Top Leadership Coach Simon Sinek Shows You How To Find Your Why in 20 Minutes

1 Sep 2026 · 39 min · 25 chapters

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In short

Simon Sinek explains why long-term decisions are hard (dopamine-driven short-term focus), argues “success requires help,” and teaches a fast “Find Your Why” method based on patterns from your past. He connects “why” to leadership, service, and difficult conversations about work and compensation.

Guests

Simon Sinek, leadership thinker and creator of the Start With Why movement; author of Infinite Games; works with CEOs, founders, and teams on motivation and purpose.

Key claims

Your why is formed by mid-to-late teens and doesn’t change; authenticity means living your values consistently; performance is secondary to identity/values; your why is about contribution and impact, not money or fame; asking for help confidently is a leadership strength; “why at work” matches “why with friends.”

Notable examples

Deutsche Bank nonprofit presentation teaching financial literacy to high schoolers; “Camp Nader” including a Down syndrome girl; Barry-Wehmiller’s human-centric culture; Henry VIII/Anne of Cleves portrait at the Louvre.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Human Behavior and Money Decisions

0:46 to 4:20

Simon Sinek discusses how dopamine impacts long-term planning and the importance of seeking help.

“I've been very excited for this conversation in particular because most people know you as a leadership expert.”

Finding Your Why

4:21 to 8:00

The conversation shifts to discovering personal motivations and identifying one's 'why'.

“We were at lunch the other day, if you remember, and I was babbling on and on about questions about Mary and Pip and the podcast and just talking your ear off.”

Exploring Childhood Memories

8:01 to 12:00

A discussion about childhood experiences that shape one's purpose and contributions.

“Well, I didn't know that by the time you were 18, your why is formed.”

Articulating Your Why

12:01 to 14:00

Simon helps Mary to articulate her 'why' by exploring her contributions and the impact she wants to have.

“and the next day and all summer we had Camp Nader and we just like got to be best of friends.”

Understanding Your Contribution

14:00 to 14:33

Learn how to articulate your personal contribution and impact.

“And so the impact for yours is we can see it, which is to make people feel included, to feel seen, to open up possibility, right?”

The Invitation Concept

14:33 to 15:10

Discover the power of inviting others into your space and experiences.

“So for me, I know what mine would say, I would say, he inspired.”

Personal Experiences and Vulnerability

15:10 to 15:51

Explore how sharing your vulnerabilities can resonate with others.

“and make people feel like they have a seat at the table of a historical, in my opinion, boys club, which is finance or even like entertainment.”

The Challenge of Translation

15:51 to 16:48

Understand the challenges of translating complex topics for inclusivity.

“So how do you go about inviting people in?”

Identifying Your Why

16:48 to 17:29

Learn to identify your core motivation and purpose in life.

“Because people don't know how to be comfortable around her and what to do.”

Aligning Actions with Your Why

17:29 to 18:14

Discover how your why should guide your actions and decisions.

“And so now that's your marketing, that's your messaging.”
Show all 25 chapters

Difficult Conversations about Money

18:14 to 19:15

Gain insights on how to approach uncomfortable conversations about compensation.

“And I've devoted my entire life and my entire career to inviting people in who've historically been left out so they can discover that they have possibilities and never knew they had.”

Value Beyond Performance

19:15 to 20:37

Understand how value at work goes beyond mere performance metrics.

“Because there's many reasons to have a money conversation.”

Finding Your Professional Purpose

20:37 to 21:40

Learn how to articulate your purpose as a professional.

“And so it's also the thing that provide the deep value at work.”

The Journey of Discovering Your Why

21:40 to 22:57

Explore the journey of finding your why and the impact it has on your life.

“And I was thinking as you were talking, one of my growing interests is just learning.”

Overcoming Challenges in Business

22:57 to 23:52

Learn about the challenges faced in business and how to overcome them.

“And so the more you can learn, the more you can translate.”

The Importance of Sharing Your Why

23:52 to 25:14

Understand the significance of sharing your why with others.

“And my fourth year didn't feel like my first three years.”

The Path to Public Speaking

25:14 to 25:56

Discover how to build confidence in public speaking and sharing ideas.

“And just like when you see a great movie or read a great book, all you want to do is tell other people.”

Giving vs. Receiving in Speaking

25:56 to 27:21

Learn the mindset of a speaker focused on giving value rather than receiving praise.

“which I didn't even know you were allowed to be paid to do that.”

The Essence of Your Why

27:21 to 28:01

Explore how your why is an act of service and not just about personal gain.

“You know, like, or people who say, people who start, their opening line is, can you please put your phones away?”

The Importance of Finding Your Why

28:01 to 28:38

Learn how showing up with a giver's heart can help you find your purpose.

“And if I suck, then you should be on social media to pass the time.”

Navigating a Changing Workforce

28:39 to 29:27

Discover how finding your why can guide you through workforce uncertainties.

“It's the value provided to the world, both through your work, but also in the lives of your friends.”

Company Culture and Personal Values

29:28 to 30:48

Explore how companies can embody purpose and the impact on employees.

“You can find ways to do it that bring you great joy.”

Defining Success Beyond Job Titles

30:49 to 31:35

Understand the importance of being true to oneself when choosing a career path.

“like even when I was in college interviewing for jobs, you look at the mission statement.”

