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Progressive Insurance Announcer
This episode is brought to you by Progressive Insurance. Do you ever think about switching your insurance companies to see if you could save some cash? Progressive makes it easy. Just drop in some details about yourself and see if you're eligible to save money when you bundle your home and auto policies. The process only takes minutes and it could mean hundreds more in your pocket. Visit progressive.com after this episode to see if you could save Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states.
Elizabeth Day
Hi, I'm Darina, co founder of Quo. If you run a business, you know the team that responds first wins the customer. You've probably opened your phone to a bunch of missed calls and no voicemails. Those are missed opportunities and exactly why we built Quo. Cuo is the business phone system that helps your team handle every call and text right away. Join over 90,000 businesses that win more customers with Quo. Try Quo for free@quo.com tech that's quo.com
Edward Jones Announcer
tech what does it mean to live a rich life? It means brave first leaps, tearful goodbyes and everything in between. With over 100 years experience navigating the ups and downs of the market and of life, your Edward Jones financial advisor will be there to help you move ahead with confidence. Because with all you've done to find your rich, we'll do all we can to help you keep enjoying it. Edward Jones Member, SIPC hello, I'm Elizabeth
Elizabeth Day
Day, the creator and host of how to Fail. It's the podcast that celebrates the things in life that haven't gone right and what, if anything, we've learned from those mistakes to help us succeed better. Each week, my guests share three failures sparking intimate, thought provoking and funny conversations. You'll hear from a diverse range of voices sharing what they've learned through their failures. Join me Wednesdays for a new episode each week. This is an Elizabeth Day and Sony Music Entertainment original podcast. Listen now wherever you get your podcasts.
Jamie Laing
Hello everyone, I'm Jamie Laing and this is Great Moments. Hey guys, how you doing? Welcome back to another Great Moments. I hope you're having a great day, whatever you're doing. Uh, now today we're sharing a little slice of my conversation with my very good friend and friend within the industry, Elizabeth Day. Now, Elizabeth Day, she's an author, she's a podcaster, she has a podcast called how to Fail. And actually, I don't think she knows this, but she was the first person to sort of champion me coming from Made in Chelsea, kind of a little bit like Marmite and definitely Marmite within the industry. But she was the one who asked me onto her podcast to talk about my three failures. And still to this day I get comments about it. So I got to thank Elizabeth Day a lot for that. Now, I think many of us in our 20s feel like we're kind of failing. I definitely did. I know that a lot of us feel like we're comparing ourselves to everyone else, and I did that as well. Especially with social media, that happens a lot. Elizabeth knows that feeling, too. So in this great moment, she talks about the pressure to keep up in the rat race that can define your twenties. But actually she believes power comes with age. So if you're feeling behind or you're feeling like you're not quite where you should be, this great moment is for you. And don't forget, okay, if you like this, check out our other amazing guests on Great Company. Just search Great Company wherever you get your podcasts. And if you like this little snippet, go and click on the show notes and listen to the full episode. Okay, here it is. Enjoy this. It's Elizabeth Day on Great Moments. Walk me through the decade. So why were your teen years tricky? Why is that a tricky? Just in general for people in general,
Elizabeth Day
because speaking from my own experience and from the experience of some other people that I've spoken to, you don't know who you are and then some in your teenage years. So you are trying to forge your own identity at the same time as you are still part of your family unit and your family unit will still encourage you to see yourself in that way. So I'm the. The youngest child of two. That will forever be my role in my family. I'm going to be the youngest. I'm going to be the baby. I'm going to be the one who in her own head, doesn't have enough agency to be herself almost. And I think your teen years are the first time that you start experimenting with those boundaries. And actually, how much do I think I'm part of this family unit? And how much is it important for me to forge friendships outside of that? And who am I within that soup? And at the same time as that happening, you're going through school, which, by the way, is so tough. I still wake up today and think, I'm so grateful I'm not at school. I. And I was of a generation, honestly. Yes. What? School is hell. You have to. It's like prison. It is so regimented. You have to get up earlier than anyone ever wants. It's often dark you have to, like, either at boarding school where you're questioning everything and like, does my family love me?
Jamie Laing
And then doing a cross country run at 6am in the freezing cold, I'm told you can't wear trousers, your knees are freezing. It's minus five. Like, what, you had a night, like,
Elizabeth Day
listening to other people shuffle, cough and masturbate, like in beds next door to you.
Jamie Laing
Theo Bossom sits on next to you and shouts, mommy.
