Michael Wolff
A Story of Hope
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 338: Michael Wolff
Hello. I’m Charles Day. I work with creative and innovative companies. I coach their leaders to help them maximize their impact and grow their business. To help them succeed where leadership lives - at the intersection of strategy and humanity.
This episode is being published on Christmas Eve, which is my favorite day of the year.
Growing up, the anticipation of everything that was to come filled me with wonder and possibility. The month long build up of advent calendars being opened, trees being bought and houses being decorated, cards arriving, then food, then grandparents. The chill in the air, and the hope for snow that stays with me to this day.
As I got older, and started to see Christmas through a different lens, I discovered A Christmas Carol by Charles Dickens. One of the most memorable experiences of my life took place on Christmas Eve 1994 when Chris and I saw Patrick Stewart’s one man performance of the story onstage in New York. I’ve never found a video recording of it anywhere. But if you’re willing to step back in time, you can buy the CD on Amazon. It will take you to Dickensian London from its first moment.
Set amongst the despair and darkness of a struggling city, A Christmas Carol is the story of a powerful man led astray by greed. He creates a world that has no compassion or concern for others.
Sounds familiar.
This week’s guest is the writer Michael Wolff. He is a former editor of Adweek but is famous for his work as a columnist for New York Magazine, Vanity Fair, British GQ, The Guardian, and The Hollywood Reporter. He is best known as the author of several books on some of the leading figures of our time. Fire and Fury: Inside the Trump White House topped the New York Times best seller list for ten weeks in 2018.
His most recent book, Too Famous, is a collection of stories and essays that he has written over the years about some of the world’s most powerful and controversial leaders - from Rupert Murdoch, to Harvey Weinstein. From Boris Johnson to Michael Bloomberg. These are people that he has come to know intimately and the effect of whom he has seen up close.
After listening to our conversation, you might believe that Michael is not a fan of leaders or, in fact, of leadership. In fact, I think it would be easy to come away from this episode feeling that some of the spirit of the early chapters of A Christmas Carol had seeped in, like frost through the keyhole.
But like A Christmas Carol, I think this episode is ultimately one of hope.
Next year is going to be chaos on steroids. The Great Resignation, work from home, vaccination passports, rapid tests, two plus years of physical disconnection, a fundamental change in the structure of society, a de-emphasis on work and a yearning for in-person experiences, the accelerating acceleration in the use of technology.
In the middle of all that, we need some people to step up and provide a way forward. We will need leaders. Brave, bold, empathetic, caring leaders who will have to do this without case studies or classes or books or mentors who have experience, for the simple reason that none exist and no one has any.
Given all of that, traditional leadership can no longer be the reference for how you meet this moment.
So how do you lead with so little knowledge of what we’re facing and amidst so much uncertainty?
The framework I think, lies in an answer that Michael gave in response to my question about how he is raising his children during the pandemic.
“Parenting is always dealing with things you didn't much expect to deal with. So I think you just go along and just try to deal. Probably one of, if not the most important message you can send as a parent is that things can be dealt with. We must deal. And deal with some grace, and some originality, and some humor.
If we have learned anything from 2020 and 2021, it is that we cannot know what 2022 will bring.
The story we tell future generations about how we met this moment will depend on how we approach what comes next.
With frustration and old rules.
Or with grace, originality and some humor.
Happy Holidays and Merry Christmas to you all.
Here’s Michael Wolff.
Charles: (04:35)
Michael, welcome to Fearless. Thanks so much for coming on the show.
Michael Wolff: (04:38)
Thank you for having me.
Charles: (04:41)
When did creativity first show up in your life? When when were you first conscious of creativity being a force in your life?
Michael Wolff: (04:48)
Well, I guess I would say I have never not been conscious of it. So therefore, I've never registered it as unusual in any way.
It's the air we breathe. It has always been part of what I do, part of my view. I don't really see the world without that. And I don't think I ever have. As long as I have been… at the earliest moments of putting things together, and thinking about how you approach the world, that was part of it.
