Welcome. I’m your host, Greg McKeown. I’m the author of two New York Times bestsellers, Effortless and Essentialism, and I’m here with you on this journey to learn how to live a life that really matters.
Today we will share this new habit of highly effective people with you, along with actionable advice for putting it into practice. By the end of this episode, you will be able to lead better, whether you are the CEO or the CEO of your own life.
Remember to teach the ideas in this podcast episode to someone else within 24 to 48 hours of listening so they can hope again.
It seems to me that for a lot of people, it’s a bit like living in a matrix like the movie. I mean that they’re just doing what they’ve done, and even the idea of questioning it is uncomfortable to the level of unthinkable.
And I say this as somebody who was raised in England and has a tendency within me to just, and I don’t mean rudely, but just to sort of question everything and just imagine a completely different way of being and living. And I remember how people would sometimes look at me in my life, or the things they might say, “Well, why do you want to do that? Why would you want to do it differently?”
And I didn’t always have a great answer for them, but it seems like just even having exposure to what would happen if we didn’t have to try and control the outcome or didn’t have to just live within the existing system but could work on the system.
I know that you have run an interesting experiment around this, the failure exercise that you’ll put students and executives through to help them to be able to take more action and be willing to experiment with their agency. Can you tell us more about that fascinating exercise?
Yeah, that’s right. So it can be tempting when you’re in a classroom, when you’re reading a book, to just sort of intellectualize things and go, Oh, yeah, that’s important. I should fail. That seems important to me in order to be able to lead change. And so after a two-hour lecture where we’ve done some case studies where we’ve looked at empirical social science research looked at one inspirational video, then at that point I go, “Okay, now there’s only one thing left to do, and that’s simply.” And then I flash up two words on a screen, and it says, Go Fail.
And students and executives sort of look around at each other, they sort of laugh nervously, and they’re kind of wondering, Is this guy for real? And I go, “Yeah, I’m for real.”
I go to the next slide, and it says, Okay, you have 10 minutes, and you have to go leave the classroom, and you have to go get rejected on purpose. You have to go ask for something and get someone to tell you no to your face, and you can’t come back until you’ve gotten that no.
And the nervous laughter shifts to a somatic response. I start seeing people turning red. Students and executives tell me that their hearts start beating a little bit faster. They’re sweating a little bit, but I go, “Okay, you’ve got 10 minutes. Let’s go do this.” And so they nervously shuffle out of the classroom, and then when they come back, the energy is just off the charts. So much so that I once had a next-door professor come by and ask us to keep the noise down because, in those 10 minutes, something really profound has happened. We, especially high achievers, spend so much of our life thinking about how can we minimize risk. How can we minimize the chance that we will fail or get rejected?
We become so good at taking the preordained path, the safe path, the path where we know that, okay, if we follow steps A, B, C, D, well, we get to the end, we’ll get a nice little recognition. And in those 10 minutes, I want to shake that up for people completely. And so when the executives come back to the room, there’s two stories that are most common.
About one-third of people, they go out, and they are positive that they are going to get a rejection. And to their surprise and delight, they get a yes. They ask for something they think is so ridiculous, but someone actually agrees to it.
I think, for instance, about the woman that walked into the gym and she said, got on the PA system and said, “Hi, it’s not my birthday, but would you all sing Happy Birthday to me?” And she got a gym of 60, 70 people all singing Happy Birthday in unison to her on a day which was not her birthday.
I think about the student who went to the local café, and she asked for a free orange juice. And to her surprise, the barista said, “Yeah, okay.” And gave her one.
She was kind of shocked because she expected to get a no and knew she couldn’t go back until she got a no. So she said, “Okay can I have another one?” And again, he said, “Yeah, okay.” And it was only when she asked for the third that she finally got her no, but she came back to the classroom with two orange juices.
That’s fascinating. What other examples? I’m loving these stories.
It was a rainy day in Berkeley, and a student walked out without an umbrella, found another guy, complete stranger, and said, “Hey, I don’t have an umbrella with me. My other class is about 15 minutes across campus. Would you walk me to campus?” And the guy, again, to his shock and delight, said, “Yeah.”
A complete stranger was willing to spend 30 minutes just to help out a stranger because that person had the courage to put themselves out there, the agency, to ask for something that they wanted. And when that’s reciprocated, that’s a really powerful thing because we so often set ourselves up for failure because we’re sure we’ll get rejected. And so we don’t even ask in the first place when, again, the empirical data at my class show about one-third of the time, even on ridiculous asks, like singing happy birthday or walking someone across campus, We actually get that, yes.
What other examples do you have of people that got yeses when they thought they’d get, No?
I’ve got a whole bunch of them. We had a student who went up to a woman and said, “I love your shoes. Could I try those on?”
