Leadership coach Jerry Colonna argues that the win-or-lose mindset destroys joy and burns out leaders. He traces this thinking back to childhood games like Risk and Monopoly, and proposes a simpler measure:
Theodore Roosevelt said, comparison is the thief of joy. I'd rather be joyful. There's always somebody who has more.
Okay, everyone, super excited to bring you Jerry Colonna today, who is known as the CEO Whisperer, which I think is a hilarious— it's a hilarious, hilarious name. But he is the CEO of Reboot and is a certified professional coach. He also played a very prominent role in the early development of Silicon Valley Valley as a venture capitalist, also worked in private equity as well. And the reason he's known as the CEO Whisperer is from what I read on the Wired article, read the whole thing, but he's worked with amazing CEOs. He's known to make them get really emotional and cry. I've actually done that in our first interaction. It wasn't even a coaching— well, maybe it was a little coaching, but work with—
Every conversation with me is a little coaching. Keep going.
Thank you for that. So he's worked with the CEOs of companies such as SoundCloud, Etsy, And he's also the author of Reboot, which is a fantastic book on leadership and the art of growing up. And Jerry, first and foremost, super excited to have you here. My friends are even texting me right now on questions they want to ask you as well. So thanks for joining.
Thanks for having me, Eric. It's really good to see you. As I used to say all the time, there's a spinning that goes on. There's a bullshitting that goes on, which is the belief system that everybody's crushing it. Here's a little truth: nobody's crushing it. There are some days that are better than others. There are some product launches that go better than others. There are some team development efforts that go better than others. But the truth is nobody's crushing it. Everybody's faking. Now, that's not a particular problem. Who cares? Except that some percentage of the people who listen to this podcast, some percentage of your friends, are slowly suffering and dying inside. And by saying dying, I'm, I'm not bullshitting. I'm not exaggerating. There are people who are legitimately worried about their own life, and that is exacerbated when we're all walking around preening and bullshitting and pretending that we've got it all figured out.
I guess I forgot who came up with the infinite game, uh, phrase, but I know Simon Sinek started—
Simon Sinek.
Yeah, I don't know if he started it or anything, I just know I think it was somebody else that started in the '80s, but would you say that's the kind of mindset you have now? There's no like exit goal in mind, it's just let's just keep playing.
Sure, if you want to say, say put it in a game metaphor, sure. But what comes to mind is a conversation I had with one of my teachers, Parker Palmer. Parker is 81, and when his book On the Brink of Everything came out, Um, I— we did a podcast conversation and we were both, you know, like old men sitting on a park bench. You know, we're tossing breadcrumbs to pigeons and we're talking and we're making this comment about how a lot of people come to us and say, in effect, what is the meaning of life? What is the purpose? And we both laughed and we said, It kind of boils down to this question: How have I been kind today? That's it. Which could not be further from a zero-sum game. How have I been kind? How have I made Eric's life a little bit easier so that the people who work with Eric go, "He's not such a jerk today. I like him." That makes me happy. That's my purpose.
You've done a really good job of that, by the way. There's a couple of times where I caught myself, so—
Good.
You've been kind many times to me.
I have enough. The question is not how much do you need? The question is what does it take to have the feeling of enough? You had a relatively lonely childhood. You found belonging, which is one of the things that we're looking for always. You found community in the gaming world.
Right.
One of the lessons you learned in the gaming world is that it's a zero-sum game. There are winners and losers. You then take all of that benefit that you had, community, you combine it in a complex system, with a zero-sum analysis, and then you're in the workplace and you think, your brain thinks, that to belong someone has to lose.
Right.
And it better not be you. But here's the truth: human beings don't operate in zero-sum ways, not healthy ones. In fact, somebody who may not be performing well today may not be performing well because they have a parent with COVID And they're scared shit. And this person may be going through a divorce, and that person may be worried about taking their child to school tomorrow, all of which impacts performance. In a zero-sum world, off with their heads, every one of them.
Yeah.
Right? But, you know, off with their head is what, what the Queen of Hearts said in Alice in Wonderland. And this ain't Wonderland. Right? This is real life. Human beings. And what we really want is to create work environments where good people get to do the best work of their lives and go home and take care of their families. That's what we want. I mean, I sit here and I wonder sometimes, does Bill Gates look at Jeff Bezos and say, if only Does Warren Buffett at 90 go, God, if I could stay alive for another 10 years, maybe I'll be the $200 billion man? I mean, like, what the fuck are we doing?
Yep.
By the way, that mindset not only does it destroy us, but it leads to the destruction of the planet. It leads to this kind of rapaciousness around each other. Now, don't get me wrong, I like a good game as well as anybody. You know, among the games I like playing were Risk and Monopoly, right? These are winner-take-all games. There's no question about that. I like competition. I like competing, but I don't need to destroy. I just need to have fun.
Bingo. That's freaking awesome. Well, Jerry, this has been great. We probably have to have you on sometime in the future again, uh, because there's a lot of time, buddy. I have, uh, what is the best way for people to find you online?
Probably Twitter @JerryColonna. I'm on Instagram, I'm on Facebook, I'm on LinkedIn, but Twitter is probably the best way to sort of stay in touch with what I've got going on.
There you have it, everyone. Jerry Colonna. Check all his stuff out. It's amazing. And Jerry, thanks again for doing this.
Thanks for having me, Eric. It was a blast.