Charles: (05:29)
Did you write as a child growing up?
Michael Wolff: (05:31)
I did. And, both of my parents were writers. So that was clearly a given in my life, and how I grew up.
Charles: (05:45)
What kind of stuff did you write about? What were you drawn to?
Michael Wolff: (05:50)
You know, I was drawn to any opportunity. I was drawn to… I think you begin to write in your mind. So you begin to recast whatever you have done and whatever you have seen into sentences. Into language. You're looking for the language about it. You know, there's the experience and then there's recapping the experience. So I think, when you're a writer, you become… at the earliest time, you find yourself recapping.
Charles: (06:25)
You're such an exceptional storyteller. I was just curious where that started to evolve for you. What drew you to storytelling?
Michael Wolff: (06:33)
Well, I think this is part of it. I mean, it's part of the way you approach experience, it's part of the way you recast it, it's part of the way you talk to people. The interesting connection with writing, and a connection that people sometimes have a hard time making, and even people who want to write, is to be able to translate your spoken voice into a written voice. That's something, I think, from an early age, you begin to fool around with. There's the story that you tell people, and you're looking for a reaction. If you're a good storyteller, and if you want to be a good storyteller, it's all about the reactions of people to the story you're telling.
Charles: (07:23)
I think it was Alan Aykbourn who once said, "I don't know what I think about something until I write it down." Does that resonate with you at all? Is that part of your experience as well? Or are you clear walking in, that this is the story that I want to tell?
Michael Wolff: (07:34)
No, no, no, no, no. And I am never clear about the story I want to tell. I mean, the best told story looks for language with which to tell the story, or language with which to match the story. I mean, sometimes you don't know where it's coming from. But at all times, it's always pieces of improvisation.
Charles: (07:56)
Have you got a writing habit? I was talking to Michael Korda a few weeks ago from Simon and Schuster, and he grew up with Graham Greene, and he said, "Graham Greene had this extraordinary discipline. He would buy these very fine notebooks, he would use a fountain pen, and every morning he'd get up and he would write 500 words in this tiny, very precise handwriting, and then he would stop. And he would close the notebook and put it away and not write another word until the next morning.” Have you got a writing habit that you've found works for you?
Michael Wolff: (08:23)
I think, by the way, I think that's a drinker's writing habit. But yeah, I think everyone who does this for a living, functions like anyone with a job. So I am at my desk every morning, at an appointed hour, and I sit there and do my work. Sometimes, some days, better work than other days. But it is as straightforward and organized and unglamorous as most anyone's job. And often anyone's menial job.
Charles: (09:03)
Do you look forward to writing on a daily basis? Or does it feel like work more often than not?
Michael Wolff: (09:08)
Well, it is work. And I think most people, their work becomes very much a part of them, becomes very much like a routine. I mean, to say routine, which has a bad sound, we all like our routines. I'm not sure we can function without routines. I mean, I'm a runner, or have been a runner, I have some knee problems in these days. And I don't particularly like to run, but I've done it for 30 plus years. And, I would perhaps often think I would like not to be doing this. But in fact, there is quite a bit of pleasure in doing it.
Charles: (09:54)
You are such a keen observer of societal shifts. How do you think society has been changed as a result of the last five years? First through Trump, and then obviously with the pandemic laid on top of that?
Michael Wolff: (10:05)
I don't think we know that. I think that's the overriding question now, what has happened to us, and then it leads into, what is going to happen to us? And I don't know anybody who has a fix on that. I mean, the symptoms are obviously that of breakdown and the country coming apart, and of fissures appearing almost everywhere. I think that that's inarguable. The question is how permanent it is, how much just a function of this strange moment this is. Or how much is a function of actually even larger things. Which we're not even aware of yet. And I think that's certainly the major question of the moment.
Charles: (10:59)
When do you think we'll start to know? What are the markers that you're looking for to say, "Okay, I can count on that, that's a permanent shift, that's a meaningful evolution?”
