#172 Success In The Second Half Of Life — Henry Oliver on John Stuart Mill, Samuel Johnson, Penelope Fitzgerald, why we shouldn't dismiss Gladwell, writing, late bloomers, the importance of finding the others, Tyler Cowen's help and the lessons from Audrey Sutherland

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today, I have the pleasure of talking with Henry Oliver. He is finalizing a book that is going to come out in the spring in the UK and in the fall in the US called The Second Act, which I'm really excited about. It's exploring the lives of late bloomers, people who got their start on their thing later in life. I'm not sure if I qualify as a late bloomer.

I sort of found my thing writing in my 30s. We'll see what Henry thinks about that and if I qualify, but excited to explore his path, his curiosity, and some of the ideas he's shared in this book today, among other things. Welcome to the podcast, Henry.

[01:53] Henry Oliver: I drink beer.

[01:54] Paul: Fantastic. So the question I always start with, I gave you a preview of this earlier, uh, what are some of the stories and scripts that sort of shaped you growing up, that told you about this is what you're supposed to do when you grow up?

[02:11] Henry Oliver: I think I was fortunate that I did not have a lot of pressure from my parents in that way, so there was a general you know, it's good to be a lawyer, it's good to be like whatever. That general kind of idea was there, but there was no overt pressure and there was very little of that kind of like, you have to do this, you have to do that. Um, and so I just followed my nose all the time really. And I was very, very fortunate 'cause I had teachers who were, uh, I don't know if they'd appreciate this, but they were like real nerds, right? They were still really into their subjects and they still really just followed their own curiosity. So I just sort of made my own way through.

I didn't feel like I was given too much pressure, but I was surrounded by people who believed they had to be doctors or dentists or accountants in order to, you know, in order for everything to be okay.

[03:03] Paul: How did you not get sucked up in that? Just your parents?

[03:07] Henry Oliver: Uh, my parents were very good. I think my mother would tell you that like there would be no point. you know, he was a stubborn child. What am I going to do? I think, uh, but yeah, they were very good about it. They didn't—

[03:23] Paul: what did they do?

[03:25] Henry Oliver: Uh, they were both lawyers, and, uh, as I say, there was definitely a sense that was like a good thing, and you, you know, you needed a secure job. And they, they sort of talked about it, but, um, they— I think they could see I was very interested in other things, and so they were pretty relaxed about it.

[03:43] Paul: That's pretty cool. And tell me about some of the people, the nerds you were learning from. It's interesting you say that. It makes me think of this Bertrand Russell reflection where he talks about everyone thought he was foolish until he arrived at Oxford and people were like, oh, philosophy is actually okay.

[04:03] Henry Oliver: Yeah.

[04:03] Paul: While getting mocked his entire life before that.

[04:07] Henry Oliver: Yeah. I had teachers who were still, so these are people, they're teaching philosophy, literature, biology, subjects like that. They were still reading widely. They were still trying to explore new ideas, right? They were still trying to push themselves, you know, to read in areas of philosophy they hadn't read before. They were always ready to have a conversation about it.

What about this book? What about this thinker? But have you considered this? Like always ready to challenge or to be checked about ideas. And so you just got this great sense of like, that's just what you do, right? Political philosophy, like all sorts of subjects like that.

And so there was much less for me of the sense that like you do these things and you pass this exam and that's That's that. And much more a sense that like, okay, we have to do the exam. That's a real thing. Whatever. But it's amazing. We're studying John Stuart Mill, Plato, Shakespeare.

This is amazing. Let's really get into this. Let's talk about the other things that they've done. Like, who wouldn't want to do that? And so just going way beyond is the exciting thing.

[05:22] Paul: That's beautiful. Uh, any of these teachers stand out particularly?

[05:28] Henry Oliver: You want me to name people?

[05:30] Paul: No, I just mean, were there specific instances, or, um, like, were there comments? I mean, to me, that does sound wonderful looking back now, but I didn't have anything close to that.

[05:44] Henry Oliver: Like, I was so lucky. I was so lucky. And it was— there were, there were like 3 or 4 of them, and it was all at the same time, uh, when I was like 16, 17, 18. So it was, I was very, very fortunate and it wasn't so much specific incidents as just like, that was just the way it was. That was just, yeah, it was really, I'd say 3 or 4. There were more.

It was really, it was really, really good.

[06:09] Paul: So you have, I've read some of your stuff you've written about John Stuart Mill. You brought him up. So I'm going to use that as an opportunity to dive right into this. Um, maybe tell us a bit about John Stuart Mill. I find his story fascinating because I mean, when I, when I started reading his autobiography, I was sort of blown away. It's like, wow, this young person knows so much more than what I did.

And it sort of broke my brain of what is possible. So, yes, I'd love to hear if he inspired you, if at all.

[06:44] Henry Oliver: I read Mill as a teenager, studied On Liberty for an exam. And I, you know, fell in love with, with him. I read the autobiography, uh, and then subsequently just carried on reading him, carried on being interested in him. I think I've read all of the biography about him. Uh, I've read, I haven't read all, like his complete works is huge, but I've read a good chunk. I'm like, like, where's the Paul Millerd?

Uh, to me, he's one of those writers. There are few people in English literature who can just, they can just do anything. Right. And Mill, he's an economist. He writes a textbook logic. He's political philosopher.

He knows a huge amount about French affairs and French literature and becomes the leading commenter on French affairs in England at the time. He knows a lot about the ancient world. So he can review very authoritatively like histories of Rome, right? Histories of Greece. And he keeps in his mind for his whole life, this like idealized vision of Plato. And this really, I think, informs a lot of the idea of like accomplishment, as you say, like really expanding what you think it is possible for someone to do.

He is drawing that, the inspiration. And none of that is his day job. That's what's so remarkable about Mill. So there are a handful of these writers that you can just keep going back to find more and more in every time.

[08:24] Paul: Yeah. And so were these sort of your role models as you were coming of age?

[08:30] Henry Oliver: I don't think I thought of it like that, but yes. Someone like Samuel Johnson, they're the people that I mean, you know, particularly admire.

