Greg McKeown, Simon Sinek
Come with me on an exploration of self-discovery. On this podcast, we decipher what really matters.
As we unravel the chaos of day-to-day work to learn how to build an essential life,
I’ve been thinking about your life.
And thinking about how easy it is to feel lost in the midst of all the busyness, how easy it is to feel like we’re languishing after a year and a half of all that has been required of us of all of the uncertainty and adaptation. And I can think of nothing more important in such moments than coming back to not just what’s essential but why it matters.
To renew our clarity in why we think what matters matters so much. So I reached out to my friend, Simon Sinek, and asked him to be on the What’s Essential podcast today. So that we can reflect on not just what matters. But why? Let’s get to it.
I am here today with Simon Sinek. He sort of needs no introduction, really. I sort of imagine that anybody listening to the What’s Essential podcast is at least familiar with Simon’s work. You know, I hate to even say it this way. But number two, TED Talk. It’s got to be number one soon, Simon. We’ve got to be close now. He’s blown up the internet on multiple occasions. But there’s a Millennials speech that’s just gone bonkers and hundreds of millions of people. And, really, I feel a sort of kinship between essentialism and the Start With Why movement. So I’m so looking forward to this conversation. Simon, welcome to the What’s Essential podcast.
What’s something essential to you right now that you’re under-investing in?
Oh, that’s a good question. For me, it’s about the essential for me that I’m under investing is, is the pursuit of art. And I don’t mean the buying of it. I mean, the seeing of it.
COVID clearly put a big damper on that. But there are other ways to pursue it, I can see it and make it. And I like making art. And I like the process, even sometimes more than the result.
And I miss it if I’m honest. And so I think I think that’s something that I could put more time and energy into.
There were a few elements of your answer. One was seeing it one was making it, what do you wish you were seeing?
Well, I think they’re inextricably linked, right? I need inspiration, which comes from seeing how other people interpret the world. And, and then I make things, and that inspires me to go see things, which then inspires me to make things and so I think I think I think it’s a virtuous circle. So, which one is more important? I think if I start with either one, the other one will follow.
I’ve been thinking a lot about this recently about how it’s difficult to even get clear about what you want, what you want, without interaction with the people that matter to you. That there’s that, that it’s hard, even, in my estimation, to find a thing that is truly independent. You know, the things that seem independent, once you get into them, are really interdependent.
Have you found that by helping people find their why? That it’s an inherently interdependent process? Or is it something you think people can find, you know, really on their own?
You know, I’m not going to be pigheaded about it and say you absolutely cannot do it alone. But I think it is very, very, very, very difficult to do alone. And it’s because none of us are objective about ourselves. And when you’re asking someone for help, I tend to recommend to people not to ask a sibling or a parent or a spouse, because those relationships are so close that sometimes they think they know better than you do and also like objectivity.
And so sometimes working with a stranger is wonderful because they bring nothing to the table except you, except the data you give them. But a friend works just fine. Someone who wants to help you or a colleague who wants to help you find your why, but in my experience, asking for help to find your why is much easier and much more rewarding, and probably much more accurate. You know? Yeah, I think that it’d be an extreme kind of personality or maybe a near-death experience that would help somebody have that kind of objectivity. But otherwise, I think asking for help is the way to do it. And again, learning one’s own why requires help, you know, finding out who you are, requires support from others, and then what you discover about your why’s that’s you actually live in service, all-wise, are selfless, you know, all wiser about contribution, every single one of them. And, and I like that, it’s, it’s the value we provide to the world, it’s the value we provide to, to the people in our lives. And the rub is that the thing we give to the world is also the thing we need the most. And that’s the difficulty of living. Starting with why,
Greg McKeown :
Can you unpack that a little bit?
