologist and writer Zora Neale Hurston attended there. And at that time, I was really enjoying studying Black women who did race work, particularly in the past. And so I was intrigued. And then I learned about the prestige of Columbia. And I was also curious by the possibility of if I could get in. I had already dropped out of school to get married once, and I didn't have any other education. And I was kind of intrigued and seduced by this idea that I might be able to get into an Ivy League school to study something that was really pulling me at the moment and continues to be such a central theme in my work.

35:26I applied and I got in and it was a really special and exciting moment of affirmation in the way that institutions often affirm us, yet they shouldn't. But also it again was another lane of possibility of like how I could learn, where I could learn, who I could meet and what I could do in my own interest of career. And Columbia was a really special place to be for the time I was there. There's this fascinating passage in your book where you talk about being shown into the library at Columbia, and you realize that you are surrounded by a wealth of knowledge, but a wealth that is guarded by elite white institutions.

36:07Can you tell us about that moment? It's bizarre. It's so bizarre to me how these universities and institutions work so hard to gather, analyze, create knowledge, and then it's not accessible to the public. I just don't know who they're doing it for or what they're doing it for. And it becomes this very eerie situation of holding knowledge and power for a society or for a culture that you say you are both part of and invested in, yet it is behind paywalls or actual the walls of the university that no one else can get through. And it's very eerie that all of that is being held in a space where it could be used even more so by politicians and how they're making laws by individuals to understand the world better.

36:57This knowledge being dispersed and accessible could really change how we all move through the world. And it was very off-putting to walk into the Columbia Library in particular because it's so beautiful. It's so grandiose. I was just all tingly excited about all the things I could read, all the things I could write, all the connections I could make, all the knowledge I could gain. And it was very much so it had this cloud of eeriness over it for me because it's just an unfortunate use of power that isn't serving. What was your experience of Columbia for the year that you were there? I was able to sign up for some really wonderful courses that challenged me and added to the material of my knowledge.

37:40One of them was looking at sexuality and gender in West African culture. and being able to find some new language and understanding about queerness and indigenous communities on the African continent and how that relates to our understanding of queerness, gender, sex here in the U.S. or in Western culture. I took a wonderful writing course that was taught to me by a graduate student, and she really supported me in my craft of writing. I don't have a degree, and so my writing that everyone sees in the world is really just whatever's on my little heart. And so I was really invested in the craft and looking to find ways to be a better writer, be a better writer and hone that.

38:19And so I really enjoyed sitting and thinking and whenever we'd be assigned a work, I always took it from a Black feminist angle and she always gave me such wonderful feedback and I was able to grow a lot in that space. I remember taking another course and I can't remember the name of it right now, but what I loved about that course is that the teacher was willing and exciting for us to be critical about the university itself, that he invited us to challenge what we understood about the university and how it related to the culture and the society that surrounded it. And I found the classroom, you know, I was older.

38:53I was, I think, 28 when I was there taking undergraduate courses with these younger students. And I feel like the students were just as prolific teachers to me as the actual professor at the front of the room. So I value the classroom so much, so, so much. It is just another one of those shaky bridges that you have to decide whether you want to cross with the underbelly of racism, the alligators of racism below the, you know, the planky bridge. It came down to that decision for me. So talking about that shaky bridge and beyond the classroom, there were a few things that struck a sort of horror into you as they should have done.

39:38One was, I think it was an induction talk where they said something about how they've not changed since 1893. Is that right? I don't want to misquote. But another one was an incident involving a young black man called Alexander McNabb. And I would love you to tell us about those two things. Yes. So the first one was, as you said, during orientation, and they were giving us the tour and, you know, doting on the university. And it was a white woman who was giving the tour at the time. And she said, you know, we're so proud that we've maintained the history of the university. Sometimes when you step on campus, you feel like you're right in the 1890s.

