347: The Power of Truly Living Your Values Daily with Drew Dudley

By September 19, 2018Podcasts



Drew Dudley says: "For most of us, the number one criteria we use to make decisions is 'what will avoid the most consequences right now?'"

Drew Dudley redefines leadership and shows what it really means to live your values.

You’ll Learn:

  1. The gross way we make decisions when we don’t have clear values
  2. How to make leadership a practice, instead of a hobby
  3. Approaches to discovering your own deep wisdom with “the edge of the bed advice” technique

About Drew

Drew Dudley is the Founder & Chief Catalyst of Day One Leadership, and has spent the last 15 years helping individuals and organizations increase their leadership capacity.

Recognized as one of the most dynamic keynote speakers in the world, Drew has spoken to over 250,000 people on 5 continents, been featured on The Huffington Post, Radio America, Forbes.com, and TED.com, where his TED talk has been voted “one of the 15 most inspirational TED talks of all time”. Time, Business Insider and INC. magazines have all included his talk on their lists of “speeches that will make you a better leader”.

Drew’s clients have included some of the world’s most dynamic companies and organizations, including McDonald’s, Proctor & Gamble, JP Morgan Chase, Hyatt Hotels, the United Way and over 75 colleges and universities.

Items Mentioned in this Show:

Drew Dudley Interview Transcript

Pete Mockaitis
Drew, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Drew Dudley
Oh, I’m thrilled. Thanks for having me.

Pete Mockaitis
Oh, well, thank you. I think we’re going to have a ton of fun here. One fun thing I want to know about you right away is all about your stuffed penguin collection.

Drew Dudley
The stuffed penguin collection. The stuffed penguin collection emerged, believe it or not, because I’m afraid of dogs.

I was dating a girl and almost every silly story starts with that. I was dating a girl who really wanted a dog. I was attacked when I was a kid by a big Siberian Husky. While I’ve gotten better with dogs, back then I was – if there was one the size of a hot dog, I crossed the street to avoid it. This was a bit of a nonstarter for me.

We were out one night on a date and we saw March of the Penguins. She leaned over to me and said, “If you buy me a penguin, I will never bother you for a dog again.” I thought, “Done.” This is a way out. Believe it or not you cannot purchase penguins as pets anywhere. I tried. I tried. I said, look, I’ll just poke holes in the front of my freezer. We’re good to go.

I was in Wal-Mart lamenting the fact that I was going to have to back to battling against this impending Great Dane that she wanted and sure enough I saw a giant stuffed penguin sitting in a box. I thought to myself, she did not specify the penguin had to be a live one. I brought it home. Every now and then as a boyfriend you knock one out of the park and she loved this penguin.

Unfortunately, what happened is – I don’t know if anyone out there has pets, but sometimes your pet becomes the communication tool between you and your partner, like “Tell daddy he’s staying far too long at work.” “Well, tell mom that if I don’t stay at work, we don’t get to-“ etcetera.

Well, one of my friends witnessed this exchange. In order to mock me for the fact that I was apparently whipped by a stuffed penguin, he began giving me penguin gifts and got all my friends on board. What I realized is that you can do one of two things when your friends are picking on you. You can either fight back, which just makes it all the more rewarding or you can lean into it.

Sure enough, I leaned into it and it became my thing. I’ve got 50 or 60 stuffed penguins and penguin cuff links. Because what happens is once you make a deal of it, every gift from every client, from every friend, anybody who sees a penguin-related thing in a store, that’s it. My penguin collection was my way of avoiding having to get a dog. I was trying to find a loophole and it turned into a monster.

Pete Mockaitis
That is wild. I would imagine if everybody just gives you penguins, because that’s what they know about you, you’ve probably got some duplicate penguins over the course of your collection years. Is this true?

Drew Dudley
Just a few actually. Somehow they got to be the big thing about three years ago. Everybody had a penguin in the front hall. Yeah, I’ve got – but what’s cool is people make little shirts for them. I’ve got one from the University of Notre Dame. I’ve got another one from the Sanitation Workers of New Jersey T-shirt. We break them up a little bit. I’ve got – I think they’ve got a little football league going on.

