101: Henry Oliver – Late Bloomers Success Stories

0:00:00 – Henry Oliver
People who spend too long exploiting. They don’t get enough breadth to like reach the best level or to find out what they’d be really good at right. They’re not sampling enough. The key seems to be that you I don’t want to say drift, but there’s a certain amount of meandering going on and you’re looking at different things and trying to explore different options and then at some point, you choose to switch into a phase where you’re like I’m doing this thing some point, you choose to switch into a phase where you’re like I’m doing this thing.

0:00:33 – Speaker 2
Do you think money takes up more life space than it should? On this show, we discuss with and share stories from artists, authors, entrepreneurs and advisors about how they mindfully minimize the time and energy spent thinking about money. Join your host, jonathan Dio, and learn how to put money in its place and get more thinking about money. Join your host, jonathan Deyo, and learn how to put money in its place and get more out of life.

0:00:53 – Jonathan DeYoe
Hey, welcome back on this episode of the Mindful Money Podcast. I’m chatting with Henry Oliver. His website says simply that he’s a writer. He writes the Common Reader, a weekly essay about literature, biography, history or whatever tickles his fancy. Henry received a grant from Emergent Ventures to write a book about late bloomers. The book is entitled Second Act what Late Bloomers Can Tell you About Reinventing your Life. Published by John Murray One. It comes out in May of 24. The moment I heard about it, I wanted to talk with him, partially for those personal reasons that many of you guys know about, partially because a second act might inspire some hope in those of us who are still trying to figure out what we’re going to do with the rest of our lives. Henry, thanks for being here and thanks for coming on the Mindful Money Podcast.

0:01:38 – Henry Oliver
Thank you for having me. I’m really pleased to be here.

0:01:41 – Jonathan DeYoe
Great First where do you call home and where are you connecting from?

0:01:45 – Henry Oliver
I live in London. We’ve lived here for many years now and we have a flat and that’s great. Where’d?

0:01:52 – Jonathan DeYoe
you grow up.

0:01:53 – Henry Oliver
I grew up in the middle of England in a much smaller place, much more suburban, and this is much more exciting.

0:02:01 – Jonathan DeYoe
I always ask the question when I’m talking to somebody from England about your team. Who’s your team? Who’s my team?

0:02:08 – Henry Oliver
Well, you, mean like football? Yes, I’m not a football person.

0:02:13 – Jonathan DeYoe
That’s what I get nine times out of 10. That blows me away.

0:02:16 – Henry Oliver
I have been to one football game when I was a child and I could see everyone was cheering and whatever, and someone scored a goal and I cheered and all of these huge men around me were like, tell that boy to shut up. That’s the other team, so not my thing.

0:02:37 – Jonathan DeYoe
Not your thing, scared you away from it. Well, I’m a lifetime Tottenham Hotspur fan, so now everyone knows.

0:02:43 – Henry Oliver
That’s London team right.

0:02:45 – Jonathan DeYoe
Yep, yep. And my son’s a man city fan, so we kind of we fight it out. He’s always at the top of the table, I’m always fifth or sixth place, always, always, always, always. It’s very it’s infuriating.

0:02:55 – Henry Oliver
You know what? My father-in-law? He’s big for liverpool, so let’s go liverpool, there you go.

0:03:01 – Jonathan DeYoe
Okay, that’s good, that’s okay, it’s acceptable. Mo sala is an incredible player.

0:03:05 – Speaker 2
Sure, I’ll take it, I have his jersey.

0:03:07 – Jonathan DeYoe
I have his jersey. He’s awesome. So I’m curious growing up, what sort of thoughts about life success did you have? Money, giving back earnings, business, entrepreneurship what did life success mean when you were growing up?

0:03:21 – Henry Oliver
I don’t know that I gave that very much thought. Or maybe my parents would say I didn’t give it enough thought. I was just more interested in reading and those sorts of things. I never felt the need to like everyone wanted to be a lawyer or a doctor or whatever. I didn’t feel that very strongly.

0:03:42 – Jonathan DeYoe
And no pressure.

0:03:44 – Henry Oliver
Not an overwhelming sort of pressure, no, a kind of normal expectation, but my parents were very good at just letting me do my thing and also, like I’m told that like I arrived as a reader and so they just let me get on with it, I think.

0:04:02 – Jonathan DeYoe
And it’s done well for you.

0:04:03 – Henry Oliver
I’m fine with my choices. Yeah, I don’t have a house or anything, but like.

0:04:10 – Jonathan DeYoe
I noticed the bookshelves. You have your books.

0:04:12 – Henry Oliver
I have my books and my kids are homeschooled and some people want a house, Some people want different things the mortgage situation and the house price situation. I’m not so upset that I’m not in the mortgage market right now.

0:04:26 – Jonathan DeYoe
Great, so give us a little bit about your background. I did my research, I looked around. There’s not a lot about you out there. Tell us about how you got here.