Michael Wolff: (11:09)
These are the questions that are answered most always, and perhaps only in hindsight. But I think obviously, the things that people are looking at is, the next election markers. And that's partly because they are markers. And they seem more significant than they turn out to be, or it's hard in the moment to actually interpret the nature of the significance. But anyway… 2020 to 2024 is certainly what I think everybody has their eyes on.
Charles: (11:49)
And, what do you think about the societal impact of people being, if not completely locked down, certainly, I think, disconnected from each other, from a human standpoint. What do you feel are likely to be the lasting impacts of that? Or at least the next wave of impacts as a result of that?
Michael Wolff: (12:05)
I don’t know. I think it is the major question. We've gone through an experience that we have never had before, that we have really never imagined having, certainly that we haven't prepared for. An experience that we are now all ready to turn our backs on, like that didn't really happen, except it doesn't go away, it continues on. And I think that actually compounds the experience. And then begins to define the experience. It's this thing that will not end. In what that turns us into? I mean, I don't think we can begin to know, first thing, because it impacts us individually in different ways.
But it impacts different segments of the population in different ways. I mean, there's people of a certain age… I have a six year old daughter. I mean, she basically now knows nothing but pandemic rules. She's in her second year of school, in which she has only ever worn a mask. So you're certainly asking the major questions of the time. But, I don't think anyone, I certainly haven't heard anybody who has the kind of answer which even begins to hint at something that sounds like, "Oh my God, yes, you've understood it."
Charles: (13:37)
As a father of a six year old, how are you adapting your parenting to make sure that she's given the best possible foundation in these remarkable, extraordinary circumstances?
Michael Wolff: (13:47)
You know, I mean, I'm not sure it's different from any parenting. You know, I not only have a six year old, I have a six month old.
Charles: (13:57)
Hm.
Michael Wolff: (13:57)
But I also have a 37 year old. and two others that fall in there. So I've done a lot of parenting. And, you know, parenting is always dealing with things you didn't much expect to deal with. So I think you just go along and just try to deal. Probably one of, if not the most important message you can send as a parent is that things can be dealt with. We must deal. And deal with some grace, and some originality, and some humor. If I can do that, then I think that's about what I can do.
Charles: (14:37)
In your most recent book, Too Famous, you write about everybody from Trump to Murdoch, Michael Bloomberg, Harvey Weinstein, Ariana Huffington. Beyond fame and money, what else do you think draws people to leadership?
Michael Wolff: (14:53)
I think that they're all egomaniacs in some way. I think that they're all… in every instance, there's a psychopathology at work. I think most of these people are not like you and me. I think that they have needs and drives that are exceptional. And I don't mean exceptional in a good way. I think that they're usually in a bad way. I think these are usually people who are not all that happy. It's compulsions that they're often dealing with.
Charles: (15:35)
Do you think at any level, you can lead without an ego, healthy or otherwise? I mean, do you think ego is just a foundational part of the capacity to lead, the desire to lead?
Michael Wolff: (15:45)
I would say yes, for sure. But I think you have to be more specific in terms of the nature of what you want to lead and what you want to achieve. I think certainly the people I have written about, and the many people in the business world that I have dealt with over my rather long career writing about them, is that they are interested in pursuing and, in many cases, need this level of personal recognition. Me, me, me. Recognition, often control, and I often find that the urge is not to be alone.
Charles: (16:39)
Oh, that's interesting. You think they're running away from fear of being alone, in many cases?
Michael Wolff: (16:44)
I think partly. I mean, I think you could probably run down, you can make a checklist of all of the fears here. Of all of the insecurities. Of all of the holes that they're trying to fill.
Charles: (16:58)
I'm struck in reading Too Famous, not only by the fame that so many of these people, or perhaps all these people sought. But by the organizations that they built. And the organizations are fundamentally built around them, they're built to define them, to defend them, usually to enable them. Effectively they create their own bubbles of validation, affirmation. Do you think leaders who desire fame can actually build organizations that are also designed to unlock the potential of others? Or do you think that one prevents the other?