[08:40] Paul: What stands out about Samuel Johnson?

[08:43] Henry Oliver: I could talk all day about Samuel Johnson, so you have to cut me off.

[08:46] Paul: Let's go. This is a nerdy podcast with a nerdy crowd, so we have time.

[08:51] Henry Oliver: So Samuel Johnson, he wrote the dictionary. One man wrote the whole dictionary himself. It took him 9 years. That is just on the numbers. That is ridiculous. It's like, it's difficult actually.

[09:07] Paul: That is crazy.

[09:09] Henry Oliver: Yeah. And we're talking like 42,000 words in that dictionary. So that's quite difficult to comprehend how he did that. There are, um, his, his innovation in this dictionary was definitions. So when we use a dictionary, it breaks down, these are all the different things this word means, right? And for some words that might be dozens of separate meanings.

Johnson invented that. Before Johnson, dictionaries were more like thesauruses. They just said, you know, here's a word that means the same as this word. And they would, and for that reason, they would often concentrate on like slightly obscure words. Johnson was like, no, I'm going to define get, right? A word which I believe has 2,500-word entry in this dictionary.

And the other thing he did that was remarkable He gave quotations for all of these definitions drawn from the poets, the scientific writers, the historians, whatever the appropriate source was. And so it's an accomplishment both of writing. I mean, how did he do that? But also of reading. He read so many things. There are 115,000 quotations.

Dictionary. And so people used to read his dictionary at just like, almost like it was a text, right? It would, it would be an education in itself to study this dictionary. Um, now, so this is like, it's difficult to understand how he did this level of accomplishment. And the definitions have real elegance to them. He didn't, he didn't just sort of knock out, you know, boring stuff.

They're still quoted because some of them are witty. And they were, I think, 1,700 of them when they came to write the Oxford English Dictionary, sort of 150 years later, something like that. I think 1,700 of their definitions, they just took straight out of his dictionary because those were, you know, still like, actually, we can't do better than that definition.

[11:15] Paul: I just pulled up, I just pulled up his online dictionary, Johnson's Dictionary Online. So I picked random words. So to bring this alive, color spelled in the British way, of course, the appearance of bodies to the eye only. And hue, dye. It is a vulgar idea of the colors of solid bodies. When we perceive them to be a red or blue or green tincture of the surface, but a philosophical idea when we consider the various colors to be different sensations excited in us by the refracted rays of light reflected on our eyes in a different manner according to the different sizes or shape or situation of the particles of which surfaces are composed.

That's pretty cool.

[12:06] Henry Oliver: Yeah.

[12:08] Paul: And that's Watts. Yeah. He's just quoting people. Yeah.

[12:11] Henry Oliver: So he, he not only knows how to give you all the specific definitions, he knows where to find the right quotation that will show you it in use. So for that to come out of one mind, it's, it's, it's quite something. He then—

[12:26] Paul: Wow. There's 17 quotes here for the color.

[12:31] Henry Oliver: Exactly.

[12:31] Paul: This is wild.

[12:32] Henry Oliver: How did he do it?

[12:34] Paul: This is such a good rabbit hole.

[12:36] Henry Oliver: Right? Now that you're on the Johnson Dictionary website, you're never going to leave. I think it's permanently open in my tabs.

[12:43] Paul: That's beautiful.

[12:46] Henry Oliver: It's amazing. That is not all that he did in those 9 years. He is very famous for writing a series of essays called the Rambi, which are on moral, political, Literary, religious, like any number of topics. It's a sort of higher version of self-help in a way. He wrote those essays at the same time that he wrote the dictionary, which is another like startling level of achievement. When he finished the dictionary, he did another series of essays.

Then he did something called Rasselas, which is a short novella that, I mean, so many people in history have said there is more wisdom in that book than in any other. He also wrote a poem called The Vanity of Human Wishes. And this is all in this 10 or 15-year period, a remarkable achievement. He then has a sort of fallow period, sort of 3 years where he seems to do nothing other than learn and get drunk, quite literally. We don't really know what he lived off, really. And then he comes back and retires.

You know, when he's sort of in his 60s and writes The Lives of the Poets, which is one of the most innovative works of literary criticism and biography in the history of literature and full of many, many wonderful passages of writing, so quotable, so, so such a high achievement. And these are just the major works. You can then get into all the volume after volume reviews and then other sermons, legal opinions. He would write anything for anyone. So a bit like Mill, he has this sort of incredible breadth piled on top of really remarkable productivity.

[14:32] Paul: Do you think the things like The Rambler, do you think the modern newsletter is sort of our modern version of those? Is that how you think of it? What do you think about yours?

[14:45] Henry Oliver: It went out twice a week. He got a subscription. He would try and, you know, he wanted them when they were really good, they'd be picked up by like regional newspapers and reprinted and he'd make a lot of that. So it's a very, very similar thing. And a similar thing, I think, as well in the writing practice, because he would often sit down while the boy from the printer was standing in the door saying, you know, I've been sent to get the copy. And he's going, 5 more minutes.

I've gotta finish writing it. 5 more minutes. So it's got many parallels to the modern Substacker, right? Working to a deadline.

[15:22] Paul: Yeah. What is a common reader?

[15:25] Henry Oliver: The common reader is a phrase from Samuel Johnson. He was criticizing a poet called Thomas Gray who had lots of fancy language and old-fashioned words. And Johnson was saying, oh, this is all unreadable. Yeah, it's all just rubbish. And then there's a famous poem called Elegy in the Country Churchyard, which I say famous, it used to be the sort of poem that every child at school in England, obviously no longer. But when he comes to that poem, Johnson says, "I rejoice to concur with the common reader.

This is a great poem." And it is only from the common reader that the final sets of honors can be bestowed. And what he means is, Johnson's very up on the idea of living in a commercial society. This is like the mid to late 18th century. So he can really see that capitalism's here, commerce is here, society's completely changed. And he's saying, look, people buy books, right? There's a market.

And this is the big thing. This is the force that decides who survives and who doesn't. Yes, we have critics and scholars and he's on the side of those people, But he's also saying, look, I'm writing off Gray. He's pompous and purple and no good, but come on, everyone loves this poem and they're right to, and that's why. And it's true. He still survives now for that poem.

