HENRY OLIVER: Your Next Starts Now

0:00It's not about, I'm going to change everything right now and get it all done. It's like, what's the one thing you can do to make progress? Hi, I'm Michael Hyatt. And I'm Megan Hyatt Miller. And you're listening to The Double Win Show. So today, we're excited to share with you our conversation with Henry Oliver. So this is such a great conversation. You are going to love it. Henry may be somebody that you haven't heard of before, but he is a prolific writer and journalist with contributions to many major publications. And he has this really interesting fascination with cultural analysis and personal development.

0:40And kind of a contrarian. And kind of a contrarian. I mean, he would describe himself as a grumpy Englishman or a pessimistic Englishman. I think that's what he said. I didn't actually find him pessimistic. I found him to be a realist. But he has a very interesting point of view. And he's the author of the book, Second Act, which focuses on the concept of late blooming. So if you're someone who, even as somebody who's probably excited and enthusiastic about achievement, maybe you feel disappointed sometimes that you haven't accomplished as much as you wish you could have at this point of your life, this conversation is going to be very interesting and relevant for you.

1:19He talks about some themes like reinvention and success throughout one's career. And he talks a lot about some kind of almost mundane ingredients to doing that well, but in ways that you've never thought about it before. I just felt like, you know, the little emoji that's like the head exploding emoji. I felt like that was my brain during this conversation the entire time. You know, I felt incredibly optimistic because I felt like, oh, my best days are ahead of me. Right. So if you feel like maybe you've peaked, I promise you, you haven't. Yeah. So enjoy this episode. Henry, welcome to the show.

2:02Thank you for having me. I'm obviously thrilled to be here. This is going to be such a fun conversation, I think, for our listeners. And I just want to start at the beginning and ask you, can you kind of share some key milestones in your journey that led you to where you are now and talking about this idea of the second act? about six years ago i had cancer and it was like not very serious but i had to take some time off work and get chemo and the doctor said look everyone comes back and says doc it changed my life it was the best thing that ever happened to me i finally you know did what i wanted to do and he said you know you're you're going to end up writing your book or something and i looked at him and i said that's not what i'm like you know i'm it's not going to change my life uh let's just do the drugs go home forget the forget the big transformation okay um it's like larry david but more grumpy you know what i mean and then with all this spare time i was sitting at home and i was like i'm gonna do some blogging because i don't feel like i can get up and do anything but i'm gonna do some blogging and it it like gradually turned into writing this book so i had to grudgingly admit yes the doctor was you know yes okay i had a i had a moment in my life when i did these things changed.

3:19But I prefer to think of it like that because rather than like, I had this big revelation, I had this big milestone. It was like, I'm sitting here, I want to do some writing, I'll do some writing. And it builds and it builds and it builds. And I think that's really important. I love the phrase, a torrent is made of drips. We all are waiting for this great moment when you fall off the horse and have your conversion on the road to Damascus. But there are many years of preparation that go into that, right? And actually, the sudden process, I think, is always a slow process as well. What was it about late bloomers that captivated you and made you want to write about them?

4:00So while I was at home recovering, I read the novels of Penelope Fitzgerald, who no one here will have heard of. She's a fantastic English novelist. And I love her work. And she didn't write her first serious novel until she was 60. And so her story is fascinating. Right. And she lived in a houseboat and it sank and they were homeless. And her husband was an alcoholic. And it was like this very difficult, very interesting life. And I was then listening to the economist Tyler Cowen on a podcast. And he said something like, people who haven't achieved anything yet, but maybe they will. and I thought oh well that's Penelope Fitzgerald right like her whole life that's her uh so I started just blogging about that and then I thought oh that's Margaret Thatcher and well kind of Winston Churchill and just names kept coming to me and I thought there's like a thing here and I so I was just blogging about it and then when I was at work my clients were saying to me I was like in marketing where's all the talent we need to recruit people where are all the people.

5:09And I was saying, well, if you look at the data, they're all like 50 plus. That's where the action is. That's where the talent's sitting in the market. We're not interested in that. You know, they were kind of reluctant about it. And I was saying, yeah, but no, but these guys are great. This is a wonderful group. They've got experience. They've got expertise. And I'm starting, and I start talking about Penelope Fitzgerald. And it's like, what the hell is he going on about. But I had this like big, crazy idea in my head that I was going to pull it all together. Right. Um, and so gradually I did.