Sure. So my why is to inspire people to do the things that inspire them. So together, each of us can change our world for the better, right? That’s what I give to the world. When I asked me when I talk to my friends, like the greatest compliment someone can give me that gives me goosebumps is you inspired me, you know. The word inspire like lights me up, I want to have I would have that tattooed on my body, you know, I have it permanently connected to me, that would make me feel fine. But at the same time, I need inspiration, I need to be inspired. So the thing that I give to the world that the thing that I need the most. So you know, depending whatever your why is to support others so that dot dot dot, you know, those people more than must be supported, you know, and that’s the hard thing about the wide is that it is a contribution, but it’s also a deep-seated need. So you have to be able to be the one who helps but ask for help as well on for the same thing.
Yeah, I mean, in a sense, you’re saying that the clearer you are about your why, you know, getting clear about your why is one decision that makes 1000 decisions because it all coalesces together in your own life. It does because you can keep making decisions that are consistent, but it’s this interdependent experience that you’re adding to that which is the people will be attracted the right people will be attracted to you. The wrong people, so to speak, will not be; they’ll say, Well, that’s not for me. You know, and they’ll go their own way.
I remember when I was at business school, we went I was in a class with called the strategic management of nonprofits. And everyone was asked to identify name there, were there we’ve, our task was to go away and find a couple of vision and mission statements from various nonprofits to come back, and we’re going to share that with the class. So you’ve got maybe 70 people in the class of this, you know, there’s like, 140 of these, we start reading them. And it basically makes people laugh because they’re either so general, you don’t know what they mean, you know, they’re just sort of corporate speak. Or sometimes they would be clear, but so unachievable, you’d have like a seven-person organization that would say, well, we’re going to, you know, solve world hunger. And everyone’s just like, “No, that isn’t what you’re going to do. So that’s not real.”
Then somebody said, “Well, you know, I’ve got Brad Pitt’s here.” And because of the sensation in the classroom, everyone was sort of laughing by this point. And they read it out, they said, you know, the, the intent of our organization is to build 250 Storm resistant homes in the Eighth District of New Orleans by this date. And it just took the oxygen out of the room because everybody knew at that moment that that was real, that that was clear, you would know, and this is what made me think of it from what you were saying. You would know, sitting there, whether that was an organization you wanted to work with. You’d know if you were the most junior person hired there how to help. You’d know whether what you were doing was supporting or taking away from the mission, even if you were trying to do something good. But that type of clarity. My goodness, I think it’s the rarest thing in the world. Your thoughts?
Yeah, that’s finite, though, right? It’s eminently achievable. And then what happens after they achieve that goal, do they shut the doors, and they may say that that may be the case, which is they may say we have a finite goal, which is once we achieve this, our mission is over, and we’ll shut the doors. However, if they have a more infinite vision, you know, they may say we believe everyone on the planet should have a place, a safe place to live. I don’t know. Right. And the way we’re going to do it is first by building 250 homes in the Eighth District of New Orleans, right? And so you can see there’s a driving belief, and that they’ve picked a very realistic goal is to goal to advance that belief. And upon achieving that milestone, we expect them to choose another milestone and another milestone and another milestone, and maybe those milestones will get bigger and bigger as they become more recognized and better funded. But all the way, all the time being driven by an infinite pursuit that is, for all intents and purposes, unachievable.
And so, you know, it’s good to have finite goals, it’s important, and they have to, they have to be grounded in some sort of reality, even if they push us and stretch us, but the context within which those visions exist, you know, again, unless the organization is a finite organization, which is upon achievement, we will shut the doors, which is totally fine as well, I have to believe that those who are driven by cause that those were there are attracted to a higher, and maybe, and maybe the people who joined, you know, somebody was working in homelessness. But so, in other words, that underlying belief that everyone deserves a safe home to live attracted them. But then the thing that they’re actually working on is building houses in the Eighth Ward and in New Orleans. The eighth parish in New Orleans, that they’re like, “Oh, I that definitely events is my cause, even though I’m not doing the thing that I used to be doing.”
So I think I think yes, it’s both.