So the common reader is the non-professional reader who wants to read the great works and who wants to educate themselves in a way. And I think if you go on Twitter, it's, that's everywhere, right? Common wisdom is a big force in modern culture.

[17:04] Paul: Well, you see people sort of, uh, try to dunk on writers that are popular, right? It's like, oh, not Atomic Habits or Malcolm Gladwell's writing, but it's like, yeah, people, people love that stuff. There's nothing wrong with it. In fact, like Gladwell's writing was sort of a portal to the deeper stuff for me.

[17:26] Henry Oliver: I think Gladwell particularly is a good example of someone who gets criticized for whether he is right, whereas the achievement is that he spread those ideas so wide you wouldn't be talking about whether he's right. You wouldn't be talking about all these theories, all this social science. He got that out there. That's really important. What's changed since Johnson's time is that, you know, as Johnson said, men require more often to be reminded than informed. He was trying to get back to like ancient wisdom, religious wisdom.

Like we know all this. We live in an age where there's a lot of new wisdom. And so Gladwell, like inevitably will be, you can look at a book like The Tipping Point or Outliers that are relatively old now. Okay. The, the research has moved on. The particulars of the numbers are no longer correct, whatever, but there's still a similarity in the ability to show people.

I think this is what's going on based on this research and it's a very high— I've written about it more than once on my Substack because I think he's very, very interesting. You have to take that seriously.

[18:40] Paul: How did you think about building a life around writing? It seemed It seemed like it was clear to you early that you wanted to do this. And it seems you majored in biography, which I've never seen as a major before. So I imagine if you're picking something like biography, you are certainly intending to build a life around the written word.

[19:05] Henry Oliver: So to begin with, I did a degree in English literature. And then I went back and did an MA in biography a few years, but it's just a very similar thing. I just did that because I was interested. I didn't really, I didn't quit my job and become a writer until I was like 35. So, and I still do a lot of freelance marketing work. I'm not one of these pure writers by any means.

And I think, I don't think you have to be. Um, so I didn't really build my life around writing. It happened a bit later and I didn't think it through at all.

[19:43] Paul: I like it. Yeah. How do you think about that balance between writing and other things? I mean, I, I like writing for me is the most important sort of work I do. I love it. It's something I can't really not do, but I still do some consulting work and stuff.

And I've never tried to solve that as sort of like, oh, I need to be completely a writer. And I almost wonder if there's some advantage to not having the pressure from writing. Did you have certain models about how you were thinking about it early on?

[20:22] Henry Oliver: I really didn't. It's, it's really a case of like earning money. Yeah. And as you say, I'm, I'm, I'm always going to write. Around whatever it is I'm doing. So that it doesn't go away when you're consulting.

And particularly the reading, right? I always think that what, half of all writing is reading, if not a much bigger number. That's always there. And I just, I think it's a very pragmatic thing.

[20:53] Paul: Do you see yourself as a late bloomer?

[20:56] Henry Oliver: Uh, maybe that depends on how successful the book is. I don't know, it would be presumptuous for me to say that I've bloomed, I think.

[21:08] Paul: Fair. Yeah. Um, well, how do you— yeah, how do you think about like success as a writer and what's your relationship with those things?

[21:17] Henry Oliver: Success means having an audience and it means, um, It means people taking you serious. There's obviously a sort of an element of money and an element of, um, being published in, you know, notable places. But I think in, in all ages, what success as a writer has meant is people will read your work. Good readers it's not just like you need good readers who are really sort of invested in it, respond to it, share it, and readers who are also writers. Like, I think all of these things are significant.

[21:59] Paul: Yeah. The, the way I think about it is who are the people I can attract with my writing that I actually wanna spend time with? Because it's, it sort of leads to this virtuous cycle of actually deepening my ideas. And I just love people. That like to think deeply around these ideas.

[22:16] Henry Oliver: There's a lot of correspondence between writing and conversation. And again, that's very true historically, right?

[22:25] Paul: Yeah. What led to you thinking about this book idea? So I think your subtitle is What Late Bloomers Can Tell You About Success and Reinventing Your Life, which is very interesting to me. Me because I'm just deeply curious about how do you reinvent your life? Um, yeah. How did, how did the idea bubble up for you?

[22:49] Henry Oliver: The sort of marketing work that I do is employment marketing. So I, I do research about organizational culture, what it is that makes a company attractive to go work at. And because I was the research and branding person this meant I would always get questions from clients about the labor market, right? And when you're in a tight market, everybody wants to know, oh my God, where can we get people? We've run out of people. Where do they all be?

And I, so you keep doing, you know, getting these inquiries and doing research and sending back slides or whatever. And I kept coming back to this like cluster of ideas around basically that said that we're not as good as we think at identifying talent. So a lot of things have changed in recruitment in recent years to do with whether you need a particular sort of degree to be eligible to go on the, you know, go on the law firm graduate scheme, whether you need to have gone to a particular sort of university, right? Is it even valuable to have a degree? Can we not just take school leavers and train them? Or Like there are so many questions like this.

Women coming back into the workforce when they've been out of work for 3, 4+ years. Have they like lost their skills or actually is it just a question of redesigning the entry point and giving them some confidence and that, guess what? They come back and they do a great job. People doing career changes in their 50s and becoming the intern again, right? When they're like, they've been in senior management. And so just in so many ways, there was this cluster of ideas that I was researching that said, actually, a lot of the things that we sort of took for granted as markers of talent and how we assessed talent, they just weren't really true, right?

All the big law firms, you had to have a 2:1 from a top 5 university. That's all gone. That's all gone. And it hasn't really made any difference to anything. It turns out you can assess for talent across 50 different universities without looking at the degree outcome. It still works, right?

And so there were all those sorts of ideas in my head. And then I was ill and I had to take a few months off work. And I reread the work of Penelope Fitzgerald, who was, I think, a wonderful novelist, a genius of the late 20th century, very underrated. You must all read her books. Um, but she didn't start writing until she was 60.

[25:23] Paul: Yeah.