5:42And I got into this concept that the late bloomers are out there and we're not paying them enough attention. Hmm. So did your ideas about late bloomers change during this recovery process as you were thinking about it, writing about it, Did you have kind of a perspective pre-chemo that was very different than what you had post-chemo and all this research and thinking and writing? Or had you just not really thought much about late bloomers in general? I hadn't thought about it enough. And I would have maybe reflexively been one of those people who says, oh, writers do all their work when they're young or whatever, right?

6:23Which is just completely untrue. um so yeah no i was i was one of those people who was stuck in this culture of not thinking about of kind of privileging youth and and all that yeah one of the interesting things to me is that it is changing right now like i think it was two years ago best actress and best supporting actress both women in their 60s uh whatever you think of the whole joe biden thing a very active and lauded president who's like what 80 plus while he's in office before anyone right uh the average age of the american workforce has crept up a little bit there are many more people over 65 working now than there were in the 90s uh you go on tiktok you see videos of like there was this woman she was a park ranger she started in her 80s and she retired at 100 like oh wow yeah no she's really you should google it she's really cool uh jerry seinfeld directing his first movie when he's 70.

7:23It's just a bit more in the culture now that like, oh, you're 60. You're going to do something new and exciting now, as opposed to, oh, are you going to retire, dear? Right? Which was kind of more of the default. So I do think I've come out of the book and been like, oh, yeah, more people are thinking about this now. This is great. Ageism is gradually declining, I think. What is it culturally that's that accounts for that shift where a, there's more appreciation for people that are older and be people that are older, don't just want to retire and play dominoes for the rest of their life. So I think there are two things.

8:03The first is that we have, um, an aging population, right? And what that means is that there are a lot more people of that bracket who have a lot more cultural influence, a lot more income, whatever. The second thing is that we've just made lots of really good progress. Yeah. So you have a longer life, a healthier life. You just have way more options available to you. You can re-educate, change careers, whatever. So people have been rethinking the like educate, work, retire model into more of a like educate, work, re-educate, change, do other stuff, have a portfolio, go part-time while you semi-retire, but everyone can travel more now.

8:48And so our expectations of our lives, like if I think about my grandmothers, it was like, they stay at home, they're very respectable, they watch some TV, they go to the shops on Tuesday, that's their retirement, right? My mother is going all over the world. She's picking up new sports. The baseline is just so different. And so as you just get a lot more people like that, your default perception of age and just the quotes, older people, there are no old ladies anymore. It's true. There's these funny memes you see on social media of love like that American television show, The Golden Girls, one of those women in their fifties next to like JLo.

9:34And it looks like your great grandmother next to your sister, you know, like it's super dramatic. And you're like, how can these people be the same age? I mean, Botox for sure, but among other things, anyway, I mean, I do think that, that, you know, 40 is the new 25, like, or 60 is the new 40. I mean, I don't, I think about my, my grandmother when she was your age and she seemed ancient, ancient, you know, she was getting her hair set on Saturday mornings for the week and you know, all that kind of stuff. She wasn't like playing pickleball and traveling the world to your point. So I really do think our sensibilities have changed.

10:11Our expectations of age have changed. Totally. So that makes it much harder to look at a 50, 55, 60 year old and be like, they're on the decline. It's not going to be the same. like actually many more of those people are just as vigorous as their younger counterparts. Yeah, absolutely. And they're still competitive, right?

10:34So you talk about this idea in the book of persistence and how important persistence is. Can you share an example that illustrates this and just kind of talk about that idea a little bit? Let's talk about Catherine Graham because she's like an American hero, right? She took over the Washington Post when she was 45 one day because her husband killed himself. And her confidence had been eroded day after day in this terrible marriage. Her mother had been very bad for her self-esteem when she was young. Her husband was was domineering and bullying. And she'd ended up unable to get herself dressed with any confidence to go to a like an event or a dinner party because she'd been really diminished.