Because you’re saying you need an infinite vision, plus a metric that so the infinite…
Infinite vision is not; we’re trying to build a home for everyone in the world because that’s stating it as a goal, right? To your point, a completely ridiculous amount is achievable. Right, but to say we believe everyone deserves a safe home to live in means we are doing a part of that work, and we expect others to do a part of that work.
I spoke at a conference of all of the heads of development for, I don’t know, 1000, 1200 charities, who knows what, right? And I remember, I came out on the stage and I said, part of my opening remarks were at least 50% of the people in this room, your organization’s deserve to go out of business. Because you’ve completely forgotten the plot, you’ve become obsessed with money. And worse, you refuse to work with each other. Like, explain to me why two organizations that believe in stamping out cancer don’t cooperate. Explain that to me. You claim to be in the do good business, and that you literally see the other the other group as your competition. And we accept that there’s a finite amount of money we accept there’s a finite amount of, and so you literally are trying to steal people away from your fundraising event away from their fundraising event. Why not work together? Doesn’t that make more sense to help stamp out cancer, but it goes back to the conversation we had before about those personalities where they forgot the plot. They made it about themselves. So to do so, many not-for-profit organizations forget the plot and make it about themselves.
You know, there’s that Charity Navigator website that I love that grades charities. And it’s it’s astonishing how many charities that are pretty well. And again, we shall they shall remain nameless, but I know some of them are they’re very well-known and well-recognized charities that such a small percentage of the money raised actually goes to the cause they’re trying to advance, and they get poor grades. deservedly, you know, the question is, they become self-licking ice creams. They become more interested in their own survival rather than advancing their causes.
Self-licking ice creams. I haven’t heard that before. But it’s an interesting idea. What else are you doing to make this vision real for you?
I think that anybody who’s trying to advance anything has to be willing to take a deep breath and blow it up every now and then. And to some, COVID was that mechanism that blew up for them if they didn’t have the courage to do it themselves, which allowed for reinvention.
Was that true for you?
Well, yes, that was true for our business.
Yeah. I mean, it must have been.
Yeah, I mean, most of our money came from live events, workshops, and things. COVID blew that up, of course. It was an amazing opportunity to say, great, well, let’s take advantage of everything that’s available now that we weren’t taking advantage of before. And let’s make it even more scalable. Let’s get the message out even more, you know, and that was a great, great opportunity.
But for me personally, it’s different. Right? So I look back at my own career. And there’s a funny pattern that, like, I started in advertising, and I did really well and got promoted. And then once I reached a level where it was like, boring, I quit. And I’d go work some shitty account at some lesser agency, and I it either work or it won’t, and I built it up, or it would fail. And I’d be like, All right, and I’d leave. And I remember I left Ogilvy and Mather, you know, which was at the time one of the most respected agencies in the world. Yeah, And when I decided to leave, they offered me all these illustrious accounts, you know, IBM, American Express, Kodak. They said, “Simon, you can work on any one of these you want.”
And I went and worked on for a lesser agency on a wasn’t a glamorous account, Upper and Heimer funds, I mean, mutual funds, really, you know, and nobody can understand why I wouldn’t take the offer to go work on these glamorous accounts to go work on this sort of less glamorous account. That was and I explained to them, because all the good, all the heavy lifting has already been done. Like, you’re going to give me a job where I get to do maintenance. And I don’t want to do maintenance. And, so I took risks with my career. And it didn’t always work out, by the way. But I took risks with my career, when things were going really well, I’d leave and start over again. And I’m in that process right now.
The way I was doing things and the way I think I want to do things, and I don’t have perfect clarity as to what will come next. So I’m in a position of discovery and reinvention, which is exciting and nerve-wracking. But when you ask specifically about the sacrifice, the sacrifice is pace, right, I necessarily have to slow down and pull back before I can speed up again. I got to find my footing, and I got to find the vehicle. You know, in other words, if I’m trading from this car to that car, I have to stop the car, get out of this car, get into that car, and I’m losing, like I could be racing down the highway. And I’m stopped, right? It’s like when people you know are on long car journeys. And I like to keep track of how long it takes, you know, stopping for gas, you want to do it as quickly as possible, because you destroy the time, you know, 20 minutes of standing here could have been how many miles could have driven in 20 minutes, you know, and that’s an I do that knowingly.