Simon Sinek's Fascination with British History

31:36 to 36:48

Dive into Simon's newfound interest in British history and its cultural significance.

“okay, what are all the different ways that you could bring that to life?”

Historical Art and Its Significance

36:49 to 37:19

Learn how historical art provides insight into society and individual stories.

“I don't think so, but that's a funny concept.”
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Transcript

Automatic transcript. May contain errors.

0:00Mary Holland Nader:The following podcast is a Dear Media production. Hey, y 'all. Welcome to Growing Interest. Before every episode, we set an intention. Today's intention is simple. Clarity. On today's episode of Growing Interest, I'm sitting down with Simon Sinek, one of the world's most influential leadership thinkers and the creator of the Start With Why movement. For years, he's helped CEOs, founders, and teams uncover what truly motivates them. In this conversation, you'll learn how to get closer to the real reason behind the goals you're chasing, the difference between what you do and why you do it, and how that clarity can change the way you think about work, money, and success.

0:36So as you listen today, I want you to remember one question. Why are you pursuing the goals you're pursuing? Or as Simon would ask, what's your why? All right, hold on to that thought, y 'all. Let's grow. Well, welcome to the show, Simon.

0:52Mary Holland Nader:Nice to be here. Such an honor to have you. I've been very excited for this conversation in particular because most people know you as a leadership expert. But what I really like about your work is it's all centered around human behavior. And obviously, a lot of human behavior dictates our spending habits and money habits. So I'm excited to dive into that today. But my first question is about Infinite Game, of course, which is one of your bestselling books that's all about looking beyond immediate results, especially in spending and money behavior, it's really hard for people to make decisions that benefit their future selves.

1:26So why is that?

1:27Mary Holland Nader:Well, I mean, we're sort of dopamine driven machines, you know, and dopamine has gotten a bit of a bad rap because of we keep associating it with, you know, social media and sort of phone addiction, which is true. It's all true. But dopamine exists, you know, if you go back sort of back to caveman times for a very good reason, which is to help us find food and to help us find shelter and to help us get things done. You know, that's why you get a good feeling when you accomplish something or just cross it off your to-do list. It's why when you find your keys, that feeling you're like, found them.

2:01Mary Holland Nader:That's dopamine. It's a good thing. And so we just naturally aren't very good at long-term planning. Short-term is what keeps us going and finding things and getting things done and staying away from danger and all that stuff. So, yeah, we're just it takes a lot of discipline and a lot of help. Right. To do things for the long term. We're not naturally good at it. And some of us are even worse like me. Well, you spent your career training some of the most successful people who have clearly gotten good at looking at their future selves. What is one habit that you see amongst the successful people you've trained or companies that you've worked with that you can attribute to their success?

2:39Mary Holland Nader:You hear this idea of like the self-made, you know, millionaire and all this kind of stuff. There's no such thing. There's no such thing. Nobody achieved anything without help. Whether someone gave them a break or some of them gave them advice or someone told them whatever you're doing that doesn't work. They gave them some hard and honest truths. When things went horribly sideways, there was somebody there to help pick them up, give them advice, shoulder to cry on any of those things. And so I think the thing that we forget that is anything we want to overcome or accomplish requires help. And the best leaders I know know that.

3:13Mary Holland Nader:The best leaders I know are willing to raise their hands and say, I don't know. And can somebody help me with this? And they do it with confidence. It's not an embarrassing thing. It's not like, oh, can somebody help me, please? It's like, hey, I don't know how to do this. Can somebody please help me? I have no clue about this thing. And they own it. And so when you go back to sort of long-term anything, the willingness to ask for help and knowing that you're doing it for someone else is actually even more powerful. For someone else, meaning like for your team. Purpose and service. So the easiest way to do things for the long term is to recognize that you're not doing it for you, but you're doing it for someone or something else, something bigger than you.

3:53Mary Holland Nader:And that helps you think more long term because when it's about me, it's all short term satisfaction. Right. Right. Of course. But you think about the sacrifices we make so that our kids can grow up, right? Well, that's because we're doing it for them. Right. And so it's one of the reasons I preach service and I talk about the why and I talk about purpose at work is because when we feel connected to something bigger than ourselves and we're doing something in service to someone else, our ability to make longer term decisions is actually much easier. That makes sense. Well, perfect segue into my why.

4:22We were at lunch the other day, if you remember, and I was babbling on and on about questions about Mary and Pip and the podcast and just talking your ear off. And you interrupted me mid-yap and you were like, well, what's your why? and I was like I don't know I have so many interests I have the podcast I have Mary and Pip I have investing I have family obligations things like that so I think that's why it's been so hard for me to find one why and I remember at lunch you were like well in a separate meeting we'll help you find your why so I thought this is that separate meeting why not let our listeners listen in and you mentioned at lunch you were like it usually takes a few hours of introspection and thinking through it.

5:04But for someone with a very short attention span, I guess, could we crank out what my why is and a few questions so that the listeners can maybe follow along and find theirs?

