Simon Sinek: The Advice Young People NEED To Hear
Guests: Simon
Full transcript · Read the full conversation in order, with its original context.
§01Transcript — part 1
The thing I think about most, especially when I'm on the go but also when I'm sat here in The Diary of a CEO studio, is the Wi-Fi and internet that we have to work with. In fact, anytime I'm filming away from the studio, one of the first things I do when I arrive is open up an app and do a speed test to see how strong the signal is.
The number of screenshots I've sent to my team about Wi-Fi signals at different locations is actually pretty crazy. It matters that much to me because it's such a competitive advantage to have fast Wi-Fi. On any given day, if I'm recording hours and hours of footage with a podcast guest, I then often have to have my team send that across to our London team who then do the edit.
So fast Wi-Fi and internet is not a "nice to have," it is absolutely business mission-critical. So when it came to finding the best provider who could supply internet and Wi-Fi to our new LA studio, which I'm sat in right now, we looked at every single option.
Of all the providers, the one that came back with the steadiest connection as well as being the cheapest was today's sponsor, Spectrum Business. Spectrum Business keeps businesses of all sizes connected with fast, reliable internet, advanced Wi-Fi, phone, TV, and mobile services. Millions of business owners already rely on Spectrum to keep their operations connected. So if you want to join them, head to spectrum.com/business to learn more. That’s spectrum.com/business. Restrictions apply; service not available in all areas.
The single greatest lesson I ever learned in my career, that profoundly changed the course of my life...
Multiple-time bestselling author, third most-watched TED Talk of all time, the return of Simon Sinek.
Thank you very much. For the last 30 or 40 years, we've doubled down on "how do I find love," "how do I find happiness." We've doubled down on selfishness. But now in a complicated, messy world, we haven't been practicing and developing the skills of taking care of each other. And that's what we need now more than ever.
Do you ever give up on someone?
I have a fear, and I've never expressed this openly. Gen Z are the least resilient generation. They're really good at presenting a confidence that they don't have. This young generation seems less capable of dealing with stress than previous generations. That is true.
Going from relationship to relationship, from job to job. There's no stigma to quitting. Flash forward five years, and what's going to happen is an employer is going to look at them and be like, "I can't take the risk." Everything we're talking about today comes right back to those human skills that we are lacking: how to listen, how to give and receive feedback, how to have a difficult conversation. And the thing we have to deal with more than anything is fear. Fear is the underlying thing why we don't have honest conversations.
Let me give you some honesty then. What is the greatest fear you have about how you're currently living your life?
I was very insecure about admitting that... I was crying as we were talking about it. That was hard.
Without further ado, I'm Stephen Bartlett, and this is The Diary of a CEO. I hope nobody's listening, but if you are, then please keep this to yourself.
Simon, good to see you again.
Good to be here.
I have to thank you first and foremost for many reasons. I'm a huge fan of all your work, but the conversation we had when we were over in LA was received so unbelievably well by the listeners on this podcast. It did millions and millions of downloads in such a short space of time that I had to nag you to get you to come back again when you were here in the UK.
Well, it's nice to be back and it's nice to do it on your home turf.
Literally in my home. There are so many things I want to talk to you about, but one of the things that I was curious about, because I've been thinking a lot about this in my life, is this idea of our "Why" evolving. What is your "Why," and has it evolved over the last decade at all?
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. It's why I wake up every morning, every day. It is the greatest compliment someone can pay me when they say to me, "That was inspiring" or "You were inspiring." That feeds me.
The interesting thing about a "Why" is because it is objective. A "Why" is the sum total of how we were raised. It's born out of the patterns and the lessons we learned from our parents and our teachers when we were young. Our "Why" is fully formed by the time we're in our mid-to-late teens, and you only have one "Why" for the rest of your life. It doesn't change.
You are who you are based on how you were raised. Now, you may not be acting as your true self—people say that to us all the time, "It's like I don't know who you are anymore." But when you are at your natural best, your "Why" is front and center. But we're not always acting at our natural best. Sometimes we make decisions out of selfishness. We take the job that pays us the most money and turn down the one to work for somebody who would probably be a better mentor.
Can you tweak the words of your "Why"? Of course, but that's semantics. Can we find better ways to bring a "Why" to life? Yes, that's the evolution. But the "Why" itself is fixed.
When you talk about the "Why" being influenced by the things that happened in our life, our experiences, our upbringing—does that mean that our trauma can influence our "Why" for better or for worse?
Always for better. A "Why" is always positive. I'll give you a real-life example of somebody's "Why" discovery that I did. One of the things I do when I do somebody's "Why" discovery is I ask them about happy experiences when they were kids. This person said, "I didn't have a very happy childhood. I had a really bad childhood." And I said, "Okay, so tell me a bad memory then."
She talked about a lot of abuse in the household and a very abusive, alcoholic father who would beat her mother and the kids. She told a story of a repeated pattern: when the father would be drunk and come looking for the kids, she would be hiding in the cupboard, protecting her brother with her arms wrapped around him to shield her brother.
At the end of that whole story, I pointed out to her that she's a protector. In these traumatic experiences, it was her instinct to protect her baby brother. And she's lived her life—if you look at all of the times that she's really thrived and where she's her best self—she's usually in a position of protection of other people. That's where she finds joy, in taking care of other people. So the experiences mold us into who we are, and the impact will be positive regardless of where it comes from. A horrible childhood made her a wonderful human being.
I was going to use myself as an example there to try and rebut that somewhat, but I remember having a very similar conversation with a very good friend of mine a week ago upstairs who talked to me about their childhood. Their father used to beat their mother up really severely. She was telling me her memories of trying to hold on to her dad's arm as it swung for her mother when she was five years old.
When you look at the pattern of what those early experiences have caused, she's obsessed with helping others. She's building these amazing businesses and is unbelievably successful at a very young age. However, that force in her to help others has meant that she's compromised sometimes helping herself. Of everyone I know in my life, she is the most successful woman I know, but she's also the woman that is most unsuccessful in all of the personal aspects: relationships, boyfriend, mental health.
So when we say, I understand the positive side of it, but the negative side of it seems to be that this unbelievable "Why" she's got seems to just honestly not be worth it. This is not someone that would say they are happy. This is someone that is in therapy and is every day in tears and upset while serving the world in an unbelievable way. So is that a positive "Why"?
So the "rub" about the "Why" is that a "Why" is basically the thing we give to the world; it's the value we have in other people's lives. Her friends would say of her that she is our protector. That is the role we fill in their lives, which is why they love us—because we're giving them our "Why" as our value.
The rub, the most difficult thing about the "Why" to understand, is the thing that we give to the world is also the thing that we need the most. It's always balanced. I would argue that it's not that she's unable to take care of herself; it's that she needs to find friends or colleagues who are committed to taking care of her.
That's where the change happens. We were talking about this before the show started: there's an entire section in the bookshop called "Self-Help" and there's no section in the bookshop called "Help Others." I believe what we need is the help-others industry.
I'll tell you something that happened to me. A friend of mine was going through a really rough patch in her life. Her marriage was struggling, her career was struggling, she was unhappy—none of the boxes were getting checked. She asked a favor: "Can you help me?" Of course, I said.
Every week we had a standing 90-minute meeting where she'd come over and tell me what's going on. I would give her some advice and point out some patterns. She'd feel fantastic; she'd leave on a high for like two days, and then it would go right back again. She'd come back the following week, and this went on for months.
Then it occurred to me—I remembered my own work. In *Leaders Eat Last*, I talk about Alcoholics Anonymous, where they have 12 steps to help an alcoholic beat this disease. AA knows that if you master 11 of the 12 steps, you're going to probably slide back and succumb to the disease. But if you can master the 12th step as well, you're more likely to beat the disease.
The 12th step is to help another alcoholic. It's service. So I decided to change things up. I said to her, "Look, I love that you come and see me every week and I love helping you. But I struggle with things too, and I don't have anybody to talk to. Would you be willing to help me? Maybe we can split the time."
She said, "Of course, yes." What started to happen is every week we got together and I would genuinely unload and tell her what I was going through and what I was struggling with. It ended up that we wouldn't split the time; she would spend 90 minutes talking about *my* stuff. She was the advice-giver. She was the one looking for the patterns. She would leave on a high, and that high would stay until the following week. It was only when we reversed the scenario where she had the opportunity to take care of someone she loved that she was able to find the solutions to her own challenges.
I'm a great believer that we have to remember we're social animals. We need each other. This is the great paradox of being human: at every moment of every day, we are both individuals and members of groups. There's a debate: do you take care of yourself first or do you take care of others first? There's a school of thought that says you have to take care of yourself first because if you're not healthy, you can't take care of others. And there's a school of thought that says no, you have to take care of others first so that when you're in need, they'll be there for you.
