THE OUTNET’S Head of Content, Claudia Mahoney, was thrilled to make some time for author, journalist, and host of the acclaimed How to Fail podcast, Elizabeth Day. In case you missed their inspiring live conversation, we made sure to save some of the best bits…

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Claudia: Good evening Elizabeth, thank you so much for joining us.

Elizabeth: It’s such a pleasure to be here.

Claudia: I am feeling under enormous pressure this week, particular pressure to introduce you. Just because you are famed for your warm and incredibly generous introductions on your podcast. I’m gonna try, ok? Are you ready? You’re an acclaimed author, a revered podcast host, you’ve been described as sort of the voice of a generation when you were writing as a journalist. So, everyone just wants to be your best friend, myself included.

Elizabeth: I don’t deserve that at all but I’m really flattered. And, it’s so lovely to be chatting to THE OUTNET. I love THE OUTNET. I’ve literally just spent a sizable sum of money on a bridesmaid’s dress for my best friend, cause I’m getting married in December. BUT, it wasn’t as sizable as it would have been had it not been on THE OUTNET and I’m very grateful.

Claudia: So, you’re particularly famous for How to Fail, your podcast and the book that you’ve written and everyone very suspiciously says ‘what would you know about failure?’ And, I think what it is, is that they’re squaring their perception of you and you know, by any standards your success, with failure. So, how did you hit upon this rich seam of failure to mine then?

Elizabeth: Well, it’s a really good question, because I’m extremely aware that I speak from a position of real privilege. You know, I’m white, middle-class, I have a roof over my head, I speak from a certain perspective which is why I seek to get very diverse voices on the podcast who I then quote in my own work and give a platform to. And, it’s interesting that perception, because a lot of the time, the culture that we now live in, encourages us to compare our insides. So, we all know our own anxieties, our neurosis, our failures, we all know that from the inside out. But, we’re being encouraged to compare what we know about ourselves, our insides, with everyone else’s outsides on platforms like Instagram, where quite often, people portray a perfected version of their lives. So, although on some levels I completely appreciate I come across as successful in the sense that professionally speaking, you know, I am an author, I’ve published books and I’m a journalist and I have a salary and all of that sort of stuff. Personally speaking, I’ve found that my life has not gone according to plan, and it was really that kind of disconnect that encouraged me to launch the podcast and to make this conversation about failure a bigger one. To cut a very long story short, I was dumped 3 weeks before my 39th birthday and I was looking back on the decade of my 30s and I realized that professionally speaking I’d done ok, personally speaking, I had got divorced, I had tried and failed to have children, this relationship was now ending, and it felt like I was staring down the barrel of an uncertain future in my 40s. And, it was really from that place that I thought ‘what if we all got more comfortable talking about failure’ and what if we realized, as I was coming to learn, that for every time something goes wrong, generally speaking, if I’m lucky enough to survive it, we can learn from it and we can apply greater resilience the next time something doesn’t go according to plan. So, that was the starting point for the podcast. I didn’t really know what I was doing so I was really relying on friends and contacts to be my first few guests. I really wanted to make it clear to them, this isn’t going to be wallowing in sadness. As the podcast has matured, it’s been really wonderful having the opportunity to talk to people who have gone through failures that they still live with on a daily basis, that still affect them. But, they choose to take some meaning from it. So, during lockdown I spoke to Henry Holland, the fashion designer, and his business recently went into administration, and he was talking to me about that as a failure while he was going through it and that’s something that I’m not sure I would have been brave enough, as a host, to do in the very beginning. But, which I felt really honored Henry chose to do because he was learning from it as he was experiencing it. 

Claudia: Do you have like a line in the sand about what you consider too far and too personal for you, because in the past you’ve spoken about death of loved ones, of friends, you talked about infertility, divorce, relationship breakdowns. Your friend Phoebe Waller-Bridge used your very personal experience of a miscarriage in Fleabag. So, do you have a point that you say, ‘you know what, this is just for me now,’ because you’ve got such a public persona as well?

Elizabeth: I think my line in the sand is much further into the sea than anyone else’s. So, I feel quite comfortable sharing but I have to be ready to share. There are certain experiences that I’ve had, you mentioned my miscarriages, I’ve had 3 now and I definitely know that I need to take time to process that myself privately before I can write about it or talk about it. That is integrally important but, having said that, once that process is done and once I’ve kind of acclimatized myself to the idea of living with it; I then really, really feel a need to share and to write to talk about it for two reasons. One is that’s how I attach meaning to something that might otherwise be meaningless and that makes it easier to live with. And, the other reason is that I am profoundly passionate about attacking the stigma and shame that woman feel when they talk about a miscarriage or infertility. And, I will talk about it forever until that becomes an easier conversation to have and I appreciate that I’m lucky enough to have a platform to do that but I’m also lucky enough to have a personality that doesn’t mind doing it. A lot of people don’t feel comfortable talking about private things, and I completely respect that and I find myself quite weird that I don’t need that, and I’m willing to do it.

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Claudia: You are undeniably a very clever, bright woman. Would you describe yourself as a Type-A personality, and if you would do you set yourself impossibly-high standards so that you’re doomed to fail?

Elizabeth: I used to be that kind of person. So, I describe myself as sort of a recovering perfectionist. I was definitely someone who felt a need for approval and when I got to school I realized that a way that I could do that was to do well at exams and then I’d get praise from teachers. But then what happens is you begin to think that that praise from teachers and doing well at exams is your entire personality and of course it isn’t. You’re out-sourcing your sense of self to external validation. I kept on doing that professionally and in relationships and I think a lot of, particularly women, could relate. You’re often the one at work who does the over time, organizes the office collection for a leaving party, who says yes to everything and doesn’t complain because they think they’ll eventually be rewarded. That was me, for 8 years as a staff writer on a Sunday newspaper. Never once asked for a pay rise because I just felt like I didn’t deserve it, which is ridiculous. And, eventually my life imploded because you can’t live your life like that. You’re actually not living your life, you’re living other people’s versions of your life, or what you perceive to be a judgement of you. It was actually my divorce that helped me get over that.