So, I’m in a position right now of trying to figure out which car to get into. And I’m fully aware that I’m not racing down the highway. So people ask me, you know, “What are you writing?” and I’m not writing anything, you know, and they’re like, you’re not writing anything, like, I’m thinking, you know, I’m thinking, and I’m putting together patterns, and I’m trying to find, and so the sacrifice, you know, there’s an expectation that when you have a certain when you’re under a certain level in your career that you have to maintain that pace all the time. And I think that’s where I think people get into trouble where either the work gets stale, or they get tired. And then, either way, it’s going to collapse.
And so I think the challenge of reinvention, and this goes for individuals as well as organizations, is such a good one. And so necessary because the world changes. And we have to change with it, we have to adapt with find new ways, better ways, you know, more fun ways, more efficient ways, whatever it is to spread our message to advance our cause. That keeps us interested and keeps those around us interested. I think people are afraid when you’re running on a hamster wheel, you think it’s you who’s setting the pace, and sometimes you don’t realize that you’re just trying to keep up. And the fear of getting off the hamster wheel is horrible. So yeah, so my sacrifice right now is is, is pace.
I relate to everything you’re describing here. First of all, the necessity to blow up success at a certain point in the cycle. I’m thinking of all sorts of examples of that. I’m thinking Steve Jobs when, when it comes back to Apple, and there’s like a veritable Museum at Apple with all of their greatest hits, you know, the original Mac and, and the mouse, and all of these things that that are really genuinely impressive. And he takes them all, and he donates them, I think to the Silicon Valley Museum, but he just literally gets rid of them all. So that is a signal to everybody. It doesn’t matter what we did before. It really could hold us back enormously if we keep thinking about that. And we keep trying to replay that. Or if we use that to make ourselves feel good that we’ve done good things. And so the innovation, you know, now is less important, and all of that. So I think that that’s sort of one level of alignment.
I mean, that’s what, that’s what you’re trying to do. It sounds like it’s somewhat of necessity, but it’s other. It’s not like a necessity. You don’t necessarily think that somehow the customers or the people around you are saying, “Hey, listen, it’s time for something new.”
It’s your own internal sense of this feels. You used the word stale, so I don’t want to now double down on that that’s not the right word. But, it’s a sense within you, within you, that you say, this isn’t this, I’m living on a momentum from somewhere before. And I need to make decisions. Now to create a new wave of momentous a new phase of what I’m trying to do.
It’s a choice. And it’s done without judgment. And what I mean is other people make a different choice, I think that’s fine. They both have value, right? This is a choice I’ve made for my life or my career. But I don’t judge the choices that other people make for their lives or their careers. Like I said, they both have value, they’re different kinds of value. And so after I wrote, Start With Why I could have serialized it, I could have done Start With Why for various environments, start with families and Start With Why for families, and I could have kept writing Start With Why books and sold a lot of books and you know, built an enterprise that start with why and, and, you know, even when Start With Why came out, people call me the why guy, you know.
And you didn’t want that because it would have fixated you. It would have kept you there.
Again, for those who have made that decision and serialized their own work. Very often, the reason it got serialized is because it’s good work. And then there was demand for all the verticals and variations. And I know there’s demand for verticals and variations for my work. I mean, on our website, we offer, Find Your WHY courses, and we have done them in verticals because we we have practitioners from those verticals. So we have Start With Why for Healthcare and Start With Why for Teachers and Start With Why for Artists because that way the room is filled with people like you as you’re looking for your cause, like we’ve done that, you know, so because there’s…but I never serialized the work because that was a decision I made. I wanted to learn new things.