Pete Mockaitis
Well, I’m just curious, if you move, are you going to take all of them with you and will you store them? This is quite a commitment that you have taken on your shoulders here.

Drew Dudley
I’m not going to lie, there’s about 48 of them that are just stuck in a storage unit somewhere. I move around a lot because I figure I can, so why not experience the world. Ultimately, after I moved out of my place that I had sort of been in for a few years, we just pack them away because now I live – I’ve got a bunch of 500 square foot little places scattered about North America where I base out of.

Pete Mockaitis
I’m just imagining the episode of was it Storage Wars or whatever that reality TV program is where they claim abandoned storage lockers.

Drew Dudley

Pete Mockaitis
Like, “What the heck is this?”

Drew Dudley
I actually am storing a bunch of them in the actual storage facility where they shoot that show. Yeah, I kid you not. If somehow I disappear in the Bermuda Triangle, dammit, somebody’s going to open it up and find a whole bunch of stuffed penguins and all of the workout materials that I’ve stuck in my storage unit because –

Pete Mockaitis
You’re not using those either.

Drew Dudley
That little ab roller that everybody buys, “Hey, that’s a good idea,” yeah, that’s what they’ll find.

Pete Mockaitis
That’s fun. Now I want to hear a little bit about your other role, other than penguin custodian, you are … the title. I like it. You have fun with the title. I do the same. You’re the founder and chief catalyst of Day One Leadership. What does that mean exactly?

Drew Dudley
I guess my job ultimately is to be accountable for how well the company makes three things happen. One, help people figure out the specific leadership behaviors that are right for them to feel like leaders and act like leaders. Two, to help people make those behaviors a non-negotiable part of every single day of their lives. Then three, convince people that doing those two first things makes them a leader.

My title when it comes to the company makes it sound like I’m in charge I think, but effectively all it means is that I’m ultimately accountable for the company’s success in making those three things possible for as many people as possible.

I started to realize this when it comes to titles. The day-to-day operations, the strategy, marketing, sales, everything that a company or organization does, those are all just logistics in service of, in our case, those three things. Whatever your job is, it’s not the tasks that you have to do, it’s how those tasks relate to the bigger mission of the organization.

Here’s the thing, if you don’t know what the bigger mission of the organization is or you hate it, quit because you’re in the wrong place. That’s it. That’s my role is to make those three things happen: help people figure out what the best leadership behaviors for those are, make them a nonnegotiable part of their life, and then convince them that doing that is in fact leadership.

Pete Mockaitis
Okay, well, you’re clear on what you’re about, which is cool. Let’s dig into some of these dimensions one by one. You sort of capture a number of these ideas in your book, This Is Day One. What would you say is sort of the main idea or thesis behind this one?

Drew Dudley
The key thing I’m trying to get – and this is everything that I do in terms of my speaking and the book, here’s the main idea. There’s a form of leadership to which we all can and should aspire. It’s defined by a commitment to acting on your core leadership values every single day because when you do that, you close the gap between the person you want to be and how you’re actually behaving.

My argument is that actively and consciously working to close that gap is what defines a leader, nothing else. Whether or not you are trying to close the gap between the person you want to be and how you are actually behaving on a day-to-day basis.

Because I don’t know the secret to happiness, but I have found that the secret to unhappiness is when a gap forms between who you want to be and how you’re acting and you become aware of that gap.

For me it happened because a seven-year-old called me out on it. About ten years ago I had this horrible time at work, like a real toxic environment. I decided I wanted to take a train ride all the way across Canada and not talk to anybody, just stick my nose in a bunch of books, all those books you were supposed to have read and just not talk to anybody.

I started out in this empty car at the back of the train and was super happy with my nose in this book. This little girl was running up and down this train, back and forth, back and forth. Then she plopped down next to me and said, “What are you reading?” I said, “It’s just a book for work.”