[25:24] Henry Oliver: So this again, for me, I was like, look, you see, here we go. This is what I'm saying. Like, no one knows. No one knew she was gonna be a novelist. It's the same thing. I was starting this, you know, it's one of those things that starts to like bug you.

And then I heard a podcast with Tyler Cowen where he said something like, of people who haven't done anything yet, but maybe they will. And I was like, yes, it's the maybe. And maybe there's no room for maybe in this discussion. And then it kind of came together in my head that that's a thing. And so I started blogging about it. Obviously at that point my clients were like, what are you talking about?

We're not gonna hire a 60-year-old novelist. What? Tell him to stop. I was like, but like it, I started blogging and then, you know, you start seeing it everywhere, you start researching it and suddenly it's like, I realized like late bloomers are a whole category of talent that just haven't been considered properly yet. I don't, I didn't think weren't getting enough attention in the workplace, even though they're a very real thing. And I hope a lot of people listening to this would be thinking that's true.

I know people who have like taken very new directions in their career at a point when You wouldn't expect it. And I think if you're inside a company, that's much easier than if you're trying to get hired in to do that new direction. And it's really interesting to me that so often the criteria on a job ad are like strict, but if the company is like in a pinch and needs to get the work done, we have someone over here, she's pretty good. Why don't we just give it to her? And you're like, what's the, what's the explanation for like Putting the barrier up. And the explanation is you can assess the person you've already got and you kind of know, yes, yes, she probably will.

That's fine. Great. The new person, it's almost impossible to know. And so that's why I got interested.

[27:17] Paul: It's almost like we, and I explore this a bit and just thinking through like, what is the default path? But I think the way I've been thinking about it is we sort of just embrace these stories and scripts of this very simple life path. And all we're doing is taking the markets, like what the market is saying for our own reality. The problem with that is it totally undermines or eliminates any space for human transformation and change, right? It's like this is a career path that is the reality of a human life. And there's actually some interesting research from Donald Super in the 1950s, and it was talking about life development stages.

And it's really funny. I'll, I'll send it to you. But basically it was like, all right, 17 to 22 is your searching phase. And that's what he called it is like you're searching for your thing and then for the next 20 years you're doing the thing.

[28:29] Henry Oliver: Yeah.

[28:30] Paul: And then somewhere in your late 40s or early 50s, just the decline, right? And it's so crazy to read this because you realize it's basically just like a company's career track.

[28:43] Henry Oliver: Yeah.

[28:43] Paul: Has nothing to do with the human, any sort of human potential or the reality of human lives.

[28:49] Henry Oliver: Yeah.

[28:50] Paul: Um, and we're a couple generations removed from that, and we don't even question this anymore. Like, we— I've talked to people in their, their 60s, and they're like, I'm not creative. Like, I'm done. I can't work anymore. It's like— and so I love what you're doing. Um, can you tell us a little bit more about Penelope Fitzgerald?

[29:12] Henry Oliver: She was born into a very sort of upper middle class or upper class English family, just in the middle of the First World War. Both of her grandfathers were bishops and her father edited Punch, which was a very dominant Victorian magazine. So she's really born into the establishment. They're enlightened about women in her family. Her mother's been to Oxford. Yeah.

And so she goes to her mother's college and obviously expectations are high, right? We're surrounded by bishops and all of her uncles are famous. You know, Ronald Knox, famous detective story writer. One of them's a spy. One of them, you know, writes books. Like she's surrounded by all this accomplishment.

She leaves Oxford. She lives this sort of bougie life in London. She gets married to, an officer in the army. This is time of the Second World War. And then he comes back from the war with PTSD and life becomes really difficult. And there's this weird period where she kind of could be writing, but she isn't writing and she's doing some reviews and stuff, but there's no, we can't really see any fiction going on.

It's difficult to know cuz she lost some of her papers, but she's doing like Creating things. She's going to pottery classes and stuff, but her husband's problems get worse and worse. He starts drinking. They have to leave London to escape their creditors. They go to the coast and they live in this very unfortunate way. She's working in a bookshop and then they come back to London because presumably the money problem is over, but they can't afford rent, so they live on a boat.

And after a while the boat sinks and they are homeless and eventually they get council accommodation and she's working as a teacher and they can sort of, you know, they, they get it together. And as a teacher, she's working in a sort of, it's like a grammar college. So like mostly girls from well-to-do families going for like Oxford and Cambridge. Intense tuition classes to get them into Oxford and Cambridge, prepare them for those exams. And so to do this, she's rereading the classic works and she's paying very close attention to them. And she makes masses of notes about how exactly is it that Jane Austen's novels work?

What is going on in George Eliot? What's Samuel Beckett doing to get this effect? She's really, really going into that. She's reading critical work, And her whole life she's also studying languages, German, Russian, traveling, going to the opera. And so there's a sense in which the two things in her life are this like personal catastrophe plus really deep learning. She just goes through the whole tradition again.

So then when she's 60, her husband dies, she's like, she's got lots of time on her hands. All of that can come together and she becomes a novelist of basically of experience. She can write from the experience of her own life, but she's also done all this deep learning. And so she does two sorts of books. The bookshop she worked in becomes a novel, the boat becomes a novel, the school becomes a novel, right? And then there are these four great novels at the end, four historical fiction set in Germany, Russia, Italy, and England, all based on her traveling languages.

Right. And so they are just, they're some of really the best historical fiction. And what critics at the time said was, how does she make it so Russian? I don't understand how, because she's so immersed in the language and the history and the culture and the fact she's been doing it for decades. And they're so short, these books. They're really like 50,000 words max.

That's almost like the best, but she can, every word is exactly the right word to make it like the one, the Blue Flower set in Prussia in the 18th century. It sounds ridiculous, but the critic who said, how did she make it so German? I mean, that is the right question to ask. It's really incredible. No one who reads that book ever forgets it. She wrote it, I think when she was 8.

And so she—

[33:35] Paul: That's beautiful.