0:04:35 – Henry Oliver
I did an English degree and then I drifted a little bit. I was a teaching assistant with some eight-year-olds. That was a really cool job. We did Shakespeare they excelled at that. I went to law school, which was okay it wasn’t for me Became a blogger at a law firm. I was kind of dull. And then I went to work in Parliament for Liz Truss, who you will have heard of because of, but I worked for her before. She was famous okay, and that was interesting for a while.

But then I moved into basically an advertising job, but not in product advertising like everyone knows about. We did recruitment and employment and business culture. So we were doing the careers websites and the marketing materials you get when Unilever tries to hire you as a grad or whatever, and I’m on the research end of that. So I’m interested in questions like what is it like to work here? What sort of person would enjoy working here? Right, and I was able to go and talk to CEOs and C-suite people and say no, but for real, like, okay, it’s diverse, it’s innovative’s innovative, it’s whatever. What? Okay, there’s, but actually what’s the money following? Who’s getting promoted? Like? What do you actually care about day to day? And that’s a very interesting.

That’s very interesting to do, and it inevitably brings you to questions to do with people like late bloomers, which is the general question of how the hell can we hire good people in a tight market? Or how the hell can we hire good people with like weird skills, niche skills, how can we hire people who can fit into our culture, whatever? And so you end up getting asked all the time where are the hidden talent pools? Where can we go right? And there’s an old thing when you look at like labor market data people who find it historically less easy to get a place in the labor market, like women, right, people of color, neurodivergent people there are many groups people like that. Their employment rates do tend to go up in tight markets, of course, sure, but I found that very interesting that people start paying attention to talent. That was always there at a time when they kind of don’t have a choice, and one of the things that demonstrates, I think, is that it’s very easy to overlook talent. You can say we can’t get people, there’s no talent out there, but that actually that can be like quite wrong, and I saw, like just personally, I saw several people who would let go and I felt that it was more to do with their age than with anything else and I saw just the general difficulty of how organizations deal with people over the age of 50 or so. And there were various questions coming in and I eventually sort of decided to myself no one is interested in late bloomers, but I think they’re a whole group of people.

0:07:45 – Jonathan DeYoe
So how do you? You have a very all over the map background. How does that coalesce into late bloomers, into the idea of late blooming?

0:07:54 – Henry Oliver
I was ill at one point and I took like four months off work and one of the things I did was reread the novels of Penelope Fitzgerald, who is a really great English novelist who could be more popular. She deserves to be more popular Now. She did not start writing until she was 60. And a book that she published when she was, I don’t know, 80 or older was a big hit in America the Blue Flower. That won prizes, critics Circle, choice, all that kind of thing. Really, really marvellous book, and I was very struck by the fact that she was such a late bloomer and the great thing if anyone’s ever taken time off work like that. I was really quite ill so I didn’t have a lot of time to think, but it does give you a bit of space to be like I’ve been thinking about these issues at work. We’ve got Penelope Fitzgerald here.

I heard Tyler Cowen say something on a podcast about people who haven’t done anything yet. Maybe they will, and I was like you know what? There are other people like that and once and I was blogging at this point and some of the magic of blogging right, you write a short post saying, oh, there’s a thing here. I don’t know what it is. But there’s a thing here and all of a sudden you see it everywhere and you’re like, oh my God, late bloomers is such a thing. So it pulled on my personal interests and my work interests.

0:09:12 – Jonathan DeYoe
The stuff you’ve mentioned so far doesn’t suggest that you would run across Tyler Cowen anywhere. How did you run across?

0:09:18 – Henry Oliver
I have been reading marginal revolution for a long time. I don’t know. Fantastic, yeah, yeah, yeah.

No, I’m a big yeah, yeah, yeah I graduated in 2008, so into the financial crisis, and so I became very interested in economics. And there are two sides to that number one. I was like I love english literature, you know, I love all of that but I was very aware, I feel, that english literature, literature, does not teach you about these sort of other things, and I was very aware of some gaps in my education. And it was all just in the news every day and I used to be a big newsreader. So I started trying to learn economics and somehow I found Modern Revolution and I was reading this blog thinking I don’t really understand any of this, but the bits I do understand are good.

And was helping me, like trying to pick up some economics, and then one day he wrote something about like he just in passing, he’s like oh, bleak House is like obviously the best novel in English and few people understand this and I was like I understand that who the hell are you? How do you understand that you?

0:10:23 – Jonathan DeYoe
right. So at that point I became he’s a genius, tyler is a genius, he is.

0:10:29 – Henry Oliver
He is a very interesting guy, but I was just so struck by his ability to appreciate Bleak House in amongst all the other right, and so at that point I was like, well, now I’m really going to get into Marshall, right, and I do think actually that the’s commentary he offers is really good. Yep, underappreciated in the book’s world, I would guess, yep. So that’s how I knew about tyler, because I’ve been reading it, for I think I mean at this point I don’t want to name it because it’ll make me feel old, but it’s- 15 years, it’s something like that, yeah, yeah, yeah I

don’t know if it was in 2008, but as part of my, I need to learn economics if I’m going to understand what’s happening here, so I came to it sometime after. That could have been three or four years, but at some point.