5:13Mary Holland Nader:Yes, we can do the simple version that will get you in the ballpark. How do I decide my why? You don't decide. Okay. So let's just take a step back and talk about where the why comes from. Okay, please. We are all products of our upbringing. You are who you are because of the experiences you had when you were growing up as a kid. the mentors you had, the people who believed in you, the things that went horribly wrong, they've molded you, made you who you are. And now you are who you are. Your why is fully formed by your mid to late teens and you are who you are for the rest of your life. Now, whether you live in balance with who you are is a different conversation.

5:49Mary Holland Nader:And that's what we mean by authenticity. When you are accurately and honestly representing your values, your beliefs, the things that you actually believe, you know, you say and do the things you actually believe, then we will say you are authentic. And so to know who you are, it's like if you start chasing money and fame, your friends who know you from way back when, they'll say things to you like, it's like, I don't know who you are anymore. It's because you're not. Who have you become? It's because you're being someone else. You're pretending to play a role, right? You're playing a role of someone else.

6:19Mary Holland Nader:And so the value of learning your why is we all sort of have been in the experience where we're in flow and everything we touch turns to gold and everything, no matter how hard the work is, it feels good, it feels passionate. That's because you're saying and doing the things that are sourced from your cause, from your why, from who you actually are and it feels good because it flows. The problem is it's a little bit like roulette. It happens sometimes. We don't quite know when and sometimes you'll be doing like, I've done this a hundred times before. Yeah. Why can't I get the flow? It's because it's not really about the thing.

6:54Mary Holland Nader:It's about what's underneath the thing, that deep-seated purpose, cause, or belief. So to articulate your why means that you get to live with purpose on purpose. It means that you get to have that sense of flow more often. You get to feel passion flowing through you more easily. Instead of just playing roulette and hoping that the thing you're doing will tap into your why, you're now doing it with the filter live so you know what to say yes to and you know what to say no to more easily. So fascinating. And it's all based on your past, right? Because as I said, your why is fully formed by the time.

7:30Mary Holland Nader:And so like doing vision boards and cutting things out of magazines, that's not how you do your why. It's not about imagining your future life. That's something else, right? But your why is like a process of discovery. You're panning for gold. I'm looking for patterns in your life. So I'm going to ask you questions about the past. Not about your desires, not about your tastes. None of those things matter to me, right? All my prep is out the window. All your prep is out the window. So those things only matter when we talk about how to implement your why. Okay. Okay. Which is a different conversation for another me.

8:00For another me. Yeah. Well, I didn't know that by the time you were 18, your why is formed. Yeah. So like people can't change.

8:07Mary Holland Nader:No, no, no. You are who you are. You are who you are. Right. Because if you could change. So like the youngest person I ever did it for was 16. Okay. And it worked out fine. And yeah, you only have one why your entire life. And you don't. People are like, well, my work why and my personal why. Like, no, it's you. It's you. It's you. There's no difference between you at work or at home. The only difference is the clothes you wear and the table you sit at. Right. And you don't change your why. Because if you could change your why, then you would never be able to form trusting, loving relationships.

8:37Mary Holland Nader:Sure. Because I fell in love with or I trust this person. But if you change your why, then I don't know who you are anymore. So true. So that consistency really matters. Okay. Technically, I guess. I never thought about this. But if you know your why and you live by your why, the trusting relationships you have should be more stable. Right. Okay, so we'll do it now. Okay, let's commence. So we're going into the past, right? Yes. So tell me something you've been involved with in your life, a project you worked on, something professionally. It doesn't matter if it was a commercial success or not.

9:10Mary Holland Nader:but something you worked on that you absolutely loved being a part of, that if everything, every project you work on in your life was like this one thing, you'd be the happiest person alive. Something specific. Okay. In my professional career? Yeah. One of my favorite things that I worked on was a presentation, group presentation that I did at Deutsche Bank, and it was for a nonprofit. It was for a school. So it was teaching high schoolers about financial literacy, about personal finance. And I loved working in collaboration with a colleague of mine. But then I also loved, I guess, translating what I did every single day for younger kids who didn't have access to it.

9:50So that was like the most fulfilling.

9:51Mary Holland Nader:So you've given presentations before. Yes. You've worked with other people before. Yes. You've given advice to others before. Right. What was it about this one specifically that made you so quickly tell me about it and talk about it with such a big smile? Probably because I knew that those high school students didn't have access to this kind of education and like didn't think that thought that because they came from families that didn't have money or went to a school that didn't necessarily teach personal finance or they didn't think that that was an option for them. didn't think that working in finance was an option for them.

10:25And then when we went and talked about our careers, what we did, how easy it is to learn about it, seeing their face light up to realize that like they had a seat at the table and they could, like it was a possibility for them, if that makes sense.

10:37Mary Holland Nader:Got it. That was why it was fulfilling for sure. Tell me an early specific happy childhood memory. Not like we went to my grandparents every weekend, something specific that I can relive with you. Okay. Childhood memory. Definitely my dad getting home from work every single day. I want something. I want one specific one. Specific childhood memory. Okay. Middle school, summer day, Baton Rouge, Louisiana. My sisters and I hosted a Camp Nader, we called it, for the kids in the neighborhood and all of the kids, because we loved just including people, being, having people around. It was a revolving door always.

11:19And I remember specifically, there was a little Down syndrome girl at our house and she was just kind of like hanging out by herself. And I just like resonated with her so much and hung out with her all day. And she was really sad at first when her mom dropped her off and we were playing in the pool. And then we were going to throw the ball around. Like we had all these activities at Camp Nader, of course, because me and my sisters were between the ages of probably like 13 and 16 and, you know, being camp counselors, which was so fun at the time. And I was just like, this little girl was just like latched onto me.