[33:36] Henry Oliver: It's really beautiful. And so she became a novelist of experience, right? Everything that happened to her, she was able to— And also, I should say, a novelist of nostalgia. You know, by the time she's writing in the '70s and '80s, she's looking back to the pre-Second World War, like that Edwardian generation that have brought her up. And that comes out a lot as well, that kind of lost ethos. And so rather than being like a lost talent who was crushed in her youth, I really came to think of her as someone who, like, the way she works as an artist is through like massive immersion, like massive input, amazing levels of knowledge and scholarship, huge personal experiences, and just is able to synthesize all of that in a way that no, no 30-year-old That's not possible to do again.

So the nature of her art is, it is late, it's late art, and it's unrivaled, I think.

[34:37] Paul: That's amazing. It, it's wild to think about this because the more you think about just potential and go throughout history, you realize, wow, there were probably so many people that either could share. I mean, it was really hard for women to share for a very long time. And now it is so much easier to share ideas. And I imagine some people would come back from a couple hundred years ago and be like, how are you creatively stuck? You can publish your stuff for free on the internet.

What are you doing? Put your stuff out there. This is something I think about. And it's like, do people know that like people used to die for the right to share their work? Work.

[35:26] Henry Oliver: I, I don't know how to think about this because, so I totally agree with you and I, and I think it's this amazing thing and it, it, um, it's, it's, but it's also like, is it too easy when, when there's a barrier? Like, that is part of how you impose standards on people and how people like have something that they have to like work towards. And that also, that barrier helps to impose the pressure of the past. Like the people who came before me were so good. I need to be so good. Whereas I wonder if the internet has like this dual thing with the benefit of being able to publish and explore and discover, but also the difficulty of like slightly removing burden.

And the burden is part of what pushes you. To achieve things. I don't know, but I wonder about that though.

[36:21] Paul: Yeah. My gut is that it's probably moved the median to the right. Like there's been a net improvement, but there's long tails.

[36:31] Henry Oliver: Oh yeah.

[36:31] Paul: Especially, especially on the left side. And yeah, you're probably right. I think there's probably some otherwise more deeper contemplative thinkers that sate enough of their creative urge with like a tweet or something. Um, I think I waited too long to actually write a book, and one of my reflections was that, wow, this really pushed me to grow and go deeper. And so these deeper forms really are powerful.

[37:01] Henry Oliver: I think so. And I think, um, I think you see this in literature in like in modern fiction and stuff. Twitter is great and it expands the reach and it, and it gives writers a new platform, but there is a risk that you become really good at Twitter instead of really good at writing a novel. And I think that has happened to some people and I think it, I think we should have it and we should explore it and we should have Twitter in fiction and, and keep going with that. But it's also like, how many great tweets do you want to write versus like a novel, right?

[37:38] Paul: Yeah. And I'd love to ask you about a couple things in the book. I think one thing, um, one thing that really jumped out to me and something I've been thinking a lot about is you write many late bloomers lack the cultural meal— I don't know how to say it— milieu. There we go. Tongue-tied this morning. That is essential to success.

And I think this is something I've been exploring a lot recently. I was reading the story of Robert Caro. He walks into the New York Public Library and he doesn't talk to anyone for a couple of days. He's super embarrassed. He doesn't want anyone to ask him how long he's been writing his book. Then somebody asks.

He says, "5 years." And they go, "Oh, cool. I've been working on mine for 9." Something like that. And he writes that this moment was like such a relief. He had finally found his people. And yeah, that line really stuck out to me when you were writing this. What are some other examples of this you've seen?

[38:53] Henry Oliver: There are several people in the book. I think sometimes people are shy, sometimes they don't know how, sometimes they're in the wrong place. Sometimes like, you know, women aren't allowed in the club. Like there are prejudices. There are so many reasons. But there's a whole chapter with people who, like Nathaniel Hawthorne, the great American novelist.

I think Henry James said, you know, he's brilliant and he's done so much, but It's a real shame because if he'd only shown someone his writing and, and, and been with other writers, you know, he wouldn't have had to spend 15 years sitting in a room on his own trying to work it all out. Um, and I think again and again you see, so one, one of the sort of theories I put forward is that late bloomers begin in an exploration stage where they're doing lots of different So a bit like Penelope Fitzgerald with all her reading and learning, right? Sort of looking around the world. And at some point they choose to switch and go into exploit. And it's just, you know, get the work done as it were. This is based on a paper by Northwestern, I think it is, out of Kellogg.

And a lot of times it's the network, it's finding your your group that is the thing that helps you switch. And a lot of times that's coincidental, right? It's very difficult to force that, and it's very difficult to like contrive it. And I think I, I can't prove— I didn't put it in these like terms in the book, because like, how can you prove it? But I think there's some— there must be something about the personality of people who bloom later that like, this is not what they're good at. Right?

This, this is something that they have to find their way with. Yeah.

[40:42] Paul: And like Hawthorne is a good example. I think he stumbled upon the, the like group in Concord in Massachusetts. There's a great book about this called, uh, American Bloomsbury. And it, it talks about like Hawthorne, Melville, uh, Marie Louise Alcott, And, of course, Emerson and Thoreau. They're all on one street. They're walking back and forth to people's houses.

They're all sorts of these cross relationships, and they're all just working on their writing. And it makes you realize how powerful that can be. And that's something I've been trying to do. I was actually co-writing with with a friend this morning and, um, trying to talk about like, how do we get more of this?

[41:40] Henry Oliver: Yeah.

[41:40] Paul: Together.

[41:41] Henry Oliver: I have a friend and he lives close by and we've known each other since school. And I, this whole book is the product of me just chatting to him. Yeah. It's really, yeah.

[41:52] Paul: How does the power of conversation shape your writing?

[41:56] Henry Oliver: Well, I mean, I think partly it's— you just, the more you babble on about something, you overhear yourself and think, oh, now it makes sense, right? Because you're forced to explain it to yourself in a way. Um, I think it's Charlie Munger. He talked about, um, you know, Warren Buffett's partner. He talked about how he has this thing, like, if you, if you, um, go into a room where there's an orangutan and you have to explain your idea to the orangutan, like after 10 minutes you come out much wiser than when you went in. I think that's a really good observation.

