How To Fail With Elizabeth Day - Monica Lewinsky - ‘I would have liked a more normal life’

Episode Date: June 25, 2025

Monica Lewinsky is an activist, podcaster and producer.  At the age of 24, Lewinsky, a White House intern, found herself in the eye of a global scandal. She was subjected to a mass public shaming -  losing her livelihood, her anonymity and the future she had once imagined for herself. Now, 51 Lewinsky has garnered a new generation of admirers, who with the advent of social media and shifting cultural tides, have rightly reinterpreted the shocking way she was treated. Her podcast, which launched earlier this year, is called ‘Reclaiming’ and features interviews with guests who are in the process of reclaiming their own narratives, just as she was forced to do. She joins us to talk about her experiences with shame, her perfectionism and why the pain she went through has given her purpose. Elizabeth and Monica answer YOUR questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com  All episodes in June are brought to you by @arlalactoFREE - all the taste, easier to digest. Listen to our bonus episode brought to by ArlaLactoFREE with Vicky Pattison here: https://link.chtbl.com/VickyPattison  🌎 Get an exclusive 15% discount on your first Saily data plans! Use code [howtofail] at checkout. Download Saily app or go to to https://saily.com/howtofail ⛵ Production & Post Production Coordinator: Eric Ryan   Mix Engineer: Matias Torres Studio Engineer: Gulliver Tickell Assistant Producer: Suhaar Ali Senior Producer: Hannah Talbot Executive Producer: Carly Maile How to Fail is an Elizabeth Day and Sony Music Entertainment Production.   Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [e-mail] Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

I'm Courtney Act. Many of you may know me from RuPaul's Drag Race, Celebrity Big Brother, Dancing With The Stars, or probably my hit album, Kaleidoscope. Well, guess what? I have got a brand new show called R&R with Courtney Act, and I want you to check it out. You know, I hate small talk. I want to go deep and I want to go quickly. And on my show, we do just that. In today's world it feels really polarised and we're more connected than ever, but really we can feel isolated and I don't like that. I want the story shared here on R&R

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How To Fail is proudly partnering with Aala Lacto Free through June. Delicious dairy with all the taste, none of the lactose. Welcome to How To Fail with me, Elizabeth Day. This is the podcast that I started because I wanted to know how other people survived failure and what, if anything, they learned along the way. This was not something that happened to me. And so it was foreign and it was terrifying. I never could have imagined the consequences being so far reaching.

Okay, how am I going to do my CV? Do I put that I worked at the White House? Do I not? My guest today is an activist producer and podcaster. She is also in her own words, the patient zero of online harassment. Her 2015 Ted Talk, The Price of Shame has to date been viewed over 20 million times. She has repeatedly spoken out about cyberbullying and the need to find one's own voice. She has a master's degree in psychology from the London School of Economics, where her thesis dealt with the effects of pre-trial publicity

on juror impartiality. Her podcast, which launched earlier this year, is called Reclaiming and features interviews with guests in the process of reclaiming their own narratives, just as she was forced to do. Because her name is Monica Lewinsky, and in 1995, at the age of 22, she fell in love with her boss, a man almost 30 years older than she was. Her boss was the then president of the United States, Bill Clinton. And by the age of 24, Lewinsky, a White House intern, had found herself in the eye of a global scandal.

She was subjected to a mass public shaming, losing her livelihood, her anonymity, and the future she had once imagined for herself. It is testament perhaps to her courage and to her determination that she returned to the public eye at all. Now 51, Lewinsky has garnered a new generation of admirers who, with the advent of social media and shifting cultural tides, have rightly reinterpreted the shocking way she was treated. She's also launched her own production company, Outending, aiming to platform others whose voices have been silenced. It is an expansive and impressive

trajectory. As Lewinsky said in a recent interview, my life is full of things other than just my past. Monica Lewinsky, welcome to How to Fail. Thank you. Thank you so much. I told you before we started recording that you have been on my dream guest list for this podcast ever since I started. So it's a real pinch me moment to have this happen and to meet you and discover that you're so wonderful in person as you are on your podcast. But tell me why that idea of reclaiming and calling your podcast reclaiming was so important to you. Interestingly, the idea actually started out as a book that I thought I might write, and then it just

started to kind of tickle me in a weird way as a thought around that it would be more interesting to explore this landscape with other people. And really, when I started to look at it and think about where does this fall into our culture, I realized there's a very elastic definition of reclaiming that I was attracted to, right? So it wasn't necessarily just someone who had a big reclaiming like mine was over the last 10 years of their narrative and their history, but I think the smaller ways that we might, the different aspects of our identity. I also joke around that when I call someone a fuck face, but I don't flip them off in the car in LA with my road rage, like, I have reclaimed my comb.