0:11:15 – Jonathan DeYoe
There’s a lot of sources that you could have stumbled upon. You stumbled upon one of the best, like I’ve been a reader of his for a long time as well, and it’s incredible. And all the stuff you can click through to learn more about like resources, links. Just genius. So quickly define. Second Act for us.

0:11:33 – Henry Oliver
Second Act tries to answer the question what is a late bloomer and how can we find more of them? It’s a book about talent, but it’s very applicable to everybody. So I’m interested in the people with very high accomplishments how do you become a novelist in your 60s? How do you become a great architect in your 70s? These kinds of questions. But I think that we learn from the best. So I think the insights of the book are to explain to us how can we go out and find this, because great late bloomers right, right, like they’re important to the renaissance, they’re important to silicon valley that this is like a really important part of understanding how we achieve major things in civilization. But it’s also all the lessons are applicable to. I’m just some person and I want to live my life differently, so like I’m reluctant to call it self-help, but it sits somewhere between a study of talent and a self-help book.

0:12:30 – Jonathan DeYoe
I mean that’s the next question. Is there a change you’re hoping to make with it? I mean, how are you, are you trying to affect policy? You know, in individuals’ view of themselves, what is the effect you want to have?

0:12:41 – Henry Oliver
I don’t think there’s a policy change that I could point to, but I would like those people who are professionally interested in talent, whether they’re investors or HR professionals or hiring managers I would like them to think differently about late blooming potential right.

And just talent in general, yeah, talent in general, for sure, but specifically this question of like bringing someone in at a late stage in their life, and I feel that all the advice on this is like, oh, you’re 50, now it’s time to like give back or slow down or whatever. And there was an article in the Atlantic saying about cognitive slowdown after the age of 50 and executive processing and stuff. I don’t want to say that I disagree with that article, but one of the things I discuss in my book is that the graphs where you see this slow mental processing speed like it goes up and then it just sort of plummets after middle age. That is an average line, yeah, and there is a lot of variation around the average line and I don’t feel comfortable with this advice. That’s like you’re screwed after this point, so you should change it. I mean, actually, a lot of you might not be.

There’s a really interesting study of it’s called the Moray House Test and it’s a wonderful piece of research where they were able to give the same IQ test to the same people some 60, 50 or 60 years apart. Wow, yeah, and many people at 70 had a higher IQ Now. There could be all sorts of things going on there, right Test conditions, et cetera, et cetera. But it is really interesting that a lot of people are able to come out better. A lot of people come out worse, and so on, and I just think the picture is much more fuzzy than the average. The average is true. I’m not trying to like, I’m not like some intelligence truther the beard makes me look like I go in for conspiracy theories but I just think there’s variation around the average and we need a little bit of appreciation. When we assess talent, which actually investors in VC, they have a lot of that right, like you’re dealing with a person, right?

0:14:53 – Jonathan DeYoe
I mean the curve can be. If you have a bell curve it can be a very steep bell curve or it can be a very flat bell curve, right, and that’s. You get the same average, but the variation around that average is completely different. This is perhaps a little bit of a turn, but my favorite line and this is probably not a line that you were like this one I hope people pull out of the book but my favorite line in the book I’m going to read it is we should not despair if we’re not everything we want to be or if we are behind our peers. That’s the kind of thing that I try to teach and try to talk about. I took it, I have it on a little yellow sticky thing and I stuck it on my computer.

So, what do you tell the kid who just put like the YouTube or TikTok video on they have a camera on the dash of their car took a video of themselves just describing how life is hard? They can’t afford rent. Their fast food retail wage doesn’t get them doing anything. They can’t afford a college. If they went to college, they can’t afford their student loan payments and it just seems like it’s just so hard they can’t get started. They can’t do it. I love the idea of second act and some people don’t really get a first act, but you talk about just patience and taking time and just keep doing things and stuff will develop and you’re going to be okay and don’t worry about it. What do you tell that kid, though?

0:16:05 – Henry Oliver
Honestly, I might tell them the story of Samuel Johnson, who he did not grow up rich as such. His father was a bookseller. So he’s not poor, but he’s not what we would call privileged. He went to university because his mother inherited some money Otherwise he wouldn’t have gone and he was there for one year and then he had to leave because the money ran out.