Michael Wolff: (17:26)
No, I mean, I don't. I think that leadership, and you might call this success, those are kind of both opposite sides of this coin. And simultaneous sides of this coin. I mean, it's hard to imagine calling someone a leader who's a failure. And I think that that kind of success is again, I think it's a function of, it's almost a particular psychopathology meets the market. And at other times, this person would be not as successful, would be a failure, or would be socialized in an odd way that is counterproductive. But this person is lucky enough to find the moment when his or her compulsions suit and serve the market.
Charles: (18:22)
History is filled with examples of leaders who have done great good, and leaders who have wrought enormous destruction. Do you think as a society, as a species, maybe, that we need leadership? Is leadership a fundamental requirement of how we exist?
Michael Wolff: (18:39)
it appears to be. I think you could probably make an argument that we would be much better off without leaders. That for every leader, if there is an upside, there is an equal downside. That they are always… the balance between constructive and destructive is always in play.
Charles: (19:07)
And what do you think are the myths of leadership? What are the great falsehoods that we convince ourselves of?
Michael Wolff: (19:15)
I think the central falsehood is that success represents leadership, start there. I think even the word leadership is a loaded word. Because it's necessarily positive, or at least in our culture. It has become something that's positive. And I think that's because the victors write history. The executives of this world, the CEOs of this world, have sought to propound their own virtue, endlessly.
I think that's under some revision now. But I think that we're still stuck with this idea that leadership is necessarily a good thing. That leaders are a positive force. That you need leaders to accomplish great things. That greatness and leadership are somehow connected. And I think that that has stood in the way of seeing so-called leaders as human beings. I mean I think actually, you can make the case that we've gone overboard now. We see these people now as monsters, all of them, or many of them. And we'd do anything to bring them down.
And so, in a way, over the course of not that many years, you know, basically a generation, we've gone from veneration of these people, building whole industries, certainly much of the media industry, to praise these people, to now building these industries to take them down.
Charles: (21:04)
And do you think that will swing back? Will we develop a more balanced sense of our expectation of leaders and what they are really capable of?
Michael Wolff: (21:11)
I'm never really convinced we ever get to a balanced sense of anything. But yeah, I think you can usually count on swings here, sure.
Charles: (21:23)
What do you think we should expect of leaders realistically? I mean, you've had such intimate access to so many. What's reasonable for us to expect of leaders?
Michael Wolff: (21:35)
That they will disappoint us.
Charles: (21:41)
And what about on the positive side?
Michael Wolff: (21:46)
I think that there is the moment meets the man or woman. And very odd people can create a significant difference. But again, I think that all of these people in their own way are problematic. And again, we get this… our inability to see these people for what they are is, I think, largely a sense of this… we capitalize these words, Success and Failure and we can't kind of see that the world is not a binary place.
Charles: (22:28)
If you survive long enough in a leadership position, is there always a fall from grace? Do you always reach that tipping point where...
Michael Wolff: (22:35)
I think so, yeah, I think so, yeah.
Charles: (22:38)
So there's a point at which you should get out if you want that to not happen?
Michael Wolff: (22:43)
No, I guess. But yes, but who does?
Charles: (22:46)
You think there is a sell by date for meaningful leadership, impactful leadership?
Michael Wolff: (22:52)
I mean, there is a sell by date in which you are no longer going to be on top. I mean, you may still be able to perform with the same effectiveness that you've always performed. But I think that the nature of the vacuum of power will sweep you into it. I think that we've just seen, for instance, Andrew Cuomo go down. We can go through the list of his sins, but I think the largest sin, the overriding sin, is that he hung around too long. Eventually, too many people want your job. Too many people want what you have. You're going to be toppled.
Charles: (23:40)
Do you think there's a line at which leaders evolve from wanting to do something positive, making a difference, to being in it almost exclusively for themselves? I mean, I'm just struck by watching Elon Musk's, I don't know whether it's evolution or just revelation. This is a man who ostensibly wants to save the planet and turn this into a multi-planet civilization. How do you look at somebody like him, in terms of what he says he wants to do and how he actually shows up?
