S2 Ep3: The Brutal Truth About FAILURE You Need To Hear | Elizabeth Day
5 Aug 2025 · 116 min
In this episode of the How to Fail podcast, host Chris Donnelly interviews author and broadcaster Elizabeth Day. The conversation moves from a powerful live moment where a guest’s emotional story shifted the audience’s energy, to a deep dive into why the show features successful people rather than those in the midst of acute failure. Day explains her "failure principles," especially the common feeling of failure in one’s 20s, and critiques the cultural fetishisation of success and arbitrary timelines like "30 under 30." She shares a personal narrative about a failed fertility cycle, how a psychic reading helped her find peace and reframe parenthood, and how this experience reshaped her sense of purpose. The discussion then explores the importance of friendship, setting boundaries, and overcoming people‑pleasing tendencies, with practical advice on saying no and managing expectations. Day describes how she handles criticism and negative feedback, using a 24‑hour response rule and viewing dissent as a sign of impact. She recounts a moral dilemma about pulling an interview with Justin Baldoni after allegations surfaced, illustrating the complexities of platforming guests. The conversation shifts to Day’s entrepreneurial side: her instinct‑driven approach to building the How to Fail brand, the creation of the Daylight production company, and the development of "podclasses" that amplify diverse voices. Finally, she outlines upcoming projects—a new novel, a secret Daylight venture, and plans to grow her audience in the United States—while emphasizing her preference for short‑term planning over five‑year forecasts.
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We live in a culture that constantly encourages us to have a goal of impossible perfection. We think that's what we should need in order to be fulfilled. Even if you're doing all of the things, quote unquote, right, life doesn't go according to plan. Every single challenge that you face is going to teach you something so meaningful in the fullness of time.
Elizabeth Day is a world-renowned podcast host, Sunday Times bestselling author, and successful journalist.
She helps people to be more vulnerable and to see their failures as a natural and valuable part of life. Much of my 20s I felt incredibly saddened when I failed, and I had spent a lot of time trying to avoid it. You're taught this lie that life is a race. If you haven't got everything sorted right now, then it's over. But I now realize that I am where I am and you are where you are because of all the things that went wrong as well as the things that went right. So I think there's a lesson there in paying attention to who you are right now and having faith that you are exactly where you need to be to learn the lesson that you need to be learning.
For the person watching who at the moment they don't feel like they've got complete control over themselves, how can they help themselves?
The first thing I would want to say to them is—
Hi everyone, did you know that 85% of people who watch the podcast aren't even subscribed to the YouTube channel? Now, I don't like asking people to subscribe to the show, but honestly, it is the single greatest thing that you can do to help us grow our podcast. If you want us to keep bringing you these conversations, the kind of stuff that you simply cannot Google, then do us a favor, hit the subscribe button and let me know in the comments who you want me to interview next. It helps us to grow the channel, reach more people, and get the best guests in the world. So let's get into the show. Elizabeth, welcome to Wake Up.
Thank you so much for having me. I'm so thrilled I woke up this morning. It wasn't a given, I have to say. I had quite a heavy night.
An evening out?
I had a press showcase, my new novel, and I had one vodka martini, but it was a healthy serving. And when I woke up this morning, I did some exercise, and now I feel much better. So it's great to be here.
Is that enough to, to have a hangover?
Not generally for me, no. But didn't expect to start in this way. I've had quite a hectic couple of weeks, and I think I'm still a little bit jet-lagged, and so it just tipped me over the edge.
I want to say thank you on behalf of my wife and I, because we obviously had massive challenges in our life with fertility, and both of us independently found your content and then told each other about your content. And I would say that in the really quite dark moments, both found a huge amount of solace in you talking about it, you explaining it. And I feel for people who probably were struggling to have our own words for at the time, we were like, okay, this is how we process it. And so I think from both of us, yeah, thank you very much.
Thank you so much for saying that. It really, really moves me. It It really does. And that you both independently found the stuff that I was putting out into the world means more to me than I can ever say, because fertility is so difficult to go through. And when I was going through it, I struggled to find my experience reflected in other people's words. And so having gone through it and having come out the other side and not having had a baby. I'm really passionate about giving the world those words, and I'm really passionate about speaking about the experience of it for people like you, or like the person that I was then, or like your lovely wife Louise. It means so much to me, and it gives my life such meaning and such purpose. It actually gives my life the meaning and purpose that I worried it would lack by not having a child. In the conventional way. So thank you for saying that, it means a lot.
I think it's also an important reminder that, you know, if you're sharing in your challenge, is going to help other people, you know.
Totally. And I've come to learn that so much because of what I do, because of the podcast that I have, which is all about looking at failure in a slightly different way. I now know that whatever challenge I experience, and it might be really, really difficult, but I know that I have the resilience and strength to withstand it. And I know that in fullness of time, living alongside that challenge will teach me something meaningful. And it might be that the only meaningful thing it teaches me is that I can survive it, that I can withstand it. But generally speaking, I think most of those experiences have taught me something else really profound, and that's been very, very helpful as a way to live life in a more liberated fashion. So instead of pretending to be perfect. And instead of constantly trying to achieve that goal of impossible perfection, I think I'm now so much more aware that I am where I am and you are where you are because of all the things that went wrong as well as the things that went right.
Yeah.
And I think it's really important to remember that.
The challenge you go through in that, you know, in this case, like, quite traumatic period you go through I think when you do come out the other side of it, I feel you're just more grateful for everything else that's going on in life.
Definitely. You know, definitely. And I think it's because life doesn't go according to plan most of the time. And when I struggled to carry a pregnancy to term, when I was going through recurrent miscarriage and failed IVF cycles and all of that, I realized the extent of which I'd held this plan close to me, and I felt that achieving that plan was my metric of success. But I hadn't really questioned where the plan itself had come from. Yeah. And actually, I hadn't really dug deep into my own soul and thought, well, is this what I want for myself? And it turned out it was something I wanted for myself, and therefore I wanted to pursue it. But I think so many of us are conditioned to believe that we want certain things, or our families have told us that we should want certain things, or culture has told us we want certain things, or we've grown up in a very sort of heteronormative environment where we think that's what we should need in order to be fulfilled. And being confronted by failure, even if you are doing all of the things, quote unquote, right, you're sort of ticking all of the right boxes, still being confronted by failure really brings you face to face with, who you actually are beneath it all.
I do really wish more people would ask themselves that question of, why are these things important to me? The goals I have for myself, the perception I have of myself, my shortcomings— like, why do I think these things are these things? And I think in so many ways, like, that is, you know, the external forcing opinions on you.
Totally. I think So much of my 20s and a fair bit of my 30s was guided by the idea of what other people might be thinking of me or feeling about me.
Yeah.
And actually, it's an impossible way to live your life. Some people call it people pleasing, and I suppose there was an element of that. I did want to please others because I thought that was safe. I thought by pleasing others, they would like me more. And in a romantic relationship, I thought if I please my partner, they would never leave me. And I thought that's what I wanted. But ultimately what I realized is that I was taking it to such an extreme. I was outsourcing my entire identity and sense of self, not only to other people's opinions, but to what I imagined other people's opinions were of me. Yeah, because you can never truly know what someone else thinks or feels, and you can never control it, and nor should you. That's what gives life its multifaceted meaning and beauty. And so actually it's exhausting and pointless. Yeah. And so I've been trying since then to decondition myself from that. Having said that, it is difficult just to let go entirely of external validation, and it's definitely something that I still struggle with. And I think it's part of my kind of life's purpose to work out that the truest validation comes from Inside.
Listen, I know that you are loving the podcast, and trust me, the rest is incredible. But before you skip, there's £200 or $200 cash depending on where you're based waiting for your business, and this is no joke. As you probably know, I run multiple businesses. I'm constantly traveling. I've got teams in different time zones and currencies flying all over the place. And if I can have an app that lets me track, manage, and control everything literally with one tap you best believe I'm going to share it with you. It's called Revolut Business. It's one app, one login, and suddenly I can send, spend, hold 30 currencies, issue virtual cards to my team, and integrate my accountancy software directly to the app for full financial visibility. It's like having a CFO in your pocket without the salary. And here's the best part. They're giving new UK and US business customers £200 or $200 welcome bonus just for signing up and topping up your account before the end of August. If you are a founder, a freelancer, or you're building something from scratch, I highly recommend you checking this out. Sign up to Revolut Business at www.revolut.com/rb/wakeup and add money to your account before August 31st, 2025 to receive £200 or $200 welcome bonus. Subscription fees and terms and conditions apply. Available for business customers in the UK and the US. Okay, let's get back into the episode. It's funny because I— if you were to look at you now and you were to hear you on stage like I did the other month and so forth, like, you do come across as so incredibly confident. And I've seen you talk about the fact that you would say you're an introvert. Yeah, sort of trained yourself to be an extrovert. But I'm quite interested as to how you got to here, you know, for someone that would say they're an introvert and probably weren't that confident to get to where you are, I think is fascinating. So, I'd love to hear a little bit about you before the podcast. I'd love to hear a little bit about you growing up. You know, I read that you grew up in Northern Ireland.
That's right.
With an English accent at a particularly challenging time.
Yes.
Which must have been difficult.
It was difficult. Yes, as you can hear, I speak with this English accent.
Yes.
Never been able to shake it. And the podcast, I'll come back to the North of Ireland in a second, but the podcast has been great immersion therapy for me in terms of getting to like my voice. And actually, I'm so grateful to my listeners and the How to Fail community that they've given me that because so many people have been very generous about how I sound. But I spent decades hating my voice. And now? Now I'm really at peace with it because I think like everything in life, it's a patchwork of all of my experiences.
Yeah.
So, a well-trained person could probably identify, in fact, I know that my accent is very difficult to identify, but a very, very well-trained person might be able to identify that I did spend time in Ireland.
Oh, wow. Yeah.
And they might also be able to identify the years I spent in London or the months that I had in South Africa when I lived there for 6 months when I was 19. And so, I, I love all of those experiences being reflected in how I sound. Um, but to go back to Northern Ireland, yes. So, I was born in Epsom in Surrey, and my father was a surgeon. He's retired now. And his mother had been born in Northern Ireland and raised there. So, there was a family connection. And when I was 4, he got a job in Derry. So if you've ever watched Derry Girls, that was my era, and I'm like the weird English cousin James. We moved out in 1982, which was a heady time in the sense that there were the Troubles ongoing. And I always think the term Troubles is rather diminishing. It was essentially a civil war. And obviously, as a 4-year-old, I wasn't really aware of the political context. And we lived in the countryside, so we weren't immediately affected by it. But Every single journey into school, there would be a military checkpoint with British soldiers with armed weaponry and tanks on the road. And I got very used to evacuating shopping centres when there was a bomb scare, there being travel delays because there'd been some terrible explosion. My father obviously treated many victims and survivors of terrorist atrocities. And so, all of that was going on, and I was made to feel like an outsider because I spoke in the accent of the British.