11:52And when she smiled and like laughed for the first time that day, like, I'll never forget it. It's, it was so fulfilling. And she came back the next day and the next day and the next day and all summer we had Camp Nader and we just like got to be best of friends. So So I think that one day, that first day where I was able to make her feel like she was a part of the rest of the group and just like make her comfortable enough to have a good time. That was it's a very specific memory, but you made me go there.

12:18Mary Holland Nader:That's nice. So you've you had a happy childhood, rich in love, rich in love. And you had a lot of amazing and great experiences and happy experiences. What was it about that one that made you want to tell me the story? What was it about that one? Just like how it made me feel when she felt like she was a part of the group and included. Like it just made me feel so my heart was so full. My cup was so full. I purposed like I felt like I had purpose and I wanted to make everyone feel that way. So do you realize that both those stories you told me are basically the exact same story? How so? So in both cases, you included others.

12:55Mary Holland Nader:In both cases, you showed possibility. And in both cases, the people who you were serving, in this case, the Down syndrome girl and the room full of high school students, all of a sudden lit up and felt included, felt like they could be a part of something. that something that they thought was closed off and unavailable to them, all of a sudden the doors were open. And you sort of showed, you opened the door to possibility. And most importantly, you made people feel seen and included. And how does that feel so far? You see? Yeah, I completely see. Yeah, crazy. And so your why is in that space.

13:32Mary Holland Nader:So the way I like to write a why, there's no right way, but this is the way I like, which is to blank, so that blank, right? So there's something you do, an action, so that and some sort of impact. And sort of most introspective people are fairly good at coming up with the impact, like the impact they want to have in the world or in people's lives, which is great. But the most important part of a why is actually the first part, the contribution, the contribution and the impact, right? And so the impact for yours is we can see it, which is to make people feel included, to feel seen, to open up possibility, right?

14:11Mary Holland Nader:Right. So the question is, what's that contribution part? And there's something to be said for an invitation. I like that word for you. I do too. To invite someone in. Right. You know, if one day after your remarkable career, they build a statue of you, the question is, what will it say on the plaque? Wow. So for me, I know what mine would say, I would say, he inspired. Right. Amazing. So what would yours say? What's that word that you would get tattooed on your body as a reminder of what you stand for is the, you know, she invited us in. Right. She showed us, she showed us that we can, like, what's, what's, what's the thing that we put there?

14:53I think invite definitely resonates now that you're saying that and through that comparison between those two stories, I'm seeing so many, like, I'm thinking of all of my different avenues, the podcast, Mary and Pip, even Love Thy Nader. And I'm thinking of what I'm trying to do in each is basically translate complex topics and make people feel like they have a seat at the table of a historical, in my opinion, boys club, which is finance or even like entertainment. I'm trying to give my full vulnerable self so that people can resonate with something they've been through on the show maybe. So I think translate, but like that seems a little cold.

15:31Mary Holland Nader:but don't worry about the language right now right now we're in concept we want to know the stuff that feels right we'll think about it later this is why when you talk about the work you're doing in finance and every time you talk about it remember when you first told me about the idea you lit up you lit up the exact same way you told me the story about the high school you lit up the exact same way you told me the story about inviting that girl to come and enjoy Camp Nader you light up when you have an opportunity to, and it's, I think translation, I would actually say translation is a how. So how do you go about inviting people in?

16:05Mary Holland Nader:Well, one of the things you do is you translate. Okay. Right. How, yeah. Because I wouldn't call you a translator, as you said, it's a little bit, it's an action you take. Yes. But the, the, but the why is, is that, is that opening of the door. I love that. It's the, it's the, it's the letting people in. It's the invitation, whatever language we want to use. Right. And that's your personality. You know, you are at your natural best. You are your happiest. And it's specific, right? You're not looking to let people in and invite people in who already have access. Right. You very much. The little guy.

16:39Mary Holland Nader:It's the little guy, the person who has historically been excluded. Yeah. Misunderstood. Yeah. Whether it's the kids in the school who misunderstood or thought that because of how they grew up that they don't have access or the Down syndrome girl who frequently gets left out. Of course. Because people don't know how to be comfortable around her and what to do. And so you are at your natural best where you are opening the door to those who don't generally have the doors open to them. I love that. So wherever a listener or myself is at their natural best and feel the most fulfilled, or would you say, like, how did people compliment you when you were a child?

17:14Like when you were your most vulnerable, normal self, I guess, before society warped you. Okay. I love that. So my why is we're in the ballpark, we're in the ballpark to invite people in so that they have opportunity.

17:28Mary Holland Nader:So they can discover the possibility that they never knew that existed before. I love that. I mean, I'm so motivated now. And so now that's your marketing, that's your messaging. Yeah. So when you sit down with somebody and they say, you know, why are you doing a TV show? Yeah. Why are you starting a financial company? Why? And if those things fit. Right. Not everything we do fits. We talked about that before. Sometimes we chase money or chase, you know, rank or opportunity, whatever it is. And we do things that are outside. And they may reward us financially, but we won't find them emotionally rewarding.