And it's like, it's also an argument for talking to yourself, right? Which again, I think a lot of people find like, I don't wanna talk to myself, but there's only so much that your friends, your spouse are gonna listen to you.

[42:48] Paul: It's interesting. I actually read my own words out loud as I'm typing. And this was something I've been thinking about recently. And I realized conversations really shape everything I do with writing. I'm sort of like talking it out to myself. How does this sound?

Over and over and over and over again. And it is a very powerful thing. It's writing is this mysterious thing that there's no right formula. You basically just have to like try stuff and treat it as this very sacred process.

[43:26] Henry Oliver: I think also like you, you, it's as you are writing that you realize what you think, right? And it's, it's the act of like moving the pencil, hitting the keys. That is the thinking. You don't have it all worked out in your head first. And I think the same is true of conversation. Like in a way, the more self-conscious you are about trying to think up something to say, the less successful it is.

Whereas if you just talk, the words come out and you think, oh great, actually that sounded pretty good. Everyone's had that in a work meeting, right? Where they say something and then they think, I have got to write that down because like if I need to say that again to someone, I'm gonna forget it. So there's a shared thing where they're both quite generative. Processes.

[44:13] Paul: I loved you pointed out in another one of your chapters was the power of being disappointed early. Like, I think that there is a quote in my first book by David Foster Wallace. He's like, the great— one of the greatest privileges in life is succeeding as early as possible so you know it's not all worth it. Um, and said with a little more, uh, David Foster Wallace energy, but, um, sure. I think that was something I experienced too, which was, okay, I'm in my early 30s, I'm where I thought I wanted to be. This is kind of disappointing.

So what, um, is that a theme you've seen in a lot of late bloomers?

[45:00] Henry Oliver: I have a whole chapter on midlife crisis and on the idea that you, you will reach a point in your life where, um, you're dissatisfied with the overall mix, right? And there are different theories. Some people think this is biological occurrence and it happens to the great apes and it's like, it's just hormones, it's just chemistry. Like, you know, don't take it too seriously. I think that the data on that are like less certain. And that the idea of the happiness U-bend is, I don't know, I think, I think it, that used to look really convincing and some of the data now looks much less convincing.

And there's an argument to be said that like that U-bend is very different across different countries, right? It's very different depending on the statistical techniques that you use to interrogate the data. It, um, and it doesn't take very much account of individual variation in it. So I sort of ended up saying like, for some people, a midlife crisis is a great opportunity and they should, they should have a midlife crisis. They should, they should like change things. I don't like giving advice 'cause I feel like, as I was saying about the happiness curve, right?

Like it's these big statements that don't apply to everyone and you don't want people to like take something from that that's bad for them. But there's, there's definitely something about like the necessity to change because whether you've succeeded or whether you haven't is no real guarantee of what's going to happen to you later, right? Just because you haven't made it yet, like, I don't think that's as strong an indicator as we think. Um, and letting it Letting it be an indicator is like, that's a conscious act, right? I haven't made it. It's not going to happen.

That attitude in itself is like, that's not just an analysis of where you are, that's creating a situation. Again, I don't want to tell everyone like, don't give up, everyone's going to get there and there are prizes for all. Like, of course not. But I think it's important to keep that in mind. And I couple— there's some other research in the book, about what's called a competency trap. So the other side of this is like, you can get really good at something, right?

You're in your mid-30s, your 40s, you've become like an expert, you've become a senior person at work, you really know what you're doing. The idea at that point of going back to scratch with something just makes you think, oh God, I remember what it was like to be 23 and I didn't know and I had to make mistakes and oh, it was just awful. I'm not gonna do that. That could be a really bad idea, right? Like the fact that it would be like uncomfortable and difficult and like you'd have to be, look like an idiot. Okay.

But you don't know that like you might not be great at that thing or that you might not just really enjoy it and that looking like an idiot is fine because it will be really fun and reward, right? Like you'll get a lot of value out of it. And so there are these two sides where like some, you shouldn't be trapped by your own competence and you also shouldn't be trapped by the sense that like, oh, I'm 40, I'm in a slump, whatever. Like don't accept that there are definitive things about either of those. It's an individual assessment. It depends so much on the situation you are in and who you are.

I've almost, I've almost like been radicalized against averages because I I worry that they don't tell you the variation. They don't tell you how certain they are and that it just looks a bit like that's the way it is for people. And it isn't.

[48:50] Paul: Yeah. Yeah. I was reading this research that said, uh, you're on our, of course, on average people's views at 19 predicted their views on money at like 30 years later. And it's like, well, like, I know for a fact my views on money radically changed. And so what other, like, conventional wisdom should I be skeptical of? Probably like a lot of it, right?

It's these self-fulfilling prophecies. But there is no actual average person.

[49:30] Henry Oliver: So there's a really interesting psychologist called Jay Belsky, and he has some work that says that, um, your propensity to be affected by, um, like trauma basically varies quite a lot. So some people, if they have a really difficult time with their parents as children, it like won't really affect them at all. And some people it'll affect them very strongly. This will then change when you're teenagers. Different people will be affected by that differently. And he has, the numbers are in the book.

It's actually really fascinating the extent to which there is lots of variation in how the same bad, you know, going through the same bad experience affects different people. For some people, it just like, it's not a big deal, but if it happens to them at a different stage in their life, it really is a big deal. And I think something like that, like we need a slightly different attitude on these things. Like what I always want to know, what is the variation? The chapter on cognitive decline in this book pushes this point that like, yes, there is average cognitive decline. Although you'd have to be an idiot to deny that there's a cognitive decline as we age, right?

Yeah, of course. But these numbers are given, there's a book about this in a piece in The Atlantic about this saying like, you reach a certain age and it goes downhill and you really need to rethink your life and stuff. And it doesn't talk about the variation, but the variation on these particular numbers is huge. And there are really good studies, the Moray House Test studies, where they gave the same people the same IQ test, I think at age 17 and age 70. Some gaps everywhere, a big gap like that, right? Loads of people got a higher score, loads of people got a lower score, loads of people came in about the same.