Yeah.
And for many people, the British military at that time were deemed as enemy occupiers, and the assumption was often made that I must be from a military family, and actually I wasn't.
Yeah.
And so, it was quite a nuanced situation within that situation. My primary school experiences in Derry were really positive. I had a lovely school. I made really good friends. I'm still in touch with them. I had a text the other day from my earliest best friend, Susan Marshall.
Shout out.
Shout out to Susan.
Big watcher of the show. Yeah.
And that was all fine. And I really, the countryside of the North of Ireland is so beautiful. The other thing that I appreciate so much about Irish culture is the emphasis placed on storytelling. They are a nation of incredible storytellers. And from a very young age, I loved books and stories and was surrounded by them. But at secondary school, it became more difficult. So I went to secondary school in Belfast, and at that time of adolescence, you are trying to find your identity, and other people are trying to find their identity, sometimes as a counterpoint to yours. And that's when I experienced mild bullying, I would categorize it as, and feeling very left out. And I was suddenly strikingly aware of my difference, which wasn't just being English. I was also a year ahead of myself academically, so I was a right, right old nerd. And, um, and I had no fashion taste and had a poster of Chesney Hawkes on my wall and stuff like that. So that was more challenging, definitely.
Yeah.
Um, and then when I was 13, because I was pretty unhappy at that school. I got a scholarship to a boarding school in England and I went to boarding school. And the irony of that experience is that from the first day at that school, I was accepted because I sounded right.
Yeah.
But I hadn't grown up there. And so I still felt like a bit of an outsider. I still felt like an observer. And that school was amazing for me. In many ways, and it was particularly good for my confidence. It was a single-sex school, and I had an English teacher— shout out Mrs. Mel Hewish, a regular watcher of the show— um, and she encouraged me to do public speaking and debating.
Oh, amazing.
And I was really underconfident, and I think she saw something in me that would really benefit from being put in these situations where I had to pretend to be confident in order to sway an audience with an argument.
Yeah.
And I'm so grateful to her for that because I think that taught me that confidence is a muscle that can be flexed. You can start by pretending, but then you get practised at how to project it. And that's why when you and your wonderful wife come and see me do a How to Fail live show, I come across as confident.
Yeah.
It's partly because I've got very good at pretending, but it's also because I've put in the hours. As Malcolm Gladwell says, if you do 10,000 hours of something, then you become the thing, you become expert. And so, I also think it's really, I have that to draw on. I have the confidence that comes from having done it before.
Yeah.
And that really helps.
Even at 12. You were messaging newspapers to try and become a columnist?
No wonder I was bullied.
Well, you said you were a nerd, but I mean, 12 is, that's young. I mean, ambitious, quite confident then?
That's such an interesting question. I wasn't confident socially, but I was confident in writing. And that's something that has always stayed with me. I think I'm much better written down because it feels calmer. I feel that I can reach for the right words and express myself in the way— I'm feeling calmer now just talking about it. That's so interesting. In the way that I want to express it. Whereas verbally, I always get anxious and nervous that I'm not going to be able to reach for exactly the right phrase at exactly the right time.
I know exactly what you mean.
Yeah.
Isn't it interesting? I've never said it like that, but I would say that would be a perfect explanation, yeah.
Yeah. And it's so interesting that we're both podcasters because that has never left me. I can draw on the accumulated hours that I've done and reassure myself that I know how to do it. But I get nervous every single time I do an interview. And I'm grateful for that. I think it's really good to have that level of healthy adrenaline. And it means you're not taking it for granted and you're not dialing it in and you're showing respect to the person the person that you're interviewing, but that's never left me. So, with writing, I think it was a self-fulfilling prophecy. For some reason, I just always wanted to write. I always wanted to write books specifically. I remember being 4 and thinking, "I want to write books." Wow. One of my many privileges is that I grew up in a household surrounded by books, and my mother taught me how to read and write before I started school. So, reading and writing was really important. And my parents are inveterate readers. And so, I just started reading a lot and still do. And then because I liked books, I would go to school and I'd be like, "I like books." And then it becomes your thing.
Yeah.
So then, if you have good teachers and you have a family who are interested, then they encourage you to write.
It gets developed.
Yeah. Exactly. And then it gets developed. And then, I was getting complimented for it, and I enjoyed that validation, so I carried on doing it. So all of those things meant that by the age of 12, I knew for certain that I wanted to write. But I had met, by this stage, a real-life journalist in, um, just down there. She came— we had Northern Ireland's only health farm for many years just down the road from us in Claudy. It was run by a lovely couple called Alfie and Claire Danton, and they had a journalist staying with them once, and they knew that I wanted to write, so they invited me to meet her. Her name was Linda Gilby, and she said, "If you are serious about wanting to write, you should start right now. And you should write to all of your local newspaper editors and say you want to write for them." And that's what I did. And the Derry Journal, bless them, gave me a job as a fortnightly columnist, aged 12. And that was the only column I had until I was in my 40s. Is that right? So, it went full circle, yeah.
I, I thought I read that you went on to get a double first.
Yes.
And in history.
Yes.
And then you worked for the Evening Standard and wrote a more like a gossip.
Yes. Well, I didn't write it all, so I, I joined the Evening Standard and I was part the Londoner's Diary, and it was, yeah, 2 pages in the Evening Standard, and it was a kind of highbrow gossip column, but many people wrote for it, and I was one of the members of staff who, that was her job. So I would go out every night to these parties. Talk about a lack of confidence.
When you, when I read that before and I saw you saying that you were introverted, I was like, you had to go up to celebrities.
Yes. And it was a nightmare. I mean, I know it was also super glamorous and it's given me so many anecdotes and that feeling of being an observer. Or an outsider, which I had got from growing up in Northern Ireland and going to school there, actually served me so well as a journalist, and it serves me really well, I think, as a writer. And I know that it's ludicrous that as kind of white, middle-class woman, I'm saying I felt like an outsider, but actually, I mean it as a sort of observer of things that she didn't always understand, but was interested by. And I would put, that part of my life squarely into that category. So yeah, I would be sent to— I got to go to the film premiere of the first Lord of the Rings movie.
Oh, wow.
Yeah.
Big fan?
I mean, it will surprise you to hear I'm not a huge fan. Or I went to just mad kind of book launches in gorgeous spaces in London with an array of celebrities, film stars, and politicians. And I would not only have to try and recognise famous people, but then you're right. Go up to them because you never got a plus one at these parties. I mean, you barely got invited as a gossip columnist. But if you were lucky enough to score an invitation, it would just be you. So I'd be on my own. Wow. And after a while, I developed this strategy of— it was almost like assuming a role. And I'm here to do a job. I'll be here for an hour. And I just have to pretend that I'm confident doing this. And I'm just going to have to go up to this person. And I had one question, which you probably know about, the one question I would always ask everyone is, who do you think is going to be the next James Bond? Because—
Great question.
Well, whatever anyone says, it makes for a story.
Yeah.
If they're famous, because either, oh, I think so-and-so would be a good James Bond, huge news story.
Yeah.
I don't know, then you're like, so-and-so doesn't know. Yeah. Or something like, it could be a woman.
Yeah, they think it might be them.
Exactly.
Yeah.
And British people are just, unbelievably obsessed with who's going to be the next James Bond. So that was my tactic. So yeah, I had a year of doing that. It taught me a lot.
Amazing when you think about it like that. You did just do the hard thing continuously, even whether you're faking it or not. You had a, like, an apparatus, the James Bond question, that you just put in the reps of probably being a bit uncomfortable.
Yes, that's such a good way of putting it. Yeah, I realize that, the truth of that, as you're saying it. And I, I know this sounds trivial, slightly weird a connection, but it's a bit like I always say, if I ever got the chance, which I wouldn't because I'm not a celebrity, but if someone said to me, what celebrity reality TV show do you think you could do? I would say I'm a Celebrity because I can eat anything, right? And it's partly because this completely unhinged. My parents sent me to Russia when I was young to learn Russian, right? And the food there was not great because Russia was going through a really difficult time socially and politically, and there was barely any food to put on the table. Now, if I can survive those weeks in Russia, I know that I can survive any plate of horrible food that is put in front of me.
Yeah.
And it's a bit like that.
Similar.
Sometimes you just have to swallow it.
Yeah.
Sometimes you're right, you have to do the hard thing. As Glennon Doyle so brilliantly says, we can do hard things. And I guess from a very young age, I've known I have that capacity, and I'm familiar with the feeling of discomfort, so it doesn't feel scary.
One of the things I think in entrepreneurship especially, I mean, and in life, is that people will compare themselves to the final version.
Yes.
And so they might be like, how on earth is she so confident when she said that she was introverted, but they sort of forget that what sounds like for the vast majority of your life you've put yourself in challenging situations that continuously got more challenging, but you yourself could deal with them more because you were practiced.
Thank you so much for putting it like that. I feel like you're helping me see the truth of myself. That's exactly—
I feel like it's me.
Well, well, I— yeah, well, game recognizes game. Introvert game recognizes introvert lack of game. But no, I really appreciate you putting it like that because it's something that I've struggled to articulate. How can I be introverted and yet be a measure of comfortable on stage? And you are right, it is that I've been really uncomfortable enough times that the discomfort feels familiar enough.
Yeah, it feels okay.
Yeah.
Yeah, you know what to do when you're there.
Exactly.
Yeah, my, my wife would always say like, uh, everyone misunderstands, but I'm the biggest introvert in the room. Yeah, but you would never tell because I do loads of talking on stage, I have lots of businesses, and so you would just never know it. But then I'm deeply aware that you will just get better at something the more you do it.
And so, yeah, I also think that there's a misperception of what introversion is. Is because introversion, as I understand it, is that in order to replenish your energy, you need time on your own or being quiet, being in a sort of safe, familiar space. And for extroverts, how they get their energy is often being in a room full of people or going out with friends, going over dinner, that sort of thing. I do enjoy it, but it often drains my social battery. And I know that— that's what I'm doing this weekend. I'm going away on my own just to like replenish those stores. Yes. And I'm very fortunate that I have a partner who completely understands that about me, even though he's much more extroverted.