The answer is you're both right and you're both wrong. It's a paradox. It's a struggle. In every day, we're faced with sometimes big but often small choices: do I prioritize myself at the sacrifice of the group, or do I prioritize the group at the sacrifice of myself?
Folks like Maslow, with Maslow's hierarchy of needs, made a huge mistake in that hierarchy. His baseline—our basic need—is food and shelter. I've never heard of anyone dying by suicide because they were hungry. I've heard of people dying by suicide because they were lonely. And yet social relationships in Maslow's hierarchy is number three. That can't be right. It seems like there's something more important to human beings than just food and shelter.
Then the top of the peak is self-actualization, which sounds like the most selfish thing in the world: "I am so self-actualized that I will literally sit on top of a pyramid and look down at all of you un-actualized people because that's my goal, to be self-actualized." He's half right. The mistake he made is he only thought of us as individuals. As individuals, yes, I need food and shelter first. But as a member of a group, I need friends and I need love. Self-actualization is not the thing I'm actually in pursuit of as a member of a group; it's *shared* actualization that I'm looking for.
Unfortunately, for various reasons, the past 30 or 40 years, especially in the West, we have doubled down on individualism. We have doubled down on my own career. We've doubled down on "how do I find love," "how do I find happiness." We've doubled down on selfishness. And it worked for a while; it worked when the economy was really good. In the '80s, '90s, and 2000s, it was awesome. Selfishness was great because it worked.
But now in a complicated, messy world where the economy isn't great and everything isn't roses, all that self-interest is now not working, except we haven't been practicing and developing the skills of taking care of each other. And that's what we need now more than ever.
We are animals in balance, and nature abhors a vacuum. Whenever I hear about these things, my question is always about the balance. Every single good thing that happens in our lives—everything—comes at a cost. There is nothing for free. Somebody with an incredible career has no relationship with their kids. Everything comes at a cost, but at the same time, everything we struggle with has opportunity and lessons that go with it. It's always balanced.
So whenever anybody tells me this great thing, I'm always like, "Yeah, but at what cost? And was the cost worth it?" Sometimes the answer is yes and sometimes the answer is no. When something horrible happens in someone's life, I always ask, "But what did you learn?"
My career—the whole Golden Circle and the concept of "Why"—came out of me losing my passion and hating work. I went through depression. I never want to go through that again, but I'm really glad it happened because look at what it's given me—an entirely new life view. I think of strengths and weaknesses the same way. It depends; life is balanced, and it's always contextual. Everything that we have that's a strength has liability attached, and every weakness we have has strength that's attached.
I could imagine that because of the books you've written and the channels you have, a lot of people come to you on a personal level—friends, family—to help solve some of the problems that they're having in their lives. Do you ever give up on someone?
I'm reflecting on my friend a little bit here and friends I've had from my childhood. I remember offering a guy, I was like, "If you can just do one month working in Subway where he was working, I'll pay for your rent so you can move out of that city and go and get a job." He didn't do the one month in Subway. And at one point I think there's part of me that's like, you know, everyone's solvable—the optimist in me. And the other part of me goes, at some point you have to give up on people.
The single greatest lesson I ever learned in my career, that profoundly changed the course of my life, was learning how to ask for help and learning how to accept it when it was offered. I think that it's not about giving up on someone; it's that helping someone is a team sport. Success is a team sport.
If you find that you're the only player in their life when they should be the primary player, you can only be the support. You can only do the assists. You'll never be the one making the baskets. That's their job. But if they won't take the pass, then at some point you stop throwing the ball.
It's not about giving up on people; it's about accountability to take responsibility for oneself. Giving up on somebody is "Don't ever call me again, you don't take my advice, this is over." That's giving up on someone. I think the other way to do it is like, "Listen, I cannot help you if you cannot be involved to help yourself."
I'll want to sit down with them and I won't criticize and be like, "You're not doing this, you have to follow my advice, you've got to go work at Subway for the week." That's not what I'd do. I'd want to sit down and understand what the blockage is. There's something else that's the blockage that I can get to, hopefully. But at the end of the day, I will say to them point-blank, "Listen, if you're not going to be involved in this, then there's no point to me being involved. This is a team, and I'm the only player here. So I will always be here, and when you are ready—maybe it's just bad timing, maybe I'm a bad fit—but when you are ready, I will still be here no matter what. But you have to call me. There's no more me throwing you the ball. You're going to have to call me."
And then they call you.
Sometimes they do, sometimes they don't.
In my case, they call me and then they say it's time, "I'm willing to accept the help," and then the same cycle happens over and over again. You go five years of them calling you...
Then they're lying. But they don't think they're lying; they always think this time's going to be different. Like I said, I want to know what else is the blockage. When there's that kind of repeated pattern, then there's something else. I think our mistake in those situations is repeating our pattern, which is, "Okay, I'm going to give you the same advice, I'm going to give you the same thing, you're going to do the same thing, I'm going to tell you the same thing, I'm going to give up on you." We're actually repeating a pattern as well.
We know this as entrepreneurs, which is you've got to try something completely, completely different. This goes back to what we were saying a moment ago, which is we are not teaching the skills of how to help others. One of the biggest skills of learning to help others is learning how to listen. Most of us are really crap at listening. We confuse listening with hearing the words that were spoken.
You're sitting watching TV and someone you love is trying to tell you something and you're like, "Uh-huh, uh-huh," and you're still watching TV. "You're not even listening to me!" and we turn around and repeat all the words back to them. That's not listening. That's hearing the words that were spoken to you. Listening is when the other person feels heard, and where you are in pursuit of meaning, not the words spoken. You're not so literal.
In the case of your friend, it's to go from an advice-giving mode—and men suffer from this more than women, our intention is to fix everything. All we want to do is fix, fix, fix. We see the problem: "Here's the solution." But sometimes that's not what people need. People need to feel seen and heard and understood. Maybe, just maybe, you're going too quickly to "fix" and he doesn't feel seen or heard or understood yet.
In this particular situation, I would go to an extreme listening: give the kid the opportunity to empty his bucket. There's only three terms you're going to use in the conversation: "Go on," "Tell me more," "What else?" Because it sounds like whatever you think the thing is you're fixing, it's probably something entirely different. And until you can get to that, you're going to give up on somebody who maybe it's just that we had the wrong strategy.
It wasn't until these examples surfaced in my life where I had friends asking me for this kind of help that I started to consider that maybe mindset itself is a privilege. One that if you don't acknowledge and understand, you'll end up giving advice from a very privileged place. You know, I might say, "Well, just work harder," or "Just cheer up." These kinds of things come from a misunderstanding that my brain is fortunate enough to think and be a certain way. I've never heard people talk enough about this idea that our mindset in and of itself is a privilege.
That's interesting. That mindset is a privilege. Is that true? If we think about early upbringing in childhood, some people have monetary privilege. One thing that your parents or your experiences might have given you is a real psychological privilege.
There are many stories of people who, when the odds were against them, whether they came from extreme poverty or abuse, rose up to have successful and happy lives. When we read about them or meet them, they talk about mindset. They talk about "My mother taught me to never be a victim. My mother taught me that I was capable of anything." And so they had a mindset where some people have a victim mindset and then that's the life they continue to live. Some people have a different mindset and it can lift them out of what we would consider unprivileged circumstances.
It makes me question then, is mindset a privilege? We both know people that have every privilege afforded to them, every one of them, and yet for whatever reason their mindset is the wrong one and they can squander all of that opportunity, all of those advantages that they've been afforded, and make a mess. So I question whether mindset is a privilege. There are a lot of privileges in life; mindset, I think, is one of the ones that is there for the taking.
I think about—so I was 18 years old, dropped out of university, shoplifting food to feed myself—and in that moment, I was entirely convinced that I was going to be a millionaire. What did I actively do?
You're just countering your own point, that mindset is not a privilege.
No, I'm saying because I think that I have the privilege that that mindset was given to me by my experiences and maybe by my biology. I'm wondering why, in that situation, if you'd put me and my best friend that I talked about with the Subway example in the same situation, one of us would have catastrophized. Me, I just saw it as this wonderful stepping stone to the point that I went around my house videoing my despair, videoing my dire situation, opening the fridge: "There's nothing in it." My first page of my diary on Facebook Notes, which I kept, says, "I'm keeping this diary because a TV production company have asked me to..." Bullshit! I lied to my own diary! Because I look back and go, this kid was sure that he was getting out of here.
I played tricks and games with myself as well. I did the same thing. I go back to the concept of "Why," which is it's the experiences we had when we were young that formed us into who we are. It wasn't the shoplifting alone; it was your parents, it was your friends, it was your teachers. Is that a privilege?