Now Johnson, I don’t know what we would diagnose him as, but he was neurodivergent in some way. He’s full of tics and twitches and maybe he has Tourette’s, we don’t know. And he’s a big guy and he has a scar on his face from a childhood illness. So he presents in a way that to begin with people are like is this guy mad? Because this is the 18th century right? Some of them are like is he a lunatic? And he has to go and make his own way in the world. And he’s incredibly well-read because he’s just literally brought up in a bookshop. But he’s very depressive. So his first book he dictates from bed to his friend, because his friend is like you’ve been commissioned to write this and you’re lying in bed because you have depression, so I’ll write, you speak and eventually you know he starts a school, the school fails, it burns up, like all of his wife’s money. So he walks to London from Litchfield, which is near Birmingham, and he becomes a hack journalist and we’re talking like he is the all time five star hack. He will write anything on any deadline, about any subject. You just say it and he right, and he makes lists of things he can write and you’re like this is he’s got so much from he can’t write and he reaches the age of like late 30s, 40. And he’s got a great reputation and all the literary people in London think he’s great. But he has done really very little of note and you would not have heard of him if he died at that point, which obviously wouldn’t have been out of the question in those days.

But he had a friend, a bookseller, and in those days the booksellers were the publishers. So the bookseller obviously knew the other booksellers and there was a group getting together to make a dictionary, because the French had a dictionary. So the English were like, well, my God, if they’re having a dictionary, we have a dictionary. But how do you write a dictionary? Right, that’s a crazy job. And Robert Dodsley, this bookseller, said look, I know a guy and this sounds insane.

But he’d seen Johnson coming into the bookshop and just he was an absolute monster for reading. He would read any book in any section. He was interested in everything. And he got that job through his network in that sense, but also just because all the things that had made him a bit weird and outsidery and made him struggle in other circumstances. Doddsley looked at those things and was like, well, if there’s one guy who can sit down and write a dictionary like it’s him.

And so Johnson wrote the dictionary in nine years. He had the help of a small number of people to do the cutting and pasting, but he wrote a dictionary himself. It took the french like I can’t there’s an odd joke about how it took the french like 40 years and you know dozens of people or whatever. And so all of those aspects of his personality came together and that was a hot streak for him. He also he wrote many other things in that. He wrote the rambler essays, he wrote restless, all these things that now his reputation really hangs on and that made him like the most famous guy in London. And he got a government pension. And this is when he becomes like Dr Johnson and they do cartoons of him and he’s in the right.

But, like, a couple of years before that, one of his old friends wrote a letter to another old friend and he said oh, say hi to Sam for me. I feel so sorry about him. He is quite lost to himself and to the world. So there was this real sense that like he was talented, bright guy but it just hadn’t worked out and that was a real shame. But that wasn’t the end of the story, right? So I think you can pull the aspects of yourself together later on. There are so many things like you need luck, you need persistence, you need determination. Samuel Johnson obviously like is a talented guy, but it’s easy to see like, oh, I haven’t achieved this, I haven’t achieved that. It’s not easy to see what you haven’t yet had the opportunity to do.

0:20:23 – Jonathan DeYoe
So this it strikes me as an important conversation to have culturally, because social media and it seems like you’ve kind of protected yourself a little bit just in your own path and your parents seem to be very supportive. They may have said, hey, law, medicine, but you were able to read and just kind of pursue your own thing. I think there’s a lot of pressure to pick. Hey, I got to do something. Now, I got to become an expert at soccer or science or STEM and we don’t really allow people just to develop and to. The humanities are at a loss right now, in the US specifically, but we don’t teach virtues patience, perseverance, humility, these sorts of things. How important are those virtues and what are we missing because we’re not allowing those things to develop?

0:21:08 – Henry Oliver
I don’t know if I agree with what you’re saying. The system isn’t so bad at letting people pursue their interests. I think the reason the humanities. I don’t believe the humanities are in crisis. By the way, I’ve written an article about this, like where’s, we’re recording a podcast and I’m talking a lot about samuel johnson.

I don’t to me like the humanities. That great Big win for the humanities Touche, and the internet is just full of this stuff. Right, it’s all over the place. There is a decline in enrollments, but I think that’s more to do with, like, choice and economic prospects, and I think maybe there was a bubble in the humanities and now that’s deflated. I think we’re currently back at like year 2000 or late 90s levels of enrollments. Now I know at the time everyone was saying like oh, the humanities are in crisis, but they were saying that in the 80s, and like it’s not a new thing for people to say that. So I think if you want to like sit around and read Tolstoy, you still can. I think maybe, though, that like we’ve realized that fewer people want to do that than we thought. Now I’m fine with that, but the consequences?

0:22:13 – Jonathan DeYoe
are greater.