Yeah, I'm the exact same.
There we go. And is your wife more extroverted or is she similar?
She will be incredibly recharged post hanging out with 20 of her friends.
Wow.
Whereas like, I'll come in and I'll be like, woof.
Ditto. We love our friends. It's amazing at the same time. But that's so interesting.
Yeah.
I also think there's something about being on stage or doing a live show that I really value because it feels more like one-on-one.
Completely. I don't know if I've ever spoken about this, but it's like I would feel more uncomfortable being in the crowd than I would on the stage, which makes me sound like a psychopath.
No, I totally, totally get it.
Yeah. But it feels like a more intimate conversation which I'm probably more in control of when I'm on the stage, as opposed to if I'm like networking in a room, which is my absolute, you know, horror show, basically.
Yeah. I mean, I'm the kind of person, if I'm networking, I'll find myself in a conversation with someone and I won't be able to leave it because I'm too worried about offending them or them being upset, or honestly, there's just no way out. If someone hadn't helped me, I could still be networking right now rather than here. I'd be networking at a conference from 4 years ago. There's just no way out. I'm like, I'm in the conversation now.
So my first, my first business, I had to do the sales for my first business. It was like a, you know, the founder-led sales as it were. And at networking events, I would go in, I would hate them so much. But again, I knew subject yourself to the hard thing and you will get better at it. And over time I did. But I was the same. I could never exit a conversation because I was so concerned how they would feel being exited.
Yes.
And the funniest one my best friend, who was my business partner, always laughs at is I spent half an hour charming the pants off this guy, talking about my business, what we could do. And at the end, we'd been talking for so long, he goes, can I get you another Diet Coke? And he just worked there. Oh, so I'd just been networking my way for half an hour into the, into the bar staff.
Oh, but that's— I bet he really appreciated it. It sounds to me like you're also a bit of an empath, and I feel like empaths path and introversion, they're these terms that have got slightly hijacked by TikTok. I'm like, no, I was both of these things before they were cool.
Yeah, yeah.
Um, but it sounds a bit like you have that ability to take on other people's energies and feelings, and I think I have that, and I think I'm extremely grateful to have that characteristic or skill because it definitely helps so much in what we both do. But it does mean that in a crowded space with lots of competing energies, that can be quite a lot to take on.
Yeah, very overwhelming.
I remember speaking to Elizabeth Gilbert once. I was lucky enough to sit next to her at dinner, and I think she's an amazing, magical person. She is all of these things that we've been discussing in spades. And I said to her, "How do you cope with that, with so many people feeling like they know her, wanting to share their stories with her?" and also her ability to empathize and communicate. And she said, "I have a secret cloak." She has an invisible cloak where she will, when she feels herself getting drawn into a conversation with someone, she puts this cloak around her and says something like, "I love you, but that's not my story." So she can be present but not take it all in because for her to take it all in, she's taking in people's traumas as well. And actually, in order to be true to her own creativity, she can't do that all of the time.
Yeah.
So invisible cloaks, that's my top tip for you.
Yeah, you'd lose yourself, wouldn't you?
Yeah.
Before the podcast, you've written for so many different publications. Before the podcast became a thing, was failure a massive thing in your life? Because it's become your brand, and I think it is such interesting apparatus to, you know, talk to people through. And I thought, you know, as we'll come on to, like, the Sally Phillips talk and her talking about her failure was fascinating because obviously she's so accomplished. But before the podcast, was that something that was a sort of ever-present thought?
Fantastic question, and one I've never been asked before. I definitely haven't thought about it as much as I've thought about it now, and it was probably something I sought to avoid, which, spoiler alert, you can't do with failure because it happens to all of us.
Yeah.
No matter how hard you try to avoid it. And when I say I sought to avoid it, it's because I think I had a fragile sense of self. And my way of trying to love myself or make myself lovable was to attempt to be perfect, attempt to succeed, attempt to constantly and consistently achieve. It goes back to those very early days at school being told I was good at writing, that became something that was important to me. It was important to me to be good at exams and to get good grades. And I sort of carried that mindset into young adult life. And so, I think failure was something that I felt it really undid me. I felt incredibly saddened when I failed and also humiliated. And actually, although there were many professional failures, I think the ones that hurt me most deeply were what I deem to be personal failures, relationships that ended.
Mm-hmm.
Heartbreak is one of the most difficult things to go through. It is a form of grief. And every time I went through a breakup, I would see that as a verdict on who I was and how I was lacking. Because I hadn't done the work of building up my own self-esteem or my own sense of self, I felt that my only worthy definition was in tandem with someone else. And so, it felt so deeply upsetting when it happened. And I remember those breakups so vividly. And actually, it was a breakup that prompted me to launch How to Fail. And I think there's something interesting about that because on paper, because I was also focused and I knew that I wanted to write and I got a good degree and I was doing journalism all through school and university. And so, I then did get this job at the Evening Standard. And after that, I worked for various national newspapers. So, on paper, you would think, well, this is someone who is successful.
Yeah.
What we mean by successful. And if you'd read my CV, you'd think, oh, well, that's fairly successful. And—
She's got it all together.
Yes. And I didn't feel like that internally. And I didn't feel like that in my personal life. And I constantly felt that I should be doing better and I should be further along. And I think that's something that's familiar with lots of people in their 20s right now, that you are taught this lie that life is a race and that if you haven't got everything sorted right now and you are not doing better than your peers right now, then it's over. And actually I now realize, and I'm really passionate about sharing, that the older I've become, the more myself I felt, the more awareness I've had of how that is true success rather than something that I can put on a CV. So, I don't think I had spent a lot of time thinking about failure because it scared me, and I had spent a lot of time trying to avoid it, which actually in my case had led me to fail more often. Because if you're seeking to avoid failure or conflict, particularly in a relationship, that's actually not a good basis for it to last.
And so for the person watching who, you know, feels that at the moment, they don't feel like they've got, you know, complete control over themselves, they feel like they're chasing those things, how can they— I mean, other than starting, you know, award-winning podcast, how else can they, uh, you know, help themselves?
The first thing I would want to say to them is you are doing doing a brilliant job just as you are. Just by existing on this planet and asking those questions shows what a thinking, feeling individual you are. The second thing I would say is that life is not a race, and I have learned to become someone who values depth above noise. We live in a noisy culture. We live in a culture that constantly encourages us to have binary opinions about things and to share them immediately online. And actually, I think that true resonance and true success comes from looking inward and digging deeper within and valuing depth over noise, valuing something that will last, valuing getting to know yourself, valuing building key personal relationships over filling your CV with seeming achievement. So, I would encourage you to spend some time time with yourself and getting to know yourself first, because that is time never wasted. And it means that you can show up in your true authenticity in whatever relationship, be it professional or personal, that comes next. I would also want to say that you are not alone and that so many people feel like this, and I have so much empathy for you. But that actually every single challenge that you face is going to teach you something so meaningful in the fullness of time. So if you feel in the grip of that challenge right now, I just implore you to cling on because the worst failure is not taking the risk of continuing. And some periods of your life, you will just feel like you're putting one foot in front of the other and you'll feel like you're stuck or you're not getting anywhere. But those periods of time are never, ever wasted. I first went into therapy when I was 27 because I felt that I was in one of those periods of my life. And my therapist at the time told me something so powerful. Beautiful about the power of gestation. She said, "You know, you've been rushing to achieve things and meet goals all through your 20s, and perhaps right now it's this period of time when you are allowing the next thing to grow. And so sometimes you need to leave the field fallow. You need to leave it in a cycle of recovery in order for the next thing to blossom." So, it's not a race. You are not behind and you are doing great simply by being open to this conversation.
I do think that is your skill, by the way, is that you allow people to feel good about being themselves.
Thank you. That's such a lovely thing to say.
Yeah. As in—
Thank you.
You're okay with the challenges or the state of being that you're in. Yeah. It's quite an amazing thing.
Wow. That means so much to me. And actually, as you're saying it, I'm thinking, I really love people. I think people—
So clear.
I really do. I mean, a sort of, it's a kinder way of saying I'm actually really nosy. But I love people and I love them because of their imperfections.
Yeah.
Like that's what makes someone so interesting and unique. And I think I think my struggle has been extending that to myself, but I'm getting better at it. And I think it's all of our struggles, extending ourselves the same compassion and love as we would extend our best friend. But actually, I've been thinking about this in the context recently, this seems like quite a cognitive leap, but bear with me, of weight loss jabs.
Yeah.
And the fact that an increasing number of people are taking them. And I think they're amazing drugs for people who need them for health reasons. And I also fully support anyone who wants to take them for aesthetic reasons, that's totally their choice. I have had my own sort of struggle with what that really means, particularly if, like me, you came of age in the 1990s or the early 2000s. You're probably familiar with a very toxic culture regarding how you look, and I think that gave rise to a lot of disordered eating thoughts in— definitely in women, and in men too. And so sometimes if you are coming to a weight loss jab from a place of that anxiety and that sadness, I don't necessarily think that that is potentially the right thing that's gonna make you feel empowered. And the reason I've been thinking about what we just been talking about is because of that idea of perfection. I've never looked at anyone and thought, "You are beautiful because you are thin." Never, no. "You are attractive because you are thin." I might have thought, you are attractive and you're thin, but they're two totally separate things. It was a really good wake-up moment for me. And that's how I feel about people. I find them so fascinating and interesting and wonderful, not because they're perfect and they've never done anything wrong, but actually because they have. Yeah. And so I think that's important to remember. That beauty is not this impenetrable, shiny, seemingly perfect, I put that in quotes, thing. It's something radically flawed and encompassing and inclusive and beautiful because of that.
How do you nowadays think about, I suppose, being yourself and being happy with where you are and not having yourself defined by your career and the CV and, and, and the being perfect? And how do you balance that with still being ambitious? Because I feel like it's something that I feel like I struggle with a lot of the time.
Yeah.
Which is I am very ambitious, but I always want to be very present and, you know, I want to be always happy. And it's so funny, like, I feel like if I was to find the happy, would my ambition just go, "Woo"?
I've got exactly the same thing.
Yeah.