So there are little moments of reclaiming too. And I think it's kind of an ethos that when you start to look at the world through that lens, you start to see reclaiming everywhere. So that was really where it felt interesting to me. I also get road rage, but I appear a very calm and reasonable person in other respects. So it all comes out behind the wheel of the car. Yeah. I don't understand why people get so mad when you want to go faster. It's not like I've, I don't, I, it's not like I've said you're bad in bed. I mean, it's just, it's sort of one of those things where you think

I'd like to go faster than you. That's also just either let me move so I can go in front of you or move so I can just go on and be out of your hair. I mean, I don't want to, yeah, I totally agree with you. And I don't want to make this profound metaphorical shift, but I'm going to try anyway. Do you think that part of it is you lost a decade of your life, at least to what I refer to in the introduction. And do you feel now that you're kind of making up for that time, that you don't have time to waste, that you need to go fast? What's interesting to me is there was a long period of my life where I felt exactly that. It was a long period of my life where I felt exactly that. And I think in the last decade, as things started to change, both in my personal work,

spiritual, energetic, psychological, psychiatric, all the work, all the things, I started to see and as my life was shifting, I think in the public arena and people were seeing me more for my true self and understanding what happened to me through a different lens, I started accepting slowing down. So I began somatic therapy during the pandemic. It's the first time in my life I found myself saying to a practitioner, okay, we have to slow down or we're at 40 minutes of the hour session. I'm done. Because I think that there was very much exactly as you're saying this feeling of I have to

catch up. I've lost so much time. I have to catch up to my peers. I have to catch up to my dreams. And fortunately for me, turning 50 was really just so much about acceptance, a really nice way. I wanted to ask you about turning 50 because when you turned 40, you wrote this extraordinary piece for Vanity Fair, which I remember reading at the time, which really reset the framework

for public perception of you. And turning 50, you've launched this podcast. And I wonder how you feel about your 50s. I'm excited. I never thought, especially not having been married and not having had kids, that were things that I really wanted in my life. And I think very much things that I saw, um, constructs in a way that I looked at the world, ways that I, I evaluated people or situations and myself to just kind of find myself in a place where that all feels okay to me is, is pretty, pretty magical. It's also really amazing for me to meet a fulfilled, brilliant, creative woman who doesn't have children.

So I don't have children either in the biological sense. I know we're both aunts. And I want to thank you for that really, because I think that even though it was sort of forced on you, I imagine, by what happened, you're such a role model. I mean, it's aspirational what you present to the rest of us. Thanks. You know, it was not by choice. So I think I just I had Chelsea Handler on the podcast and we had a discussion. I don't know if you've had her on yet. Not yet. Okay, well, I will I will plug you to her.

She's an amazing woman. And we came at this same kind of conversation from these two different places of Chelsea really knowing she didn't want to have children. And for me, I did really want it. And I froze my eggs. And my therapist said something so helpful to me. I repeat this all the time. I think there was a small period where I was toying with the idea of do I have a child on my own? And we had this discussion about regret. And she said it's a mistake to think that making the right decision means you won't have regret.

That's so wise. I don't know if this will make sense, but it's like regret seems to make our decisions binary in some way. And that's how we define it, right? Like, well, the wrong choice is regret and the right choice, I won't have regret. And that's not accurate at all. I know we're going to get more into this later, but your sense of acceptance more generally, I read absolutely zero bitterness in you. Yeah. Not today.

Well, you're not driving. Right, exactly. I mean, it's there sometimes, but overall, it's one of the ways I consider myself so lucky. I mean, I've had a fuck ton of unlucky things happen, but I consider myself really lucky to not be bitter, to still be able to open my heart, to still be trusting, sometimes too trusting. Because when you're talking about having frozen your eggs and not having got married or had

the children that you yearned for, that you'd always have, that can be laid squarely at the foot of what happened to you when you were in your early twenties. Well, my best friend from college will often say, well, it was always going to be hard for you. Really? Really? Why? I think I'm a pretty, many of us are complex. I think my complexities are pretty unique.