Elizabeth Day
And you go, what the hell is this? Theo bottom.
Jamie Laing
Theo bottom.
Elizabeth Day
Oh, my gosh, it's an actual person.
Jamie Laing
Yeah.
Elizabeth Day
Shout out to Theo Bossom.
Jamie Laing
Theo Bossom. You love him. Yeah. Shuffle and masturbate.
Elizabeth Day
So you either that or you're at a day school and you have to schlep out often, like getting buses before dawn to get this lesson, and then you're forced for years to study subjects you're not good at until you can finally give one or two of them up. But then you'll still. And then it's just. It's just so weird. And I understand, it's the best system we have. Yeah. But I hated it. I should say I hated school as a concept. The second secondary school I went to was actually a really good school and I met some lovely people and it was really good for me, but I just didn't like school. But they had a course that was lessons called Life Skills. Now the only thing I remember being taught in that lesson was how to put a condom on a piece of plastic. I don't remember being taught about taxes. It was such a shock to me when I was like, I have to pay taxes. I'd love to have been taught key accountancy skills or the importance of collaboration, or dare I say it, like, the limits of fertility.
Edward Jones Announcer
Yeah.
Elizabeth Day
Whereas it felt like all of my education was about double maths and don't get pregnant as a teenage girl. So much of it was that. And obviously that's important, but I think that there needs to be a little more balance. So I think that's why teenage Dom is quite tough. And then you enter your 20s and you are out of school and either you're in the world of work or you're at university and that kind of forging and discovery of identity continues. And then it's your first experience of adult life. And adult life is bafflingly free of signposts and exams. So there's no exam that you can take that will tell you that you're doing a good job at adulting. So in your 20s, all you have to compare yourself to it's the example of your parents, if you're lucky enough to have parents or it's cultural signals. So rom coms like the stuff that you watch on television, what that's telling you or it's your peer group. And in the age of social media that's so much more pressured than ever before. Yeah. So you will My experience and that it was a world before Instagram was very much like I'm not doing as well as X. I'm not as far along in my career as I should be because of why I am not having a footloose fancy free life of the sort embodied in Sex and the City or friends like I. And. And should I also be having a long term relationship or should I be having one night stands? Like I just don't know where I sit in this. And so that's why your 20s, I think at times.
Jamie Laing
So you constantly think you're failing all the time?
Elizabeth Day
Yes.
Jamie Laing
Because you don't know what's right.
Elizabeth Day
Yes. And interestingly, when I started how to Fail my podcast the first few seasons, so many people came and chose their 20s as one of their failures and it became something that I'm really passionate talking about because I think so many people in their 20s feel that they're the only ones feeling that they're failing. And I promise you that you're not. And also I think that we've been sold a myth that life is a race that we need to be achieving greater things younger than ever before. And I think that comes from the wrong headed idea that as we age our power somehow diminishes. And that has been the opposite of my experience. I feel that I have got more powerful, know myself so much better the more that I age and my success, conventional success, like conventional CV on paper success has only really come from my late 30s onwards.
Jamie Laing
That's amazing. You're so right. I love that that power is with age and it's not the other way around. The power isn't with you when you're young and you are with Fed Lies.
Elizabeth Day
Yes.
Jamie Laing
If you're not Mark Zuckerberg and you're not a billionaire by the time you're two, you know you haven't been a success.
Elizabeth Day
Ye.
Jamie Laing
And so that's driven into us. But that's one person out of seven and a half billion. You know what I mean? It doesn't matter. And actually I completely agree with you. In my 20s I was doing lots of different things and there were things that I was doing that I was like, well I'M successful now because I have an office. I'm successful, but actually I just was. And now that I'm 35, I realized before everything was just nonsense. And actually, what is success? There's lots of things, but knowledge is 100% everything.
Elizabeth Day
That is such a good way of putting it because obviously I spend a lot of time thinking about failure and that means that I've spent a lot of time thinking about its shadow twin success. And how I think of success has radically changed. I saw something on Instagram yesterday saying that the true mark of success is a calm nervous system. And I thought that was so good because that comes from knowledge like the ability to retain your inner calm even when there is outer noise, the understanding that you don't have to take on everyone else's opinions, that everyone else isn't right and you're somehow wrong. That is success. That is a measure of authenticity that only age. And doing a podcast about failure really has brought me, because now to go back right to what we were talking about at the beginning, I feel so accepted by a community of people where I am able to show up as myself, as my deeply flawed self. And that's been a revelation to me and something I'm forever grateful for.