I'm extremely ambitious and I can be very competitive. And I don't always like my competitive streak. And I understand now, I think the first step, in answer to your question, the first step is self-awareness. So, I'm aware that I have that. I'm aware that my competitiveness comes from a time in my life when I felt felt deeply insecure and worried that there wasn't enough space for me to be lovable. And so it comes from that. It comes from feeling like I have to prove myself, and I have to prove myself to be better than in order to gain love. And the awareness is half the battle, because it means that I can have compassion for that part of myself. When I feel myself falling into that trap, because it is a trap, of thinking, "Well, I feel like that was a really good episode of How to Fail. Why is that not number 1 in the podcast charts? And why is it the fucking Goal Hanger crew with..." Why is it The Rest Is History? I love history. Anyway, no, but I'm being facetious because obviously those Goal Hanger podcasts are absolutely brilliant. And the flip side of that is that my competitiveness gives me drive. So, I'm constantly striving to be better. And I'm constantly striving to think, "Well, those podcasts that I really admire that are at the top of the charts, what are they doing? What can I do better?" So, there's an opportunity wrapped up in it, which becomes ambition. And I think ambition is a great thing to have. It's a form of motivation. It's when you turn it inwards and become your own worst critic. That's what I'd categorize as sort of competitiveness. Because ultimately, who am I competing with? I'm competing with myself and making myself feel less than purely because I feel like that's how I'm going to get results. And that's not true. So I think the awareness is key. The other piece of it that I have now understood is that my work is about lived experience.
Mm.
And my work is about individualizing that and understanding that every single person has a story to tell that is deeply resonant and meaningful, and to try and draw that out of them or to tell stories that help people feel seen. That's the value of my work. That's what has to drive me. And in order for that to be true, the only thing I have to have done is to create change in one person's life. And I know that I've done that. And I'm so grateful to know that I've done that because my community tell me, you told me when we started this podcast, That is my meaning. And so, that really helps me in those moments when I am falling into old habits. I remind myself that I value that individual interaction, that level of meaning, and that depth over noise.
Oh, brilliant answer.
How do you struggle with it? Like, how do you— No, I'm really interested in asking other people. 'Cause it's helpful to me.
Mine just comes in like unbelievably distinct seasons.
Right.
As in, I am very, very good at doing nothing.
Are you?
Yeah. Like an absolute professional. But then when that fades, I go back to being like a complete and utter workaholic.
You are leaving the field fallow and then you are blooming again.
Yeah, it's bizarre. As in, I can take like full breaks from life months. And my wife has a more normal job than I do. And so there'll be periods where I'll be like, I'm going to go and go away for a month. And I can just like chill for a month, not think about anything and read. But then when I come back, it's like a, you know, okay, here we go again. And it's, my life has always been in spurts. But I'm always trying to find the balance.
But I really admire that. I think I'm also good at doing nothing. I just haven't created the opportunity for my being able to do that.
Yeah, I suppose it's come, it's come very much off the back of like exiting companies. So yeah, when I sold my first company, I had an earn-out period, and then because I was so annoying, they were like, you should leave early.
Okay.
And so I then was like, oh, I can't do what I'm doing. I hadn't really thought about what I was going to do next, and I was like, oh, well, I'm going to do nothing. And so I just did nothing for a long time and then built another company. And then after that company I left, I had another big nothing period. And so yeah, I mean, that's kind of the cycle. Haven't worked it out yet.
What— I'm not interviewing you, sorry. What does your wife do when you're away? She just carries on with her normal life?
Nowadays she just comes with me a lot of the time. Now my wife is the head of product at a company that I founded 5 years ago, which is helps elderly people find care. And so the company is called Lottie. My wife is like the nicest, kindest, most incredible person ever, and she is so driven by the mission of that company that she ended up staying longer than I did.
Beautiful.
Yeah.
Well, I think that really relates to the previous question, mission and purpose. That's— and actually, that's the advice I'd give to someone going through a challenging time now. Is to try and work out what your mission and what your purpose is, because that means that you never feel you're failing. If you can, if you can remain aligned to that, whatever challenges you experience, I believe, are only going to bring you closer to that.
And that's been a really helpful thing for me in all respects, sort of reminding myself of what my purpose Yeah, and I do think, like, I, I would never say to people that you have to be so distinctly purposeful the whole time because sometimes you don't have the privilege to be. I would say that nowadays I was able to take a step back and say, what's important to me? What do I care about? But in many ways, I, I had already got myself to a position where I was comfortable and settled and so forth. And so I feel like a lot of my purpose nowadays is helping people realize that they can become entrepreneurs, that they can become the best version of themselves, and it doesn't necessarily be defined by money.
No, not at all. And I think anyone watching this, and even if they're not watching this and they have a job that they hate, that they have to do because they're paying the rent and they're keeping a roof over their kids' heads, even that, in that situation, there is so much purpose. That person has so much purpose to give. And it could be that your purpose is not driven by what you do for a living. It could be the joy that you bring your kids or in your friendships or— and I think it's really important to start thinking of life in the wholeness of it where, you know, we live in a world where so much emphasis is put on work and what we do. And actually, there's so much more depth to it.
I wanted to talk about a period of your life that was probably a lot more challenging, which is interesting because having been through something similar, I obviously read that your friend Phoebe wrote her, uh, Fleabag, and she, she wrote about, well, about a moment of yours accidentally.
Yes.
I was interested because having been through something similar a few times. It's one of the worst experiences that you could ever go through. I was amazed and like so proud of you that you were okay with that being shared, because in it being shared, again, you made so many people feel better about themselves.
Oh, well, that's a really kind thing to say, and I'm very lucky in that I have amazing friends in my life. And one of them who ironically I met at a 4-day conference, the kind of thing that I would never want to go to. But I was in a dark place in my life and I was like, it was an all-expenses-paid trip to Vegas, so, and it was a competitive interview process. I was like, yep, tick, tick, tick, my competitive muscles are flexed and I get a trip to Vegas.
You did a 4-day interview in Vegas?
No, sorry, I've told that story so bad. It's this thing, it's called this, it's called the British American Project. Okay. Every year they get about 40 people from the UK and 40 people from the US together, and they're meant to be under 40, and they're meant to be going somewhere interesting, sort of in life. And, um, in the UK there's— you have to be nominated by someone who's been before, and there is this competitive interview process. And one year I was nominated, and actually I just had my first miscarriage. And at the beginning of that year I'd had two unsuccessful rounds of IVF, and then I got pregnant naturally, and and then I miscarried at 3 months, which was horrendous and a really awful 2014. And so I thought, "Well, I've got nothing to lose. I'll go to Vegas." And that's where I met Phoebe Waller-Bridge. And we became instant friends. It was like falling in platonic love. She is such an amazing person. Everyone knows that she's a creative genius now, but I am always struck by her generosity and kindness. She's just a really phenomenal woman, and I'm so lucky to have her in my life. Anyway, back then, Fleabag was a stage show, so she hadn't written it as a TV show. And then, subsequently, she did. And then she wrote the second season, which I think is one of the greatest pieces of television ever written. And before it aired, she called me up. She said, "Elizabeth, I think I've done something." weird. And I think you told me this story, and I'm so sorry, but I think I've put it in Fleabag. And it was a story I had told her.
Yeah.
Actually, it was a story I told her, I think, the first day I met her, because that's how bonded I felt to her, about how I— when I experienced that miscarriage at 3 months, I was just about to go in for my 3-month scan, and I started bleeding, and I went in for an emergency scan, and they said, I'm really sorry, but the baby stopped developing. And it was the first time I'd heard of a missed miscarriage. That's what they call it. And they said, we're going to have to book you in for a medical procedure, um, to remove the fetus. And there were various complications, which is why I had to have the medical procedure. And they said, "Um, so we'll try and do that. We'll book you in, but you can kind of go away and come back at the allotted hour next week. If in the meantime you start miscarrying, come into A&E immediately because it can be very distressing." And I went to brunch the following day with a friend of mine who was over from Australia. And I went to the loo, and I realized that I was starting to miscarry. And I went back and sat down and I didn't say anything because it was more important to me that I had this brunch with my friend and that I didn't bother her with it because she was over from Australia and we'd made this plan and we had to stick to the plan and it was going to be fine. Now that is evidence, I think, of how far I had got in my journey of insecurity, lack of self-esteem, people pleasing, just want— wanting everything to be perfect, but also increasingly aware that it couldn't be. And I didn't tell my friend for— I could— I don't know, for a good half hour. And I think maybe she said something in the end, and I said, I think I'm having a miscarriage. And she dropped everything and was like, "We're going to hospital right now." Got me in a cab, took me to A&E, and I'm so grateful to her for that. And then my mum came and met me, and it was a very traumatic weekend. And I stayed overnight in hospital. And I had told Phoebe that story. And if anyone's seen Fleabag season 2, you will know that in the opening episode, Fleabag's sister experiences a miscarriage as she's sitting down at dinner, and Fleabag goes and finds her in the restaurant toilet. And her sister initially is like, "I don't want to make a fuss. I don't want to go to hospital." And it's Fleabag who insists. And so, Phoebe called me up and said, "I've used—" [Speaker:CHRIS DONNELLY] "I've written this up." [Speaker:KARA WILSON] "I've written this story. I'm so sorry. Is that okay?" And I just said, "That is great." And I was so— Immediately? Immediately. Wow. Because I knew that in Phoebe's hands, it would become something that so many people would relate to and see themselves in. And it was a way, genuinely for me, of making an experience that was so challenging and upsetting and full of grief into something really meaningful and beautiful. And so I'm very, very grateful to her for, for doing that in the way that she did. And I think it also says something so, um, beautiful about creativity, that it can come from the most unexpected places, and sometimes you don't even remember where it came from, but it becomes something more more in an artist's hands. And so yes, that happens. Yeah. And then I went to a special screening and was so moved by what she'd done with it. So that's how I felt about it. And also, it, I prob— it probably helped in that I was at a different stage in my life. I was still in the thick of fertility stuff, but that experience— there were a few years between my having gone through it and then it being reinterpreted in that way.