So without getting into it a lot more, but I just always thought that was funny and I love that she says it to me. Yes. Because it makes you more than what happened to you as well. I think so. I think so. And I think those, I think when you have any kind of a big identity shifting loss or failure or any of those things that it is always good to be reminded of all of who you are. Yes.

Right? Even if it's negative, right? So I mean, she says it to me lovingly, but it's a good reminder that I can't blame everything on. Like, I was kind of fucked up before too. So I mean, and also, you know, without getting into too many details of things, I also think that there was a brokenness there that led to what happened. Right. So... Well, now that's all I wanted to know about. I think I'm being respectful.

That's for our record. That's for drinks. Sometimes. No Frills delivers. Get groceries delivered to your door from No Frills with PC Express. Shop online and get $15 in PC optimum points on your first five orders. Shop now at nofrills.ca. Well, let's get on to your first failure and who you were as a child. And I love this failure because it's your first memory of failure and they're so potent.

And I also have my own first memory of failure. And yours dates from first grade. So how old are you for English listeners? So six or seven. How's that? Great. Okay. Perfect.

So you're six or seven and it's a Friday afternoon at school and it's show and tell. And what happens? Well, in order to go to the show and tell that's happening on one half of the classroom, you know, where there's the rug that you take the naps on and the other half has the desks, is the girl who's show and tell it is that day and she's brought in a bunny.

But the rest of us are still sitting at our desks and we've been given a new math assignment and you can't go to the show and tell on the other side of the room and play with the bunny until you finish the math assignment. In a very weird twist for me, like math and school things just came quite easily to me then. I couldn't figure out the math problems and so I would answer them and every time the teacher would come around to kind of check it, she'd be like, nope, that's not it.

I couldn't figure it out. And so then I started to panic more and more because it was this spiral of this hasn't happened to me before. I've lost at games, but losing and failure are two different things, right? And so it really was the first time that I remember this concrete failure because everybody else finished before me. And I think that my anxiety

and panic started to grow too because I had always been able to rely on my intellect. I think to understand the landscape of this story, that it was just this, this was not something that happened to me. And so it was foreign and it was terrifying. Tell me quickly whether you ever got to cuddle the bunny. I did. But what I couldn't remember was I remember starting to cry eventually. And what I couldn't remember was if I got the math problem finally or they just finally said

to let me go, which is sort of interesting to me. My guess is it's the latter because I feel like I might have had a memory of accomplishing something or I just blocked the whole thing out because it was so, it was really traumatic for me. Yeah, funnily enough, I actually ran into the girl who was there with the bunny, randomly at a spa. She looks exactly the same as she did in first grade. And so we had a nice reconnect. I mean, I hadn't seen her since third grade. So, but... I think what you're saying is so interesting and I relate in a certain aspect in that as a child and probably still now, I didn't have a great deal of self-esteem, but I was good

at school and being good at school became part of my identity. It's what I relied on to give me the data that I was lovable in a way. And obviously it's a conflation of different things. Being academically successful doesn't make you lovable. Spoiler alert, sadly. But I wonder if that resonates with you. Oh, absolutely. You know, I think as I've, you know, one of the interesting things, I guess if you're an introspective person about getting older, is you also have these opportunities to relense early experiences all the way up, right? You learn more things about yourself and you start to see things differently. And so,

I had had a period in second grade where I was very competitive with who my best friend at the time was. And I remember she kept sort of getting better scores that we were like doing some dinosaur thing and you'd get a Jolly Rancher or a smelly sticker, whatever the thing was. And I actually, I stole the answer book from the classroom and took it home so that I could, it's like making me emotional. I feel it. So that I could get, and it wasn't so much that I wanted to beat her,

I just wanted to be, it was like perfect, it was some version of perfect. Of course, I look back now and I wonder, there are a bunch of things for me from my earlier years that I know problematic things happen and I don't know what they were. And so I look at that time period or even back to first grade and I think, well, maybe something was happening around that. And so that it was really more of a

Well, maybe something was happening around that. And so that it was really more of a telltale sign that there was a problem. But we just kind of we didn't live in a world that looked at things that way. I mean, I had and have very loving parents who, you know, very, I think, very, my dad spent a lot of time with me doing the projects for school, the dioramas and all those things. And my mom was very attentive, but parents just didn't have a kind of a way of looking at things back then. You mentioned your parents, and I know that they got divorced when you were a teenager. So I wanted to know whether that, what kind of effect that had on you, if any.