11:21and all of her friends and people around her are saying, well, you've got to sell the paper, right? You're not going to take it over. And most of us in that position, I think, would say, my God, what am I going to take over this business? Because it's not just the newspaper. They own Newsweek, they own TV, they own radio, like it's a media organization, right? But she had this deep set of beliefs from her childhood. It had been her father's paper. She'd been brought up with amazing privilege, like servants in the house. She'd been very well educated and she loved the news. I mean, she just, we think we're obsessed with the news today.

12:01She just could not get enough. So her response was, the hell am I going to be the one that sells my family newspaper? Now, this is rock bottom for her. And what she's relying on, more than any like skill set or anything like that, What she's relying on is fierce determination. She has been through so many difficult things in her life, and she's like, well, why would I quit now? And this is really what saw her through decades of becoming the most successful CEO in America. Huge, huge financial returns. Warren Buffett invests. And he said to her, I didn't invest in all those idiots out there. I invested in you.

12:46Now, this is Warren Buffett. This is not some throwaway remark. And underlying all of her ability, obviously very well educated, very capable woman. But underlying that is this huge determination. She saw down a really, really fierce strike that would have bankrupted the company. She decided to publish Watergate. They were doing an IPO and the government was giving them very heavy hints. if you publish this stuff, we'll take away your license to do TV news. And that will sink your IPO. Right? So she is making these decisions. These are not decisions for like a major intellect or someone with great strategic genius.

13:25These are decisions for someone who is made of steel. And that's what she had. And she just persisted for years and years and years. And she went from being this diminished person to being like, if you want to be someone in Washington, you have got to go and see Catherine Graham and get anointed. You know what I mean? That's just, there's no other way. There's no other way. So she's a great example of that. I don't know if you're familiar with Arthur Brooks, professor at Harvard who wrote a book called From Strength to Strength. And in there, he talks about fluid intelligence and crystalline intelligence.

14:06And so he says that it's like two different ways of being and of working. And usually a lot of innovation comes in your early years, but a lot of wisdom comes in your latter years. So I'd love to know your opinion of that. And also, I'd love to know how that kind of integrates with your concept here of late bloomers. so i argue against brooks in the book but i don't do it super openly because i don't believe in having those like those sections where you're like oh this guy is wrong and i'm gonna take i just i'm very much though putting forward the opposite point of view i think there are a couple of things um like yes that is what the graphs about intelligence show us okay but how important is intelligence.

14:56There's really interesting data, not like brilliant data, but really interesting data that the political leaders who become the most eminent, the most significant names like Harry Truman, are often the least educated. And part of that is because you can be really, really clever and become a leader like Woodrow Wilson with his PhD and everything. But there are other qualities that are important to leadership that intelligence cannot solve. And one of those is being a really good decision maker. Now, Truman was a great decision maker. He'd been in the army. He'd been in business. He'd been in the Senate.

15:40He dealt with the very dirty politics of his home state. Like he had a lot of experience that made him really good at, you know, sniffing out when someone was full of it and when they weren't. um so i would just say like does fluid and concrete intelligence matter very much in that context probably not the second point and this is a much more direct response to brooks is these are averages okay and we live under the tyranny of the average um and what his book which was originally an article basically says is look at this average curve it dips i can't like in in midlife and it goes down, that's going to be you.

16:21You need to think about what you're going to do. And I have data in the book where I show, it's fascinating, a group of people in Scotland, the same people were given the same IQ test 70 years apart. Now, some of them got lower scores because intelligence declines as we age, like the graph says. Some of them got the same score and some of them got a higher score. And in a way, the actual thing you want to take from this graph is, Yes, on average, there is a decline. Obviously, at some point before you die, you lose executive function and you lose memory and you lose all of these things. But there is also a lot of variation around the curve and you don't know where you are on the graph.

17:05No one has measured you. No one can point you to where you are. Right. So this like big generalizing idea he has where he's like, that's the curve, guys. Make your choices. I'm like, that might not be your curve, actually. That's quite a big statement. This isn't like we discovered a law of thermodynamics. Like this is an average. so yeah some people will look at themselves at 55 and say you know what i am a little bit further down the curve i shouldn't be the ceo i am going to rethink the way i like split my time or whatever some people will look at themselves and think if i could partner up with a 25 year old colleague and they bring all the fluid intelligence and the sparkiness and i bring decades of knowledge and experience, we could be a phenomenal team.