And I remember, you know when I wrote Leaders Eat Last, my publisher showed me the designs for the cover, and it looks exactly like Start With Why it’s like Leaders Eat Last, you know? And I was like, “Wait, why is this? It’s a completely different book with completely different ideas. Why are you making it look the same?”
Like, “Well, Simon, you know, this is how we keep we build a brand.”
I’m like, “Nah, man, that’s not how you build a brand.” You know, making my cover look the same. But even the publishers are tempted to serialize it, you know, and so I, you know, one of the nice things about having success from one book is I get to say, No, I had very little say on the cover design of the first book, but the second book…So yeah, I wanted to be entirely different. And, like, there’s a couple of funny little things that only I know. But they they’re they make me smile, which is why every book I’ve published is a different size. So none of them stack up next to each other neatly.
You did that deliberately?
Yeah. Every book is a different size for a different reason. Because different sizes have different feel. Right? So Find Your WHY is big because I want it to feel like a workbook because that’s what it is. Right? And The Infinite Game is long. It’s a longer book because I want it to feel more like a manifesto.
I’ve noticed what you’re describing. I didn’t know it was deliberate.
Leaders Eat Last is like a fat book because it’s a dense sort of pursuit. You know, Start With Why is a relatively small size because I wanted it to fit under your arm and throw it in your briefcase, it’s not to be put on a shelf and kept behind glass. It’s supposed to be used and abused and dog-eared.
You know, Together is Better is horizontal because it’s a sweet little book inspired by a children’s book. I mean, they’re, they’re all different for different reasons. And, like, I was thinking about something new, a new project, and I was like, “Okay, what is what?” It’s not gratuitous? Like if I, if I realized it needs to be the same size I want to go there I’ll do it. Yeah, always based on whatever the books trying to communicate that I try and match the feel the size of the book to the feeling of the book.
But yeah, I can’t but I but you know, it’s only I knew that I guess more people know now. But because for me, it’s it goes back to intention, which is I want, like I said before, I want the book to feel like what it is, you know, and these are subtle little things that most people won’t recognize. But they would know if it wasn’t there. Like if I made, if I made Start With Why a fat book, it wouldn’t feel right because it’s it’s not that kind of book. You know, or if I made Infinite Game more squared. It’s not, it’s not how it is, you know? So yeah, it’s the same with color and touch all of them have. What’s it called? I forgot what it’s called, but it feels more like skin than paper because I wanted all my books to have humanity to them. You know, and so the new books Leaders Eat Last and again, they both they both have this they’re called soft touch on the cover. Because I wanted to feel have a humanity to it. I mean, it’s silly little things like this.
Yeah, but you say silly, but it’s being deliberate and thoughtful about the choices that you’re making and the trade-offs that you’re making so that you don’t just get stale so that you don’t just live in momentum. I mean, I remember Bill Gates saying that success is a very poor teacher. And I think that, at least to me, feels aligned with what you’re saying because instead of just doing what success tells you to do, okay, more of what I’ve been doing, more of the same things, you have to go back to clarity, you have to go back and say, “What is this really about? What am I really supposed to do next? What is the right thing to do?”
And you’re guided not by it, not even by the momentum, which is very easy to be guided by momentum. And instead, you’re saying, “Okay, let’s go back. What do I feel is the right thing to do? What does my conscience counsel me to do? What is the right next thing for me to do?”
I think there’s some elements of truth that I don’t know what to do, but I do know what not to do. Yeah. And, what not to do is what I was what I’ve been doing, right. And, you know, and this is where the danger of defining yourself by your work, in which so many people do, which is our identities, become tied to the job we do? So I am a public speaker. So what happens if I stopped speaking publicly? What does that do to my identity?