0:22:15 – Henry Oliver
Yeah, like if you get an English degree today, it will affect you differently in the job market. And I think people have picked up on that and, like you know, they’re studying computer science or psychology. I don’t see that we need to be upset that young people have decided to pursue those subjects. That sounds fine to me. As for the cultivation of virtues I talk about virtues at the end of the book and the pursuit of excellence. I think it is very difficult to pass this question Again. It’s very easy to see the ways in which distractions today divert you from, you know, sitting quietly with a book or pursuing excellence in other forms, but it is also very difficult to see that the really excellent dance videos that people put online are a form of excellence. Dance videos that people put online are a form of excellence, and to people like me, it’s very difficult to see the difference between the various types of online content. Right, but to the kids? But?

you know, to the young people who are involved in that culture, it’s much easier to see, like, where the excellence is and isn’t. I also am very pro young talent specializing Really If they want to. Yes, what I would like to see is like a more Catholic appreciation of talent. So I’d like I agree with those people who say it’s all 30 under 30. Where’s the 50 over 50? Right, but I don’t want to abolish the 30 under 30. I just want to have both. I’m out here saying let’s have more late bloomers, let’s invest in people in like the last third of their life. But I also think it’s fantastic that there are like young people who are deeply specialized in STEM fields and doing amazing things, and I don’t see why that can’t coexist and why we can’t sort of accept the multiplicity of these things.

I was a kind of generalist when I was young. I did we had a levels in england. So we do you pick like three or four subjects to sort of pre-specialize in before you go to university and a lot of people do humanities or science. I did two, two humanities, two science. I mean again like I don’t know that was a sensible idea, just like being, not becoming a lawyer. I don’t think that was like a good move necessarily, but no, like I think that would still be quite possible. It’s just that young people are making different choices and it’s great, like a lot of them are doing very well, I just worry a little bit that some of the young people aren’t making their own choices.

0:24:50 – Jonathan DeYoe
It’s like oh, look at that, you can juggle a soccer ball. So you’re going to play football for the rest of your life and we’re going to start that when you’re six.

0:24:56 – Henry Oliver
Oh, you mean intensive parenting.

0:24:58 – Jonathan DeYoe
Yeah, it’s guiding kids to focus, and way too early. And it’s when, when they’re eight or nine oh you like math, well, you’re definitely going to be doing this, and they don’t really explore outside of that, then for the rest of their lives to know that they oh, I would have liked dance, but I never danced.

0:25:18 – Henry Oliver
Yeah, okay, I mean, I don’t know enough about that to have a good opinion. I do, anecdotally, agree with you there’s a lot of organization on the parent’s side and I agree that children do very well when you leave them alone and let them get bored and let them follow their own interests.

0:25:32 – Speaker 2
Yes.

0:25:33 – Henry Oliver
I also think that sampling is good, yeah, and that children should be encouraged to do more of that.

0:25:41 – Jonathan DeYoe
So I actually, when I started reading and maybe you got this from sort of the intro I wanted a prescription, like I wanted you to tell us what do people do when they’re struggling and they can’t find their path. But I didn’t find a prescription. So is there anything we can do to like move ourselves in the direction of a second act that we know?

0:26:01 – Henry Oliver
I mean I tried to put a little bit of a prescription in the introduction and then the conclusion and I think if I’d been more prescriptive the in the introduction and then the conclusion and I think if I’d been more prescriptive the book would be more successful. But again, I’m very, I’m slightly, hostile to prescriptions. I think there’s a genre of book that’s like here are some studies, this is what they say Push the big red button and you will change your life. And it’s like well, a life is a big, complicated thing, my friend. Friend, you might push the button and find that like nothing happens right. All those studies might be grossly overhyped and it turns out the effect size is not very much or whatever. So I wanted this book to be more of a like. You can take from this the things that are relevant to you and you can hopefully change your perspective a little bit. But I don’t expect to like convert people. If there is a prescription, though it says that and I sort of outlined this in the introduction Late bloomers begin in an explore phase and at some point they switch into an exploit phase.

And I took this from a paper that came out of Northwestern two or three years ago Dash and Wang and some co-authors which was a study of hot streaks and people who spend too long exploring, like they become dilettantes and like fine, if that’s what you want to do, like, that’s great, right, that’s a good life. People who spend too long exploiting they don’t get enough breadth to, like, reach the best level or to find out what they’d be really good at right. They’re not sampling enough. The key seems to be that you I don’t want to say drift, but there’s a certain amount of meandering going on and you’re looking at different things and trying to explore different options and then at some point, you choose to switch into a phase where you’re like I’m doing this thing, and so if you’re a scientist, maybe that means you leave, like if you think about some of the talent in AI, they leave their university position and they go and join like Google or whatever, and so now they’re in an environment and a bureaucracy and a set of resources that’s really set up for like, let’s exploit what you know and deliver and do some cool stuff, whereas in the university it was all read stuff, figure it out, experiment, play around, whatever. That is a really good paradigm for thinking about late bloomers, and I read that paper very close to the end of my research and I was like, oh, that’s what I have discovered. I just didn’t have a way of framing it so neatly, and you see that again and again, so I think that’s really important.

I would also emphasize late bloomers are often quite weird, whether because they didn’t have the opportunity, they didn’t have the money, they didn’t have time, they just weren’t capable, but like, the ordinary path in some way was not open to them, right. And so the idiosyncrasies are more free to be developed and this can lead them to what it is that they become. And I think you see that the main chapters are about Catherine Graham, who ran the Washington Post, frank Lloyd Wright, the architect, margaret Thatcher, the British Prime Minister, samuel Johnson, the dictionary writer, and these people are all a little odd in their own way, and in a wonderful way. Right, I mean brilliant, but it was the idiosyncrasies that made them successful.