I remember she looked at me and said, “You get to read books for work? My dad has to go to an office,” which is one of those cool moments that remind you of how awesome your job is. I said, “Yeah, yeah, I get to read books for work.”

She said, “Well, what’s the story?” I said, “This book doesn’t really have a story,” because it was some academic research thing. She said, “Well, don’t all books have stories?” I said, “No, some just have knowledge.” She says, “Well, aren’t stories knowledge?” I was really thrown off by that because the last thing I want to do is send this kid away thinking that stories aren’t knowledge.

I said, “Actually a really smart friend of mine said once that ‘The story is the basic unit of human understanding,’” As soon as it came out of my mouth, all I could think was, “Dude, she is seven,” but this girl was amazing. She just looks at me and says, “I think your friend is very, very smart.” I said wow, this girl is incredible.

I said, “Why are you running up and down the train?” She says, “My parents say I have this very big spirit. They say my spirit is way too big for every room that I’m in. A train’s just a big long hallway, right? Anytime I’m in a place where it’s not big enough for my spirit, and no hallway is big enough for my spirit if rooms aren’t, I run to remind myself that I’m free anytime that I want to be.”

I said to her – because there was something – she didn’t do it to be pretentious. She didn’t do it to try to sound impressive. When you work at a university, like I did, all anyone is trying to do is sound pretentious and impressive. It was just the way she said it, “I’m always free if I want to be.”

She said – I said, “I think I’m like that too. I think the problem is I’m not spending time in places where it’s big enough for my spirit.” She hops down off this chair and looks at me and says, “Drew, I don’t mean to be rude, but I don’t think anyone whose spirit is too big for a hallway would ever read a book without a good story,” and then disappears.

It was weird because I had always seen myself as someone who gathered stories, who gathered insights, who shared them with other people. This is a fundamental part of who I am. This seven-year-old pointed out that I’d gotten on a train, gotten a single sleeper car, hadn’t wanted to talk to a single person. There was a gap between who I wanted to be and how I conceived of myself and how I was actually behaving.

It changed so much about how I treated that trip and made me so much more aware of where real leadership lies and the really big struggle in our lives is becoming aware of where that gap is between we want to be and how we’re behaving and doing something about it.

In the book – I know that was a long answer to that question – but it’s really about how I try to address things in the book is here are the stories of these extraordinary leaders that I’ve picked up along the way. They don’t all look like we’ve been taught leaders look like. There’s a seven-year-old and there’s a cab driver. Each one of them has sort of given me a little bit of an insight. The idea of This Is Day One is based on this.

We all wake up every single morning and we have done absolutely nothing to deserve the title of leader that day. Nothing. Whether we’re a CEO or we’re the person who just got hired in an entry level job, when you wake up in the morning, you have done nothing to deserve the title.

Ultimately that came from one of the first times I ever went to a meeting about my alcohol addiction. A guy said – he was talking afterwards – he said, “I’ve got 36 years in.” A guy next to me was also at his first meeting, he said, “Wow, 36 years.” The older guy looks at him and says, “Son, I have just as much time in today as you do.” There was something that really resonated with me at that.

When it comes to leadership, we all get up at the exact same place. That – a lot of Day One comes from that experience recovering from addiction, is that if you don’t want to have a drink for the rest of your life, choose not to have a drink today. Then treat every day as if it’s the first day of your recovery because every day one has an inherent commitment, humility, forgiveness.

If you screw up, you just recommit. You don’t throw away everything you had before. If you’ve got 25 years in of being sober or rising up through the ranks and running an organization, yeah, you’ve done all that stuff to get here, but when you wake up in the morning, you haven’t done a damn thing.

That’s what the book is about is saying, “This is day one and if you want to be a leader, you want to close that gap between who you want to be and how you’re behaving, you start today with nothing on the score card. You’ve got to earn it again.”