It was all very complicated. And kind of once, actually when I was in my 40s, it also became clear in a therapy session, I was saying, I've talked about this before, but I was saying something to my therapist and about having lost my virginity. And I was like, well, I was 19. I was like, well, technically I was 14, but it didn't count.

And so I realized later that some of what I had labeled upset from the divorce was actually this thing that happened to me at camp the summer before my... Yeah, thank you. It was complex because we didn't have language for things actually this thing that happened to me at camp the summer before my... I'm so sorry. Yeah, thank you. It was complex because we didn't have language for things back then, and I had liked the person, but I had clearly, I was 14, I didn't want to have sex. I didn't know that's what was about to happen.

And I tried to dismiss it away with my therapist of like, well, he stopped when I said to stop and you know, she's like, no, that's an unwanted sexual experience. It was very hard for me to accept that. And so, so yeah, the divorce was was not an easy thing. I don't think it's easy for anybody. But it also was necessary. Thank you so much for sharing that, which I mean, I know so many people will feel seen by what you have been courageous enough to talk about just there. And I just want to

reach out to 14 year old Monica and give her a hug because that was so much for you to go through. Your intellect got you to achieve academically and you ended up as a White House intern, which brings us onto your second failure. But before we get onto it, I just want to say that I am really aware that you have had to talk about this so much. And I wanted to check in with you about how that felt for you. Even the fact that I write an introduction and it's mentioned in it, and you're so much more than that. And I just want to see how you are about it. Yeah, it's such an interesting thing because it's been, I think, 27 years now, and it feels

different. It means different things. It has less energy around it for me now. Would I like there to be a point where that's not the first thing that's part of the story? Sure. And there's also an acceptance of that's so much of the work I had to do in, I think, in the deeper healing work I did of recognizing I couldn't run away from what happened. I had to integrate it.

Yeah. So it's fine. Do I cringe a little inside? Yes, I had to integrate it. Yeah, so it's fine. Like, do I cringe a little inside? Yes, I do. You know, but it's, it's one of those accepting what is, right? Yes. So. Your second failure is about a time when you had done your master's degree in social psychology at LSE, and you were trying to get a job, and you weren't able to.

Tell us that story. In the first few years after 98, I felt like I didn't have a choice but to lean into being a public person. It just became really clear around, started around 2003, really clear 2004, this wasn't going well. I think going to graduate school really felt like I was going to be turning the page on this public life. I was going to have this degree. It was going to be a scaffolding upon which I could kind of hang a new identity.

And when I got out of graduate school and started to job hunt, it just became clearer and clearer how hard that was going to be. You know, I remember somebody asking me of like, well, if you were a brand, what brand would you be? And at the time, it just felt like it was not intended to be a complicated question or anything that would sort of incite panic in me, but it did because it just felt really loaded. And it was a totally appropriate question to have asked me. I was looking to go into marketing and advertising and branding. So that makes sense.

But I found, you know, so it was from that I found there were particularly some of the nonprofit places that I interviewed asked me, one place asked me if I could get a letter of indemnification from the Clintons because they were worried that if Hillary had won in 2000, because she was running to be the candidate, this was in 2006 and 2007, before Barack Obama became our candidate and then our president, there was concern that if she won, that they would lose their funding. And so that there would be like some sort of backlash that way. So it just became more and more complicated and more and more obvious that

a traditional job was not going to be an option for me. And that was that was terrifying. And it was kind of an epic failure that in a weird way, felt not of my own making in some sense. Like most of the time, I think the failures that I think about are kind of were direct result of something I did. And while yes, obviously I made bad choices, I just think I never could have imagined the consequences

being so far reaching. We were now 10 years out from what had happened. And also just the complications of things of, okay, how am I going to do my CV? Do I put that I worked at the White House? Do I not? Do I put my name? Do I use a different name?