I've seen you say before that the fertility stuff is like having a second job. Yes. Obviously, for the last 2 or 3— 2 years or so, Lou and I have felt like we've had this second job. I mean, especially her, obviously. There is so much complication and so much noise in the clinic, and so many tests, and so many opinions, and so forth. And I think that without things like that, without Fleabag, without you being so— open about your struggles. I think you can become so insular about what's happening to you. And what's so interesting is like, we had a situation where they effectively said that the, a chemical miscarriage was going to be like a heavy period, and it was like the counter-opposite to that. It was like trauma. And I feel like it put both of us into the weirdest place in our life, as in like the lowest of low, you know, life loses its color type situation. And again, I would still point back to being able to read and watch your stuff at the time was amazing because it was like, oh, people do talk about this. And then I was doing a like business talk at this— I was helping a friend launch a book. I mentioned it because it was clearly just on my mind. I hadn't planned on saying it in the thing, and I had hundreds of people, predominantly guys, being like, I'm going through it, or I've been through it, like, thank you so much for talking about it. And so like, I do feel like the, the trauma and the challenge of these things when shared does help.
A thousand percent. And I want to thank you for being open about it right now because it is so potent when a man does that. It's incredibly powerful when a woman does it, but I know that for men it is such a difficult form of grief because a lot of the time you don't feel that you're worthy of it. You want to be there for your partner if you are in a heterosexual relationship, and that's a very difficult ambivalence to carry. And I know that the fertility treatment I did with my now husband, I know that he really struggled with that because he wanted to be there for me and he wanted to protect me. And so it's difficult to know where to put your sadness. Yeah. And actually having these conversations helps so many people and it helps me too. It helps me process all of that grief and it helps me understand and it helps me feel less alone. And that's why what you do is so crucially important. And it's why I do what I do because connection is the thing, really. And these conversations about vulnerability are the antidote to shame and the antidote to loneliness. And I, I really passionately believe that. So thank you, thank you for opening up as well.
It's an interesting thing about, I think, the power of, uh, content. Like, I, I was at your show, uh, with Sally Phillips, who is awesome. She is, even though she doesn't think so herself.
No, she doesn't.
The ultimate irony. But it's funny, I mean, when, when we were walking out the show, I could hear people saying how amazing she was, how amazing you were. I feel the sense that I got was that in seeing that two people who are so successful, you know, objectively, can have so many failures and think those things of themselves, I felt like I was in a rabble of people walking out being like, they've just normalized it being okay way. Yes, to, to have failures and to have challenges and insecurities. And like, when Sally Phillips talks about how she didn't have a solo comedy career because of these challenges, I was like, you know, eye-opening stuff.
Yes. Well, you've just absolutely nailed what How to Fail should be, so I'm thrilled about that, and I want to come back to it. But I also want to just say the hugest amount of credit has to go to Sally Phillips, who was the most amazing guest who came so willing to open up and be vulnerable and be hilarious. And she is so beloved. And it was very interesting for me as well that she doesn't always feel that, understandably, because she's human. And there was this one point that I still think of where she was talking about how she wanted to be taken seriously as an actress. And she'd done this audition for a director she admired, and it hadn't gone well. And she had visibly shown that she was upset. And the director had been nice to her, and she realized that he pitied her.
Yeah, he hugged her.
Yes. And she was crying as she was telling this story. And I could feel the audience chemistry change. I could feel the power of that connection and how they were swelling to give her this support and this validation that she had needed all of those years ago. And I remember when she said, you know, "And I've just never been a serious actress," they start— the audience started shouting, "You are, Sally, you are!" It's so beautiful. And she said, this is like a therapy session in front of 1,900 people. It was so beautiful. I'm so glad you were there for it. You've absolutely nailed the premise of How to Fail. And I'm often asked why I have successful people on the podcast. Why don't I have someone in the grip of quote unquote real failure? And I'm like, well, that's interesting. First of all, what would someone consider a real failure? What is that for you? And that's an interesting question in and of itself. Secondly, someone currently going through a really terrible challenge might not want to come on a podcast and describe it in detail. Yeah, in the moment. In the moment. And nor would I think it was particularly ethical of me as an interviewer to do that. Like, actually, I think most often we get the meaning when we've processed the thing. And so often I speak to people about failures that they've experienced in the past, because there's a sort of depth of interpretation you can get through hindsight. Not always. And sometimes I do speak to people who are going through current failures and who talk about it in a really eloquent and insightful way. But I always do that with their permission and with enough of a feeling myself that they are equipped sort of mentally and personally with enough support to do that. That. But it's also because I think we live in a culture that fetishises success. And so, we often think when we see a celebrity on a red carpet that that person must have the most amazing life. They must have it all sorted and they're so together. Quite the opposite. Exactly. If only I could be like them. Yeah. And actually to take that same person, to pluck Kate Winslet from the red carpet and put her in the How to Fail studio and have this amazing conversation. She's such an Incredible Woman, where she is talking about the things that went wrong in her life, the unbelievable toll that media obsession about her weight played on her, how she feels about parenthood, how she failed to keep up with her tap dancing lessons, how she feels about herself. That, for me, is breaking open the lie. And I really want it to help other people feel less alone and feel seen in those stories and feel that, okay, well, if this person felt that way and they are where they are now, maybe there is also real hope for me. That's what it's about, as well as seeking to tell the truth of someone away from a manicured, manufactured media image. I actually want to know what really makes them tick. So that's why I have interviewed really successful people. I'm very interested in the fact that the common denominator is they have handled failure and they've chosen to learn from it. And I think there's a lesson there for all of us.
I would love to go through your, like, failure principles. I think I could probably name them.
Well done, because I sometimes forget.
For me, you never came across someone that was, like, into, uh, like, psychic readings and that type of, I suppose, release, as her. And then I saw that you had had a reading. Yes, that had quite a big impact on you. Huge impact. And I was like, does that— that doesn't square with the image of her that I have in my head.
Oh, interesting. Actually, I've always been interested in, in that realm of— let's put it as spirituality. What I firmly believe is that as human beings, we don't have the capacity to understand absolutely everything or explain absolutely everything everything that exists and happens on this planet or in this universe through the prism of materialist science. Mm. That's my belief. I believe there is a whole realm that is unexplained and underexplored that is to do with consciousness. And I'm wary of calling it spirituality because that immediately puts some people off. Mm. But I think consciousness is an extraordinary thing. It's mysterious and magical and unbelievably powerful, and it's expressive, and we're just at the beginning of understanding what consciousness is and what it can do in terms of communication and meaning. And for that reason, I've always been open to other ways of seeing and believing. Psychic's part of that for me. Not for everyone. Yeah. In the same way that prayer is part of that for me. In the same way that I have tried to meditate so many times. Yes. And I will get there at some point, even though that's not the premise of meditation. It's never to get there, it's to be there. But yes, I've had a few psychic readings and two of them have been particularly good. One of them has been utterly exceptional. And that's the one that you are referring to. And that person came into my life at a really key point, and it was at the beginning of 2023. And my husband and I had just gone through a failed cycle of egg donation, and it was so, so hard. Even getting to the point of finding an egg donor had taken the best part of a year. It had been so unbelievably stressful. And And then everything seemed to be aligned. The— you will know all of this language, but the hormone levels were right and the embryo was like A+++. Yeah, yeah, successful embryo.
Great CV. Yeah, the amount that you learn. So much. You think, God, I knew nothing about nothing.
I know, I know. And for me, the amount I learned about my own body, and I was like, God, I've never been taught this. And also the amount that medical professionals still don't know, particularly about women's bodies. Anyway, that's a different podcast. Um, we just had this failed round, and it was so devastating when it didn't work, and I felt really lost, and it was one of the lowest points in my life, and I wasn't sure what to do next. And the advice from the fertility clinic, such as it was, was just to kind of keep going, just trying the same thing to eventually something might stick. But that's— I mean, it's, you know, it's so much emotional stress to go through, and it's so much money to spend, and it's so much of your life to commit to it. And I just wasn't sure whether that was the right thing, um, either for me or for my partner or for our relationship, which is incredibly precious to me. And my husband already has 3 children I have many children in my life, and ultimately we decided that we were probably veering on the side of stopping fertility treatment. But I still wasn't sure, and I was so obsessed about it, and I just was looking for guidance. And I also have therapists— a therapist. So I have fortnightly therapy, and actually my therapist, to her immense credit, was like, maybe you should go and see a psychic. She was like, I'm done with you. No, she's just someone who also also has this greater spiritual belief. And a friend of mine who had gone through fertility treatment recommended this woman who called me on the phone from America, where she's based, not knowing my name and not seeing my face. She just had my phone number. And she called me at 7 PM on a Wednesday and said, what's your name? I said, Elizabeth. She said, is that your real name? I said, yes, it is. She's like, okay, let's see what's here for you. And I didn't ask her a single question because I'd had a few psychic readings before and I was like, the key is not to ask a question so that you can trust it, so that you are not giving them guidance. Mm-hmm. The first thing she said to me was, well, you love words. And I was like, I do, I love words so much. Yeah, yeah. The whole first half of the reading was so spot on and accurate. And it was a lot about my work life. Yeah. And some about my personal life. Life. And then about halfway through, she said, I feel like you're grappling with letting go of a lifelong desire. And she said, I don't know if it's to do with children, but if it is, I firmly believe that you were a mother in a past life, and you were the mother of six, and it almost melted you. That was the word that she used. And this life has been offered to you to live on your own terms. She said, I don't know how old you are you are, and I don't know if you've had fertility treatment, but if you have, you might have experienced it not working, and you might have experienced miscarriage, because it's almost like you're being protected. And I was blown away. And when she said the mother of six, that also made sense to me because I had had 3 miscarriages and 3 failed rounds of fertility treatment. So technically I'd been pregnant 6 times, which fascinated me. And from that moment, Chris, I— this is not a word of a lie— from that moment, I've been at peace. I was at peace with letting go and saying, I think my journey with this kind of parenthood has ended. And actually, what's that— what that has opened up for me is a journey into a different kind of parenthood, where, as I say, I've got so many children in my life. There are so many different ways to parent on this earth. And there are also so many different ways to create. And I'm very aware that my life has meaning because of all of those things. And my life has meaning because I can speak like this, because I can be the voice for whom it didn't work out, but it also worked out. Yeah. And I'm very passionate about that being part of my purpose now, to speak to those people who are in the midst of it, like you and Lou, and to say to them, it's going to be okay. Whatever happens on the other side, it's going to be okay. And I have that psychic to thank for it. So yeah, it was very meaningful.
It takes the pressure off a lot.
It was exactly— it was as if someone had given me permission. But it also is beyond that because it felt so in alignment.
I actually meant for your listeners.
Oh yes, also that. Yeah, then, you know, you're—
because you're saying it's fine if it doesn't happen. Yes. The worst thing when you're going through it is the idea that it doesn't happen.