Everybody has a "Why," and everybody's "Why" is affirmative. Like I told you about the abuse story, something really positive and someone really positive came out of that trauma. So I'm struggling to use the word "privilege" to mindset. Because what you're saying is anyone who's had any kind of luck or turnaround has privilege, where anyone who hasn't and has failed, it's because of their lack of privilege. There's too many other factors involved in those comparisons to oversimplify it and call it privilege. I'm sure there are privilege components sometimes involved in that for sure, but when we're strictly talking about mindset, I don't think so. Because the control of our minds is the one thing that we own. It's the one thing that is not—we can change the way we view ourselves and how we treat others.
What's important is I think we have to have love in our lives, from someone. Even people who—like I have a friend who came from a very abusive household, he found his grandmother stabbed to death and the knife was so deep that she was attached to the bed. That's how bad it was. And yet he had a coach who believed in him. And so I think to have someone believe in us—to have one person see a spark in us—helps us recognize the spark in ourselves. It just takes one person, whether it's a friend or a coach or a parent, a boss sometimes, who takes a liking to us. Almost all of us can remember one person in our lives, whether it's a coach or a teacher, who took us under their wing and saw something that we didn't see. Every single successful person on the planet has that person. But I think most of us do. Most of us have somebody who saw something in us, and we are in part because of that person.
Having someone in our life... kind of links back to something you were talking about earlier about trying to be less individualistic in our approach to our lives and our careers. Lots of your work—I was on your video subscription library—has that as a through-line about connection and people and teams. In the backdrop of the remote working world we're living in, how do you think that this post-COVID world has been impacted in terms of connection, community, teams, and that unity that should be on the bottom level of our Maslovian hierarchy of needs?
Well, obviously it took a step back. Though there are, again, I always think of things in terms of balance and cost, so it's not good or bad, it's both. Of course, we have freedom of schedule now that we didn't have. We have freedom to live wherever we want which we didn't have. We have freedom to pick up our kids from school or go to the dentist where we used to have to ask permission or take time off. We have that freedom now that we didn't have.
For people who are introverted, they like that they can get their work done in the privacy of their own home. There are many advantages to remote working. The sharing of ideas is much more difficult. A brainstorming—really, really hard to do in a virtual scenario because it's hyper-polite. You can't interrupt somebody as easily. When you have a real brainstorming, it's messy, it's loud, you step on each other's words, you interrupt each other, you have an idea—like "No, no, no!"—and nobody cares. It's the mess, it's the joy of it. In an online scenario, it gets—you literally can't hear people if everybody's talking at once. And you're constantly apologizing: "No, your turn." You don't have that wonderful energy. So I think brainstorming's suffered.
And then the obvious one, which is for a lot of people—and I think it dramatically affected younger people more, but for all of us—when you're done with work, you go out with your friends for a bite to eat or the pub and you bitch about work and you bitch about your boss. Totally healthy. And you do it with the friends—whether it's a good job or a bad job, it doesn't matter—you have a place separated from work, that's your friends that you go and get it all out, and you feel supported and loved and heard and all that good stuff. That went away completely.
So what ended up happening—again, if you didn't have a family, if you were living alone, all these things just get more and more exaggerated—what ended up happening was, especially young people but for a lot of other people too, we spent more time with people now at work on Zoom with them all day and sometimes into the evening. We now started looking to work to be that therapeutic outlet.
So what so many people did is, first of all, gossip starts to swirl a lot more because we're now venting and bitching to each other as opposed to our friends. So, especially if somebody's young or susceptible, gossip can take off much quicker, which is very dangerous to a culture. But what I've seen is that we find one empathetic person, a good listener on the team, and we call them up and we bitch about our job and we bitch about our boss. But then it keeps going: "I don't know what I want to do with my life," "I hate my boyfriend," "I hate my girlfriend," and all of a sudden you're dumping all of your life's problems on somebody from work who just happens to be a good listener.
What we're doing is we're increasing the stress on that person. We suffered it in our company and I've heard it from many other companies, which is those people, those empaths, they're quitting. If you ask them, "Why are you quitting?" they go, "Because I'm burnt out." And you're looking at their workload and being like, "I don't understand how you're burnt out." They're burnt out from taking on all of everyone else's stress because they're empathetic; everybody else's stress becomes their stress. That's the problem with this.
It's good that as COVID eases up, going out with our friends and having that safe space to vent away from work is really important. So from a cultural standpoint, it's very hard to control for that. I can't interrupt it, I can't tell them they can't. They don't want to go to their boss to talk about these things. But what—especially young people—they're recognizing that there are boundaries at work. By dumping on one person that they should take on all your problems and they listen and they listen and they listen, and sometimes they give bad advice but they listen and they listen—we're doing a great disservice to that other person to make ourselves feel better for a few minutes.
It's one of the first times in my life that I've started to think again about culture design. It's funny because I ran a business post-COVID for seven years; we had almost a thousand people. I then left in the middle of COVID and now I'm launching businesses after COVID. It seems that not all of the rules apply, and a lot of that's because of comparison now.
A modern employee is comparing the working culture that they're seeing on TikTok and LinkedIn to their own. It's almost as an employer we're competing with a false TikTok social media narrative that is—and people never really know what they actually want, I think, as it relates to culture, even me. So if you ask someone what they want from their working culture, would it meet their fundamental needs? Probably not. So my question to you is, how are you on a practical level—what changes have you practically made or believe are necessary in a post-COVID world that you wouldn't have maybe stated in a pre-COVID world, if any?
Let me come at it from a slightly—so if you go back a bunch of years, our lives looked very different than they do now, obviously. We got our sense of purpose from church, we got our sense of community from, you know, whatever, bowling league, we hung out with our neighbors—they came over on the weekends and had barbecues with us—and work was a place that we went to make money to pay for our lives, to pay our bills. It was also a different time where we were super loyal to the company and the company was super loyal to us. And that was life.
Then church attendance started to decline, bowling leagues basically are gone, they've disappeared. We don't go to community centers anymore. We don't have our neighbors over on a weekly basis. And so all of those things we started to look to work to replace. So now we say to work, "You have to give me a sense of purpose, you have to give me my social life, you have to give me a sense of community and belonging."
And now it's—we've added things to that list now since COVID—it's like, "And you have to agree with all of my politics, and by the way, you also have to be my therapy now. You have to be my place for therapy," which is what we were just talking about. And it is an impossible standard to put on any culture that they can do all those things for you, just like we've put impossible standards on romantic partners: that they have to be my intellectual equal, they have to be sexually compatible with me, they have to be emotionally compatible with me, they have to share all of my interests, all of my politics, we have to vote for all the same—these are impossible standards to put on another human being. We're literally setting people up to fail. We're setting up business cultures to fail as well; literally no culture can live up to that standard.
In pursuit of that, the grass is always greener. You have people who are going from relationship to relationship to relationship. Worse, from job to job to job to job. When I was younger, if you didn't like your job or if you didn't like your boss, the bad news was you had to stay there for a year because if you left in anything less than a year, you would hurt your CV. They would be like, "Why did you leave in under a year?"
Now, again, particularly young people, there's no stigma to quitting. And it happens sometimes too quickly. If you're confrontation-avoidant—and I've seen it happen—confrontation-avoidant: "I'm too afraid to ask my boss for a raise, so I just quit." I've seen it happen. Or, "I've been here for four months, I don't like the culture, I quit." Or, "I got in trouble at work, I hate my boss, I quit."
People are quitting so much. My fear—I don't mind if something's super toxic, get the heck out of there. Most places are not super toxic. Imperfect, yes. But toxicity is like—there's a standard and it's a high bar. "Or this doesn't fit my values," or "This disagrees with my politics, I quit." My fear is that if we flash forward five years, there's going to be a disproportionately high number of people who have eight jobs in five years. What's going to happen is an employer's going to look at them and be like, "I can't take the risk that you're going to stick around. I'm not hiring you. You sound like an amazing candidate, but you're too high-risk for me."
And because you've had so many jobs over such a short period of time, you actually haven't stuck around long enough to build up a skill set or know what it's like to manage a storm, because you've stuck around in the good times and bailed in the bad times. So you have now been in the workforce for five years, but you don't have five years of work experience; you have four months of work experience. So I don't want you either because you've never been through a battle.
I see it happening. A young person who's been at a company for eight months goes to their boss and says, "I want a raise, a significant raise, because I'm doing the same job as those people. Those people have been in the workforce for 10 years. I know, but I'm doing the same work as them and I'm doing good work." That's true. You are doing the same work as them and you are doing good work. The difference is I'm not paying them just because they've been in the workforce for 10 years. I'm paying them because you know how to hoist a mainsail in calm waters and you can hoist a mainsail in calm waters as well as they can hoist a mainsail in calm waters. The difference is they also know how to hoist a mainsail in a storm. I don't know if you can hoist a mainsail in a storm. I pay them more because I know that if we run into hard times, I know that they know what to do and I can trust that we can navigate. I also know that they will teach you how to hoist a mainsail in a storm. It's like the same reason I buy insurance: I don't expect my house to burn down, but I pay just in case. I'm paying them more for a skill set that I hope they never have to use. That's why they get more.
