Ep 184: Michael Wolff - In 15

Edited highlights of our full conversation.

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. 

Michael Wolff 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.

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.