Exactly. And it was the worst thing for me as well. I was like, I, I remember saying to Justin, my other half, if this doesn't work out, I will need to radically change my I will need to go— I thought I just need to up— I need to go and live somewhere different. I need to become a ceramicist and live in Ojai or something. And it hasn't been that. Actually, the radical shift has been internal. And I totally appreciate that psychics aren't for everyone, but she really helped me in a way I will never fully be able to thank her for. And I've subsequently given her number. I'm very specific about who I give it to. I've given her number to some key people in my life, and they have each had had a life-altering— oh my goodness— reading which has been fully accurate for them. So I'm very grateful.
God, what an incredible story.
Yes. How do we get into that?
Wait, spirituality. I suppose one of the things I've really liked about your, your work is like, I feel like if you're in a failure, sometimes you can't see the wood from the trees. And I quite liked when I read that you actually had almost written out the different types of failures that you're experiencing. Yes. What the one that I think probably resonates with everyone is like, everyone feels like they failed in their 20s. Yes, Failure Principles.
That's what we were talking about.
Yes, well done. Yes. Yeah, um, because I feel like that's true. Like, you just— you, again, it's your comparison to what you think other people are succeeding at and achieving at, and you're not. And yeah, 20s is such a weird time to be doing so many things, you know. You've got to find a partner, and make money and have fun. And nowadays it's like, and travel and be an influencer. Totally, you know.
Yeah, that's what you're being told, and it's exhausting. I was lucky enough that I— my 20s were pre-social media for the most part. I mean, I think Facebook started when I was in my 20s. Um, you all know this better than I do. I think that started when I was in my 20s. But yeah, most of it was just kind kind of a Hotmail account.
Yeah, yeah, MSN. And so I didn't even have that pressure.
But you're right, one of the failure principles— I wrote a book called Failosophy 2 years into doing the podcast because I realized that there were 7 recurring themes. And so there are 7 failure principles, and one of those is that almost everyone feels they failed in their 20s because it came up again and again as a subject matter when I interview people for the podcast. And as you rightly identify, why it's a time of immense pressure. For many of us, it's the first time out of full-time education, and so you are in that mindset of studying and doing exams, but you can't take an exam to show that you're nailing adulthood. And so you're pitched into this world of work without the familiar metrics. And because we live in such a hustle culture, but we also live in a wellness culture which is constantly encouraging us, as you say, to like find time to do reformer Pilates and, um, go on a mini break with your friends and drink green juice and then post about it on social media to build your brand so that you're also doing— and so you're also showing everyone else that you're doing well enough. And it's so exhausting. And I just really want to tell people that most of your peers are probably feeling similar, even if they don't always show it. And that actually so much of our life— and this is another Fader principle— is predicated on the notion of who we're going to be in 5 years' time. So we constantly make plans for the future versions of ourselves, and sometimes those plans are really unrealistic. It's a bit like getting a pair of running shoes for Christmas and then saying, I'm going to run 5 ultramarathons in May. And that's, for many of us, impossible to do. By the time May rolls around, we've overwhelmed ourselves to the extent that we've barely gone on a jog because it feels impossible to obtain this goal. In the same way, I found that in my 20s, I had these infinitely detailed 5-year plans of where I would be, and then in 5 years' time, I wouldn't be there. Yeah, but I'd actually be a slightly different person. I'd want slightly and things, but I'd still feel like a failure because I wasn't chief political correspondent at The Times. You know, I was like a feature writer somewhere else. And so, I think there's a lesson there in paying attention to who you are right now and having faith that you are exactly where you need to be to learn the lesson that you need to be learning. And you will meet your 5-year self in 5 years' time, and you'll be able to assess what your 5-year future self needs then. But not now. And so, it's about paying attention to the present and also letting go of the idea that you need to have achieved everything by 30. Yeah. 'Cause I definitely had that feeling. I was someone who was routinely told, gosh, it's so impressive, you're so young to be doing this. You're so young to be a staff news reporter on a Sunday national newspaper. And I used to get an internal glow from that. I said, thank you so much. Yeah, yeah. And I remember my colleague at the time saying, thing, finding out I was born in 1978, being like, 1978? How were you born in 1978? And it's the reaction I now have when someone tells me they were born in 1996. I'm like, what? How is that possible?
Anyway, it's quite young though, 96, isn't it?
96 is so young. That's what I mean. Yeah, as in like, now 1978 makes me like a village elder. Well, you don't look like that. That's very sweet of you. Thank you.
It's just how I'm 46.
I'm 46. And that you need to let go of the idea that you have to have everything achieved by 30. Those lists, those Forbes 30 Under 30 lists have a lot to answer for. Because yes, there are some people who have achieved great things by the time they're 30, but it's a completely invented metric. Spoiler alert, time is invented. It's something that human beings have put on our daily existence to try and control the random chaos of the universe.
Yeah. Okay?
So actually, maybe your greatest achievements, they might be in your 30s, they might be in your 40s. Maybe your greatest achievements won't be something that you can measure by time. Maybe it'll be something that just grows in a really beautiful way throughout the course of your life. And that's something that I feel everyone should know, that it is just never too late to try something. And my 40s have been my quote-unquote successful decade yet, I think because I feel most at peace with myself. Yeah. And that's something that not many people get in their 20s because your 20s are a decade of experimentation and finding out who you are. And so just don't beat yourself up about having that and experiencing it.
COVID was like a, a very interesting period for me because is up until COVID, I had— well, I'd worked for myself since I'm 16, so I never had a job. I just worked like a maniac. What did you do when you were 16? Like, ran online businesses.
Okay. Yeah, not a paper round. That's my 1978 birthday.
Uh, no, I did a little bit of work in bars and restaurants and stuff, but had a proclivity to get fired quite often. I worked insanely hard. I mean, I don't know how I managed to be with Louise for 13 years over the whole way through, but I worked 70, 80-hour weeks from, you know, 20 through to COVID, basically. So like 10 years. And COVID happened, and for the first time ever, I couldn't really work. You know, like the, the fabric of all the work that I was doing just dissipated. Like, you couldn't do marketing for a store because there were no stores. And so I remember thinking like, oh, I'm a massive failure because I failed at this thing. And in a weird sense, like, it actually made me confront a much bigger failure, earlier, which was the fact that in COVID I reconnected with all of my friends. I hadn't really seen my friends for a decade, and it's amazing. Even now, like, I'll be in the group and they'll make quips about how, like, oh yeah, he disappeared for 10 years, or— and now that I'm back in the group, it feels so nice. But also, I, I sort of now appreciate that the more important thing was my friends and my and I don't know why all the nicknames are the nicknames, you know, like I missed that. Yeah, because I was working. Yes. And so like, I actually— it took like failing at my work to then be like, oh wow, I have all this free time and I don't really have that many friends. And because I'd worked so hard, it didn't, it didn't exist. So I feel like from that moment onwards, I like confronted quite a big failure, which was like not being present for my friends, prioritising, you know, probably money and success over everything else. And since then, I would now say like, okay, I focus on friends and family and Lou, and then work and all the time that I don't. Great. And I would say I'm very lucky though that COVID happened. Yes. It was quite the leveller.
That's really interesting. And as you know, because you got very sweetly got my books there, I'm obsessed with friends friendship and think it is so undervalued. Less so now because more conversations are being had about it, and I'm proud to have been a tiny part of that. But it is so undervalued in favor of obsessing over a romantic love. And actually, my friendships have been the loves of my life. They've been there the longest. They've been the most consistent. They've been there when my heart has been broken by a romantic partner. They've been there when I felt like a professional failure, and they're still here. And I'm so grateful to them. And I think your story shows many things, but within every challenge there is such a blessing. If you look hard enough, there's such a blessing. And the fact that you've reconnected with your friends is so important, but also the fact that your friends welcomed you back. I mean, I'm sure you have the piss taken out of you. Yeah, yeah. But that, for me, is the most important quality of friendship, that generosity of spirit. And it's something I rely on with my friends because if I do have an addiction, it is to work. And I think this is a broader conversation. Sometimes I worry about how much of my identity I might hang on that. Yeah. Because sometimes I think I feel anxious if I slow down. So that's something that I need to address in my life, and I'm very aware. Why is that? Because I have guilt about it. Yeah. I have guilt about wasting time. And because time is, as much as it's a construct, it's also finite. And I want my life to have meaning. I want to leave a legacy behind, if that doesn't sound too sort of self-involved. And momentum matters. And momentum matters. And also the fact that I'm not going to be a parent in the biological sense has made that more acute for me. It's almost like, well, I need to prove that I'm worthy of being here. That's in my harshest moments. But it's also that I have this yearning to create and to leave something behind, to leave something in place. So I think it's that, but it's also a fear of not having enough, of losing everything, which again, And a lot of that comes from our upbringing, but a lot of it comes from a freelance mindset as well. If I say no now, I might never get asked again. Again, I'm much, much better at that. I've got much better at that. Yeah. But it's also kind of the flip side of gratitude. I'm incredibly grateful to be getting these opportunities. So, I think all of that goes into it. Plus I'm married to someone who works incredibly hard, who set up his own business. It's celebrating its 10th year this year. I'm so happy. Clear score. Clear score. I'm so enormously proud of what he's achieved and in awe of it. So, if he's working and I'm not, sometimes I feel a bit like, "Well, I must be doing something." Anyway, like you, I'm also good at doing nothing. So, I do balance it quite well. Like weekends are sacred for me and I try not to work over weekends. And I'm good at relaxing. I know what I need to do in order to relax. So I need and value in my friends, I need them to be generous in thinking if I haven't got back to their text in the requisite timeframe, it's generally that there's something else going on for me, but I love them. And I need them to know that and to carry that with them. And when I do get in touch with them and when we do see each other, we can hit relational depth really quickly because we have that generosity of spirit for each other. And that's something that I do with my friends and for my friends. And it's something that's incredibly important to me. And I've realized that friendships can't work for me, sadly, if their most valued metric of friendship is seeing someone regularly or having long phone calls. I just don't have capacity for that right now in my life. However, I make time for my most loved people, and that is probably my number one priority. And they know that I will always drop everything if they really need it. And I also am looking forward to a time, the sunny uplands, like when everything's sorted out. And maybe I'm happily retired, when we do have so much more time together, and they have busy lives as well. And so I think it's sort of holding that in your heart and creating space for each of your friends to evolve and live their own lives, and then welcoming them when they come back into your life yours, which is a great place to be because you have almost sort of established your way of life and the friends that you have understand that.