18:01Mary Holland Nader:And at some point it won't feel like it's worth it. But these things you would do for free. Of course. That's how powerful it is. Yeah, it's amazing. And so when people say, why are you doing any of these things? Why are you doing all of these things? Why are you doing one of these things? Right. The language is, you know, I recognize that for whatever reason, some people either are left out by society or feel that they are left out for some experience they had when they were younger or some narrative they have in their mind. And I've devoted my entire life and my entire career to inviting people in who've historically been left out so they can discover that they have possibilities and never knew they had.

18:35Look at that, Simon. So good.

18:37Mary Holland Nader:Which is why I started this business, So That, dot, dot, dot. So that, dot, dot, dot. Which is why I do this show, So That, dot, dot. And those become the proof points of your purpose and your cause. And you now have the responsibility now that you know that to ensure that as many things as possible in your life will bring that to life. Wow. Okay. So you mentioned earlier, like in a relationship or something, your why can also contribute. Similarly, it's obviously your why leads how you lead as a leader. I have been having recent conversations as a new leader myself, and some of the hardest ones are around compensation.

19:10That was the hardest conversation I had when I first got to Wall Street, negotiating for myself, asking for more money. It's a conversation that's uncomfortable at first, you know, negotiating a salary on either end, how would you apply that clarity of having your why to conversations around comp, for example, or money with your partner, like conversations about money with your partner or outside of like a career driven, why am I doing what I'm doing perspective, but just in one-on-one money conversations, how could I apply that clarity?

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19:40Mary Holland Nader:So that's a loaded question, isn't it? Because there's many reasons to have a money conversation. And I think we have to be careful about conflating the personal conversation with the work conversation because the work conversation is like I would like more please because I'm doing more you know and a you know relationship it could be like hey you're spending too much right right right so you know very different let's use uh work cop okay as the example so the funny thing about your why at work is your why at work is the same as your why with your friends, which is it's the thing that makes you valuable, right?

20:18Mary Holland Nader:Your friends love you because they are, uh, they either resonate with the thing or you give them that thing that they need in their life. So I love doing a why discovery with somebody I like because what I discover is the reason why I like them. Right. Right. And people who want that in their lives, you fill that, you fill that gap. Right. And so it's also the thing that provide the deep value at work. So if you only define your value at work based on your performance numbers, I mean, that's good. Right. But that's, you know, what if you have a bad month? Yeah. Then your identity is out the window and your argument's out the window.

20:54Mary Holland Nader:And performance matters, but it matters second. Right. So assuming you work for an organization that you feel like you belong. Right. Assuming the organization cares about these kinds of things. Assuming you work for a boss that sees your value beyond just being a machine that punches a clock and produces numbers. Assuming those things, that's where you would want to start, which is one thing you may or may know about me. I wake up every single day to invite people who've historically been left out for various reasons, and I want to show them the possibilities that exist. One of the things that I love about working at this company is that you've given me an opportunity to do that professionally.

21:41Mary Holland Nader:And if you look at my book of business, for example, in your case, my client profiles look a little different than most others because you can see I'm bringing in new business in a way that has never been done before because I'm finding possibility and they trust me because that's who I am. and I'm quite frankly I'm doing it at a really high level amazing wow so you can start conversations that way I mean there's all kinds of other techniques about how to have difficult conversations and uncomfortable conversations which we can go into if you want we have so many more conversations to be had the why is wonderful it's super helpful for pretty much everyone and that's why I'm doing this podcast is to translate like have experts like yourself on to be able to give people access who might not listen to well listen to a bit of optimism if you haven't, obviously, but who might not have heard of you before.

22:29And it's like, I feel so lucky. And I was thinking as you were talking, one of my growing interests is just learning. Like, I'm so curious and I love learning from people like you and just any book, any podcast. I'm just such a sponge. And I think one of the reasons why I like learning is because I love telling it to other people.

22:48Mary Holland Nader:We're learning about your house, right? We know that one of your houses being a translator and we know that one of your houses curiosity or soaking it in or learning whatever verb we find. And so the more you can learn, the more you can translate. Wow. So we're starting to paint a picture of your full golden circle. Not only just your why, which is that deep-seated purpose, cause, or belief, but your natural strengths, your values, the things that, you know, in combination make you really good at bringing that why to life. So we're starting to learn more about you as we go through this conversation.

23:16I'm curious, when you found your why, you weren't in corporate America.

23:19Mary Holland Nader:I had my own business. You had your own business at that point. And that was like a revelation, your discovery. and then you were like, oh my gosh, this is the reason I've been doing this the whole time? No, I wish it were like that. No, no. What happened to me was the opposite. My career is an accident. This was not a commercial or intellectual pursuit. This was born out of desperation and need. I had my own little business. We'd been in business for four years and most businesses fail in the first three. So I now joined an elite club in America of the company that's revived. Well done. I have three to go.

23:54Mary Holland Nader:And my fourth year didn't feel like my first three years. My fourth year in business, I'd lost my passion. And I was embarrassed because superficially, things were good, right? Like I had my own business, my own boss, like all the things that some people dream of, I had. Right. Except I didn't want to wake up and go to work anymore. Wow. And it was a very dark time. And I didn't want to tell anybody, as I said, because I was embarrassed. Right. And so I don't, you know, I'm sure you know this, which is if you're in a dark space and you don't tell anybody, it's darker. Yeah. Exactly. And it wasn't until a very dear friend of mine, after about three months in this really dark space, a dear friend of mine came to me and said, something's wrong.