You know one of my fears at the moment, which is perfectly linked to what you're saying—I have a fear, and I've never expressed this openly, so this is the first time. I have a fear that Gen Z are the least resilient generation that I've ever seen. A lot of it—and this sounds so stupid and not evidence-based—but if you look at what TikTok is telling this generation work is... There was a video that went viral on Twitter the other day out in Silicon Valley where it shows like a Facebook employee, one of the big tech companies: she arrives at work in the morning, she takes a photo of her latte, "Oh, all these free muffins!" She goes and has the free muffin. It shows her in her TikTok literally doing like 30 seconds of work, then she's out doing some like pottery-making class that work have put on, she comes back to the desk, does another 30 seconds of work, then she's off to her work social.
I reflect on the storms that my father went through at work, and I just know so deep inside of me that there's no way some of these younger Gen Z people could weather such a storm without quitting, doing a long LinkedIn post to criticize their employer, then quitting. I just fear that Gen Z—when I'm hiring people that are in that generation, I almost need to go to an extra length just to check that they can cope with a high-intensity culture where demands might come on a Saturday, because the world doesn't stop on Saturdays and Sundays. I wanted to get your take on that.
So let's examine both sides. Again, let's think of what's the balance and what are the costs. It is a generation that already was starting to ask these questions, but COVID forced the rest of us to ask these questions too, which is what is the definition of work? What does a full-time job mean? These are unanswered questions. Right now everything is in flux and things have not landed yet. What is the definition of a full-time job? The definition used to be I come in at 8:00 or 9:00 and I leave at 5:00 or 6:00. That was a full-time job.
How much work I did between those hours was "face time." We know that because we've all had jobs where we stuck around until 7:00 so we got face time so our boss liked us. We've all done it. But face time is not a thing anymore. And so I have a full-time job and I'm offered another full-time job and I took it. We see this: employers who have productivity issues and then they say they're burnt out, and "I know how much work you have, you shouldn't be burnt out." Do they have a second job? And why shouldn't they have a second job? Well, we pay them benefits. So what? As long as they're getting their work done, do we care when? People all have side hustles. Even people who've got full-time, come to work—everybody's got some sort of little side hustle.
So the definition of what full-time employment is, is up for debate. I think young people feel in particular that "Why shouldn't I? It's my time, I can do what I want with it." Or, "I only work 40 hours because those are my limits, respect my boundaries." The problem is I think all of it is so literal. Yes, boundaries are important, but the edges of the boundaries are fuzzy. It's not like, "I don't work on Saturdays." Well, I agree with you, I don't want you working on weekends. This one weekend I really need your help to finish this project so we can get it out the door. Or, "I don't take meetings after 5:00." I agree with you, I think we should have that life balance, but today I just need you to work till 6:00 to get this one project done.
To recognize that—one of the things they're getting right is that we're married to work and we take our phones on holiday, we take our computers on holiday with us, and that work has ultimate say on our time. I agree, that should go the way of the dodo. But the extreme is not to put these hard lines everywhere and say, "I don't do this." As an aside, the irony is they demand that we respect their boundaries and yet they seem to step on every other boundary about bringing emotional professionalism at work and dumping all of my problems onto my colleagues, which is emotionally unprofessional and that's a boundary you can't cross.
But there is good evidence to your assertion that this young generation seems less capable of dealing with stress than previous generations. That is true. They are good at curating—they've grown up in an Instagram, Facebook, TikTok world where "I'm really good at showing you the life I want you to think that I lead." And so they're really good at presenting a confidence that they don't have. They sound like they have all the answers when they don't.
But then I see you presenting that life to me if you're a fellow Gen Z and I go, "What? My life's stressful and difficult and I had to work really late, and you're having a frappachaka-latte-latte whatever at 3:00 AM doing pottery lessons. I need to quit."
It raises the question: what do you want from your life and what do you want from your work? Why do you have this job? If it's just to pay the bills, I mean, I hope we've moved—I know that is the case for a lot of people, that I have to have a job to pay the bills. And I hope that employers are good enough that even survival jobs are a nice place to work. Trader Joe's: great company where people who have survival jobs still have a nice place to work.
But I think the question is, what is the life that you're trying to build? If you want a job simply to pay your bills and—there's this concept of "quiet quitting." Have you heard this one? Quiet quitting?
I've heard this term, but I've maybe heard you talk about it.
It's been written about. It's not my concept. Quiet quitting is this thing where I don't quit the job, but I basically will dial back my effort and give you the minimum. So you pay me to do this job and I will do the basic minimum amount to do the job where you can't really fire me because I'm not really doing anything badly or wrong, but I'm also not going above and beyond at all. So there's this concept of quiet quitting where people are coming to work and they're just doing the minimum, doing their hours, doing their job, not volunteering or raising their hands or going above and beyond. That's it.
It raises the question: is that bad? I'm a great believer that it's all about expectation management. Like I get asked about Amazon a lot: do I disagree with how Amazon is run? And my answer is always the same, which is they never lied. They didn't tell you it's a magical place to work or it's all kumbaya and we all hang out with unicorns every day. It's really amazing. They are very open about it: that it's very, very aggressive and very rough and very competitive. And even the people who love it only last two years because they burn out. Because they don't lie, you know what you're going to get if you go work there. And if you like that kind of culture, then go work there. If you don't like that kind of culture, then don't work there. But don't take the job and then say "I didn't know," because you did.
Like Apple: people say Steve Jobs used to drive his people really hard. But you ask the people who loved working there, they will tell you, "Yes, it was hard and there was a lot of pressure, but I did the best work of my life and I'm glad I worked there because I never would have been able to work to that standard if I didn't work at Apple back in the day."
The important thing is that companies are honest about the kinds of cultures that they have. It's the lying. It's the "Look how everything is kumbaya." No culture's perfect. Even good ones have problems and even bad ones have advantages. But I think it's about managing expectations. And I think it's okay for somebody to say of themselves, "Look, I'm not a careerist. I am okay with the fact that I will never be an owner or a senior manager. I want to be paid fairly, I want to do decent work, but I want work to fit neatly in my life and not overwhelm it. And I'm going to look for a job where that is possible."
I don't think we're at the point where we have total honesty on both sides yet. I hope we can get to that point because there's still stigma. Because the older generations like you and me are looking at—if somebody were to say to us, "I only want to work 40 hours. I'm willing to push my boundaries occasionally, but really this is just to..." we would be like, "Well, you're not working here." So it hasn't normalized yet. But I think it's just a question of being honest with oneself. And you're allowed to change your mind as well. Like, "I've decided I *do* want to be a little harder-driving and I do have more ambition than I thought," or less.
I think it's just about honesty. This point of view is as true in personal relationships as it is in our professional relationships. I had a conversation with somebody recently that I found absolutely fascinating. She is polyamorous. She has four boyfriends. And she is very open about it. One of the things that she explained is you have to be very honest with everybody so that everybody knows what the deal is. I think what a lot of people do is they're dating somebody, it's new, it's casual, and they're dating somebody else that's new and casual, but they don't tell them about each other. So they both think that they're more special than they are, or they both are driving towards something that may or may not be true because you're dating two or three people and you're going to wait and see which one works out.
In the poly world, what I'm learning is you tell everybody everything so everybody knows. And it's very open and honest, and everybody knows where they stand. You can say, "I'm not into this, I want to be the sole," or "I'm okay with this, and maybe something will develop, maybe it won't." But the point is it's on the table. And I admire the level of communication. What I'm hoping is that we do the same thing in our professional lives, so you sort of have "poly work" if you will. I have two full-time jobs, or I have three things going, or I only want this kind of relationship. And it works if both parties are really open and honest. Because it's all about managing expectations. "Hold on, I thought that you were going to give me all of your attention and all of your effort and all of your ambition, and you're telling me you only want to work—you want to treat my job as a casual job?" Just replace "relationship" with "job." All the same rules seem to apply. But if I knew that, I would have been fine with that. I would have given you a different job and had different expectations and wouldn't have pushed you really hard. I would have given that work to someone else because I'm assuming you want to live your career like I live my career. Like I assume that you're getting into this relationship and you're getting into it for the same reasons as me, because we never had a conversation.
We are nowhere near that in terms of social acceptance for that kind of conversation, but I aspire for that. That somebody sits down and says part of your CV and part of your interview says, you know, "What kind of work-life balance do you aspire for and how do you view work?" Even if you change your mind. And then as long as expectations are managed, then what's the problem?