0:29:22 – Jonathan DeYoe
And the introduction of the opportunity, like it’s really important. And you talk about luck being a big driver and you mentioned it here already right, Whether it’s country of origin or socioeconomics, or the schools and mentors you have, or just in terms of your lucky break I think, the stories of Ray Kroc and Catherine Graham and Maya Angelou. You reference those three as making their own luck. So what is the part of luck and then the part of luck that I create?

0:29:49 – Henry Oliver
So there’s a section where I can’t remember the name. I think he was a scientist who wrote a book in the 60s about the four types of luck, and his framework really made this clear to me that we all face dumb luck. Stuff happens, you get your opportunity, you take a chance, whatever. But the busier you are, the luckier you are Right, and the more intense you are, the luckier you are, and sometimes making decisions for the quote wrong reason. So he picked the hospital he worked at, which was ideally suited for discovering penicillin because of the way the labs were organized and the sort of work they did and the layout of the building. He didn’t pick it for any of these like professional reasons. It had a pool and he liked to swim right.

0:30:42 – Speaker 2
So weird kind of luck.

0:30:44 – Henry Oliver
The other thing with luck is that, like, there are always these opportunities around, but are you actually ready and able to take them? So the Maya Angelou story is interesting because she’d been trying to be a writer for a long time she’d been on the west coast, the east coast.

She’d met other writers like she keeps going, she keeps going and it’s not working and she gets depressed about it. And her friend, james baldwin james baldwin, the titan of the american literature, but he’s their friends. And he comes over and he says you’re coming to this dinner party. And she’s like I don’t want to, I don’t want to go, just shut up and go. So she goes and she gets there and there are two publishers there and they want to hear the story of her life. And of course, at that point you’re like can you please sign a contract right now, I mean before you leave, please? She’s ready to tell the story. She’s been in the writing world for years. She’s been in the writing world for years, right, this is a lucky opportunity.

But for many people they don’t turn up with the material. They don’t turn up with having done the graph, they don’t turn up having, however, like indirectly, having, prepared themselves, right. So the way to think about luck is if I drop you into the dinner party, are you ready to just like, talk and be interesting? And she’s not. It’s not cynical, it wasn’t come and network come and it just happened? Are you ready, when it just happens, to take advantage of it? And the point is that if you’re ready, the opportunities actually are created by that readiness. You never quite know who you’re talking to. You never quite know, right. Samuel Johnson’s just sitting in the bookshop reading. He doesn’t know that Dodsley’s going to turn him into a dictionary writer.

0:32:27 – Jonathan DeYoe
Did you ever run into any pushback, whether it’s in the research or in the presentation of this material, where it’s easy to pick out a few examples, or many examples, of people who successfully get this lucky break? But there’s millions and hundreds of millions and even billions of people on the planet that don’t ever get or don’t ever see, or can’t perceive or aren’t prepared for or whatever don’t get their lucky break.

0:32:54 – Henry Oliver
Well. So let’s split this out though, because there’s privilege and then there’s making your own luck, and I think they’re different things, and what I’m trying to emphasize is that, like when Catherine Graham’s husband shot himself and she inherited the Washington Post, everyone said you should sell it, and she said I can’t sell it, it’s the family paper. And she became Catherine Graham and Steven Spielberg made a movie about her.

Warren Buffett invested and she did Water and she did the Pentagon Papers and like whatever, she did not start from zero. She was an oppressed person and her husband had treated her awfully, but she had been so fascinated by the news for her whole life and partly that was a result of privilege and growing up Really rich and in a newspaper family, but partly she just had the news bug and she’d always followed that interest Right, and so she was much more prepared For that opportunity than she realized. Same thing with Ray Kroc. When he turns up to the McDonald’s parking lot and he sees this fast food restaurant and he has spent years preparing himself for this with his milkshake salesman job, which sounds ridiculous, right. But if you think about issues of franchising, issues of trying to expand the restaurant, it’s all the same with the milkshake winches that he’s selling, and at that point the one thing that is holding back the fast food industry is franchising.

People say that he stole McDonald’s from the McDonald’s brothers. What really happened is they had created like the kitchen had been. It was a model that had been perfected over decades in various places. They had taken that to like a really high level of perfection. The mcdonald’s kitchen was choreographed down to the step. It was incredible. But they could not franchise it. They tried and it failed. And every time they got like they got to like six stores or whatever. Someone stops running the process properly and so when you go to that McDonald’s it’s not really McDonald’s anymore and the food’s not very good.