Well, if I use a different name, what happens when I walk in for the interview and the person sitting there going, I don't know, Cheryl Smith sure looks a lot like Monica Lewinsky. How do you even do that? You know, so, and then you've also started out a professional relationship with a lie. So, you know, there was complication there, then there was, okay, in which states could I, you know, interview for jobs?

Because I can't not have a support system somewhere that wouldn't work to be, to do kind of what I did when I went to college. I moved to Portland, Oregon. I didn't have a support system there, but that was fine. I wouldn't be able to do that post-98. And so you wouldn't be able to do it because you felt so fragile. I think the fragility was certainly a part of it, but it was also there were times where something would happen in the news and this would rear its ugly head and paparazzi would show up somewhere.

So if I didn't have a support system in the city who was going to come help me. And I just think that for me, the way I became a public person and was a public person, I was just more vulnerable. I didn't have the resources. Most people who end up with a level of name recognition that I had at that time have an enormous amount of resources, an enormous amount of people around them to help with the complications of not being anonymous. Yes. And choose it. They choose the fame and you did not. I grew up knowing what happened to you. And it was impossible not to because the media landscape was such that there was such an obsession with you, Monica, not with President Clinton, 27 years older than you. It was with you. And I heard an interview where you said the Washington Post printed 127 articles about you the first 10 days after this came

out. Yeah, about the scandal and yeah. Google had just launched the web traffic doubled overnight. Right. That was when the Star Report came out. Right. Yeah. So I mean, it's all part of the same thing, right?

It's so hard to remember a time when a story could have legs for almost a year or over a year practically. I mean, now there were new things that kept happening, right? There was an ongoing trial and then the Star Report came out eight months later, nine months later, whatever it was. But it was this ongoing onslaught and the media was not kind. No. I do not know how you got through it. I don't either. I think that I come from a long line of very strong women who have faced adversity in myriad ways. And I think, you know, my therapist will say sometimes that, you know, the very things that helped me that I learned how to do as a child that then helped me survive 98 are also some of the things that wreak havoc for me in present time. But I think that being able to dissociate, being

able to sort of check out helped at times. And I had an extraordinary family, you know, and have, who was supportive. And I think that had my family not stood by me, and it would have been... I wouldn't have been able to survive on many levels. You described it then as falling in love with someone who just so happened to be the most powerful free leader of the Western world. Do you still categorize it as love?

It was 22 to 24 year old young woman's love. I think probably everybody can relate to this. The way we see love evolves with every relationship we have. I know, it's sort of, I don't think I know one person who has said, oh, this relationship I'm in now, this love that I'm in now, this is so much lesser than this one from 10 years ago, because we change as people and we evolve and every time we fall in love, it changes us anyway, and the person said those things. So I see what happened.

I see it as something different. But yes, that's what I felt was like, I think there was some limerence there and all sorts of other things, but that's how I saw it then. And I think, you know, it was also an abuse of power. It wasn't a relationship of equals. No, but I think that's the power aspect, but it wasn't sexual assault. So particularly when we have conversations around me too, I think that that's something we're looking at. But it

was considering that even though it was a family friend who was a big donor who had recommended me for the White House internship program, I had written an essay that had me writing, not Xeroxing for the internship and that I then got a job on my own before the relationship started. So my very first job out of college was working in the White House. So I don't think that that's the kind of trajectory that someone thinks then, you know, 10, 12 years later, that person's not going to be able to get hired. No. So, and, you know, and then I worked in the Pentagon as well and traveled the world with my boss, who is

the Pentagon spokesman, and we traveled with the Secretary of Defense. I think there was by no means a genius, by no means going to be the cream of the crop, but I wasn't a bimbo. I wasn't a dumb bimbo. So I was portrayed to be, and that was a big struggle for me to deal with that. And you were often portrayed as that by other women? Often by other women, but I think that that was a narrative that was crafted and put out by the White House. So I think it was picked up, that mantle was picked up by a lot of women. What do you think this whole period of your life taught you about love and trust? Because there were so many ways in which you were betrayed.