You've answered one of the actual number one questions I wanted to ask you about today. Because when I read your book, *The Infinite Game*, one of the big things it changed in my life was—I remember I was on a plane, I read the book, started writing some stuff, came back to our office in the UK, and I did a big presentation to all my teams about how we create a sustainable company. Because if what you're talking about in the book is true, then we're not playing a finite game here. How do we redesign the business from the ground up so that it is fundamentally sustainable?
I came up with this thing called W.W.W.: Work, Welfare, and World, which is the three reasons why we exist. We made 2020 goals for each of these areas. I'm thinking about it again a lot now, which is like: if I was to design my business in a way where my team members would stay working here forever, how would I go about that? You've just answered it by saying the point about honesty, expectations, sitting them down and saying, "What do you want from your life?" because I've never asked that. I'm assuming they want what I want.
Exactly. A, you want to create a place in which if people want to stay, it'll be an enjoyable place that they can make a career and grow within the organization. For some people who don't have aspirations for leadership, that they can come and do good work every day and get fair raises on a regular basis with cost-of-living adjustments, etc., that they would want to stay there even if it's a middle level. Not everybody aspires to be a hard-driving owner.
I think it's about making it a conversation. We never treated work like a conversation. We treated it like a speech: "This is how it's going to be." One of the good things that's coming out of COVID and young people is they're asking questions about "Why does work have to be that way?" and employers are rebelling against it because it doesn't fit the way *we* grew up and doesn't fit our understanding of relationships. It's just a conversation, that's all it is.
By being honest up front, then you can say, "I don't think this is going to be a good fit for us. I don't think you'll enjoy working here, and so if I employ you knowing what I know now, we will both get frustrated and I will either ask you to leave or you will tell me you're going to leave. That's how this will end because of misaligned expectations." So I think being honest about what you want and who you are and what your ambitions are, even if they change in the middle—you can knock on the door and say, "I've changed my mind. I think I want to stay here forever. I told you I didn't, but I really love it here."
I know this from the military: some people join the military because it's a steady job in a bad economy, or because the military will pay for you to get a college education and they didn't have the money to get it without it. So they join the military. And then when they're there, they fall in love with it. They never came in for service. They discovered the service and the brotherhood and the sisterhood and decided to stay. Work should be the same.
I think there needs to be honest conversation about—and like I said, I've had debates even with my work partners. When they say, "Well, if we're paying them a full salary and giving them benefits, they shouldn't have another job," my question was, "Why not?" As long as our work product doesn't suffer as a result. Like, if they're phoning it in, missing all the meetings, then yes, absolutely. We're paying for a certain expectation of performance but not necessarily of when they get it done. And so why shouldn't they have two jobs?
But I think, again, there has to be honesty, which is, "We have an expectation of X, and if somebody says I don't want to meet that expectation because I want to have two jobs," then you can adjust for salary that way. You can be like, "All right, then how about we pay you less and you can have all the freedom you want?" And again, it's a conversation. We don't make these things conversations; we make them one-way communications.
That's from the employee to the employer too: "I demand X." Somebody asked me recently, "I want to ask my boss for a raise, how do I do it?" I said the problem the way most people ask for a raise is like, "I want a 20% raise. I did my research and my job, the average salary on my job is X. My friend gets paid X, I know somebody who I work with, I'm doing the same work as them, so I want to be compensated equally and I want a 20% raise." They're positioning the question that leaves the employer no choice but to say yes or no. Even if it's, "I can help you get that, but this is how it's going to be," like you're going to have to reach certain targets, it still comes across as a "no" because the request was binary.
So the advice that I gave to this person was: stop thinking of your job as an event and think of your job as a career, think of your job as a continuum. Go to your boss in the middle of this continuum: "I've worked here for two and a half years. I've been here through high times and low times. You know I'm loyal. And my aspiration is to stay here and grow with the organization. Can you help me figure out a path that gets me to this salary?"
It's not a "yes" or "no" now. Now it's like, "Absolutely I can. I can give it to you today. No path necessary." Or, "Absolutely I can. We're going to set some target goals that I want you to hit, and if you can hit them, then you'll absolutely work to that salary." But again, it's allowing for conversation and it's allowing somebody to recognize that you view your own career with the organization as a continuum—that I've been here and I want to continue to be here, so can you invest in me, can you take a bet on me rather than meet my demands?
I think a lot of these things fail because they're poorly presented. And this goes once again to this younger generation, who seem to lack the skills for coping with stress, not very good at asking for help, very confrontation-avoidant—so afraid sometimes to ask the boss "Can I have a raise?" that they would rather just quit. And it's often with an email that says, "You don't appreciate me, you don't pay me enough." Like, what? You just had to ask me and I would have given you a raise!
I think part of it is also that when somebody is anxious about something, they *do* poorly present. They *do* make things binary because there's fear, or anxiety, or stress, or fear of rejection: "What if my boss says no? Can I handle it?" All of these things that come into these very binary aggressive things. I always equate all of these challenges at work to personal relationships. Like, you can't go to the person you love in your relationship and say, "I demand this." It's just not going to go well. But you present a situation and you say, "I want us to move through this and how do we work through this together?" I think that's how these difficult work conversations need to happen. A work relationship is a relationship like any other relationship. There's trust, there's anger, there's care, there's good days and bad days—all of the same nonsense and messiness in our personal relationships is at work as well. There's slightly different standards of professionalism and emotional professionalism and things like that, but in terms of it's a relationship like any other relationship, you have to treat it like a relationship. In fact, go read relationship books if you want to fix things at work.
When I read about our history as sapiens, it appears that we weren't with one partner. We were with multiple partners. We now live in this society where we're told to be with one partner. Is that natural? Is it human? Does it work? The stats seem to suggest it's not really working so well. If I bought a TV and they said "Oh, by the way, there's a 50% chance these are going to break," I wouldn't buy the TV. I'd maybe rent one.
Esther Perel, who's wonderful if you don't know her work, she talks about the changing definition of monogamy. Monogamous used to mean "I'm in one relationship for my whole life." Now monogamy means "I'm in one relationship at a time." So even that definition has changed where monogamy—and people who consider themselves strictly monogamous—have 15 monogamous relationships over the course of their lives! "How many close..." "I've had six close relationships." "They were all monogamous." So these definitions are evolving anyway.
I like that we are having conversations about the health of relationships like we're having conversations about the health of work. These things have always existed; the difference is now the stigma of talking about them seems to have dissipated. At least in the United States where I live, it's amazing how many people are talking about open marriages, open relationships, polyamorous relationships, consensual non-monogamy. I don't even know what all the differences of all these words are, if I'm honest; there's so many words that seem to mean similar things. But the point is it's amazing to me how many people are raising the question of what is a healthy relationship.
I think one of the things that boils down for me is it goes right back to what we were talking about, which is it's based on both parties and they both get a say. If you say, "I want to live this kind of lifestyle," and you're upfront about it, and somebody says, "I'm cool with that," then great. But if you lie and say, "I want to have this kind of—I want to be strictly monogamous," but you don't really, because you like the person a lot and you think that if you tell them that you want a different kind of relationship you're going to lose them, the conversations we have are largely born out of fear. "If I tell her what I really want, she won't like me and then I won't get another date." That is a possibility, but if I tell her exactly who I am and what I want and she likes me for who I am, then isn't that better?
I think it's the same thing that we're talking about with work. I don't think it's right for us to say we should be strictly anything because some people want one kind of relationship—let me rephrase that—both people in that relationship want that kind of relationship, and both people in the other kind of relationship both want that kind of relationship, then we just have to respect that we have different points of view about what brings happiness. As long as you're happy and it's consensual, I think we're done.
Usually the problems arise when somebody has—most of these problems are born out of fear, fear of loss. Insecurity in a relationship. Jealousy, for example—this is the other thing: that friend I was telling you about who's super open and honest about her life, I was talking to her the other day and she says, "I'm jealous. I'm having jealousy, and I'm trying to figure out where it's coming from." And what I found so fascinating about it is she treated jealousy as a *feeling*, like happy, sad, angry, where in most monogamous traditional relationships, jealousy is usually an *accusation*. "I saw you look at the barista that way!" Jealousy is born usually out of fear and hyper-protective possessiveness. It's born out of fear, fear of loss.
What I found so fascinating was she didn't blame her partner for her feeling of jealousy; she wanted to understand where her feeling of jealousy was coming from. It was a feeling and not an accusation. I think the same is true: all of this, whether we're talking about work or personal relationships, everything we're talking about today comes right back to those human skills that we are lacking.