Long answer because I love to tell stories, but that’s really what the book talks about, how to close that gap, how to give a step-by-step guide of exactly how to do that.

Pete Mockaitis
That’s what I found interesting is that these are big questions and heavy and tricky and can take some – a lifetime to figure out, but you have laid out a bit of process or ‘process’ as Canadians say. I love it.

Drew Dudley
Do we say it different?

Pete Mockaitis
You do. It’s a long O instead of a short O. I actually like it better that way.

Drew Dudley
I didn’t realize we did that. I know that we throw U’s in words you don’t. Apparently, we say ‘about’ although I don’t know what that crap’s about. I did not realize we said ‘process’ different ….

Pete Mockaitis
Most Canadians I do hear it. One time I was even chatting with some folks and I made reference to a process and I pronounced it with a long o and they said “Pete, are you Canadian?” I said, “No, I just like the way Canadians say ‘process.’”

Drew Dudley
You know how you can spot a Canadian right now?

Pete Mockaitis
Do tell.

Drew Dudley
We don’t have our head down on our desk banging it slowly as the chaos descends around us.

Pete Mockaitis
Okay. Noted, thank you. What I want to discuss is you have a process or a ‘process’ associated with getting to the bottom of some of these questions in a step-by-step rigorous way. I’d love to hear what would you say are the first steps to zeroing in on these values and associated leadership behavior?

Drew Dudley
Well, I think the first thing is to actually identify what your core leadership values are. Most people haven’t.

One of the things that sort of drives me as a person is this theory is that when you don’t know what to do in a situation, ask yourself what would the person who I want to be do in this situation and then do that.

But what I found is that because we all went through an education system that asked us what you want to do when you grow up and taught us that you should focus on the things on which you’re going to be tested, well, we never got tested on what our values were. We never got tested on who we want to be.

We never got tested on what criteria are you going to use to make big decisions, so most of us, especially high performers, actually never had time. We never sat down and thought about what are the values that want to drive us.

What I talk about in the book is how to actually figure out what those core values are. That’s where it starts because values are criteria for decision making. What real leaders do is they identify their values and they define them because then you use them as criteria for decision making.

Every single time that you face a challenge, you face a decision, you pivot to your values and you say which one of these options is most consistent with my list of values. The challenge is that often that option sucks. It doesn’t allow you to look good, avoid punishments, keep the money, stay in the job, but it’s always the decision that you are proudest you made five years from now.

The first step that leaders need to do for their day one is say “These are the values that are nonnegotiable for me. Here’s what they mean,” and then make sure, that’s what the book talks about, the process of actually living them every single day.

Because if you don’t do that, if you don’t use your values as criteria for decision making, the question that I love to challenge people with is “what criteria have you been using to make decisions every day for your whole life so far?” What I realize is for most of us, the number one criteria we use to make decisions is “what will avoid the most consequences right now?” That is not how leaders make decisions. That’s why that’s where you start.

I talk about how in the book, but mostly it comes down to self-reflection, not on what you think, which is how most people think about self-reflection, we get into our head, but self-reflection on how you have behaved because your values are indicated by how you behave, not by how you talk.

In the book I talk about how to use a reflective exercise that looks not at “Oh, what are my values? Let me think about it,” but it looks directly at “What have I done in my life?” because that’s a better source for figuring out what your values are.

Pete Mockaitis
That’s so intriguing that notion in terms of in the absence of clear values that is the default, what will avoid the most unpleasant consequences for me right now. It’s really not at all inspiring.

Drew Dudley

Pete Mockaitis
It’s like in terms of just selfishness and shortsightedness. But at the same time a lot of times that answer is an okay one in terms of “Well, not lying about how I just screwed up would avoid the most consequences because if I lied about it then I’d really be up a creek.”

In a way I think that’s – that shorthand default gets you to some decent decisions somewhat often, but it sure doesn’t make your chest rise in pride as to the person that you’re being.