Claudia: Do you feel fulfilled if you can tick off your plans or is it the surprising diversions that life throws at you that give you the most happiness?

Elizabeth: For me, personally, it’s the latter. So, I used to be someone with a 5-year plan, life threw me a series of curveballs, as it does everyone, and I came to realize that actually I wanted to be in a space where I could respond to those curve balls in the way that I wanted so that I didn’t feel trapped. The problem with a 5-year plan is sometimes, we are thinking of a perfect projected vision of ourselves that will never fully exist and we set ourselves such unrealistic goals that we then feel like failures because, according to our own metrics, we get there and we’re like, ‘oh, I haven’t won a marathon.’

Claudia: Is there one piece of advice that you’ve got out of all the interviews that you thought ‘that has literally stopped me in my tracks and has made me rethink my whole life philosophy’?

Elizabeth: There’s a couple actually. One is something that one of those incredible women in their 80s told me, Gloria Steinem. Casually name drop that, CLANG. We were talking about fear because she famously coined the phrase ‘feel the fear and do it anyway.’ And, we were talking about fear of failure and how that really hamstrings some people and she said, ‘you know, the thing about fear is that it can often be a signifier of growth.’ Because, often you’re fearful of the unknown and what unknown means is that you haven’t grown into it yet. And that blew my mind. The idea that you can feel fear, I think especially professionally, sometimes you’re very fearful about doing things, I’ve got a live show coming up at the London Palladium on the 2nd of October, I am terrified. BUT, I really want to do it because it’s an amazing opportunity and I’ll grow into it hopefully. So, that’s one piece and another piece of advice comes from my all-time-favorite guest, a man called Mo Gawdat, who developed an algorithm for happiness. And, he said to me that ‘you are not your brain.’ What he meant by that was you are not your anxious thoughts, your brain pumps though around your head in the same way that your heart pumps blood around your body. They’re both organic matter and you wouldn’t think that you were defined by your blood so you shouldn’t make the same mistake of thinking you’re defined by your anxious, narrative thoughts. He came up with a way with sort of training his brain to be happier, which was to give it a name. So, he calls his brain Becky because there was an annoying girl at school who was always pointing out everything that went wrong. Now, whenever he gets in that anxious, narrative loop of, you know, he had an argument with his daughter and he was walking down the street afterwards and his brain was saying ‘you’re a rubbish parent, she doesn’t love you anymore, you’re such a failure.’ And, he stopped himself in the street and he said ‘Becky, I would like you to provide me with objective evidence for that assertion, because if you don’t have objective evidence, I want you to take that negative assertion and replace it with a positive one.’ And, in that way, you can train your brain to be happier. And, it works, I’ve started doing it.

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Claudia: Talking about life philosophy, I’m going to take a neat Segway into your next amazing achievement, you’ve got a new book coming out, do you want to tell everyone what it’s called, because it’s the best pun ever?

Elizabeth: I’ve got a copy right here! It is called ‘Failosophy’. You see what I’ve done there? I love a pun. It’s out on October the 1st, and basically, it’s a handbook for when things go wrong. It contains seven failure principals that I’ve developed from doing the podcast. It’s got loads of amazing quotes from my incredible guests and it’s beautifully hand illustrated by the illustrator Paul Blow. And, it’s just like a perfect little gift size, fit it into your OUTNET handbag and go off on your day.

Claudia: I wanted to ask, are clothes important to you? Do you have emotional attachment to them or are they just literally something you put on at the beginning of the day and get on with your day and don’t really think about?

Elizabeth: Oh my gosh no, I think about it loads! They have massive emotional resonance for me. The ones that are coming up for me right now, when I started doing live shows and Paul Smith were kind enough to say, ‘if you have any events, we can dress you for them.’ And I was like, ‘actually, I love the idea of a really powerful trouser suit.’ I love Jessie Ware’s style, and Jessie Ware has a lot of like tailored, just beautiful clothes that are empowering for women. So, I have a selection of amazing Paul Smith trouser suits, including a gorgeous bronze tuxedo. Those come now with enormous emotional attachment because some of the most memorable nights of my life had been wearing those clothes and then I have a Victoria Beckham dress, I love a Bella Freud dress, these are things that are obviously not everyday purchases. But, I increasingly think of a piece of great clothing as a piece of art, and a memory. So, sometimes I will invest money in something that will last forever, and I definitely include great clothes in that as well.

Claudia: I’m going to leave you with one question. Do you, like me, think that people who have got no failures under their belt, that they’re, basically, one-dimensional, boring people?

Elizabeth: Well, first of all I think they’re lying. And, yeah, I feel that what makes us interesting is our experience and what makes us real and beautiful are our imperfections. I mean, that’s where the source of our greatest connection as fellow human beings comes from. So, I absolutely agree that it is in learning how to fail that we learn how to be more human and more fully ourselves. Even if you feel in the darkest place right now, I urge you just to cling on for that little bit longer because it does get better and you are really, really strong, and you’ve got this.

Claudia: I don’t think there are wiser words that we could leave on. So, I’m just gonna say thank you, thank you so much. You’ve been brilliant, thank you so much.

Elizabeth: Thank you for having me and thank you for such brilliant, brilliant questions. As I say, I do love THE OUTNET, so thank you for all the work you do.

Claudia: We love you, and we’ll dress you for your live shows from now on! Send me a note, after this.

Elizabeth: Oh, thank you! GREAT! Even better.

Claudia: Bye!