Jamie Laing
30 is a weird age when you hit it and you're not in relationship and you're not married or whatever. It's not married, but not in a relationship. It feels a bit weird when I turn 30 and I, I had just broken up with my ex girlfriend. I remember lying in bed and my dreams would be that I was just going to be alone forever.
Elizabeth Day
Jamie, you know that was one of your failures when you came on to fail. I looked them up recently. Your third failure was, I'm 30 and I've still not had a successful long term romantic relationship.
Jamie Laing
Was that it?
Elizabeth Day
Yeah. And I felt really moved and proud of you that now here we are five years later.
Jamie Laing
That is so interesting because I remember for me it was something like again, we go back to this being drilled into you, okay, you know, go to school, you then go to university, you come out of university, you have a degree, you get what they call a normal job, you get the normal job, you have the normal friends, you suddenly get a mortgage with a flat or whatever you can afford, and then you get married and by the time you're 32, you have a kid. That's what I thought life was. And so when I had hit 30 and I didn't have a normal job and I wasn't in a relationship, I suddenly Thought, well, this is scary. And actually I am so happy that actually I found love a little bit later. So I fell deeply in love and married so for the age of 34, 35, but obviously I was in love before that, but married at 34, 35. And actually as we talk I understand myself a lot more. And I think for people listening who are single, perhaps in their 30s and worried about it, actually I think it's a good thing. I really think it's a good thing.
Elizabeth Day
And I think as well as I've mentioned, I'm 45. So when I was in my 30s, it was a different economic climate and I do actually think that that has an impact. So it was easier for my generation, our first step on the property ladder and it is so difficult for people now. And I, and I, and I think therefore one of the knock on effects of that of not being able to own your own home until you're 85 is that your, your sense of life stages has probably shifted a bit. So maybe that's why there are more single people in their 30s now. And I salute and applaud you. I completely agree with you that it took me, I think it definitely took me until 39 to have a relationship that is fully functional, healthy, loving, accepting. And that's partly because I don't think I knew myself until then. And I had to be knocked around a bit by life and I had to be humbled by some of the things that I went through and I had to think, oh, I failed here, why is that? And be really honest with myself, not pretend to be honest, which I was doing for a long time. Yeah, but be really stripped back and honest and thank goodness I went through that. And thank goodness I went on a hinge date, age 39 and met my husband.
Jamie Laing
And why do you guys work?
Elizabeth Day
When I first met Justin, and we laugh about it now, but he is a big believer in pacing and appropriate pacing. And I'd been very used to thinking romance was love bombing and narcissism and chaos. I'm like, let's fly to Rio tomorrow and go and live there. And I'd be like, oh my God, he loves me so, so much. And then Justin again because he was a grown up and had been through lots of life, he was just very considered with the pacing. And so we took it for me really slowly. And to begin with I couldn't understand that and I didn't know if he was into me for months.
Jamie Laing
You build that slow, it relates to everything. People want a viral hit on TikTok. It's a bad thing. People want to have a hit now in music and number one hits.
Elizabeth Day
A bad.
Jamie Laing
You want to have that slow growth. And in a relationship, that's why when you meet a friend and then you suddenly fall in love with a friend, it actually turns out that it probably works better, is you've had that slow growth, you know each other much better than that instant flash in the pan. And that flash in the pan. Romance is. Isn't healthy.
Elizabeth Day
Totally. I mean, exactly that. And that's another thing that I think our popular culture has done us a disservice because it's made us think of what romance is in a certain way. It's made us think that it's fireworks. And actually with Justin, I think I have a slow, burning, steady bonfire. And I love that.
Jamie Laing
It's not boring.
Elizabeth Day
No, I love a bonfire. It's not boring at all. And it is so much more exciting because we feel safe enough to experiment. Now I'm sounding really kinky. There you go. But I just feel like experimentation and communication, like I know that I can talk to him about anything. And that's amazing. And I also know quite early on in our relationship, he said a couple of things to me that have stayed with me ever since. One time I was feeling really overwhelmed with work and demands, and he said to me, you'll get through it. And just remember, I think you're amazing. Even if you never do anything ever again. I just think you're amazing because that's you. It's not about the things you do. That is like such a. Such a meaningful thing. I'm speechless just saying it again. Like it gave me permission to just be myself. And then another thing he said to me, I've sometimes worried in the past. You know, I'm very emotional, not in a kind of sexy Italian way, but in a, like, weepy. I'm going to cry now because I'm just feeling like everything's too much way. Okay. And I. I sometimes worried about that in the past. I'm just like, too much in that way. Like I will cry at anything. And that's how I process stress anyway. And I remember sort of saying that to Justin. He was. He would say, I actually love the fact that you're so emotional because I think that that makes him feel safe, that I'm not hiding anything, that it's coming through, and that it's taught him a lot.