24:35Mary Holland Nader:Something's off. I don't know what it is, but something's not right. And I took advantage of the safe space that she created and I came clean. And it was a huge weight off my back to just say it. and all that energy that went into lying, hiding, and faking every day, I invested that energy in trying to rediscover and reignite my passion. I didn't know where it was. And I had this idea about the why. Right. And somebody helped me find why because you can't do it for yourself because you can't be objective about yourself. When I discovered my why, more importantly, I not only figured out how to find my why, I figured out how to help others find theirs.

25:15Mary Holland Nader:And just like when you see a great movie or read a great book, all you want to do is tell other people. I'm like, you got to go see this movie. You got to try this restaurant. Right. Why do we do that? Yeah. It's because we want people to have the great experiences we have. Totally. I mean, we're sharers with people we love. That's what we do. And so that's what I did. I shared it with my friends. And my friends wanted to share it with their friends. And so they invited me to their apartment. And I would stand in someone's apartment in New York City. And we had one of those who are like, you know, those things you buy, you know, in the supermarket.

25:39Mary Holland Nader:You know, pop it open. Classic, yeah. You know, the dips and things. Yeah. And I would talk about this thing called the Y and help people find their Y for$100 on the side. And people just kept inviting me to help them. And then somebody invited me to come talk to their company and was willing to pay me to do it, which I didn't even know you were allowed to be paid to do that. I thought you had to like swim across the Atlantic Ocean. That was the beginnings. I never imagined I'd be a public speaker. I never imagined I'd write a book. I wasn't one of those people who thought I had a book in him.

26:08Mary Holland Nader:I just didn't think that. but I was obsessed with this thing called the Y and it resonated with people and I love the impact that it had in people's lives. They were inspired, which in turn inspired me. Right. And I just kept saying yes to all the opportunities and here we are today. Wow, that is so impressive. I've been overcoming my fear of public speaking and I remember you told me just practice makes perfect. You used, at one point you were nervous to public speak. Yeah, of course, everybody was nervous. Everybody starts off at an amateur at some point. Yes. Nobody's naturally good at anything.

26:38Exactly.

26:38Mary Holland Nader:But it's also my disposition, right? Like every time I give a talk, every time I go on stage, I say to myself under my breath, out loud, you're here to give. And I remind myself that I'm not here for me. I'm here because I have an idea or a point of view that has real value in my life and I think it'll have value in others. And so I'm here to share it. And if you disagree, that's okay. I don't need your love. I don't need you to follow me. I don't need you to buy my book. I'm not here to get anything. I'm here solely with a giver's heart and I remind myself that every time I go on stage I'm here to give and that helps the nerves go away because the reason we're nervous is we want people to like us and I hope they get applause and I hope they buy my book and I hope they follow me on social media blah blah blah blah blah it's all about you and when it's all about you people can tell like I can always tell when speakers make it about them right they show up on stage and say well in my book you know and like they show up in the back you know the screen behind them has all their social media handles and you know their their website, their QR codes, and you know, and you can tell that they're selling.

27:41Yeah.

27:42Mary Holland Nader:You know, like, or people who say, people who start, their opening line is, can you please put your phones away? All I ask is for your attention for one hour. Right. My attitude is, that's kind of my job. Like, if I'm really compelling on the stage, you won't want to pick up your phone. You don't have to ask that, yeah. And how do I know you're not taking notes? Right. Or tweeting? This is the best thing I've ever seen. Like, I should let you do that. Totally. You know? And if I suck, then you should be on social media to pass the time. because I'm boring. Also, if you say don't get on your phone, the first thing you want to do is get on my phone.

28:11Mary Holland Nader:So like I always think that's very funny. Like your job is to be compelling. But anyway, the point is, is you show up with a giver's heart. You show up to give. This is why we talked about right back to the beginning of where we started, which is starting with why is the thing you give to the world. Totally. That's the purpose you have in the world. And it's also an act of service. Your why is never about you. It's never about your product. It's never about your company. That's like when people say my why is to provide financial da da da da. No, no, no, no. That's one of the mechanisms you found to bring your why to life.

28:41Mary Holland Nader:You're not defined by the product. It's the value provided to the world, both through your work, but also in the lives of your friends. I mean, everyone dreams of loving their work and loving what they do. And I feel like the answer to doing that is finding your why and going from there, especially as the workforce changes so much. He knows what the workforce is going to look like. So now more than ever in such a period of uncertainty where AI is taking so many jobs and you disagree. I'm just like, my thought process is if you have your why, then whatever the workforce looks like that you can find.

29:15Mary Holland Nader:That's true. And, you know, your why doesn't mean like the whole company has to, you know, sort of help you bring your why to life. That's ideal. But there are people who work with dysfunctional companies that all they care about is, you know, the quarterly results and will then bring your why to life for your teammates. Sure. You can find ways to do it that bring you great joy. One of my favorite companies, on the planet is called Barry Waymiller. My mentor, Bob Chapman, he ran it for many, many, many years. And it's a manufacturing company. Sure. It's a manufacturing company in the Midwest, like blue collar factories, like every stereotype you have in your mind.