Well, I, again, I’ve been aware of that for a while. And so if you notice it, whenever I blurb a book, every time it says Simon Sinek optimist, and author of because I never want to be defined by what I’ve done, I want to be defined by who I am. And regardless of if I stopped speaking, stop writing, stop doing anything that, you know, people might know, might know me for. I’m always an optimist till the day I die. And so I am because I made decisions a long time ago to define myself by who I am not what I do. And it allows me to, it allows me the freedom to stop doing anything I’ve done. So I’m, you know, I could stop public speaking, I could stop writing books. And that doesn’t mean I won’t spread my message, it means I’ll find new ways to spread it.
But that’s a scary thought for some people, for a lot of people, because accidentally, they’ve commingled their identities with their with their work. I am a lawyer, I’m a doctor. So if you retire from being a doctor, who are you? You know, and you see this a lot. You see this a lot with very successful people, wishes, they’re so intertwined with their work that when they retire or they have an identity crisis, and they try and live in the past. Remember, when I did that I was the first person to do this. I was the first one to do that. Well, that was 30 years ago.
Well, and just connecting all the dots here. You said a moment ago that this could be scary for people, you know, someone might find this a terrifying proposition to blow things up before they have to and so on as if it isn’t for you. And I just want to challenge that a little bit because what I sense in you is one that it does make you feel quite comfortable. There is a part of you that goes, “Yes, this is the way I do it. This is what feels right to me. This is what the daemon says not to do. And I’m following, so I have that.”
So there is something that feels quite a piece as I’m listening to. But the second side of it is, that doesn’t mean that it doesn’t require courage. You know, it does require courage, it is requiring courage. And I can sense that in you, as you say, I don’t have the answers. I just know I’m not going to just carry on doing what I’ve been doing. So I’m making that choice. It does require courage. Innovation requires courage. And, and I personally relate to it. I say that I’m sort of going through a renaissance in my life right now, and my teenage children are like, “I think you might mean midlife crisis.”
And I don’t know exactly who’s right or who’s wrong with it. But I know that sensation Many times over in my life of blowing something up. That’s too negative of a connotation. But definitely saying, I’m not going to continue doing this, even though it’s successful.
We can be more romantic about it than blowing it up. It’s changing routes. You know, but, you know, don’t give me too much credit. You know, courage is not the absence of fear, courage is being afraid and acting anyway. And then, it raises the very interesting question: Where does courage come from? And I do not for one minute believe that courage is a deep internal fortitude, dig down deep and find the courage. You know, I don’t think that’s the case. You know, I think courage is external, where you have the courage to jump out of a plane because there’s a parachute on your back. Like, it’s the external thing that gave you the courage to jump out of the plane, you know.
So there’s not a foolishness to reinvention. It’s not gratuitous. You know, a world-famous trapeze artists would never try a brand new death-defying act for the first time without a net, no matter how skilled they are. It’s the net that gave them the courage. Because when you push boundaries, necessarily, you’re going to fall. And so the courage to reinvent requires really good relationships. And I would not be able to do or have done any of the reinventions or challenges that I put to myself without a group of people around me who say, “We believe in you.” who says, “If everything goes south, we’re still we’ll still be there with you. We got your back, you got to do this.” Because the days I hesitate, they go, “You have to do this.” You know, and it’s the quality of the friendships and the quality of my business partners. And my team, that gives me the courage to change routes, blow it up, find a new direction, stop the car, or whatever analogy we want to use. And if I didn’t have them, I wouldn’t do it. Because it would be just too overwhelmingly scary. And I do not think, I think, the number of people who have the courage to act without the love and compassion of those around them, the safety of those around them. It’s probably more foolish than courageous.
Yeah, I really concur. And I love that. And it makes me think about the times that I have blown up the path of success deliberately. And as soon as you say that, I think about the people that were there, even if I didn’t really think about it at the time, the support system, the support group, and how vital it is to create that kind of community and network if you possibly can.
Simon, it’s really been fun to talk today. And I have valued your openness. And I am so genuinely curious and interested to see what will come next. And what the invention will be,
Oh, that makes two of us.
Simon Sinek, thanks so much for being on the What’s Essential Podcast.
Simon Sinek :
Thanks for having me. Take care of yourself, take care of each other.
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