I hate the term "soft skills." "Hard skills" and "soft skills" we talk about. "Hard" and "soft" are opposites. I think they're "hard skills" and "human skills." These are the hard skills you need to learn to do your job and these are the human skills you need to learn to be a better human being. We're really good at teaching hard skills; we're junk at teaching human skills. Human skills include things like how to listen, how to have a difficult conversation, how to give and receive feedback, how to have an effective confrontation.
These are skills that most people lack. We saw it after the murder of George Floyd: the number of leaders who, after George Floyd was killed, did nothing. They said nothing to their teams. Not because they're bad people; it's because they weren't taught how to have a difficult conversation, and so they were so afraid—there's that fear again—of saying something wrong that they would accidentally offend someone or inflame the situation that they chose nothing.
I think the same goes in our relationships. We make too many decisions out of fear. As entrepreneurs, we understand risk. We understand risk and that big reward comes with big risk, small reward comes with small risk, no risk you're leaving it up to somebody else. To get over the fact that if I tell somebody who I really am, that they may not like me—well, don't you want to find that out sooner rather than later? Because they're going to find out. The truth is always revealed. Sometimes quickly, sometimes slowly, the truth is always revealed eventually. But think about the magic of being able to say the kind of job you want to have and the kind of life you want to lead and the kind of relationship you want to have, at the risk that they may not hire you or they may not go on a second or third date with you. But think about the opportunity if you do take that risk.
I'm thinking about all the people listening to this right now who are in a relationship, they've been there for 15 years, it's become loveless, maybe they're not having sex anymore, and they're driving on the motorway now listening to us speak and they're thinking, "I really want to have sex with someone else, and if I go home and tell Jane or John or whoever it is that I just want to have sex with someone else and I also want to keep them around, they're going to leave." So I can't be honest, Simon.
Right. So once again, it goes like asking for a raise. If you make it binary, you're giving somebody—you're backing someone into a corner. "I realized our marriage is loveless, so I want to start seeing other people, and you can too." What you're doing is you're making a binary—you're forcing somebody into a binary "yes" or "no," which is unfair to somebody and you're setting yourself up for probably failure.
As opposed to saying, "I love you, you're my life partner, you're my best friend, I never, ever want to lose you. At the same time, our relationship is loveless and I'm struggling because I crave love and I crave that kind of affection and we don't have it. And so I'm struggling and don't know what to do, and I want to know how you feel and I want to know if we can work on this together."
So you're making it—just like the raise: "Let's make this..." Now, if you hate the marriage, then get out of the marriage. If you've tried the counseling and it's broken, then that's a different conversation. But if there is the desire to stay in the loving relationship in some way, shape, or form, but you're looking for to fill a place that's missing, then that's a conversation. But it is not a demand or a request. It's a "Honey, I need to have an uncomfortable difficult conversation and we may not get it resolved today, but I want us to promise to stick through this together so we can figure it out together. It might take us a day, it might take us a week, it might take us six months, but I'm going to be here throughout and want to go through this with you because I am struggling in this relationship." Somebody else has the right to know that their partner's struggling in the relationship. And odds are if only one person is struggling—there is no scenario where only one person's struggling. It's like when we have a problem with an employee: they hate their job too. It's not a shock.
To start the conversation like, "Listen, I'm struggling with you, I know you hate it here," it can't be one way. That doesn't exist.
I'm pretty sure most of the issues I've had in my life stem from the fact that I didn't have an honest conversation sooner.
Me too! Of course, me too! I made the mistake in my life that I didn't—and it was well-intentioned—I didn't want to hurt their feelings, I didn't want to offend them or upset them, and so I dealt with the difficult thing in my head and tried to come up with the solution that I thought best looked after my needs and your needs. But if I told you this, I would burden you with the stress of having to figure this out, so I'll figure it out and then I'll make the decision that I think is best for... Failed every time. Because the mistake that I made is I treated the relationship as an individual when it's not; it's two people. The problem with a relationship with two people is I'm not in total control of the relationship. I'm a member of a team. I'm not in total control of everything and I have to relinquish some control.
The thing we have to deal with more than anything is fear. It's fear that is the underlying thing why we don't have honest conversations. It's why we are hyper-aggressive or make things binary. It's because we fear rejection, we fear loss, we fear whatever it is. And we can ask for somebody to reassure us. And we can deal with the fear first. By saying, "I'm going to stay here," and an employer or a lover can say, "I promise you I will stick through this with you as well, I will not abandon you, we'll get through this together"—that takes the fear down a notch, that we *will* do this together.
In my own relationships, COVID—all the bad that came with COVID, again, you know how I see the world, I see the world as balanced, there's good and bad in everything—all the struggle and bad that happened in COVID, there was tremendous good also. And in my own life, I had the opportunity to stop, get off the hamster wheel, and then look backwards and say, "Do I want to get back on the hamster wheel?" or look at all my relationships: "Why weren't they working? Where's my accountability in this? What was I doing wrong?"
I realized that one of the things I had to do was I had to be a better listener. My girlfriend, when we first started dating, she's a terrible listener. Terrible! We joke about it. I would say, "Babe, I need to have an uncomfortable conversation with you, there's something I'm struggling with, something you said or did that is making me uncomfortable and I need to work it through with you," and she would start telling me a problem she had with *me*.
So what I would do is just hold space for that and the conversation would just change entirely. But what I learned about listening is that it's "holding space." To learn to hold space for someone, as if holding a baby. To let someone feel safe telling you what they need to say without you trying to fix something or disagree with something or correct something. "Go on," "Tell me more," "What else?" was the most valuable thing I learned in COVID.
The nice thing is when you give that to someone, they by some weird osmosis, they gain the capability to give it back to you. Because you've done it, if you do it enough times, you can say, "I hear what you're saying and I want to talk about that, but for now I want to finish the thing that I started talking about. Can we just start with that?" And you can say it politely, and they recognize that you've held space for them so many times that they'll offer you that service and they know how to do it because they've seen it modeled.
The really interesting thing about that, I was thinking about my own relationship with my partner, is the reason why that's so true for me is because most of the time when someone is talking and talking and repeating themselves, it's because they don't feel like they've been heard. So in my relationship with my partner, the fact that we do exactly what you've described where we literally go "Give me a safe space" and then I talk, means she only feels like she has to say it once because she feels like it was heard the first time.
In my previous relationship, I remember being—I'm going to be honest—I was in the wardrobe one day and I've locked myself in there. My girlfriend is banging on the door repeating herself. Context: I said I'm going for New Year's Eve, me and a client are going out to Singapore, it's their birthday, it's the biggest client in the world, they've asked me to come, it's their birthday. She goes, "I want to spend New Year's Eve with you." And I go, "Yeah, but I've told them that I'm going to Singapore." She goes, "I want to spend New Year's Eve with you!" and that just went on and on. And at one point she starts screaming at me, so I just go and hide in the wardrobe. She spent all night banging on the bloody door repeating the same thing over and over.
In my new relationship, we communicate with more context and we actually listen when the other person is speaking, so it only needs to be said once. And then she can speak, and then I listen and I repeat it back to her, and then I speak.
Same! The thing that I learned about being in a relationship: I used to come home and do the same thing. "Hey babe, I got a thing on Friday with a client," or an even simpler one, "The Joneses invited us over for dinner on Friday, I know that you're free on Friday so I said yes." And hell ensues. And I was like, "But I know we have no plans!" So now what I've learned is when the Joneses call me and say "You want to come for dinner on Friday?" I go, "My God, I'd love to, let me check." And I come home and say, "Hey, the Joneses have invited us out for dinner on Friday, but I want to check with you first." "Oh my God, I'd love to!" "Great, I'll call them and confirm."
Instead of me well-intentioned making all the decisions, even though I know the answer is going to be yes, what I'm doing is including the other person in the relationship. That's all it is. It's making someone feel seen and heard and included. And there's so many great lessons we can learn from our personal relationships which we can apply at work because I view it all as human beings interacting with human beings. All the anxieties and fears and egos—it applies everywhere.
What's the most difficult conversation you've had with someone when we're talking about that honesty and communicating as authentically and openly as we can as soon as possible? Or a conversation you had maybe too late down the line and you thought, "I wish I'd had this conversation sooner."
Talking about George Floyd to my team. Talking to George Floyd with my Black friends. That was really hard. And I made mistakes. I remember with one of my friends, one of my Black friends, I was crying as we were talking about it. And I said to him, "Why aren't you crying?" And he said, "Because it's new for you, it's not new for me." He says, "I'm exhausted." "I'm glad you're having your experience, but that's not my experience. You're seeing this for the first time; I've seen this my whole life." That was hard to have that being told at me, to me.
But my conversations are the same as yours. The difficult conversations are about honesty in relationships, about honesty with someone on a team. If something's not working out, or if you have to give somebody really hard feedback—somebody who you are really close with. Doesn't mean you're letting them go, but like, there's some really hard feedback you need to give to someone and learning to deliver it with love, learning to be matter-of-fact.