40:14And I remember me and another Black student being like, why on earth would she say that? And if that's the truth, then I need to rethink the fact that I'm here. And that kind of tone deafness, that type of lack of consideration really concerned me. And then, of course, the incident with Alexander McNabb was what ultimately had me leave the university, not only because of the way he was mistreated by the guards, the security guards on campus, where they assumed he was a random Black man just trying to get access to the library, but he was an actual student who had every right to be in that space, yet they had wrangled him and accosted him, then the way that the university responded to it was really a nail in the coffin, so to say, because the response essentially was, you know, we're working harder at diversity and we invite students to join these diversity groups.

41:12And it's like, well, it's not the students, it's your staff and you need to fire them and you need to make a declaration that you will not accept any forms of racism. And that lack of critical, thoughtful response moved me to leave the university and start reimagining my own education and pursuing something much more autodidactic and much more rooted in my values and the people I actually want to be learning from. You also make the excellent point that part of your decision making was shaped by the fact that this institution along with many others whilst they might have lots of courses and workshops for students from different backgrounds students of colour to know how the institution runs and how to quote unquote fit in actually what they should be doing is introducing anti-racism workshops for the white student body so that we are not racist in what we do.

42:10And I just thought that that was a really necessary point to make. When you left Colombia, it really was the start of the person you are now in so many respects, isn't it? Because you essentially invented your own syllabus for life. Yes, maybe. Yeah, I think I might agree with that. So tell me more about how you started sharing what you were doing online. You know, I really feel like my work is to think, learn and feel out loud and to invite others to join me. And leaving Columbia, I had to start getting creative about how I'd want to learn and not just learn, but learn critically. And without the shape of an institution holding me, I could be more pointed in what I wanted to learn and who I wanted to learn from.

43:01And I started to take on these subjects that I was interested in, everything from the real birth story of America. What is this without the whitewashed lens of the celebration of the founding fathers? What don't I understand yet? What can I know to give me a better context for what I'm experiencing now? looking at the history of black cowboys in the American West and how they helped shape our understanding and our ranch culture and how we were able to tend to the land, looking at the ways indigenous people use their fire knowledge to help control the wildfires happening in California and when and why they have and haven't been heard by the government, even with their wealth of knowledge.

43:45These are the conversations I want to be having, and I want to be learning them from indigenous people, from Black people, from disabled people, from these voices that often are quieted because white male voices are centered and celebrated as the canon. I'm very intrigued by what another canon will look like that gives us the baseline for our understanding of the world. I really did have to create a syllabus for myself and my work ended up being inviting others to join me along in that. You quote your mother in this chapter of the book saying you can't build your truth on what other people think, which I loved.

44:27I almost wanted to print that out and laminate it and frame it for myself. That idea of removing yourself from the colonization of other people's opinions and other people's version of history is a very potent one. Your third failure are your first attempts at business. So why did you choose this one? What kind of failures did you have? Oh, I had so many failures. I had so many failures. My first attempt at business was right after my divorce, and it was my first time making money by myself and for myself. And I was both thrilled and terrified. And one of the easiest things for me to do, I was 23 at the time, one of the easiest things for me to do was babysit.

45:13And so outside of my office job, I was doing this side hustle of babysitting to try to make money. All of my friends, of course, were starting their graduate programs and starting their PhD programs. And so I was very intimidated by who I would be in the world next to these people who seemingly got a head start on me since I had spent so much time away being married so young. And one of the first spaces of agency for me was financially. And so I started to really look into entrepreneurship and be curious about whether it was something I could do or wanted to do. and it became a challenge for me not only to be able to support myself financially but to also I thought the coolest thing about entrepreneurship was that I could also pay other women.

46:00I just thought that was so exciting that I could create something that would benefit us. So I ended up babysitting and I would like make these forms and try to create these processes and I would get so much critical feedback from these parents who are like, no, that's not going to work. Or no, this isn't what it should look like. And even all of the ways that your ideas feel good in your head, but they don't look good on paper. They don't look good in real life. And these failures really shaped me as a designer of things, as someone who creates something. And I really enjoyed the opportunity. Business has always felt like a space of creativity to me.