Jamie Laing
It's amazing. I actually spoke to someone yesterday who said we all react in different ways. And I can get quite emotional and people.
Elizabeth Day
In a sexy Italian way.
Jamie Laing
Yeah, not in a sexy Italian way, but. And, and, you know, maybe it's in a business setting, whatever. But they said, oh, I feel like that's a weakness.
Elizabeth Day
Yes.
Jamie Laing
It's not a weakness.
Elizabeth Day
I totally agree.
Jamie Laing
It's not a weakness. And people feel sometimes that vulnerability or emotion is a weakness. And it is totally the opposite.
Elizabeth Day
You have to be so strong to show up vulnerable in a business setting. And actually that's one of the things that I talk a lot about when I talk about failure in companies. I say a lot. If you take the risk of being vulnerable with your team, I guarantee you that that will be paid back in spades, that they will then feel permission to be vulnerable with you and to admit when something goes wrong, rather than trying to cover up, cover it up and making the problem worse. And actually, there's so much solidarity that comes from that and such a sense of community. And that in turn makes for a far more successful business.
Progressive Insurance Announcer
This episode is brought to you by Progressive Insurance. Do you ever think about switching your insurance companies to see if you could save some cash? Progressive makes it easy. Just drop in some details about yourself and see if you're eligible to save money when you bundle your home and auto policies. The process only takes minutes and it could mean hundreds more in your pocket. Visit progressive.com after this episode to see if you could save Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states.
Edward Jones Announcer
A rich life isn't a straight line to a destination on the horizon. Sometimes it takes an unexpected turn with detours, new possibilities, and even another passenger or three. And with 100 years of navigating ups and downs, you can count on Edward Jones to help guide you through it all. Because life is a winding path made rich by the people you walk it with. Let's find your rich together. Edward Jones Member, SIPC hello there.
Jamie Laing
Ben shepherd here. And me, Joel Dommet. So Christmas is here. And while you're wrapping gifts, it's time to wrap up your business goals too. If you want to know exactly how to prepare for your, ahem, money resolutions before the end of the year and start January ahead of the game, listen to our podcast, the Businessman. So grab, grab a mulled wine, hit play and make this Christmas the start of your best business year. Search the businessmen wherever you get your podcasts or watch it on YouTube.
Progressive Insurance Announcer
Say hello to Samantha.
Elizabeth Day
Hi there.
Progressive Insurance Announcer
Samantha built a SaaS platform that helps small businesses manage their workflow. But she needed a smarter way to reach decision makers.
Elizabeth Day
That's where Acast came in.
Edward Jones Announcer
They helped me produce a professional audio
Elizabeth Day
ad which played to business owners and ops leads using their audience attributes targeting tools. Suddenly my platform was showing up in the ears of the exact people I needed to reach.
Progressive Insurance Announcer
Now that's streamlined marketing. Samantha, what's your tip for scaling smart?
Edward Jones Announcer
Solve a real problem and make sure
Elizabeth Day
the right people hear about it.
Progressive Insurance Announcer
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Release Date: March 29, 2026
Host: Jamie Laing
In this deeply insightful and relatable episode, Jamie Laing sits down with acclaimed author and podcaster Elizabeth Day to unpack the challenges and transformation of your twenties. The conversation covers why our twenties often feel fraught with pressure and comparison, what it means to “fail” at life’s milestones, and why true power and self-acceptance often emerge with age. Through candid anecdotes, moving personal stories, and heartfelt advice, Jamie and Elizabeth challenge cultural myths around success, share the value of growing older, and offer reassurance to anyone feeling behind.
Jamie and Elizabeth’s warmth, humor, and candor make this episode especially reassuring for anyone struggling in their twenties or questioning their path in adulthood. Both urge listeners to reject toxic comparison, accept the messiness of self-discovery, and embrace the power, success, and wisdom that come with time.
This episode is a soothing listen for anyone feeling behind, uncertain, or overwhelmed by societal expectations. Power, fulfillment, and love aren’t reserved for the young or the early achiever—they grow with you, slowly, authentically, and on your own terms.