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On what it takes to find success later in life

Prelude

Henry Oliver is the author of Second Act. He writes the literary Substack The Common Reader, which has been featured in places like the Atlantic, the Sunday Times, and GQ.

Conversation

On what it takes to find success later in life

Author Henry Oliver discusses the difference between motivation and success, navigating a midlife crisis, and learning from your disagreements

April 23, 2025 -

As told to Denise S. Robbins, 2393 words.

Tags: Writing, Family, Process, Focus, Time management.

Do you consider yourself a late bloomer?

We’ll have to see.

You’ve written a lot about late bloomers and what it takes to find success creatively and professionally later in life. If you had to give one piece advice on how to become a late bloomer, what would you say?

Whatever it is that you’re going to do, you’ve already done something that’s relevant. You need to work out what that is and turn it into something productive.

How does one choose?

I’m always tempted to say that you shouldn’t have to choose. Also, people often conflate two things, motivation and success. I joked that I’m not a late bloomer yet because I haven’t bloomed. But clearly I am in the sense that I wanted to be a writer and I’m doing it, whether or not I become rich or acclaimed in the New York Times. That’s not what it’s about. I have motivation. I’m following the motivation. I’m doing the thing. I earn money by writing. That’s what I wanted to do. I’m not Malcolm Gladwell. That’s a separate point.

People often ask, “How do I find the thing where I’m going to be successful?” And it’s like, what does successful mean? Doing what you’re motivated to do? Or does it mean meeting certain external measures? If you’ve bundled these two things together, that may be a mistake.

What would you say to people who might ask, “Why focus on late blooming? Why not just focus on acceptance of current circumstances?”

Clearly plenty of people don’t accept their current circumstances. To me, it’s obviously inherent to a certain type of person to not accept your circumstances. That’s why people crossed oceans and founded new places. I think that’s an essential part of being human.

You’ve written about moments of crisis being important moments for people to change their lives and blossom. Is a logical conclusion that we should all be having life crises at age 20 and then again at 40 and 60?

I don’t think everyone should be doing this, but there’s a prevailing idea that a crisis when you’re young is an opportunity to rethink, explore, and do new things. But a crisis when you’re middle aged is generally seen as, well, don’t screw it up. You know what I mean? You’ve got to get through that. I think a lot of that is now becoming psychologized. This thing that gets called therapy talk and “doing the work.” It sounds like what people are doing is trying to turn the crisis to some kind of new state. But I suspect that a lot of the time, it doesn’t really lead to very much actual change in your life. It may lead to reorganization of how you think about some personal relationships. But I think there should be more of a sense that if someone has a midlife crisis, sometimes that is a signal that you should make some changes.

A midlife crisis might be less dramatic than the way it happens in the movies—new cars, divorces, all this stuff—but maybe it’s a good old-fashioned feeling of, “My life has lost all sense of purpose. What am I going to do?”

Obviously it’s not simple to actually then undertake those changes. But not all crises are crises that you can analyze your way out of.

There’s long been debate over whether suffering is necessary for art. How do crises fit into that? You have kids and theoretically you want them to be able to find something meaningful in their lives, without going through a crisis or suffering. How do you get them there?

I don’t want them to suffer. But your children will suffer, you will suffer. The people you know have suffered, your parents have suffered. It’s really unpleasant when your children are really sad about something. But it’s also how they grow up, how they learn. It gives you very good opportunities to talk to them about the way things are or what you know. I’m not convinced most parenting talk makes much difference. But sometimes when they’re really upset about something and you just say one thing, it can make a little bit of difference. So you have to learn to live with their suffering sometimes. It can be very sad. But that’s not their fault. That’s not their problem. That’s my problem.

Did you have a life crisis that inspired you to write this book?

In a very small way—and this is what I mean about small crises—I was just bored. I think boredom is genuinely bad for people. I was so bored, I was on the edge of tears. It was just so dull. And I was convinced I’d need a different job. And I had cancer about seven years ago. I didn’t think that was one of those turning moments. The doctor said to me, “You’re going to come to me afterwards and say this is the best thing that ever happened to you. You’ll write your book.” I said, “Just tell me what time to get here and how bad I’m going to feel. I’m not going to have a spiritual moment.” But I did start blogging while I was having my treatment, again out of boredom more than anything else. So I wasn’t having dark nights of the soul or whatever. It’s very hard to make a movie about someone going through a crisis of boredom, but I think it’s happening a lot and it’s absolutely corrosive.

It’s all too easy to treat boredom with stimulation. Social media, YouTube, TV, what have you.

But also, chatting in the pub.

So how did you avoid those usual drawbacks?

Who’s saying I avoided them? The biggest thing was the confluence of factors. I wanted to change my career. I was incredibly bored. I’d started blogging. I’ve written in my book about nuns. There is a moment when they’ve discovered their vocation, but either before or after that moment, there’s a prolonged period of becoming. The vocation coming to be true or coming to be real. It’s not, “I woke up one day and found God, so now I’m a nun.” It’s instead, “I realized my thing. Now it’s going to take quite a long time to work through that.”

Do you have to fall in love with struggle or the challenge?

I think you have to have motivation. I interviewed the economist Robin Hansen, and he told me motivation is the closest thing we have to magic. I come back to that a lot. If you have motivation, the struggle is not really a problem. A lot of what people complain about at work is that usually you like something about your job, something motivates you, but it’s encrusted with all sorts of other stuff to do, bureaucratic, administrative, making your laptop work. You have zero motivation for these tasks. So you can feel miserable in a job that you love. It’s more about getting the balance right between doing things you’re motivated to do with the things you’re not. I don’t think you can learn to love the struggle as such.