One of the mistakes I would always make: you know these theories about the compliment sandwich? Tell them something good, tell them the thing you want to tell them, tell them something good. Doesn't work because it's bullshit-generic-something-good, really specific-something-bad, and bullshit-generic-something-good. It doesn't work. Like, "You really have a nice smile... also you're a terrible listener." "I really like that you show up to work with a smile, but there's one other thing I need to tell you."
What I've learned is when delivering good news, be very emotional. And when delivering bad news, remove the emotion. So like bad news at work especially, when we sit down with someone: "Uh, so, uh, I don't want to belabor this, you've been with us for a long time, I need to, uh, this is really hard, I need to give you some difficult feedback." I'm infusing all of the emotion into this. But to be dispassionate about it: "Hey, I need to give you some difficult news. I need to just have a really blunt conversation with you about something that's going on at work and it's going to be really hard for you to hear, but I need to tell you. Boom, here it is." People appreciate it when we're just straight with them and not infuse all the extra emotion.
I've always found that I struggle to use the word "employees." And you just went to use the word then and you changed it to "team." Is that something that you also—the reason why I struggle... I will never in a chat call the people that work in my company "employees." It seems to be somewhat of a violation of my values somehow. And I just noticed you went to say the word "employee" and you went "team, someone on my team." That's what you did.
I mean, I do the same. When I show up to a group call, I'm like "Hey team." "Employee" to me is a technical word. I don't mind talking about employees when we're talking about generic company stuff. I don't mind referring to employees when I'm talking to an insurance—when I'm talking about insurance or benefits. It's a technical term that I think is totally fine to use in technical times. But when I'm referring to people, and those people have names and faces, then they're the team.
Do you—this Andrew Tate thing. This Andrew Tate guy has been in a lot of the headlines. Do you know who he is? Probably a good thing you don't. He's this guy that kind of came out with this kind of pro-masculine approach. His basic thesis I guess is saying that young men and men generally are missing something in their lives that the modern world hasn't given them. Jordan Peterson has alluded to similar things. It's got me thinking about gender differences in our needs in the world. A lot of people in the self-help space are saying men have these unmet needs because the world is becoming more equal and they are lacking their sense of purpose.
When you look at the suicide rates in our country, the single biggest killer of men under the age of 40 is themselves. It's suicide. Is there gender differences in your view? And are men in particular having certain needs go unmet because of a changing world?
Everybody has unmet needs because of a changing world. Fact. Are there gender differences? Of course there are gender differences. And how we respond to men versus how we respond to women is different. A friend of mine who was in the military, three things happened to her simultaneously. Any one of those things would be difficult, but all three happened at the same time. She was promoted to senior management, she became a lieutenant colonel. She was deployed for 12 months. And she was given her very first command.
Any one of those things is a trial and all three happened at once. She took over a job where the previous five leaders had all been fired. It was a poorly run group. She would be working with people from different forces, so she's in the Air Force, she'd have Air Force and Army reporting to her, some of whom were much older than her and much more experienced than her. She is a hard-driving, passionate young officer who said, "I'm going to turn this group around and I'm going to prove to everybody that I can turn it around."
And it was a failure. People were ignoring her, they weren't taking her seriously, and no matter how she powered up, it didn't work. Every night she would cry herself to sleep and started regretting being in the military. All she wanted to do was go home. She didn't want to be stuck on deployment anymore. What was something really exciting now became a regret. She didn't know what to do. She was failing.
And so she decided to give up. And she said, "I will not turn this group around. So if I'm going to fail at my job, I might as well, and I'm stuck here for another six months and so is everybody else, I'm going to change my mandate. And instead of turning this group around, I'm just going to ensure that the rest of their time here they really enjoy it. I'm just going to make it more fun for them to come to work every day because they're also away from their families and stuck."
And then something strange really started to happen. They started to listen to her, take her seriously. They started to respect her more. And she ended up being very, very high-performing at the end and the group completely turned around. On her way in, she made it about herself and she made it about the metrics and she made it about the performance. The lesson she learned was if you make it about the people, then the people will take care of everything else.
I remember I sat down with her a week or two after she got back and she's telling me this whole story for the first time after she got back, and she started crying. And she said to me, "I have never felt a joy so deep as seeing someone discover that they are capable of more than they thought they were." Which is very different than "I'm going to turn this around." In her telling me this, she said one of the big lessons she learned is there is such thing as female leadership.
She had a conversation with one of the soldiers: "Why didn't you listen to me? Why was it so difficult? Why did we struggle?" And he said point-blank to her, "When a male officer yells at me, I take it, I hear it, I move on, it's fine. When you yelled at me, I felt like my mother was yelling at me, and it was more difficult."
So there are gender differences in how we respond to each other. Because it is a mom-dad thing. We respond differently. Traditional male leadership qualities are things like decisiveness, aggression—those kinds of things. Traditional female leadership qualities are things like patience, maternal instinct, empathy. I think the mistake we've made across all leadership is we teach male leadership. We teach decisiveness and we teach aggression, and we teach that to everybody.
The reality is what makes great leaders is they have a balance. And what we should be teaching is more female leadership. All leaders should take on the qualities of patience and empathy. Women get my work a lot quicker than men. When I was starting my career, women would just nod and be like, "Yeah, of course." And men would be like, "What are your case studies? In what case studies do you have to prove your model?" Men would fight me on some of the details and women just inherently, intuitively understood that the humanity of the work that I was preaching just made sense. And there's space for that. But yes, there are differences and they cannot be discounted.
It's difficult to talk about them, though, isn't it? It feels like a minefield. Even when I talk about gender differences, it feels like I'm going to step on a mine somewhere. But you're entirely correct. My previous company, our managing director was a woman and I think the business was more successful because of those qualities you've suggested: empathy, care, patience. She was much more honest about forecasts and how the business was going to perform versus a male managing director we had who was extremely exaggerated and very, very ambitious about forecasts that were never realized.
That makes sense. That's consistent. I think there's lots of data on this: men, when they apply for a job and they say "We need these ten things," and if they have six out of the ten, they apply for the job. And women won't apply for the job unless they have nine or ten of the qualities. Men are a little—I've seen it happen in meetings where there's a male entrepreneur and a client is saying, "We'd love this for—we'd love to have this," and they kind of have it and the guy goes, "We can totally do that," and they'll sell it right there and then figure it out later. I've sat in meetings with a female entrepreneur who has almost that—like they're really close—and somebody's saying "We would love this" and I'm like "You have that" and they're like "It's not—we haven't tested it yet." I'm like "You *have* it, tell them you have it!" and they're like "Well, it's not perfect yet."
I have a female entrepreneur friend who has a theory—and I have to stress this is *her* theory. She believes men make better entrepreneurs than women. And the logic is that when we're young, traditional roles for the most part still exist. If you want to go to the prom, generally the boy asks the girl. It's softening, but traditional roles are still there. Which means from a young age, boys learn to muster up courage, take a risk, and get rejected. And then they have to do it again. And then they have to do it again.
So you flash forward to adulthood, and men who learned that skill of taking a risk, facing rejection, being rejected, and then trying again, makes them resilient entrepreneurs. Where, again assuming traditional roles are played, if a woman who hasn't learned the skill of risk-rejection is more afraid of the risk as an adult. Now, we could argue that with online dating, swiping left and right, that everybody is losing the skill. That nobody has to take a risk because you just swipe right—you don't know that they swiped left on you, they think maybe they just didn't see you. So you only get the "Oh, we connected!" but nobody ever gets rejected.
So are we building—it goes back to the original conversation of a young generation that's less capable of dealing with stress than older generations—there are fewer opportunities to risk, reject, have to try again. The things that we learn as kids, these social interactions, they do become skills as adults. So is it a softening of a generation? Should we not be asking *both* boys and girls to learn to take risk as opposed to taking the risk away from everybody? I don't know.
You know what, the one thing I will say is I've had two very successful women entrepreneurs on this podcast who have said the same sentence, which is: as women in the workplace, we typically don't ask for raises as much as our male counterparts. And that kind of supports what you're saying there, which is men have at some point learned to just ask for the things that they want, whether it's a raise, whether it's a job, whatever it is.
I think the theory here that my friend posed is: does it come from our experiences of dating when we're younger, that we build these skill sets that benefit us later in life as entrepreneurs? The whole—it's not risk-reward, it's risk-rejection.
Whenever I speak to someone that does a lot of interviews and conversations and talks online a lot, I always try and think of questions that I would ask them that they've never been asked before. And one day I remember—it was actually after you left when we were in the studio in LA—I thought to myself, "If I was going to interview myself, it would probably be the most interesting interview in the world because I know all the bullshit and I know all of the stuff that no one's ever asked me that I've maybe skirted away from." If you were sat in my chair and you were interviewing Simon today, what is one question you would have asked you to get the most interesting stuff out of you? Just give me one question.