18:01Why isn't that his answer, right? So I just think, be aware of it, but make your own choices and have honest understandings of what you are like, and be aware that there's a lot of variation around the average. Well, it seems like those thoughts could become limiting beliefs. Like if I think that I'm going to decline cognitively, that I'm going to probably see myself decline cognitively. Right. I mean, the limited belief is going to have an impact. Well, your behavior and your choices could follow that belief. Yeah, exactly. Like you stop doing things that would keep your mind sharp, that would be interesting to you, that would be innovative.

18:40And therefore, you do less things that are innovative and forward thinking. So the way I see it is this, like I've consulted with lots of organizations and I've met lots of people at C-suite level. right? A lot of them are of an age where they should be skidding down that slope. But when you're in the room with them, it's like the dude's at the top of the curve. He's fine. You know what I'm like? I'm not worried about this guy. He's pretty sharp. It would be insane for someone to say to this person, oh, well, according to the average, you should be retired. Like, what? Crazy advice. Like, make your own judgment about who you are.

19:21I really, really object to this, like, as I say, the tyranny of the average. I think that's a fascinating perspective. And I like that there's a little bit of room and flexibility in that, that we can use our own judgment and factor in the unique ingredients of our own life to assess ourselves. Not to toot my own horn, but I'm 69, and I taught in the last two weeks two four-hour workshops on artificial intelligence. And I've really done a deep dive into that, and I feel like I'm at my peak cognitively. Well, just to further that point, I was in the car last night with mom, your wife, obviously, father-daughter, just in case you didn't know.

20:12And we were on our way to a yoga class and I said, man, don't tell dad this because, you know, he's just going to get like a big head about it. But he is freaking genius about this AI stuff. Like I can't, like, I think he takes for granted what he already understands. And I had this realization as I was building something with AI yesterday, I was like, oh, and I texted you about it. I was like, oh, I think we actually need to like dumb this down a little bit because you've taken for granted some of the steps here that our team, who are, by the way, all under 50, you know, and most of whom are between probably 35 and 40, are struggling conceptually to wrap their head around.

20:54Whereas to you, it's like, oh, yeah, well, you know, blah, blah, blah, blah, it's easy peasy. And so, I mean, I think that's a good example of there's nothing right now that's happening that's more innovative than what's happening with generative AI. And you're just like, yeah, you know, I got it. And so I think, anyway, I'm not, I'm not saying that to toot your horn, but I think it's a good example, Henry, to your point that the averages in this case do not apply for actually all of the experience that you bring to the table uniquely positions you to understand it because of your programming background.

21:29You've always been interested in technology. So like your age is actually an asset, maybe not actually your age, but your experience is an asset. But also you have the cognitive ability to think about it, you know, as a new technology. This is such a good example, because that curve of fluid intelligence is one thing. But clearly, one of the other important things is that you are high in openness, and you must love AI, right? These are two other factors that Arthur Brooks can't take into account, because what he's trying to do is take this one narrow thing and give you a straightforward... It's this smart thinking genre.

22:09Here's a study. It explains something about your life. Push the button and it will change your life. And you're like, yeah, in your book where there's no other consideration, that's fine. But in my life, which is a really messy, complicated thing with loads of other factors, the button might just not work. Right. And if you're high in openness and you're like really interested in something, maybe this curve is just completely irrelevant. And so that's the message I want to get across totally. That's good. I love that. I mean, I think that's really hopeful. Okay. So you've mentioned openness a couple of times, and I'd love for you to talk about that idea and what that has to do with being a successful late bloomer, you know, somebody that really has a second act.

22:55Yeah. And just to add to that, you talk about this explore-exploit dynamic. Yeah. Yeah. Yeah. Yeah. Okay. So I'll start with explore exploit because I think that leads to openness quite nicely. The explore exploit thing comes from a paper that said, why do people have hot streaks? Sometimes a sports person or an artist or a scientist, they go into this 5, 10, 15 year period. Everything they touch turns to gold, right? Why does this happen? And the conclusion they came to after looking at a very large group of people across all these disciplines is, First, they're in explore mode, which is just looking around, trying stuff out, being interested in different things, not necessarily trying to achieve anything, just just burrowing away at your own thing and looking at different stuff.