How young were you when you started writing?

I don’t really know. I’m not one of these people who knows a lot about their childhood. Some people can be like, “I wrote my first story when I was 4, and it was about a caterpillar in Wellingtons.” And I’m like, how do you know? I don’t remember.

You might have written that.

Yeah, I probably could have done, but I have no idea. I don’t understand how people know these things. What I really was and am is a reader. I think that’s the essential thing. I think what I’m doing is being a public reader more than anything else.

Do you think that reading can be a creative act?

Some people would say so, but I think what they really mean is that your response to the book is the creative act. I think creativity means you make something. And I think reading isn’t quite like that. If you have an idea about what you’ve read and you tell that idea to someone, that’s creative.

You’ve quoted Samuel Johnson as saying that all young men should read five hours a day. Do you read five hours a day? Did you ever read five hours a day?

I may even read more now than when I was young. In a good week I read for 20 or 30 hours or more. I can go to the library and do seven hours of reading and that is actually a sensible use of my day.

What is your usual daily schedule between writing and reading and other things?

I am very messy. I see all this advice about getting a schedule and habits and I’m the polar opposite of all this. I just do whatever is most worrying me on the to-do list. A lot of times the to-do list is not that urgent. So I go to the library and read and write and do whatever I want. I like to have screen free time in the library. No phone, no laptop. Other days, like today, I owe a lot of people a lot of things. I’m going to have to scramble through my list.

You’ve written that expertise can lead sometimes to illusions of competence. Do you ever worry about your own illusion of competence?

All the time. Well, that’s why I try to read so much. I don’t think someone writing criticism should stop learning.

So reading is the way to counteract that.

It depends on what you read. For literature, what I try to do is keep following footnotes and keep reading people whose work I’m unfamiliar with, whose ideas I might not like. I try to understand other ways of thinking.

Does anything come to mind of a writer or idea that you were skeptical of at first, but then came to appreciate?

Modernism. I hated modernism. I thought the whole thing was just a terrible mistake. Now I quite like it. I’m still fundamentally very different to a lot of the post-modernists and the literary theory people, but I do try and learn from them. I don’t do a good job. Substack is good for this because I have a lot of people reading me now who have a wide range of literary views and they’ll leave comments or disagree with me on Notes. And I think that’s very useful. That’s what I like about it. The other day I said to someone, “I really liked your review.” And they were like, “But I thought you hated that. I thought you loved that book. And my review said that I hated the book.” And I was like, “Yes, I did love the book, but it’s good to read a review that’s like, no, this is trash.”

You’ve also written about the importance of connecting different areas of thought. Like how Michelangelo started by painting bodies and then becoming an architect. Do you have any strategies to diversify your areas of thought and intelligence and keep it fresh?

I don’t need strategies for my own interests, but I do need to find other ways of writing about them. I helped to write the Progress studies Wikipedia page last year, and that whole area is kind of absent from my work because I’ve become a bit more focused and specialized. I used to write more about those things. I might have a piece coming out soon about related topics. Also, I’m quite interested in AI and a lot of literary people aren’t, so I might be writing more about that as well, but I don’t know. Some people hate me for that.

What is your take on AI and the opportunities that it presents?

My take is basically, it’s here, it’s not going away, and it’s not just slop. You’d be insane to just ignore it or think that it’s only a lot of scams. But I am seeing literary people saying this, and I’m like, guys, they’re trying to cure cancer with this. What are you talking about? Give me a break. How it applies to literature, I think there are two ways. The first is that literary culture was changed hugely by things like photography, radio, the movies, and television. And literature always incorporated that and responded to that, even if it was hostile to it. With the internet, though, the novel has not done a good job of writing about the internet. And if it keeps doing that with AI, that will be a mistake. But sometimes it takes novelists some time. In Charles Dickens, famously, the first train to appear in his work is in Dombey and Sons in the late 1840s, quite late compared to how long trains had been around.

I’m not saying writers have to turn around and say AI is amazing. But I don’t really see how we have a viable literature if it’s all set in 1974, technologically. That’s just weird, isn’t it?

If you had to reinvent yourself right now, and take on a completely new vocation or passion, what would it be?

Well, because of AI, I might have to. I would quite like to be a gardener. I used to do a lot of gardening, and my wife is very talented at it. So I’d be the helper. She’d be the thinker. I don’t know if I’d be good, but I’d enjoy it very much.

What do you like about gardening?

I like the arrangement of shape and color, and I love growing things. I love being with the soil. Robert Frost, one of my favorite poets, wrote a lot about soil. Writers today, they don’t understand that stuff at all. The earth, plants, all that kind of thing. We have a very urban literature. But it would be good for them to get a new pastoral tradition.

Henry Oliver recommends:

Watching Totoro with children

Izaac Walton’s Life of Donne

The roast chicken recipe from Julia Child’s Art of French Cooking

Lichfield (for a daytrip)

Kew Gardens in bluebell season

Some Things

Related to Author Henry Oliver on what it takes to find success later in life:

Poet and DIY gallerist Sommer Browning on aligning your life with the things you find important Musician and author Michelle Zauner on finding ways to keep going Composer and guitarist Marisa Anderson on the benefits of being a late bloomer

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