I think you've done a pretty good job. I think the best interviews are conversations. I think the best interviews have no agenda, but the interviewer has genuine curiosity. I think the best interviews are open-ended questions that are difficult, and in this case of your interviews, you are pretty blunt with a question that doesn't leave a lot of wiggle room. A lot of questions I can wiggle out of, and yours less so.
But they give an opportunity to me to think out loud. I think a lot of the questions you asked today I haven't thought about, or if I have I haven't sort of codified them. And what you heard were not answers but you heard me *thinking*. If you go back and listen to them, I probably sort of bounce around a little bit because you hear me trying to get to an answer. They're not answers, I'm trying to get to an answer. Those for me are the best, because I walk away feeling enlightened because I got to think. Where usually the answers, the questions are—I've heard them all before, they're very focused on my work: "When you wrote this, when you wrote that, what were you thinking?" and I don't learn anything. So when you ask me about my work, I know the answers. When you ask me not about my work, you ask me about life and you ask me about challenges that the world is facing, that's what I love. So I think you've done that.
I will ask you the question that I would ask myself: what is the greatest fear you have about how you're currently living your life?
That I'm not 100% honest with myself. Because if I'm not honest with myself, I won't be honest to others. When somebody asks me a question that I'm afraid of the answer—not because I'm afraid of offending them, but I'm afraid of how I feel about the answer myself—I think that would be it.
Have you got a suspicion that you're not being completely honest with yourself?
I think that all of us have a capacity to rationalize. It's one of the genius things about being a human being. We can rationalize anything. I can make any decision the right decision. And I can convince somebody of it as well: "Like, this is definitely the right decision." And I think it's that gut, that deep down inside, to be truly honest, even if the answer is "I don't know" or "I'm scared" or "I'm uncertain" or "I want this and I feel like I shouldn't want it." I think confirmed, I don't think it's a suspicion. I think I, like every human being, have elements of self-doubt and insecurity, of course. And I can convince myself of anything.
You have self-doubt?
Of course!
Where?
That's none of your business. Those are my—I'm pretty open, but there are things that I want to resolve with myself before I'm able to share them, because if I share them it has to benefit others. And I'm happy to share stuff that's in my life if I believe that that conversation, even if it's unresolved, has benefit to others. Maybe it does, maybe it doesn't.
I find it really interesting where my line is: what *won't* I share? And there are things I won't share. Maybe I'm bullshitting myself, maybe there's quite a lot of stuff I don't share or I twist it to make myself look better. People like to be a hero, you know?
I think we live in a world that we have confused vulnerability with broadcasting our feelings. And going on a podcast, or worse, sitting in your bedroom with your phone on self-view and broadcasting your breakup or your anger or whatever it is on TikTok or whatever your medium of choice is, is not vulnerability, even if you're crying. Have that exact same conversation with those exact same words with somebody you love and see how difficult that is. That's vulnerability.
The idea of broadcasting everything—putting pictures of me as a baby and my dad holding me and "Happy Father's Day Dad, I love you"—my dad's not on freaking Instagram! Why don't I just call my dad and say "Happy Father's Day, I love you" as opposed to... I think it's hilarious, our need to broadcast everything. And we think that's vulnerability, and it's not; it's broadcasting our emotions, which is different.
So those conversations that you're struggling to have and the ones that I won't share—it's not that I won't share them with *anybody*, it's that I won't share them with *you*. Because I like you, but you're not my soulmate, you're not the person that I confide in. I will absolutely share those deep things that I'm struggling with, but I'll share with somebody who can hold space for me with love, not with the desire to make a good podcast.
So the mistake people will make is to not share them with *anyone*. When I say it's "none of your business," it doesn't mean it's none of *anyone's* business. I absolutely do share those things because it would be unhealthy not to, but I want to share those things in a really safe, really safe magical space with somebody who loves me no matter what and cares for me no matter what and will stand by me no matter what.
As you know, we have a closing tradition on this podcast where the last guest asks a question for the next guest. They have no idea who they're asking it for.
I'd love to know how somebody answered my question last time.
I'll tell you after. This is a slightly interesting one because it feels like something we've discussed in many respects: "What's one conversation you haven't had which you know you need to, and why haven't you had it? Are you willing to have it?"
Yeah, won't share the answer, and yes I will. Because I'd rather have it with the person. To me, to broadcast it now before I've talked to the person seems unfair and disingenuous. It's kind of like when there was a tragedy and people were killed and they don't release the names before they've told the families. They tell the families first and then they release the names, just out of respect. I think the same goes for these kinds of conversations, which is I think we owe it to the people in our lives we love and care about to let them be the first to hear the thing that has to be said rather than the second or the last. I think it's just respect. So yes, there are things, and they will be said.
I completely agree, and it really ties in nicely with your earlier point about having a conversation as soon as possible, but also making sure they're the first to know and they don't find out via the grapevine or a podcast.
Can I just share one funny story about being honest before we close? Honesty always has to be honest, right? Like honesty is really easy, just tell the truth. But honesty doesn't have to happen in the moment. And this is a lesson I've learned. So I went to see a friend of mine's play, and it was easily the worst thing I've ever seen in my entire life. I mean, if she wasn't in it, I would have walked out. It was awful.
At the end of the performance, I hung around with the close friends and family in the foyer and she eventually came out still in costume, still in makeup. And she knows I'm an honest broker. So after the "Thanks for coming," the first question was, "What did you think?" Now, I'm an honest person, but she's all jacked up on adrenaline, she's all jacked up on emotion—now is not the time. But the problem is I can't lie. We lie all the time to protect other people's feelings. You know, you get given a gift, it's the ugliest sweater you've ever seen in your life, and they go "What do you think?" you go "Oh my God, I love it, thank you!" You don't love it, so don't say you love it to protect them.
But you don't have to be honest in the moment. So what I said was, "Oh my God, I'm so proud of you. It was so amazing to be here and watch you do your thing. I've never sat in the audience and seen you do your thing before and it was so much joy to see you on stage." All of that was true. And that was it, done.
The next day, when all the adrenaline had come down and there was no more emotion, I called her up and said, "Can I tell you what I thought of the play?" She goes, "Yeah." And then I told her point by point why it sucked. But we had a rational conversation the next day. I think we make this mistake all the time in our relationships, which is we think we have to be honest in the moment, but we don't read the room and understand that there's too much emotion involved to have a rational conversation. You meet emotion with emotion, you meet rational with rational. You can't mix the two. Sometimes we're rational but they're emotional, which means we have to stand down. What I've learned about honesty is we have to be honest, but we can actually delay. You have to meet rational with rational and emotional with emotional.
Let me give you some honesty then. I went on your video subscription library, absolutely love it. I'm a member now—you'll see my name in the back end. Watching loads of the videos, it feels like it's too cheap, to be honest. The amount of value there around things that are foundational to my life, my business, my relationships, everything. It feels like it's a little bit too cheap. It's like a couple of cups of coffee for a month and I can just binge all of your content and you've got all these other instructors on there. The only thing I thought was, I don't know if this is the best name: Video Subscription Library. "Subscription" for me is a bad thing.
Done. We'll change it. I have no emotional connection to any of these. It's a technical thing and we called it a technical thing.
I watched your last episode and you talked about honesty in it, and I was thinking this is way better than it sounds. You've distilled your books into actionable courses, there's live classes, everything you've ever done. It feels like I'm ripping you off by being a member. I genuinely think if I hung around there for an hour a day, my life would be better.
§02Transcript — part 2
So basically we'll change the name, which will make people feel even more value, and then thanks to this conversation, we're going to charge people more.
You should! Genuinely.
I know that our "Why Discovery" course—there are people who offer all kinds of purpose-finding courses that they charge $1,500 for. And I know, because I've been told, that our course is like a thousand times better, and yet we charge like $20 something for a month. The reason is because I believe I have a responsibility to let everyone who wants to learn their "Why," learn their "Why," and not those who can just afford $1,500. $1,500 is exclusive. And I would rather try and make it up in volume because I want more people to learn their "Why." But I appreciate the feedback. It is important for me to keep prices relatively low because it's more important to me that people learn the stuff than don't.
The price is fine, it was actually the name I felt did it a disservice.
Simon's Library or Simon's University. Done. I have no emotional attachment to it whatsoever. Thank you very much for the feedback.
Thank you for coming again, Simon. Honestly, it's a huge honor. I learn so much from these conversations. I actually need to go back through this episode with my own notes so I can change my business and my life for the better. Thank you so much.
It's a joy. I learn as much if not more than you do, so I really appreciate you having me.
Amazing. We'll do it again sometime.
I hope so.
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