And again, she thought this was a super safe bet because who would let someone wear their shoes? But I guess with the compliment, the woman said, “Yeah, okay, you can try on my shoes.” Leaving my student to feel uncomfortable, being like, do I actually want to do that after all? I’m not sure about that one.
And then there was this student who, there’s some construction going on campus, went up to someone conducting or working with a bulldozer and said, “Hey, I’ve always wanted to drive a bulldozer. Could I drive that?”
And to my relief, as the faculty member in charge of their safety, the person said no. But it led to a conversation, and the person got to actually jump up on board on the bulldozer, take a look at it, not drive it, but at least got part of the way there.
We had students ask, for numbers, for Snapchats, for Instagram and get yeses. We had one student who went out asking for $5 donations to a favorite charity, and he came back with, I think, $30. He had six people that decided to donate.
Then one, I encouraged because he came back so quickly, he got it very quick. Now he asked for a million dollars. I said, “Okay, but that’s not that hard of an ask. A lot of people say no to a million dollars. Here’s what I want you to try. Go around and ask people to act like their favorite animal. So if it’s a grizzly bear, act like a grizzly bear. If it’s a pig, get down on the ground and oink like a pig.”
And so he got probably five or six different people to all act like animals in the courtyard.
I can’t get enough of these examples because it’s really interesting to experiment with what you assume will happen, but you never risk asking for, you never risk the interaction. And so you’re living in a world that does not operate the way you think it operates because you’re never actually interacting with it. You’re just going along, not wanting to get out of the stream or change what is normal for you. So then sometimes you have, of course, the whole point of the exercise, which is to do something where you actually get a fail right now. Tell us more about what happens in that scenario.
So in that case, again, we take high achieving executives, high achieving students who are used to getting a lot of what they want, perhaps because they tend to play it a bit safe. So they’ll ask for something. And again, they tell me afterward that they’re sure that someone will laugh at them or mock them or get angry at them. But in most cases, they just get a no, just a rejection. The student who asks someone, “Hey, could I have a drive to this other part of town?” And the person kind of thinks about it, and they go, No, I don’t think so.
And that’s it. That’s the end of the interaction right there. It’s not painful. It’s not nearly as painful as we set our rejection out to be in our head when it happens. And as change makers, if you’re going to lead any type of meaningful change, you are going to fail so many times along the way, doing anything meaningful, whether that’s starting a new organization, leading a change initiative at work on digital transformation, or doing something like you and I both have writing a book, it’s filled with rejection. And so the mark of a change maker isn’t whether or not you get rejected, because to be sure, if you are going to do something that’s pushing the status quo, you will get rejected.
So Samuelson and Zeckhauser have done great work on the status quo bias. So we know that people tend to overvalue the things they already have. They don’t like to shake up the status quo, but the more comfortable you can get with it becomes like a muscle. Once you’ve gotten your first, second, third rejection, then you go on a path where the 78th and 79th rejection feel a lot less painful. And we know this in service of a greater purpose on the other end.
Yes, I think this ability to get comfortable with making asymmetric bets, that is, bets that have low downside but potentially really high upside. So by definition, they’re very low-risk experiments and bets to play. This ability to get comfortable with that to reduce the cost of getting a rejection. The major cost of rejection is the emotional cost. It’s the embarrassment you feel or the fear that you think you would feel terrible and ashamed if this thing didn’t happen. But then, if you actually experiment with it, you find yourself, Well, I didn’t die. None of these executives that you had go out and get rejected actually died. In fact, what they experienced was the opposite sensation that they feel excited, exuberant. There’s an energy flow that comes into them. And it reminds me of a video series, a YouTube series that my son has been watching and has been really inspired by.
In a sense, it’s a strange undertaking. It doesn’t sound like some great academic insight or something like that, but Mr. Beast has challenged this individual. I think his name is Ryan Trahan, and his whole thing is, Can I get across America within 30 days, starting with no money? Well, starting, I think, with literally one penny. I think that’s the situation. And so he has this huge journey, and he can be reset so he can start earning money, and then for various ways, by people simply making a donation to Feeding America, he will suddenly go back to zero. He has to give away his money. And again, back to zero has to raise the money. And, of course, you’re seeing this in a single day, so that he has to raise enough money to be able to stay at a hotel that night or whatever he has to do.
And so what you get to see, and you wouldn’t normally get to see something like this, is somebody who is starting from zero to a hundred dollars again and again and again. It’s a brilliant insight into these asymmetric bets. And all he really does is a few simple things to get this going. He’ll ask somebody to give him a bottle of water. Okay, now he has a bottle of water, then he’ll try to sell that for $1. Now he’s got a dollar if he can go and buy two bottles of water for that dollar, now he has $2, and he just repeats, repeats, repeats until eventually, he has $30 or $50, and then he can buy something else with that money, and he can buy a bike and then he can start delivering with that bike. And so he can earn money from that process. But underneath all of it, what I think you’re seeing, although it’s very entertaining, is someone who is comfortable with change, who is bringing about change, who has a very high sense of their agency as it relates to going from $0 to a hundred or 200, a thousand dollars. And to be able to watch that experiment is really quite a scientific type process that we are seeing.