And that graph that just shows cognitive ability going down on an average curve, it doesn't tell you that crucial bit of information, which is a lot of people, this isn't true, like a lot. And, and that's what I worry about is is the idea that, like, like, we used to have this thing where people would say, oh, growth mindset is real. And then people started saying, what's the effect size? And, and the answer was, well, it's quite small, it doesn't really make a lot of difference. I think we now need a phase where people say, okay, but what's the variation? Like, right, how many people is this really, really true for?

Because we're giving this advice and I don't think we know.

[52:12] Paul: Yeah, it's like how most stuff is. I feel like the deeper you go into anything, it's like, well, ultimately we don't know.

[52:21] Henry Oliver: We have a pretty good idea. And as I say, like, cognitive decline is real, but—

[52:25] Paul: oh yeah, for sure.

[52:26] Henry Oliver: I was just fascinated that, like, really quite a lot of people seem to be higher scoring in older age.

[52:33] Paul: Well, this is the idea of there is no actual average person, because we're so multifaceted. We have thousands of things that describe us, right? So we're going to be like, inevitably somebody is going to be good at something at an older age.

[52:52] Henry Oliver: Yeah.

[52:53] Paul: And it's sort of just this acknowledgement that, yeah, there is beauty in all of us. I may not be able to be a sophisticated researcher and nonfiction writer when I'm older, I don't know, maybe I'll be good at speaking and mentoring and conveying different energy to different people. And we'll have to find out. We'll have to reconnect in 40 years for another podcast and see how we aged.

[53:20] Henry Oliver: You can tell me how you became a late bloomer.

[53:25] Paul: Yeah. What— how did this book change you?

[53:32] Henry Oliver: I don't—

[53:33] Paul: Books always change people in the process of writing it, don't you think?

[53:38] Henry Oliver: I don't know. I don't think of myself like that. I think a lot of the ideas that I've expressed in this conversation would've been quite alien to me before I'd written the book. So I think it probably changed me, changed what I thought. But I don't know. I don't know if I'm self-reflective enough to give I could answer that question.

[54:00] Paul: That's, that's a, yeah. And it's still to be published. So I found that it was after publishing and actually talking to many people about my book that really sort of helped me think about it in new ways and apply it to my life even more.

[54:17] Henry Oliver: What kind of things? What, how did it change you?

[54:20] Paul: So I think it's, I mean, when you're writing, you're sort of, it's such a personal act. Right? And you're exploring these ideas and you then put them out into the world and random people start telling you what different things meant to them and asking you deeper questions about what you've already written and realizing. And then just noticing, I think actually publishing and putting my book out was the first time I was really like, okay, I am a person who writes and shares ideas. Now I am not strongly identified with that. I don't care about the identity of being an author or anything like that.

But it's like, yeah, this is like a chapter of my life. And I am not afraid to be seen as a writer. I didn't really grow up in like a scholarly background. So it was like, Yeah, I'm doing this. I'm going to keep going.

[55:22] Henry Oliver: Yeah.

[55:24] Paul: So yeah, I don't even know. It's hard to think about, but yeah.

[55:28] Henry Oliver: I think I have a lot about that in the book as well. The way that you, people change very incrementally and you look back after 10 years and say, oh, look, this person became a late bloomer by doing all this stuff. And it took them a long time and they like, they can say like, oh, I've become, I've become a writer and I've put my ideas in public. You would never have anticipated this, but there's equally no moment where like it changed that day. I think that's quite important for, for like, you talked earlier about like transforming your life. I think it happened.

I think it happens like through sampling and through incremental changes.

[56:09] Paul: What role did, uh, Tyler Cowen have in helping you, uh, do this project?

[56:15] Henry Oliver: No Tyler Cowen, no book. Uh, very important role. He gave me a grant from Emergent Ventures, um, so that I could just quit my job and, and write it. Um, and Tyler is very, uh, very supportive. You can email him, ask him things, send him things to read. Like, he was very good on all of that.

Um, but yeah, no time and no book for sure.

[56:42] Paul: Yeah, I love his, um, quote. He said it in a number of different places, but it's like, one of the most important things you can do is raise the ambitions of other people. And I think being on a creative journey, I've realized how rare that is and how special there are people like Tyler doing that. For other people. And it's really something I'm trying to embrace too, is like, part of why I do this podcast is like, I just get excited about what people are doing. Like, I love your writing so much.

Like, I want more people to read it. And it's like, I get so excited about that.

[57:20] Henry Oliver: I'm very pleased to hear it.

[57:22] Paul: Yeah, it's so powerful. It sort of goes to what you were saying about the late bloomers and like finding. Those people to be around. And it sort of does like happen by accident. It's kind of crazy.

[57:38] Henry Oliver: It happens by accident. And this is where the internet is wonderful. The internet just creates so many accidents for you and it gives you a way of like, I can just email Tyler Cowen. I shouldn't say that because like loads of people will email him. But like the fact that you can just email him.

[57:56] Paul: He responds to everyone. I've emailed them too, but you know what I mean?

[58:00] Henry Oliver: Like you can just, you can be nobody, you can be online reading, you know, looking things up, email someone who's interesting. Like this is an unprecedented level of, and yeah, sure, a lot of them don't reply, but you know, I, I was working on the gender pay gap a few years ago in my job. And I emailed Claudia Goldman, the Harvard economist. I had two like That's a niggerty question. She got back to me that afternoon and was like, yes, but you've forgotten this point and look at this paper. It was, you know, it's incredible that you can do that.

And I think it's under— still underrated. Like email is still underrated. Yeah.

[58:46] Paul: What do you think Samuel Johnson would be working on today?

[58:49] Henry Oliver: It's an interesting question because he was fascinated most by biography, and biography had a boom in the 20th century. There were the Michael Holroyd generation, uh, these big, vivid, well-researched biographies, and this whole generation of people going back and actually writing about figures from history who were gay, actually taking seriously the women of history, right? This whole We had a great boom of biography. I don't know if we still have that, and I don't know. I think AI is a very interesting challenge to the biographer, but the major difference is that these biographies are all huge. The modern biography is like 1,000 pages and sort of intimidatingly long, whereas Johnson wrote, I mean, what we would think of as one chapter maybe, would be his whole biography.