I’m intrigued then. Let’s hear it. First, when you say values, I’d love to get your take on – there’s many you can choose from. Perhaps an infinite amount in terms of ways you could articulate it. I’d love for you to first give a few examples of “here are four different values and what they mean.”

Drew Dudley
Sure. In the book, I actually focus on six. The idea is that each individual, you have to identify your own and then there’s a process to embed them into your life. But in order to demonstrate the process, I say here are six, like here on day one when you put the book down, this is what you could actually do right away. They are impact, courage, growth, empowerment, class, and self-respect. Those six values.

Impact is a commitment to creating moments that cause people to feel as if they are better off for having interacted with you.

Courage is a commitment to taking action when there is the possibility of loss, which gets educated out of us as we grow older.

We go through the education system that teaches us you’re going to get evaluated not on how good you are right now, but on how few mistakes you made along the way because every time you make one along the way, we take points away. Even if at the end you’re the most talented, hey, if you lost the most points, it doesn’t reflect.

Yeah, we talk about growth, which is a commitment to increasing the capacity to add value. Leaders add value to other people’s lives. That’s ultimately your goal. Now, in the process, you add value to your own. Any time you get better at the ability to add value, you are embodying the value of growth. That means any time that you’re a catalyst for learning, you effectively have helped people grow.

One of the big ways that you can help people grow is to change how you ask questions or sorry change how you – that’s one of the big talents, sorry, is to learn how to effectively ask questions.

Leaders, I think we get confused and a lot of people walk away from the idea of leadership because they think they don’t have all the answers. One thing I really want to tell people is that leaders do not have more answers necessarily than other people, but they do ask tremendous questions. They’re better at that and they ask a particular kind of question.

The best leaders I know – and if you’re listening, think about trying to get better at this – asking questions, where the person being asked learns more than the person doing the asking. Usually we think, “Okay, if I’m asking questions it’s because I want to gather information,” but what leaders do is they ask these powerful questions that help people understand things about themselves they didn’t know.

I give a bunch of examples in the book, but the one I really like is “Why do you matter?” That’s a deep ask question, but most of the people I ask, 95% of them, cannot give me an answer to that question or they’re making one up on the spot. Ultimately, the reason I ask it isn’t to get an answer necessarily, but to make people realize they don’t have one. No one’s ever asked them before and your kids don’t have one either.

If they’re under the age of five, go ahead, ask your kids that question, they will give you an amazing answer. But once we send them to school, they stop believing that why they matter is up to them and it’s supposed to be evaluated by somebody else. Because all of us spent 20 of the most formative years in our lives in that system, we don’t unlearn that lesson. We spend the rest of our lives waiting for someone else to evaluate how much we matter.

Ultimately becoming a great leader I think is finding out a way to ask those questions where the person who’s being asked learns more than you do.

Empowerment is a commitment to helping other people reach their goals. It’s a commitment to acting as a catalyst for the success of others. Ultimately what that means is unlearning this competitive process that we also learn through school, this idea that we’re – there’s a finite amount out there. We live in this economy of scarcity and if you don’t get the job, if you don’t get the money, somebody else will. Ultimately, you have to outperform other people.

What that makes us do is that we stop seeing empowering other people as a fundamentally good thing in our lives and what we do is we think helping other people, what we’re doing is we’re holding ourselves back, particularly in the job world.

One of the things when I get invited to have the opportunity to speak to business schools, because business students are a special breed—ultimately they’re being taught this idea of compete, compete, compete, be the top, have the best resume, that’s what’s going to help you.

One of the things I tell – if you want to be great at your job and if you’re in one of these positions where you actually create a culture at a job, a manager or an executive, don’t try to outperform other people because if you can outperform 90% of the people on the planet, great, or in your organization, great. You’ll make six figures.

But if you can become the type of person where everyone who works with you outperforms everyone who doesn’t work with you, then you’re indispensable. If you want to be great at your job, be indispensable. Don’t necessarily be someone who’s at the top. Be indispensable.