I don’t know if you’re familiar with it, but what the effect of it has been for my son is his sense of agency has increased. He actually, at first, he’s like, I’m doing this. I want to actually go and try this experiment. And he did. He spent a couple of days doing this, actually getting water and buying it and selling it and learning how would I earn money.
And beyond that, of course, it increases your sense of initiative, the power that’s in. You don’t just have to wait for somebody to offer you something. You don’t have to wait to get some, amazingly, a job is going to land in your lap. No, you are going to go and do it. You go have the awkward conversation because what is the worst that can happen is that you can be rejected. And once you’ve experienced that enough times, you go, That is nothing. That is something that, in fact, is even neutral or can even be inspiring. What’s your reaction to all of that?
Oh, I love it. What you talk about reminds me of the story of Demi Skipper, who’s a TikToker who traded her way from a single bobby pin into a house.
And so, again, there’s magic. What you’re talking about magic at the margins with each individual trade, you just get a little more margin all because of that sense of agency. And then that margin pays off time over time, over time.
And as I think about taking those risks, you know, always think about what’s the downside, right? So if someone says, No, someone rejects the water bottle sale, whatever, but we often forget about is the power of agency in the margins. So something I experienced myself, as a first-time author, I had the experience to reach out to a couple of authors whom I deeply admire, authors whose work has shaped my own, asking them if they might be kind enough to write an endorsement for the book.
And as I did, that’s a risk putting yourself out there. But the way I sort of calculated it was, at the very worst, if all they do is read my email and ignore me, they will know that I was deeply touched by their work and that they inspired me to become an author. And if that’s the worst that happens, well, how could I not take that chance? How could I not write that email?
It connects you back to the idea that Brene Brown talks about. She says that we often see vulnerability as courage in someone else but weakness in ourselves. And so sometimes, when we think about agency, we think it has to be courage all the time, that we are just super courageous. But in the example of Mr. Beast and Demi Skipper, we can think about it on that micro level that’s just little moments of courage, little moments of vulnerability where the potential upside is there, and we take that risk, we take that chance, and then we parlay at time after time, after time after time. And we look back, some pretty amazing things have happened.
Beyond what we’ve already talked about. Help me to turn this into an actionable practice that people listening to this can incorporate on a regular basis so that this isn’t just the concept of agency and the practice of going out and failing in small ways. How can this be implemented into a team? If there’s a CEO listening to this he wants to apply in his team, there’s a CEO, and she wants to be able to implement it in an organization that somebody wants to do it in their family, how would you suggest they do it?
What’s the one best practice for how to begin?
So, Greg, you and I connect around our shared love of ritual. So let me suggest a ritual for your community to try out. It’s two questions you ask each week in a weekly team meeting.
The first question is, what was your win of the week? What’s something you did which brought us collectively closer to our shared goals?
When we lead change, it can feel so overwhelming to think about the big scale we want to get to, but let’s make sure that we know how all of our collective little victories add up to something really substantive.
The second question to ask is, How did you fail this week? Asking people how they failed as part of the regular routine normalizes the fact that we want people to question the status quo and to have a sense of agency to try things out. And it creates psychological safety because people know that not only is it okay to fail, it’s expected to fail as long as it’s in service of trying something bigger, of trying to lead and shape change. So my suggestion is each week, ask these two essential questions to your team. What was your win of the week, and how did you feel forward this week?
I love that idea of not just normalizing failure but celebrating it, expecting it, getting to the point, I suppose, where one could be disappointed if there hasn’t been a fail of some kind.
Exactly. Right? It becomes clear that if someone, week after week, either doesn’t have a failure or the failures are very safe and very marginal, then you can actually have a talk with them and say, “Hey, I want you to think bigger. I want you to fail bigger. Cause that’s what our team needs right now.”
There’s some evidence to support the idea that the only time learning takes place is when we experience expectation failure. That is the portion of life’s experience that we are learning. The rest of the time, you’re just repeating. And so there’s no need to update one’s mindset, update a world view or the complexity about how the world actually works. It’s in failure that we have to do the updates. And so, pushing and challenging our experience in life deliberately to experience failures seems to be absolutely necessary if we want to learn.
And surely that is deeply entrenched in what it means to have a meaningful life or, indeed, to become a change maker. Alex, thank you for being on the podcast,
Greg, thank you for having me.
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