Exactly. When I was watching or reading your stuff as well, it seemed like you weren't always like that.
No, that's a really good point. I've always struggled to verbalize anything uncomfortable that might lead to conflict. I'm extremely conflict I don't. So even though I'm a good communicator, that's where I struggle, the conflict. And so if there was ever an issue in a friendship or in a romantic relationship, my tendency in the past would be to try and process it silently myself. Yeah, without raising it as an issue. And now I've realized that doesn't serve either party well. And now I've realized that there is a way to communicate with love, even when you're communicating a conflict, that doesn't make it feel like a fight, that doesn't trigger defensiveness in the other person. And so I've got so much better at communicating my way through that. And again, I'm so grateful to my loved ones for creating safe spaces for me to do that, because in past relationships and maybe even some past friendships, it hasn't been safe for me to speak up. And so that has a long tail and it has a kind of long impact and long effect, whereas now Now I have amazing people in my life who, who make me feel that there is space in our relationship for rupture, then repair, and that they're not going to love me less for it. Also, a great way of communicating how you feel about friendship is to write a book about it and to interview your friends for it, which is what I did. And it was almost like a sort of just a love letter, a missive out there, and it really helped me clarify me how I thought about friendship. Because as I said, not that much has been written about friendship. Not— not— there, there are hardly any academic studies, for instance, about friendship. They're generally about romantic love. And what academic studies there are are completely fascinating. And I really value the chance to kind of dig deeper into what friendship really is. So it also clarified my own approach.
So for someone would self-identify as like a people pleaser then or now, how do they get to a place where they can say no, they can, you know, protect their own, you know, outcomes better?
Okay, loads of things I want to say here. One of them is taught to me by my best friend Emma, who's also a therapist, and she said this thing to me once, which is a boundary is a point of connection. Oh, isn't that good? So you saying no to something you don't want to do do, actually it does two things. It makes the person you're saying no to know that they can trust you. It makes them understand that you are being honest and your authentic self. And then it does the second thing, it makes that person feel closer to you because you've shown up in this authentic capacity. And they then know that when you say yes, you are fully committing to that yes, and you are fully committing to being there in all of your myriad ways. And that's an amazing thing. So that's one thing that I remember, that a boundary is not always selfish and it's not always going to push someone away. Quite the opposite, it can bring them closer. The other thing I would say is that you don't need to over-explain. That if someone's inviting you to a party and you don't have anything else on, you just feel completely depleted, you can say, I'm so sorry, I won't be able to make that. Full sentence. If you want to, you could experiment with, I'm so sorry, I've taken on too much these past few weeks and I'm feeling so depleted and I really need a night to replenish the stocks. You could experiment with that because someone who really loves you or a really good friend— Will get it. Will totally get that. Yeah. And I really value it when people say that to me. I'm like, absolutely, totally got it. And actually, I often say to friends, I operate a no-responsibility cancellation policy. Like, you don't need need to explain. You can just cancel, and I will just take it for granted that you've got a good reason for doing that. Yeah, it's not whimsical. Yeah, it's not whimsical. Yeah, you, you don't need to over-explain, um, nor do you need to please everyone. In fact, by pleasing everyone, you're actually cheapening what you do have to offer. You're cheapening your approach to friendship, because as a friend of mine put it, you're letting everyone in, which means you have no standards. And so it means that the real friends you do have are like, What? Why? Chopped liver? You're just letting everyone in. Yeah, yeah. So, actually saying no to things and having appropriate boundaries and expressing all of that with love, that's the other key part of this, is that you don't need to be mean or cold. And if there is some kind of conflict, you can start by saying something like, I'm so sorry if that hurt you. This was the reason. Or, um, you know, I really love you and I can't do tomorrow, but can we get a date in the diary for 2 months from now? Because I've got a really busy patch, but I really want to see you, and if we do that, it will just make me feel calmer. Something like that. There are just so many ways to express yourself that don't have to be cold or unfeeling.
How do you feel now with, like, boundaries and obviously having a big audience and having big, you know, it's like, uh, so many people can have an opinion on you. Yes. How does that, how does that feel? Because I've obviously read your stuff, I've watched your videos, I've been to a live performance, like I've seen so many different, you know, uh, elements of the audience. But it's a big audience, a lot of people have an opinion. Like, how do you, how do you deal with the boundaries now?
First of all, thank you for being one of the few men in that audience. Thrilled. I know I get more men who listen and watch the podcast, but fewer turn up to live shows.
It's quite the energy in the room, 2,000 women.
It is. It's an amazing energy.
Yeah, yeah. I mean, it is. Love that. As a man, you're a bit like, "Phew." Yeah.
I know, you have to be careful. You have to, yes, be careful to behave. No, it is an incredible energy. And actually, in that particular scenario, a live show is so incredibly special because it's a self-selecting audience. Yeah, I mean, they're your super fans and they're amazing. I love them so much. And they have taken the time to come for an evening out. They've spent money on tickets. Yeah, they've arranged a babysitter or they've booked the train ticket. I think it was a Friday night. Yeah, even, even more extraordinary. Yeah, it was to go out on a Friday night.
Yeah, I mean, it was amazing.
It was amazing. And I'm so grateful for that. And it is such a special atmosphere, it really is. And I, I actually feel feel as safe as you can feel in an auditorium full of 2,000 people in, in that environment because of all of those factors. And they're often people who've been with me since the beginning of this journey, so they've really, they've really held my hand through this evolution. I get a lot of DMs, and often I get DMs from people who are going through challenging times, and I have just had to accept the fact that I can't reply to every single one, because to reply to every single one would take my entire life. Yeah. And if it took my entire life, it means that I can't put out the work that actually will help that person. And it's a really difficult thing for me to accept because I want to reach out and message every single person. But I have had to accept that, that there's— that I have to protect the time it takes to create meaningful work that will eventually reach that person and be there for them to return to. And sometimes I do reply to DMs because it's particularly important that I do. But that's just something that I've had to take on board as, as part of the deal. Um, in terms of opinions, I've learned that if I encounter a negative opinion, which it's part of putting yourself out there, but putting myself out there is more important to me than the potential danger of someone criticizing it. And because I write books, and as you kindly pointed out, I'd written a number of books before I launched How to Fail, I got used to reading horrible reviews. I've had, like, awful stinking reviews for my books. Not all of them, I've had some amazing reviews as well. But I remember my first novel came out and the two first reviews, one was on a TV program in Ireland and one was in the Evening Standard, and I still remember the name of the person who it. They were savage. They were absolutely savage. And actually, it was so difficult to go through at the time because it's so exposing, writing a book. But I'm really grateful for it now because honestly, getting through that meant that nothing else could be as bad. Yeah. That was written about my book subsequently. And so it's proved to be. And a good friend of mine gave me a really good piece of advice, which is that I'd provoked something in them, and that's so much better than not provoking any response whatsoever and being kind of mediocre and middle of the road. The work that I do might feel scary to them, and they might have a negative opinion of it, but actually that doesn't mean that I shouldn't be doing it. Yeah, if anything, I should probably be doing more of it. And I've learned to metabolize those negative responses more effectively. So they still hurt me. Yeah, and of course they're still going to hurt me because it's important that I still feel feel, and it's important that I empathise, and it's important that I take on board constructive criticism. If I've done something wrong, I need to be open to hearing that and rectifying it. So, I understand that it hurts me, but now what I do is I always leave it at least 24 hours before responding. Yes, smart. And having left it 24 hours, most of the time I don't feel the need to respond anymore. Anymore. I've been able to metabolize it, and I've been able to understand that that person on that day was in their own world of pain and felt that they had to say this thing to someone they don't know. And that is helpful, that 24-hour period. Yeah, it's actually something that's helped me. It's helped me in other ways as well. Like, because we live in a culture of immediacy, there's a sense that we have to respond whenever we're asked something in the moment. And actually, I've realized that the kind of personality type I am My default is I always want to say yes, but I don't always have capacity to say yes. So now if I'm asked something and I, I'm not— I got that slightly tense feeling of like, I should say yes, but I'm not sure I can. I say, can I get back to you in 24 hours? And by then I feel so much calmer and clearer, and then I know what to say. And that's how I cope with it. At the same time, I'd like to wrap this whole answer up in saying I'm incredibly grateful that there are more people that have opinions about me because it means that my platform is bigger and my audience and my community is bigger. And that's an extraordinary thing and one of the greatest gifts of my life because the majority of that audience have accepted me for who I am rather than who I was pretending to be. And, and that's been a really beautiful thing.
I think that's great, uh, practical advice if someone has a challenge or a negative comment. I do the exact same thing. I will often in the moment write the response. Yeah, almost immediately, you know, like, and then I'll say I'll send it tomorrow at 5:00, um, and then by the time it comes around tomorrow, I'm like, exactly, whatever.
I also think this is where your friends and your loved ones come into play because because it's important to have your cornerstone relationships. Totally. People who really know you. Yeah. And if you're unsure, you can say to them, you can check in with them and say, have I done something wrong here? And they will say, you might want to pay attention to that. Or they'll say, of course you haven't, and that person's just lashing out. And that's really helpful, having those people that you can trust. The final thing I would say is that I find this a very helpful thing thing when it comes to opinions. I love cheese so much. I'm a savoury person. I'll put cheese on a hot buttered crumpet and I'll be happy for hours. I absolutely love all kinds of cheese. There is some person in this world who don't— there are some people who don't like cheese. There is— that's just a fact. There are some people who don't like cheese and that's their opinion, or they're lactose intolerant, which is a different thing. That's their opinion. Now, I can't understand that. Yeah. But I have to allow that there is space for that opinion. And that genuinely has really helped me because one person's cheese is another person's vomit, basically. And so, if someone doesn't like a book that I write or an episode that I put out, it could be that it's their cheese, but it's also my cheese and I love it.
I saw, like, you did an episode with Justin Baldoni. Yes. And that was pre- the argument sort of swinging.
It was pre-Blake Lively's lawsuit.
Yes, you did it and he came out as the bad guy.