It’s like cold or it’s soggy right, no one had solved that problem and Ray Kroc solved it. And he solved it with all the stuff he’d learned through his years in sales and doing milkshakes and so forth. Now, is that luck or is that? Ray Kroc has like grafted for a long time and he found that opportunity. He made that opportunity Right. It’s easy to see that like. Oh, that landed in his lap because he turned up there. They called him and said we need I think it was eight milkshake mixers and he was like who needs eight milkshakes? That’s a crazy order. I’m going to fly to the other side of the country and visit this family restaurant. Most people just don’t do that. Most people just say sure.

0:35:50 – Speaker 2
I’ll sell you it.

0:35:50 – Henry Oliver
Great, great, great, right, ray Kroc’s like who the hell are these guys? I’ve got to get down there. So on what side does the luck come from? I think that’s actually a really interesting question. It reminds me of Eisenhower, who didn’t get promoted for 16 years and then, when the war started, had a phenomenal ascent and became Eisenhower right and Supreme Commander and everything. But in those 16 years he was so obsessed with tanks, which obviously were a huge part of the Second World War he stripped a whole tank down and put it back together because he wanted to see how a tank was built. Yeah, yeah, he was a real tank nerd, I can tell you, all the people who did not have Eisenhower’s career in the Second World War were the ones who did not strip the tank down. Okay, and so there’s something about these people that, like, I don’t know whether the luck came to them or they created that luck, and the more I think about it, the hazier that gets. Actually, yeah.

0:36:50 – Jonathan DeYoe
It’s a heavily debated topic. It’s very debated.

0:36:53 – Henry Oliver
It’s very debated, but I think it’s debated in these black and white ways and actually to me it’s just all grayscale now. Separate to that is privilege. You will know that these people are, yes, they’re all white Americans, they’re all operating in I mean for two of them in the post-war boom where, like I mean, yeah, sure, great environment, right, and that is a huge factor of course. But what I am just trying to get at is ways that we can expand this a little bit. And on the question of you know, it’s all selective and you can just pick the good examples. You don’t know what happens to the bad examples. Again, like I think that’s reductive. I think if you go back a few hundred years and you look around and you see what people are doing, you can say like, well, this is civilization, like this is what it is.

You have no idea of what people are going to be capable of in the coming centuries, right? No one’s sitting there predicting like the Flynn effect.

Oh yeah, no, everyone’s just going to get a whole load smarter over three generations. No one thought that was possible. When Beethoven composed his music, particularly the piano music, people were like this is unplayable. And Beethoven kind of reveled in that. He was like, yeah, good luck, right, you can’t play that. You can now get many, many good and excellent recordings of that work. And there’s a quote from JS Mill. He says just look at history, look how adaptable people have been, look how changeable people are in different centuries, different cultures, different times. I mean no one thought women could join the labor force and the people’s view of women has been drastically unthinkable. In what 150 years? I mean it’s insane how much that changed.

0:38:37 – Jonathan DeYoe
There’s a thread underneath it. I don’t know if this is intentional, but I’m hearing this. We’re talking about the second act for a person who is neurodivergent, or whatever the cause or reason is, but I hear you kind of saying that there’s a second act for culture.

0:38:54 – Henry Oliver
I guess my bigger point is like the graph looks the way it does now when you measure talent and what it can do. But that’s a snapshot. That’s not like yeah, it’s not like a finding in physics where it’s like that’s what an atom is. We know what that’s like. No, that’s just you measured the temperature of the water today.

You don’t know that. I would not predict so much based on that, and hopefully what my book will do is I’m not trying to prove it one way or the other. I think that would be crazy. What I say in the introduction is I want to get you to perhaps Yep, I remember Yep, okay, just perhaps because we don’t know how many more people could be late bloomers. But if we find like a small number of them, if we find another six like the people I’ve profiled, the big profiles, another Frank Lloyd Wright, yeah great, I’m not going to quibble about oh, it’s not possible because of this thing. No, if we can find another Frank Lloyd Wright, another Margaret Thatcher, that’s great, let’s have them.

0:39:52 – Jonathan DeYoe
So we’re sort of coming close to a closing spot here, but I wanted to ask there’s all kinds of noise out there in the world and if you were just magically able to tell you sat in an airplane with somebody transatlantic flight long time, chatted with them they’re in their fifties you could tell they’re primed for a second act. They’re primed.

0:40:12 – Henry Oliver
What is one thing that they could do to embrace the possibility, to be curious, to say perhaps I have a phrase you don’t spot talent by what persistently happens to them, but by what they persist at. Now there is something that you have been persisting at in your life, right, something. I don’t know what that is.

I’m not going to get to that Particularly if I, maybe if I meet you on a plane and we chat for a long time but, like, I don’t know what it is that you’ve got in reserve. But you’ve got something in reserve and that’s your route, that’s your thing. It never turns on the head of a pin without that quiet preparation. First, right. And there are some examples in the book of, like people who come back to music later in life, people who decide to take a vocation as a nun, and these decisions happen. You know that old phrase at first very slowly and then very quickly, right. That’s the key. You have to switch, you have to decide, like I’m switching from the explore to the exploit phase. But what is it that you’ve been exploring? What is it that you’ve found? You’ve got something. You just need to work that out.