29:50Mary Holland Nader:Yep, it's all there, you know? Yeah. And so like they make machines that put like labels in ketchup bottles, like that's fulfilling nobody's why. Right. Right. But for the fact that the way the culture exists is that they all take care of each other. And it's a human-centric company. So people who love to take care of people and want to be taken care of and are willing to ask for help and willing to sort of put themselves out there, love working there. Yeah. And so the company is defined by how they touch the lives of people, not by how many machines they make. Right. You almost wish that everyone's LinkedIn just had their why.

30:21So you can know who to hire, know what companies to work for.

30:24Mary Holland Nader:By the way, in my ideal world, I want companies to put their why. Yeah. And I want people to put their why. in my ideal world, that's how we would link up. Yeah. I mean, the good news is the work that I do is having an impact on companies where now everybody has a purpose statement. Now, they may not follow it or believe it. Yeah, yeah, yeah. But the fact that the social pressure to have one means that the work is going in the right direction. Right. And even people who are interviewing, like even when I was in college interviewing for jobs, you look at the mission statement. You're like, how do I align with that mission statement?

30:56And I think it's just so important. Yeah, if you're graduating and you don't know what to do, what the hell to do with your life. Try and find the reason companies are operating or trying to peel back the onion of the culture a little bit so that make sure it aligns.

31:09Mary Holland Nader:And our guidance counselors, you know, well-intended aren't helpful. Yeah. In fact, our parents aren't helpful. Right. Like they say to us when we're little children, like, what do you want to be when you grow up? Yeah. Here's the five options. Like I have to pick one? Yeah, exactly. Or, you know, what do you want to do when you graduate school? Right. What do you want to do? Nobody ever says, who do you want to be? who do you want to be when you grow up? What kind of person do you want to be? Mic drop. Now the question is when you know that, okay, what are all the different ways that you could bring that to life?

31:40Mary Holland Nader:And that's called possibility. Right. And that's what allows for a wonderful career, which is you find that there are many ways to bring your why to life. Right. But when it goes right back to the beginning of the conversation, if you have that filter, it's not happening by accident. Oh my God, I love my job. Well, you just got lucky. Right. You can actually make decisions. I love that. before with purpose on purpose. Wow. Well, I feel inspired, that's for sure. And a bit of optimism. The last question I ask all of my guests going forward, since you're the only second guest. You ask all your guests.

32:12I ask all my future guests. Starting, yeah.

32:14Mary Holland Nader:You will ask all your future guests. Exactly. Is what is a growing interest of yours? Anything new that you're exploring? Anything at all? It could be a show. It could be a form of meditation. It could be type of music. Could be traveling. Anything that you're interested in newly yes tell me uh i've become sort of mildly obsessed with british history like cool the tutors in particular okay expand i don't even know what drew me to it was it traveling no no it's like henry the eighth and so interesting elizabeth the first and shakespeare they all that was a lot of tea uh a lot of tea and and sort of and there was a a lot of incredible art that came out of that time.

33:01Mary Holland Nader:Hans Holbein and a lot of incredible, you know, Christopher Marlowe and William Shakespeare. And this time period really had such an impact in the world that we didn't even realize. Freedom of press and freedom of speech and freedom of expression started to come out of this time period. They were taking risks to say things. Didn't always work out that well. Sometimes you get your hand cut off. But they were experimenting with this, you know. French used to be the dominant language in the world and in court. And it was this time period where it started to become English. Interesting. Well, Henry VIII also because he was the one that started the Church of England.

33:38Mary Holland Nader:And one of the things they did is they translated the Bible into English for the first time. And so now average people could have access to God and you didn't have to rely on the clergy and the priests and ruling classes where you didn't know what the Bible said because they had to be translated. But now regular people could read, could read the, which gave rise to literacy, you know, things like that. So it was an amazing time period. Plus the art was incredible. So fascinating. Where have you been learning about it? Like reading books? I mean, watching documentaries. I'm not a very good reader.

34:09Mary Holland Nader:Watching a lot of documentaries. Historical fictions are fun too, but I know that they're historical fiction. And quite frankly, I've been learning about it through the art. So like I was recently in Paris and I went to the Louvre and I went and looked at all the, old northern european paintings and so for example there was a painting by hans holbein of i'm really getting nerdy now no i love it this is now going to get boring for everybody present you know but here's the picture of uh anne of cleves henry the eighth has already um divorced his first wife because he couldn't get a son uh which is catherine catherine of aragon and then killed his second wife anne boleyn cut her head off because she was having an affair supposedly she probably was you think i don't know i believe her and now they needed he needed to remarry and so they sent Hans Holbein off to Germany to paint portraits of paint a portrait of this and of Cleves to see if the king should marry him and so he brings back this portrait and they show the king this portrait and he's like she's hot I want to marry her from the portrait shut up right and so they bring her all the way from Germany to marry the king he said after he met her I like her not because apparently she wasn't as hot as her portrait.

35:24Hans facetuned it a little bit.