So, yeah, so I did an interview with Justin Baldoni after It Ends With Us had been released. Yeah. And at the time, he was the internet's hero because winning awards and— yes, and he had spoken up for survivors of domestic violence, and he was getting a lot of plaudits for that. At the time, Blake Lively was enduring a lot of heat from TikTokers who felt that she hadn't got the tone of the movie or the promotion of the movie right, because ultimately, it is an adaptation of a book that has, at its core, a storyline involving domestic violence. So, I interviewed Justin Baldoni, and we put the interview out, and a lot of people loved it, and a lot of the comments were like, "He's amazing. What a hero. Thank you for everything you do." And then, I can't remember the exact time frame, I think it was a month or two later, Blake Lively launched her lawsuit, and The New York Times reported it, and it was a few days before Christmas. And then the internet caught fire, and suddenly, in the blink of an eye, someone who had been getting so much praise, was suddenly getting criticized for serious allegations of sexual harassment on the set of It Ends With Us. And so, that pitched me into a moral quandary because obviously, when I had recorded that episode, I could have had no knowledge of something that hadn't happened yet. If I had had knowledge of the thing that hadn't happened yet, I absolutely would have asked him about it. [Speaker:CHRIS DONNELLY] Yeah. [Speaker:KARA] But as it was, was I started being accused of and being criticized for platforming an alleged abuser, which is not something that I ever want to do. Yeah. At the same time, it was a legal matter, and part of me felt like, well, we need to see what happens in the legal proceedings, because as serious and distressing as these allegations are as a woman to read about, they have to go go into a court of law, and someone has to decide whether there's merit to them or not. And so, I wasn't sure what to do, but ultimately, I thought it made more sense to take the episode down and allow the legal process to play itself out, and then to take a decision. Now, I didn't know then that the legal process was going to take well over a year. Dominate the world. Yes. I also did it because I didn't want to trigger anyone who is a survivor of sexual harassment, sexual assault, sexual abuse, or domestic violence. I didn't want to trigger them if they saw that episode or heard it. And I had to be cognizant of the fact that that might happen. And so, I made the decision that felt right to me, and it was completely my decision. And I took it down just before Christmas. Also, it was Christmas, and I was like, I was like, I just— this— there's too much noise around this. And I didn't feel I could be silent about it either. And so I took it down. And then obviously the internet has now swung in all different directions the other way. And who knows who's going to come out of that story. But I can't even imagine what it's like for those— for the people involved to be going through that right now, the amount of attention and scrutiny it must be absolutely horrific. So that's the story. But I do think there's something interesting about questioning what we're being told there, because, you know, I'm like anyone, I really enjoy a good scroll through TikTok. But we need to question the narrative sometimes. Sometimes what is gaining traction on TikTok is not actually the multifaceted, nuanced truth of a situation, which is so much more complicated.
I mean, nuance is lost in social media. I mean, this sometimes—
sometimes it, it is in the name of entertainment. And actually, we all like to belong to groups of people, and we all like to feel that we're uncovering something that we haven't been told. But sometimes there are other things going on, and I just counsel everyone to question what they're being told and, and work out their own opinions.
Finish on talking about something that I don't see you talk about very often, which is that you are an out-and-out entrepreneur, like incredible founder. And I think because you're a podcaster, because you're a writer, because you talk on stage, I think people forget that while you might be the talent of the business, as it were, you're also the person that runs the business. Wanted to ask like what it's like doing both those things, running a business where, you know, you are the front person, but for your own business?
First of all, thank you, because it's so nice to be asked about that, and it's so nice to be spoken of in those terms. And I think I have struggled to claim that for myself, um, which is an interesting thing, isn't it? It's almost like I don't feel that I can be a real business person because I hate Excel spreadsheets. I now realise that being an entrepreneur entrepreneur is creativity, and that's why I love it. And I love being surrounded by entrepreneurs. I love being surrounded by people who have an idea and who come up with a strategy to make that idea exist. That is so exciting to me. And I love what I do, and I'm incredibly passionate about the business side of things. And part of the reason I'm passionate about it is because I'm extremely instinctive about about it. And that's something that I've learned on this journey, that the world of entrepreneurialism, but specifically business, is still a world that was created along male-dominated lines. And so it feels like there are still these kind of gatekeepers who say things like, well, you can't possibly be in business or be an entrepreneur unless you know how to do accounting, unless you do know, like, how to do an Excel spreadsheet and what the little adding symbols mean, unless you do have a very clear notion of what your projected figures are for the next 10 years. And all of that has its place, of course. You absolutely have to nail that and you have to be clear about what your profit and loss is. But I think that that really marginalises what might be seen as a more female-focused idea of, like, following your instinct first. And your community. And my community, exactly. And that's something that I know I'm good at. I love having ideas and I feel like I can have ideas that take the temperature of the time because I have access to this extraordinary community and because I ask questions of people and the world. And so I have conversations about what's happening. So that's all a big preamble to saying that, yeah, how to fail deal, I started on my own drawing a rosette with felt-tip pens as my logo and DMing a hummus company on what was then Twitter to be my first sponsor. And I learned about deals that I could do to get sponsorship for entire seasons and to cover my costs in the first 3 seasons. And then I started turning a profit, and then I understood that not only was How to Fail my passion project, it was becoming my business. In fact, it became the most successful thing I've ever done, which is deeply ironic. And it became something that through its growing listenership also grew my book readership. My book sales increased as a result. So it's really the tentpole for so much of what I do. And now I have a partnership with Sony, who I produce the podcast with, and that's been a very interesting experience. We're about a year and a half into that partnership, and I've understood that my role, as well as being talent, you're right, is managerial too. Like, I'm across every single aspect of my podcast because it is so personal to me. So every single social media caption, like every single edit of a trailer every single word in a show note. I do all of the research, and I will write the introductions and do all of the questions. Like, all of that is deeply personal to me, and I will be across everything. It's incredibly important to me. And perhaps I'm a bit of a control freak.
Can you hear? That's why you're as successful as you are, though.
Well, thank you. And I feel that I know my people. Yeah. And so I— and I want them to feel like they are seen and that I am No matter— the podcast has grown, but I'm always loyal to them. And off the back of that, because I'm so appreciative of the success that's come from How to Fail, which I could never have anticipated, I noticed that the top of the podcast charts in the UK was still overwhelmingly dominated, no offense, by white men. And I wanted to do something about that. I noticed that I was very often the highest charting solo female podcaster. And you know, because you've been to one of my live shows, that men, straight men generally, won't always choose or won't often choose to listen to a podcast that's fronted by a woman, which is so fascinating because I constantly listen to podcasts that are fronted by people of all genders. It's the same thing in the book world. So I set up a production company called Daylight, which seeks to elevate diverse and female voices in podcasting. And again, I was so passionate about it, I launched it before a wiser-minded, more experienced business person might have suggested I launched it. I launched it with a website and my own money. And I was like, well, let's see what happens. And I had this idea of a podclass, a podcast masterclass. The idea being that I would make expertise accessible and entertaining, and that the kind of experts I would have would challenge our very notion of what an expert is, because we still wrongly believe that experts are generally like white professorial middle-aged men. And actually, I'm really passionate about challenging that. So I've produced two podclasses now, and the first was called How to Write a Book, and the second was How to Date. Yeah. Um, and the first podclass was fronted by three incredible women who each phenomenally talented in their own field, an agent, an author, and a publisher, and they all happen to be Black women. And we got into the top 10 of the UK podcast charts, and I'm so proud of that. And it teaches you everything that you need to know if you want to write a book, or even if you just want to tell your story in some form. And it takes you right through from idea to plot development and all of the rest. And How to Date does what it says on the tin. And it's a boot camp for anyone who is navigating the jungles of dating right now. Now. It's everything I wish I had known when I was single in my late 30s. It's sort of 8 weeks with 1 bonus episode, and it takes you chronologically through: are you ready to date? How to get ready for the first date? How to meet someone? How to navigate the apps? How to spot red and green flags? And I co-host that one with Mel Schilling, who many people will know as the brilliant expert on Married at First Sight Australia and UK. And it was her first ever podcast So I was very honored that she trusted me with it. And that's been really fun and a lot of work, but it's work that I find so inspiring. And I actually really have discovered that I love platforming others. I loved co-presenting How to Date, but ideally, I wouldn't co-present them. I just— I'm really— I love seeing other people being brilliant. Brilliant at what they do and being given a platform on which to do it. So I want to do more of that.
When you look at what you do, sometimes it's not overtly obvious how brilliant your business actually is. Oh my gosh, thank you! Tell me more. Well, I think most entrepreneurs, like, if you were to go out and ask 100 entrepreneurs, what's your biggest problem, they would say customers and sales and marketing. It's like the always stated problem of— whereas what you've built is like a self-fulfilling community and business where now you have an incredible community that trusts you and support you and have such depth with you that when you do do a live show or you do launch a new show, your audience comes with you. You can't buy that.
Well, thank you for saying that, and I get— like, thank you, and it's true. I mean, I feel so, so grateful to that community for multiple reasons, but probably right up there at the top is the fact that they trust me and I never want to let them down. And, and the Podclass is a really important part of that. There are lots of free resources that you can download. There's a website that I built called thepodclass.co.uk, just get that in. And, um, with How to Date, there are all of these free worksheets that you can download. With How to Write a Book, there are these reading lists and all that sort of stuff. So, where I can, I want to make things readily available. And very often I get people coming up to me and they might see me on the tube or on the street, and they will say to me, "I feel like I know you. This is probably really weird, but I feel like we're friends." And it's not weird, it's beautiful because they do know me. They do know me because they've been with me for so much of my life and they've listened to me and I've been open because they've made me feel that I can be. So that's something that's really precious.
And so what's next for you?
Well, as you know, I don't like to have a 5-year plan. I like the next 6 months. Okay, next 6 months. Um, I have a book coming out. I do have a book coming out. I've got my new novel coming out, which I'm super excited about. That's coming out on the 25th of September in the UK. It's called One of Us, and I had a lot of fun writing it. It's the first book I've written since deciding to end the fertility journey, and actually I can tell because I— that's where I put my creativity. It was, and I, and it was joyful actually writing that book. So yeah, that comes out in September. Then I do have another daylight project. It's not a podcast, but it's simmering away, and I think people will be really excited by it. It's a mashup of two different interests of Can't say too much more about that. I think that's it for now. That's the next 6 months. That's enough. Yeah. I'm really keen to build the podcast audience in America. So, I've just come back from a few recordings I did in New York, and I think I'll be doing more of that. I love the American market in terms of creativity. I think it's a really interesting and innovative market. Creative space. So I'll be doing more of that and, yeah, building my entrepreneurial reputation and business.
Chris Donnelly, amazing. Well, thank you so much for coming on the show.
Thank you so much for having me. I've loved it.
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