46:40It felt like an art form to me, a place to be creative. And so I failed in so many ways. I had so many spaces that, you know, I had to deeply apologize to people who I failed in one way or another and to get a, I hate to say thicker skin because I don't necessarily feel like it's a thicker skin, but I had to be able to weather the criticism that would refine me. And so as I continued to grow and learn in business, I had to get comfortable with sitting in a space of knowing nothing. I would sit in front of my lawyer or even with the foundation, I would sit in front of my advisor and they'd say, Rachel, that thing can't work.

47:22That's not how it is. Or for them to be talking to me to be like, wait, I don't know that word. Wait, I don't know that concept. It was so hard. It's so hard to have to sit with what you don't know. But I had two businesses before I created Loveland and it was a babysitter placement agency, which I really enjoyed the opportunity to serve parents and pay mostly other women to be doing the work. And then I had the same business model with virtual assistants where I would match really high-end executives in New York City with administrative support in my hometown of Ohio and getting them really good jobs and getting them really good support.

48:01And neither of those were able to grow the way maybe they would with my understanding now, but they certainly ushered me into how I understand myself to be as an entrepreneur and a businesswoman. So how do you set up a business then? Having learned what you did, how did you go about setting up Loveland? What were the things that you knew you had to get right? It again started with studying other people, with studying and seeing who was doing something that inspired me and how could I, as I say in the book, take the meat and throw out the bones of their approach, take what applies to me, take what aligns with my values and try to build out something of my own.

48:41And I studied Oprah a lot. I was so intrigued by the fact that Oprah, aside from who she is, who we understand her to be in the world, I was really just intrigued. She seems to do whatever she wants. She seems to have so much fun. I was like, she has a TV network and she has a pizza? How does that work that she just has this space to do whatever she wants? And I wanted that type of freedom, that type of sovereignty in my career. And so I really looked into not what Oprah was doing, but the shape of her company. And so I really modeled the shape of my company after Harpo, which is her umbrella company that holds all of her other ventures.

49:19And so that's what the Loveland Group has been, an umbrella company that gives me space to create businesses that align with not only my values, but whatever I might be interested in at the moment. So if it's something new that I want to run for three years, it can happen under the same umbrella as where my bookstore is living, as where my online learning platform is living. I really studied and looked around at these entrepreneurs and I was interested in the shape of their company because as an entrepreneur, I'm less interested in what I do, but how I feel. I feel like I could do anything. I could do many things.

49:53I have a bookstore. I could have an ice cream shop. I could have you know there's many ways that I could do my work but I'm interested in how I want to feel in it and I wanted to feel grounded I wanted to feel meaningful I wanted to feel free and I value so much that I called it Loveland because I really see my career as a landscape as opposed to a lane I have to be in or some race I have to run I really view Loveland as this landscape and there's these plots of land that I get to tend to my bookstore is a plot of land the foundation's a plot of land. I invite people to help me till the ground of this space.

50:26I can plant new things if I want to. I can expand and I can grow or I can make it smaller and I can, you know, there's a expansiveness and a knowingness. And I think that Loveland has become this landscape that I feel very grateful to get to tend to. I love that image of a business as a landscape. Can I ask you just a really prosaic question? Do you worry about money? Because when you are an entrepreneur and when you are a CEO, you have many people's livelihoods depending on you. Yes, you do. I'd be so stressed. You do. You do have a lot of people to consider. And yes, I think, yes, I am stressed.

51:08To answer your question, yes, they're absolutely a stress. And I think that in capitalism, which is a whole other podcast, but you know, that is a necessity to keep you a little bit stressed to keep you doing the work. So I think we all feel that by design, not because of anything being wrong with us, but by design, capitalism insists that we stay a little bit stressed to keep doing the work that it wants from us. I do feel that pressure. I'll speak to one of the really special things about my company as well, is that when I started to explore what a career might look like for me, who I might be in the world, I used to have these team Rachel meetings where I would invite all of the people who believed in me, all of the people who had proven that they believed in the work that I was doing.