35:25Mary Holland Nader:Exactly. And so he married her and it didn't last very long. Did he kill her? No. Divorced, but had died. She died. No, sorry, Jane Seymour. Sorry, I left out a wife. So he was married to Catherine de Aragon for many, many years, but he couldn't get a son. And so he wanted to divorce her. And the Catholic Church and the Pope wouldn't allow him to divorce her. So he basically started the whole Church of England just so that he could divorce his wife. Shut up. So the whole Church of England became because Henry VIII wanted to get a divorce that he couldn't get. You're kidding. No, that's how the Church of England began.

35:54Mary Holland Nader:Oh my God, T. So the rise of Protestantism also is this is the reason, right? Okay. Then he, so divorce beheaded. So he killed Anne Boleyn. Then he married Anne Boleyn's lady-in-waiting, which is Jane Seymour, which is his true love. His true love. Right? And Jane Seymour gave him a baby, which was, he gave him a son, which he was really happy about. Good. But Edward. But then she died. So the love of his life died. And so the fourth wife was then. Was the one that he said, never mind. Which is Anne of Cleves, right? In real life, she wasn't as hot as the portrait. And then, and so he married her and then divorced her pretty quickly.

36:29Mary Holland Nader:And so he was the original online dater, you know, where you meet the person and they're just not as hot as their picture. The original catfish. So OG goes back to the 1500s. Wow. You know. There needs to be like a new show. Is there? Is one of those British shows about this? I don't think so, but that's a funny concept. That is hysterical. And so anyway, the point is the reason I went down. So you saw the portrait. Yeah. At the Louvre. Now I see the value of the portrait. So that was very necessary to answer. At the Louvre, they have the actual painting by Hans Holbein. The actual painting of Anne of Cleves that Henry VIII looked at and was like, she's hot, I'll marry her.

37:09Mary Holland Nader:Shut up. The actual painting. What did you think? She's hot. She's hot. Yeah, she's total cutie. I have to go to the Louvre and see this painting. And the funny thing is because everybody just wants to see the Mona Lisa. Right. There's nobody there. And it's one of the most historically important paintings in the world. Now I'm hooked. That is like, if anyone's going to Paris this summer, Louvre, Anne of Cleves, essential. By Hans Holbein, yeah. Wow. Okay, so history. Now I'm going to go down. I'm totally into British history right now. Ew, I'm obsessed. For no reason whatsoever. Now I'm, have you heard like Stuff You Should Know and Hardcore History, the podcast?

37:36Mary Holland Nader:I haven't heard that one, but there's a fun - Hardcore history is fun. There's a British history one that's fun too. Okay, love. Well, that will be a new growing interest of mine. So thank you, Simon, for coming. Sorry to all the listeners. No. Who now... I have a feeling we're going to have some secret history nerds that really enjoyed that. So six wives. He had six wives. Six wives. Crazy. And the Protestant church because of it. Well, not the Protestant church. Because he wanted six wives. But the Church of England. Oh, sorry. Church of England. But most importantly, the translation of the Bible into English.

38:05Mary Holland Nader:That was because of Henry Gates. I mean, of course. That's the most important. So the King James Bible came out of... Sure. King James. King James. James. Wow. Even though it was really from Henry VIII. Oh my gosh. I mean, this is like a whole new rabbit hole that I'm going to go down after this. This is crazy. It's a rich history. You have to send me the documentaries you watched. I will. And I'm going to force my sister to watch. I know what to show you that will get you hooked. You know? Yeah. Okay. Would it get my sisters hooked? Yeah. I mean, there's a historical fiction about Oliver Cromwell called Wolf Hall.

38:34Okay.

38:34Mary Holland Nader:It's Henry VIII. Wolf Hall. And there's two seasons. Okay. And like, it'll get you hooked. We'll put all this in the show. I was into it and I watched that and I'm like, oh, this is good. Obsessed. Well, thank you, Simon Sinek, for joining us. Thanks for having me. Hey, everyone. Hope you enjoyed this conversation. The biggest action item from this episode is simple. Find your why. Grab a friend and ask them these three questions. Professionally, what's a project you worked on that you absolutely loved being a part of? Early childhood memory. Get specific. And last but not least, what would your plaque say?

39:07All right. See you guys next week. Thank you.

From the publisher

Simon Sinek sits down with Mary Holland Nader to help her answer one of the biggest questions we face in work and life: What is my why?

In a first-ever abbreviated version of Simon’s famous Find Your Why exercise, he walks Mary through the process of uncovering the experiences, patterns and values that have shaped her sense of purpose—and shows how you can start finding your own.

Simon also breaks down:- What great leaders have in common- How to start finding your purpose at work- Why our upbringing shapes who we become- Why we struggle to make decisions that benefit our future selves- How to have difficult conversations as a leader- Why your “why” is a process of discovery—not something you simply inventWhether you’re questioning your career, looking for more motivation at work, or trying to become a better leader, Simon offers a practical framework for understanding what drives you—and how to use it.

Keep Up With Mary Holland

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LinkedIn: @MaryHolland

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DISCLOSURE: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. All investing involves risk, including loss of principal. Guests and the host may own securities discussed on this show, and nothing said here is a recommendation to buy or sell any security. Always do your own research and consult a licensed financial advisor before making financial decisions. This podcast is not produced, reviewed, or endorsed by Mary & Pip Investments LLC, a registered investment advisor, nor its affiliates. Nothing said here reflects the views, advice, or services of that firm.
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