Mm-hmm. I think that I... I think they were very deep wounds, and they're both really... were really intertwined from that whole period. And it's something that I still work on, you know, I mean, and the, I think we've been having these kinds of conversations publicly more, but with the somatic therapy, it's bringing in, you know, my nervous system and my body and listening to my body and trying to reconnect in different ways because of betrayal and because of love and those things. So I think it's ongoing work for me. I think it's ongoing work for probably

everybody in different ways. What is somatic therapy for you? Oh, so it's okay. I'm probably not going to give the best definition, but how I think of it is, you know, when you go into therapy, you're talking about your, your thoughts and your emotions, and you're sort of using your emotions as the landscape to have those discussions. And somatic therapy is really about the body. your emotions as the landscape to have those discussions. Somatic therapy is really about the body. It's checking in with the body.

It's being aware of what the body is doing, what the body is reacting to. Yes, you use words and their images and all sorts of things to communicate that to someone. It's not necessarily nonverbal, but it's really reconnecting. It's sort of remembering that these are all the parts of me. So that's what you work on, calming the nervous system, toning your vagus nerve. If you could take away this period of your life where you were unable to be anonymous, you were unable to get the job that you deserved because of what happened, would you take it away?

Oh, sure. You would. Yeah. Yeah. Even though it's made you who you are now. Yes. And I love and appreciate who I am now. But I think for so many different reasons, I would have liked a more normal life. I would have liked to have had a more normal trajectory. So decade of lying low and a decade of what sounds like healing. Mm-hmm.

Well, I think those two were one in the same. Yes. So, and then the last decade has really been the reclaiming, but I think the decade before was part of the preparation. And that's one of the things that I love about reclaiming too, is that it encompasses all of these things. To have something, right, definitionally, you get back something that was lost or taken from you. But so you have something, you lose it, you go through the grief of the loss, you have to be resilient, you eventually have to heal, you usually have some kind of strategy and ultimately and perseverance and ultimately you triumph.

But I think that that decade was preparing me to be able to reclaim. Yes, so well put. You mentioned karmic, like something karmically earlier on. And I wonder how much you believe that we live several lifetimes. And you do, so do I. Oh yeah. Several lifetimes, I believe different dimension. I'm like the multiverse is real. I loved the movie Arrival with Amy Adams and really where so much of the film was talking about time being circular. So that's very much something I don't put into practice enough, but I 100% believe. So I wonder if I could ask you the final question on this failure, whether you feel that in this multiverse of dimensional time, that

part of your purpose in this specific lifetime that we're talking about right now, right here in this podcast studio, is to have traveled this path so that you can speak in this way for others. I think there is part of me, like a higher version of myself that has worked to try to accept that more and more because that is, this has ended up being part of my lot in life. And I have had the privilege of being able to see how I can use my pain to sort of serve a purpose and to help ease other people's pain, which is it's not something I ever thought I'd be able to do. And it's very rewarding. So I see that.

I don't know at the end of my life. I don't know where I'll fall in thinking about it all that way. Your final failure, we're going back in time. Because this dates from 1999 when you launched a handbag company. And the bags were called, what were they called? Made especially for you by Monica. Yes. And what kind of bags were they? So they were unstructured bags made with upholstery fabric and they were unstructured.

And it kind of, so it came out of everything that happened. It started because of what happened in 98 that I couldn't leave the house and my stepmom taught me to knit. And I had seen a bag that I really wanted to carry my yarn around, but it was too expensive. So I had done costume design in high school. So I designed a bag and I made it on my stepmom sewing machine. And then, you know, a couple other friends wanted it and eventually it became a business. And I loved doing it. I loved that, um, the creativity that was in there. There's something about creativity and failure that I think is really beautiful and intertwined

because creativity in a way it, it's, it's, it relies on you being liberated enough to make mistakes. And so do you think it opened up that part of you again? It was like, it's actually okay for me to explore. opened up that part of you again that was like, it's actually okay for me to explore. I think what comes up for me that is more reflective of that is I started doing my own sort of self-directed art therapy a couple years ago and the fact that I, you know, it's just for me, there's not an end goal with it. And it's just sort of, I hate the word honoring, but it's honoring the creative process. Yes.

Or the kind of creative process within me, you know, so. I don't know if you know this, but there's a whole corner of the internet devoted to how great your bags are. Oh. And how they deserve a reinterpretation. Oh, I didn't know. And they're being sold on eBay and stuff. Oh my gosh. Oh, wow.