23:43You then choose what it is you're going to work on and you go to exploit mode. So if you say you're a research scientist, there are people in AI like this, right? They spend 20 years at the university doing their research, just getting into their thing. And then at some point, they say, I'm going to a business. I'm going to a corporate lab. I'm going to make something. I'm going to have a team around me. They've got a logistics operation. We can do delivery. The infrastructure is not I'm doing my thing and writing my papers. It's when are we shipping? The paper says the key thing is that you make that switch from explore to exploit.

24:22And that's like, that's what gives people a hot streak. And I was like, Oh, that's kind of what my book is saying. Actually, I found this paper at the end. And I was like, Oh, this is amazing. Like, this happens so often with late bloomers. And I think it tells you that openness is a good thing. But it can be a trap. Right? Before you get into that, will you just say what you mean by openness, just in case anyone is like, what exactly does that mean? It's like I'm interested in lots of different things. I'm a curious person. I'm not just going to stay with what I already know and like. If you come to me with different ideas, different experiences, I'm like.

24:59So a good example is I went to Dublin recently and I shouldn't say this. I didn't know that there was much of cultural interest in Dublin. And I went to the National Gallery and I was like, can you show me where the Irish art is? Because I don't know anything about Irish art. I was blown away. And some of the stained glass was just life-changingly good. that is an example of like openness to this new type of art that previously i'd have been like i don't know do they have any art i don't know whatever um that's so rude i've got lots of i am like part irish i'm not just being an awful english colonialist so this can be really good right because openness brings you to new ideas and new thinking but it can be a trap in the sense that you can become one of those people who lives entirely in explore mode and sort of dabbles around in different things and like gets lots of different experiences but doesn't do anything with it right and like if you want to achieve something if you want to make build create whatever you do in fact need to sit down and like do the logistical stuff think about when you're going to ship all that kind of stuff and that's not really openness that's something else um so you have to use openness as a driver, but like set deadlines, get stuff done.

26:26Right. And that's a very different part of your personality. And I think we're very keen on openness in modern culture, but we're less keen on the more prosaic side of delivery. It's almost like openness that doesn't, you know, flip into exploitation of some sort is kind of dabbling. Yeah, exactly.

27:01But you talk about the idea of networking numerous times in the book. So can you talk about what that means and how it helps us to build leverage later in our lives? we think of networks as all being about connections right partly because in the tipping point Malcolm Gladwell talked about connectors and I think that idea really broke through and people still retain that in their minds those those people who can always give you oh I know someone who can help you with that I know a guy I can put you in touch right and online you're always making connections on on social media and stuff what the latest research shows is connections are like obviously important but what really matters is influence are you connected to the person who can actually influence you so you guys if you recommend something to each other there's like a good chance you'll take that recommendation seriously right if you go one degree removed two degrees removed how seriously you take the recommendation starts to drop off quite quickly.

28:10And what we talk about is we talk about six degrees of separation in a network being the like the magic number. You're not listening to anything anyone says three, four, five degrees, right? So you have to really think, who is it in my network that has the influence that I need? And the mistake because we have the connection mindset is like, I need to know the person at the heart of the network, the most important person, someone senior, something like that. But actually, the most influential person might just be like if you said, oh, I've got a friend and she can recommend this great book on AI to you.

28:47You'll be like, well, I trust you. So your friend's probably an OK. Right. That's maybe she's not a very significant person in anyone's network, but she actually is the one person who you want to send your AI book to in this instance. And so thinking about that is a bit more subtle and a bit more difficult. and it's not so easy to like make LinkedIn posts about why that's the magic, but that is the magic. Um, and what it means if you're looking for like a takeaway on that is you might be the most influential person for someone in your life right now in a small but significant way, even though you're not like a big shot.

29:31Um, there's, there's George Elliott in her, in her wonderful novel middlemarch says this at the end she says that things are not so bad with you or i as they might be depends on the unhistoric acts of all the people who've gone before us and what she's saying is you go around and you're like a good person or a bad person just in your daily life you're nudging the world one way or the other and that's pretty influential and that does in fact make a difference to people. And it turns out networks are a bit more like that and a bit less like, I got 10 ,000 connections on LinkedIn or whatever. Because like, just because you do that doesn't mean you get invited to the White House party or some other, that's not how it works.