He had the, the really the art of concision. And I think that will become much more important in the age of AI, right? You versus ChatGPT, probably you shouldn't write 1,000 pages. Um, and Johnson would've been really good at that. He was, he was absolutely brilliant at, uh, short writing. So I think he'd be thriving.

I think he'd be doing really well. He'd put The Rambler on Substack and he'd be great.

[01:00:20] Paul: I'm sure somebody has, uh, The Rambler as a name. If they don't, I'd be surprised. But, um, yeah, that, that's beautiful. Any other, uh, like for people on, like I write for a lot of people that are sort of carving their own path, some people still doing gigs on the side, some people still trying to find their thing, some people finding their thing and trying to build a life around that. What are some of the lessons from the, the late bloomers you think somebody in the modern world should embrace?

[01:00:56] Henry Oliver: My favorite— I think my favorite late bloomer is Audrey Sutherland, who was a kayaker. She ought to be famous. She is famous among kayakers. She ought to be famous among everybody. She went in an inflatable kayak to explore the coast of British Columbia and Alaska throughout her 60s and 70s and into her 80s. She'd never kayaked in cold waters before.

She was doing this on her own. She had bear encounters. Like, it was really fantastic, and her memoirs about it are so worth reading. And she was a single mother. She, like, she had a job, but she wasn't like, you know, well off. She had 4 kids and, uh, she only started really doing these kind of coastal explorations and kayaking in her forties.

She'd been a very competent swimmer before that, but she really developed throughout her life and she used to give talks. Yeah. And at the end, kayaking talks, right? About how to do particular things. But at the end she would say, close your eyes, someone's going to give you $5 million. Okay.

Think about what is it you're going to do with your life now that you have the $5 million. This is like back in the '90s. So whatever the number is to, I don't know the number, but like, what are you going to do?

[01:02:19] Paul: Billion.

[01:02:20] Henry Oliver: Yeah. But like, you know, I'm just kidding.

[01:02:22] Paul: It's like, I think $5 million would still do it.

[01:02:24] Henry Oliver: $5 million is still pretty good.

[01:02:26] Paul: I would do stuff for far less.

[01:02:28] Henry Oliver: But then she says, okay, so open your eyes and tell me, like, why can't you just do it now?

[01:02:36] Paul: Right?

[01:02:37] Henry Oliver: And one time, this grumpy man stood up and said, I'll tell you why I can't do it. I said, I have a wife, I have children, I have bills to pay, my parents are elderly, I've got a mortgage, right? All the usual stuff.

[01:02:52] Paul: Yeah.

[01:02:53] Henry Oliver: But of course, he's saying this to Audrey Sutherland, who's a single mother with 4 kids and she knows much better than him, like these problems. And she said, okay, you have to find something that you can do today. You have to just, where can I start right now? And she was always like, if she saw good rope that someone had discarded on the side of the road, she would take it. Anything like she would take it, repair it, make use of it. She would study maps.

She would go to the sea near her house and practice capsizing and bringing herself up. Anything, anything you can do, you just constantly, these marginal gains, to the extent that her table, her dining table was glass topped and under the glass were the maps of British Columbia and Alaska. So she's always just trying to make these incremental gains. And that's how she ends up doing what she does. And I, you see this in several of the case studies and I think it's really the most important advice. It's not a question of how do I quit my job today and do my dream?

It's a question of a torrent is made of drops, right? And you've gotta keep going with anything you can do right now.

[01:04:10] Paul: I love that example so much.

[01:04:11] Henry Oliver: It.

[01:04:12] Paul: Resonates with my story. I think one thing I've tried to pull out in this podcast is I think the 'I quit in a bold moment of courage' is sort of a fake story because— and I think why it gets told is people expect that story and they think they're supposed to tell that story. But I'll always say, like, what is something that happened 3 to 4 years before you quit or 5 years or 10 years, there's always something.

[01:04:45] Henry Oliver: Yeah.

[01:04:46] Paul: There's always these small moments and you don't see it looking forward, but you do see it looking back. And I think knowing that sort of with what your book is saying too, can give people confidence that it isn't these bold moments of courage, it's these small moments of just sort of following your curiosity and also adopting the idea that it's not over. Like you're not, your current path is not your final path. But so I don't know.

[01:05:18] Henry Oliver: Go back to Penelope Fitzgerald where we started. She publishes this, her first novel when she's 60, but she's had years of the houseboat and homelessness and all these difficulties. And what is she doing? She's teaching herself German. She's reading great literature. She's going to the opera.

She's building it up day by day. That's exactly as you say. If there is this one moment, it comes at the end of a lot of preparation, acclimatization, accruing what you need to do it.

[01:05:52] Paul: Do you have any path role models?

[01:05:54] Henry Oliver: What do you mean?

[01:05:55] Paul: Yourself. Do you look at Samuel Johnson as I I sort of want to craft a life similar to his.

[01:06:03] Henry Oliver: I don't know about a lot. I don't think his life— his life wasn't very enviable. But no, I know in terms of like how to live, not in that way, but like people like Samuel Johnson are sort of role models in the sense of he was so dedicated to learning and to wisdom and to his work. Yeah, I do. I do think of like that.

[01:06:26] Paul: Beautiful. Where can people follow you to learn more? And please talk about the book and when the book's going to be out.

[01:06:35] Henry Oliver: The book is out in May in the UK, September in the US. It's called Second Act: What Late Bloomers Can Teach You About Success and Reinventing Your Life. Pre-order it now so that you get it as soon as possible. Get more than one copy. Give it to the late bloomer that you know. Um, my Substack, The Common Reader, is where you can follow me.

I'm on Twitter, but I'm not good at Twitter. Much better on Substack.

[01:07:01] Paul: Beautiful. Well, really enjoyed this conversation. Um, I have a lot of ideas flowing now, so need to sit down and take some notes. But appreciate your curiosity, inspired by your work, and thank you for sharing this book with the world.

[01:07:16] Henry Oliver: Thank you, Paul. I'm really glad to be here. This was a great conversation.