And they're great. Oh, thank you. I will tell you this, they are sturdy motherfuckers. They are really sturdy. A bit like their creator. Yes, exactly. But I think that's the benefit of upholstery fabric and having, you know, a kind of fabric story on the inside and one on the outside. It's a very sturdy bag. So why is this a failure? Because we, you know, the beginning launch went well and then Henry Bendals wanted the bags and we had an amazing launch there that was very much, as you were saying before,

a pinch me moment was pretty magical. And ultimately, my partners and I had very different visions on how to grow the business. And so we ended a failure, you know, to me to close a company was not by choice, you know, so it was heartbreaking. I actually really love it when people choose business failures for this podcast because they are so personal and it does feel so devastating. And you said to me in the email that there was something to do with not taking the advice of your lawyer. Right. Well, I had, I think that I was very eager to get going and was in business with really wonderful people.

And so I, you know, just I kept saying nothing's ever going to go, like, this is all fine. I wouldn't listen to them. They wanted to make changes in the contract. And I was like, no, no, it's fine. It's fine. It's like, what the fuck did I know? These are people who went to law school, who work in a very good law firm because they know what they're doing.

And it ended up making things very complicated on the exit. So I exit as if I exited, as if we sold the company, but in the dissolution. But that's all water under the bridge. I still am in touch with them on occasion. So I've seen them since then. And great people, we just came to have different ideas on how to grow something. What do you think that failure taught you?

To listen to my lawyers. In fact, I even recently had an instance where my lawyer had been pushing me to button something up a little more. I was like, no, no, it's a friend. It's fine. It's all fine. Then I felt a little burnt after. Maybe I'm not always good at learning those lessons. It taught me to be, to try to, I haven't perfected it, but I think to try to find a balance of

being hopeful and dreaming, but also having my feet on the ground and also being really really mindful of when I think when something goes wrong in a business, it needs to be addressed, whether it's sort of communications or other issues and I don't think you can just kind of keep moving on from that. So that's very wise. And I also think talking about this just makes me meditate on the idea of instinct. Because I think, particularly with women, we often have very strong instinctive responses and thoughts and feelings and beliefs. And yet, many of us have been socially conditioned out of trusting them. And you had an extra layer of being conditioned out of trusting your instinct, I imagine. And I wonder where you're at with trusting your instinct now.

Yeah. You know, I think that there are some lanes where I feel very confident trusting my instinct. And then there are ones where I doubt myself and I'd say 60% of the time, I was wrong to have doubted myself. I'm not always right. My instinct wasn't always right, but right more often than not. And I also, I think sometimes what's a little complicated

is there could be a murky place between wishful thinking and intuition and trying to kind of tease that out and remember that intuition is usually a whisper for me. And so, if I've gone looking for the whisper, it's probably not a whisper. But I don't know it. Yeah, I'm not sure if that makes sense. But it does make sense. Yeah. And I think that's very wise that generally if something shouting at you is because you want it to be true, or it's just you behind the wheel of a car, right? Yes. Shouting at someone else who's going too slowly. Exactly.

Exactly. I have absolutely loved meeting you and talking to you. Honestly, Monica, I cannot thank you enough. And I wonder if we could just wrap this up by asking you what the process of thinking about failure for this podcast was like for you. Well, I struggled at first. So I think it was, I was to, you know, have it my publicist the day before. And I emailed her and I was like, I'm having trouble coming

up with things. So I this is going to have to be tomorrow. And I felt a little more clearheaded and and it was, you know, then the failures just kept rolling. So it was failures, a disappointment and has consequences to it that can be really painful and challenging. But sort of like making mistakes and apologize, I kind of get that that's part of life. But I do always want the A+. Yes, I hear you. I really do. And I'm going to give you an A+. Oh, thank you. For this episode of How to Fail.

Thank you. Thank you. I'm going to give you an A+, and a metaphorical white bunny. Yes. Monica Lewinsky, thank you so much for coming on How to Fail. Thank you so much Elizabeth. Thank you. Thanks so much for listening and watching. This tune on How To Fail, we're all about celebrating wellness from the inside. If you'd like to hear more on this, go and listen to my episode with Vicki Patterson, brought to you by Ala Lacto Free. The link is in the

episode description. Please do follow How To Fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music or wherever you get your podcasts. Please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.