0:41:24 – Jonathan DeYoe
It’s like the person who’s been writing whatever plays their whole life, but they’ve been working at this job and that job and this job and taking care of their parents and doing this thing and another thing, but they’ve been writing in the background this whole time.

0:41:41 – Henry Oliver
And then, okay, you’ve explored, you’ve been writing, you’ve been writing. Now let’s exploit that writing that kind of thing. And personally I find it amazing how often you discover, like when I had an office job, like oh, my colleague here, I didn’t realize but she’s like inches away from being a qualified sommelier, or this guy is like a massive World War I nerd.

People have all this stuff right Now. Not everyone’s going to become some great, successful thing. You don’t just wake up and it’s like oh, you’re Tony Morrison, well done, but there’s something there and you have to choose to go with it at some point and all the usual stuff applies. Like. It’s not easy, it might not work. You have to do the work, you have to adapt. Maybe you’ve been writing plays, but what you’re really going to end up writing is like a sub stack or whatever, but it’s already there.

You have to choose to switch. The other thing I would say is there’s a whole chapter on. This is to do with sampling. So if you take the example of Audrey Sutherland, she is not very well known but she should be really famous. She should be taught. You know, we should tell kids about her because she lived in Hawaii.

She flew over one of the islands one day and she saw a piece of coastline and she said I want to explore that. You couldn’t get to it very easily. So she flew a plane, landed at the old leprosy hospital and went down and did her exploration. It was going to take her a few days. She had a pack, waterproof pack, so she could swim for the bits she couldn’t walk. This was a crazy idea. Okay, she nearly killed herself jumping off a cliff. She got dehydrated. She didn’t go back for several years because it was a dangerous expedition.

But from that point on she is always exploring, practicing. She gets a kayak. It’s inflatable so it’s light enough for her to use right and she just builds up her skills bit by bit, like marginal gains. Everyone was talking about marginal gains a few years ago. It’s a classic example and she becomes a really proficient kayaker, a really proficient explorer, although in these warm waters, when she was 60, she flew over a piece of coastline in British Columbia and Alaska and she said now I want to go there. No one had seen this coming. I spoke to some of her friends and relatives and I said, when she started they were like oh no.

No one had anything. She didn’t know, we didn’t know, and, of course, going up in the Arctic is a different thing and she had to learn new skills and she’s doing this solo, right. So bear encounters, solo right, capsizing in Alaska waters solo, like all this stuff. And she has just developed this year after year. And she used to give a talk and she would say close your eyes, what would you do if you have $5 million? Okay, open your eyes and tell me why aren’t you doing it right now?

And one day this grumpy guy was like I’ve got kids, I’ve got a wife, my parents are old, I have to pay rent, all the stuff that everyone listening to this is like that’s me. And she said, okay, well, what can you do now? You have to do something today, just anything that will get you closer. She took this so seriously that her dining table was glass top and underneath it were maps of British Columbia. She was always looking at the map, always thinking about the expedition, always planning the route. If she saw rope on the side of the road, she would go out. It’s good rope, I’ll take that. I can use rope Like always, always thinking, and that’s what I mean. Right, how do you end up kayaking solo in British Columbia, first very slowly, and then, okay, I’m going today.

0:45:08 – Jonathan DeYoe
Andrew, just before we wrap, what was the last thing you changed your mind about?

0:45:13 – Henry Oliver
Oh boy, I don’t know the last thing. I so many things. I’m reading this book called Mozart the Performer. I’ll hold it up. It’s very good. It just came out from Chicago. It’s by Dorian Bandy, and I’m changing my mind about the central role of performance to the way Mozart fought as a composer, and I’m on my way to being persuaded that his ability to improvise was somehow crucial to him composing music.

0:45:44 – Jonathan DeYoe
That’s probably the most academic answer I’ve ever gotten. That’s awesome. Is there anything that people don’t know about you? Or maybe you told them and they don’t remember that you really want them to know? Read my sub stack.

0:45:56 – Henry Oliver
It’s called the Common Reader. That’s the center of what I do, so if you’re interested, you can get more.

0:46:02 – Jonathan DeYoe
That’s who you are. Yeah, how can people connect with you? Just on the Substack? The Substack is good.

0:46:06 – Henry Oliver
I’m on Twitter, but I’m not a good at social media and, I don’t lie, I’m grumpy about it, but the Substack is the best place. My email address is available online. I’m always happy to get emails.

0:46:18 – Jonathan DeYoe
I’ll just challenge readers or listeners to go and check out the Substack it’s very fun and then check out the book. Henry thanks for coming on the Mindfully Podcast and I just really appreciate it, Really appreciate your time.

0:46:29 – Henry Oliver
I had a great time. Thank you for talking to me.

0:46:40 – Speaker 2
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