The Secret To Scott Galloway’s Success

“On your last day on earth, the person you became will meet the person you could have become.” — Anonymous

I try to live my life in fear of this statement, just as I believe Steve Jobs did when he said in his famous Stanford speech:

I also believe Scott Galloway tries to live this way.

Therefore when I heard him say on the MFM podcast:

“I wish I had been more forgiving of myself when things didn’t’ work. I have trouble forgiving myself, and I struggle with anger, and the person I get most angry at is myself. And I struggle with getting past shit.”

He then cited his NYU colleague Adam Alter who’d done research on palliative care patients and asked about their regrets, and said one of them was not being so hard on themselves.

This sentiment is also backed by Bronnie Wares work on the dying where she reported one of the regular regrets of her dying patients reported:

“I wish I let myself be happier.”

However unlike Scott, I’d bet most of those folks weren’t building large companies, doing activist investing and joining the board of the NY Times.

In hearing him say this after he said all the bold and daring projects he undertook (mind you, on the podcast, he reported his book just hit #1 on Amazon as well), I couldn’t help but think if he didn’t have that anger and wasn't hard on himself, could he have accomplished the things he’d accomplished and would the people around him wanted to have been led by him as well?

Good leaders lead by example and followers love to follow those they admire, so wouldn't it only make sense that he uphold ultra high standards?

According to the research done by Dr Nassir Ghaemi, author of A First Rate Madness: Uncovering the Links Between Leadership and Mental Illness, Ghaemi’s main argument is:

“The best crisis leaders are either mentally ill or mentally abnormal; the worst crisis leaders are mentally healthy.”

It seems like many great leaders, Galloway did everything he could to maximize his potential and grew to love the pain.

He described companies he built with a hundred or more employees, and doing activist investing in partnership with a hedge fund where he’d have to go in and shake things up.

This is extremely difficult work.

Who are the bold and audacious who do that kind of work? Reminds me of Columbus or other risk takers who venture into unchartered territory.

Whether it was in 1492 or 2024, getting large numbers of people to work together toward a complex goal is one of the hardest things one can do, and in a competitive open market dynamic where you have to be the best, it's even harder.

As he said in the podcast:

We went out and put together the world’s best data set that no one could compete with us on.’

It seems to be a bit of a contradiction, no?

On one hand you’re trying something very difficult, thinking you have to be the absolute best in the world at it, are committing your whole life and soul to it, and on the other, you expect not to be hard on yourself?

My question is: if you’re going to do those hard things, why wouldn’t you also expect to be hard on yourself? Wouldn't it be naive not to be?

As I see it, why wouldn’t you be hard on yourself given the bold audacious moves you were making? Is there any other way? Would those people have followed you if you weren’t hard on yourself (and therefore them, by example)?

In the old days, pressure had your survival at stake. In 2024, pressure is the privilege.

This is not an argument to say people working on big complex goals in a competitive environment should be hard on themselves.

This is an argument to question if it’s realistic to expect anyone daring enough to venture out into unchartered territory in a competitive environment to not also be predisposed to being hard on themselves.

Would they do it if they weren’t hard on themselves in the first place?

Dipping your toe in the water is one thing, but crossing that point of no return as Galloway regularly did is a whole other beast.

The difference between wantrepreneurs and entrepreneurs.

The difference between the dreamers and the doers.

Galloway is a doer and I think it was the curse of his anger and voracious excellence that got him there.