Michael Wolff: (24:09)
You know, I never take whatever anybody says they want to do. It is, let's face it, is significantly off the mark. I think we can just safely assume this. And what they are doing, or what they actually want to do, or why they are doing what they're doing. I mean, I think Elon Musk is an attention seeker, a press hound, a promoter. Let's just call him a promoter, that's what he is, and that's what he has done successfully. Incredibly successfully. So, if you look at what he's doing now, I don't think… this is not necessarily erratic. It seems to me quite strategic.
Or at least that he has… I think that these guys usually go on instincts, sometimes the instincts go wrong. But the instincts are to keep doing what has always worked for you. And for Elon Musk, it's to call attention to himself. It's to try to take the next step, which everybody goes, “Oh my God, what is he doing? Oh this will… et cetera, et cetera.” I think you just have to say this is Elon doing Elon.
Charles: (25:27)
Are you fundamentally optimistic or pessimistic about where you think society is headed?
Michael Wolff: (25:32)
Well, let me put it this way, for a pessimistic guy, I actually find myself always very optimistic. You know, you get up the next day, things happen, we never know what's going to happen, it all turns out to be pretty surprising. I mean, I'm 67 years old, I've never missed a meal. I have wonderful children. You know, what's not to like?
Charles: (25:59)
And what do you see as the future of leadership?
Michael Wolff: (26:04)
I mean, an extremely good question. I mean, we're in this moment where all people in those kinds of roles are in fairly precarious positions. I think they're all grateful, frankly, to live another day. I think it can all end, and they all see themselves now, or certainly should see themselves, in somewhat of an existential predicament. The end can come anytime. And it can come from all kinds of different directions. And so, I think that probably we are seeing, without quite being able to see, a kind of reluctance. Anybody with an amount of caution is saying, "I don't necessarily want to go there."
And then one of the effect of this is that we're going to get more people without any caution. So, that sounds probably bad to me. But I don't know. Maybe, this is the other thing, you know, the idea of risk takers. Risk takers are the people who take risks, and therefore create those unexpected things. So, that brings us back to that real idea, there's a premium on psychopathology in leadership. Those are the people who will do what ordinary, more ordinary, cautious, responsible people, feeling people, concerned people won’t do. I.e. leaders are crazy.
Charles: (27:51)
If the leader of a business that had, say, 1,000 employees came to you today and said, "2022 is going to be filled with uncertainty. What shall I worry about most?" What would you say to them?
Michael Wolff: (28:03)
They will worry most about the thing that they are worried most about. Which is, living another day, staying in business. At the end of the day, the only real thing that the person in the leadership role is most worried about. And the idea that there are some leaders who've risen to a place where you think that they can have the luxury to think about other things, I think that that's probably not true. I think Mark Zuckerberg is sitting there and thinking, “This could all collapse. If not tomorrow, in six months or a year.” It just goes south. So I think that's what they're thinking about.
Charles: (28:50)
How do you think about fear?
Michael Wolff: (28:55)
Well I think that there's usually reasons to be afraid. And, if you're not afraid, you're either foolish and sometimes that pays off. You know? Normal people are afraid of things that are worth being afraid of. And the people who aren't, usually die. Or are destroyed. But sometimes they're not. Sometimes there's that person who is not afraid of what we are all afraid of, takes the risk, and realizes the reward.
Charles: (29:32)
And what are you afraid of?
Michael Wolff: (29:35)
Virtually everything.
Charles: (29:41)
How do you get up in the morning, being afraid of virtually everything?
Michael Wolff: (29:47)
Well, that's why I get up. I wake up worried.
Charles: (29:53)
Michael, I want to thank you so much for joining me today and coming on the podcast and sharing your insights. You've obviously lived an extraordinary life, and seen the world, and people who have massive impact on us, from a remarkable vantage point, and I thank you for sharing today.
Michael Wolff: (30:07)
Anytime. That was nice. That was fun.
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