51:47So this was like, you know, my lawyer who was giving me some pro bono work, the PR agent who was offering me like super low points of her time in order to support me, the advisor who was just there and loved the work that I did and was willing to support me. And I would have these team Rachel meetings just to say what was going on, ask if they had any advice or any insight, questions on what directions they might give me. And that very team that was coming to my team Rachel meetings, as soon as I started making money, the majority of them came on as full-time staff at Loveland. And so I had this intention and this pull towards what I wanted.

52:25And I think that that momentum kind of brought towards me this type of people who would be invested in the work that I'm trying to do in the world. Okay. Thank you for answering that quite nosy question. There's a quote in your book, which comes from someone else and it made me laugh, but it also has such a grain of truth in it. Is it manifestation or is it white supremacy? Have I got that right? Okay. Because I think a lot of listeners might think, isn't Rachel amazing? She manifested this. She had the idea and then manifested it. But my understanding of that quote is actually that's a privileged position to come from.

53:05A white person can quote unquote manifest something much more easily because there are all of the structures and systems in place that are already in our favor. Whereas you were someone who had to be so intentional and work so hard. So I just wanted to ask you what you thought of manifestation culture. I love manifestation culture. I love the conversation of it. I love the thoughtfulness. I think it provokes the thoughtfulness that someone might need that little bit of magic to insist for them, I do think that there is value and truth in the concepts of manifestation. And I think that we could be critical about who and how people are able to manifest opportunities and what positionality exists to make things easier.

53:48You know, me and my friends often laugh about how particularly, and as a nanny, I've seen many, many kids across the city, particularly these very rich white families who put their kids in the best theater school and they have a tutor after school and they say, oh, my kid is so smart. And they've gotten into, like, no, he's not any smarter than the black kid three neighborhoods over. He just had every single resource possible to ensure he succeeded. There's a difference. There's a difference. And so it's not just a manifestation, but we can have this very same conversation around talent. We can have this very same conversation around someone's ability to succeed in any space.

54:30Is it that you were just inherently so talented or is it that you had every single resource or many more resources at your disposal than some other marginalized group? Because I can promise you, if you put anyone in that situation, they will thrive. And that's what everyone deserves actually. Yes. And I think it's a really key conversation to have around the notion of failure too, because I'm very aware that I, as a white middle-class person with a roof over her head, I'm given multiple opportunities to fail and to fail upwards, whereas others are not. And actually, I suppose that leads me onto my final question, which is, I wonder what the concept of failure and its shadow success, what they mean to you?

55:18You know, I'm 34 now. And I think that in this time, especially with the passing of my mother and having a particular empathy for her failures that might've felt sharper when she was alive. And that kind of get faded away after the passing of someone. I find so many nutrients that's so nourishing these failures. It's kind of like what it's making me think of is when we burn the land in order to burn off the crops and the ash offers nutrients for the ground, but that doesn't make the fire any less hot. It doesn't make the burning any less crisp. It's still the fire. And so these failures, I feel like the fire and it takes a lot of intention and heart and stomach and gut to be able to suss out the nutrients of it.

56:09But I think that it's possible. And I think that's a practice we can do to really sit with failures and say, I failed, I failed and sit in the sorrow and the frustration of that. And then to take some time to say, okay, well, let me spread the ashes of this to give some nourishment to whatever might come next. Rachel Cargill, you are a dazzling ray of wonder. Thank you so much for giving me your time and your brilliance. I can't think of a better metaphor for failure. I'm going to use that all the time now with appropriate footnoting. And I'm so grateful to you. And I just can't believe you're 34.

56:46And I'm excited about meeting the future older version of you too. I can't imagine what you're going to be like at 70. It's going to be wild. I sleep about her all the time. Hopefully I'll be in a flowy caftan on a boat somewhere, but I'll reach out and let you know where I'm at. Please do stay in touch. I want to see that flowy caftan. Rachel Cargill, thank you so much. And everyone must rush out and buy a Renaissance of our own. I can't recommend it more highly. Thank you for the work that you do and the person that you are. Thank you for having me. This was wonderful. Thank you.

57:24If you enjoyed this episode of How to Fail with Elizabeth Day, I would so appreciate it if you could rate, review and subscribe. Apparently it helps other people know that we exist.