When you create a career where every day you could identify something you did to make someone else move closer to a goal, what you’re doing is you’re creating a career where when other people get promoted, you get promoted too because people remember who made them better at their job.

Class is a commitment to treating people in situations better that they deserve to be treated.

Self-respect is a commitment to recognizing you cannot add value to other people’s lives until you’ve added enough value to your own. When you are empty, you have nothing to give.

That is the six that I use as examples within the book. Each one comes with an accompanying question to make sure that you can give yourself evidence you’ve lived it. But the idea of the day one process is you get to figure out your values and you can figure out what they mean and then you can convert into your own things that drive you every single day.

That really is the key to what the book, my work, and my company is trying to do is give people this direct guideline every day of how to live like the person they want to be through their work, not necessarily on top of it. You can answer all these questions and live these values through the work that you do every single day.

If you don’t know what the values are, you don’t know how to define them, the last like 40 pages of the books is basically a list of 40 of the most common values I’ve been given over the years and sample definitions for them along with the questions you can use if these are the ones that are important to you.

Pete Mockaitis
Well, then this is intriguing. Maybe no need to offer all 40 definitions, but of those 40 could you share a few more because I have a feeling as folks listen, some folks will be like “Yes,” like by hearing a little bit of a laundry list, some of them will naturally have more of a resonance than others. I think that could be valuable if you could maybe rattle off a few more.

Drew Dudley
Yeah, sure. Adventure, a commitment to seeking out new or exciting experiences. Accountability is a commitment to acknowledging responsibility for the outcomes of your actions. Perseverance, a commitment to overcoming obstacles and enduring discomfort. Rationality is the commitment to making decisions based on logic and reason.

Mastery, a commitment to seeking continuous improvement. Mindfulness, a commitment to being conscious aware and engaged in any given moment.

You’ll notice that they all start with a commitment to. We use a lot of these words – integrity is a big one, integrity or honesty or compassion. We throw these words around and we use them to evaluate our behavior and to judge other people, but we honestly very rarely identify what those words actually mean.

What I often will tell people is to envision a hypothetical where someone follows you around for 30 days out of your life and at the end of those 30 days, and you weren’t aware of this, I asked that person what are the three values that this person puts out into the world every day. What are the three values this person uses whenever they have to make a difficult decision? What would they be? It’s always integrity, honesty, generosity, kindness.

But if you ask people, “All right, finish this sentence, ‘Integrity is a commitment to…what?’” We have been using these words to judge ourselves and our organization and other people and we have never actually identified what they mean.

The problem is if you haven’t identified what one of your values means, turn it into a finish line so that you can actually recognize when you cross it, you can’t make it a target, you can’t strategize on how to get there, and most of the moments where you actually live up to it will be completely ignored and uncelebrated.

In order to actually live our values – yeah, because look, it’s the celebrations in our lives that drive us forward, that give us momentum. Setting goals is planning celebrations. When we don’t identify what our values actually are, we deny ourselves the opportunity to celebrate the moments when we are the person that we want to be. Some days, that’s the only thing that we get to celebrate. Some days the world blows up in our face.

That’s why I think it’s really important that what guides your behavior every day is a commitment to making sure that you can give yourself evidence at the end of the day that if you claim to be someone of integrity, honesty, empowerment, in my case, growth, courage, empowerment, at the end of the day you have to be able to give a specific example of when you were that.

Because when I ask you, “Okay, you’re someone of integrity. Give me three examples of integrity this week.” “Well, hold on. It depends on how you define it.” “No, it depends on how you define it.” But ultimately if you can only give me two or three examples of you living your values in a given week, then leadership isn’t a practice, it’s a hobby.

Really what I want to talk to people about is moving leadership from a hobby to a practice because I have six questions that drive my behavior every single day. With a laptop and a phone I can answer those six questions tied to my values in less time than it takes me to empty my email inbox. But for most of my life I prioritized emptying my email inbox ahead of being the man I want to be every day.

What I found is that most people, even very successful people, that is what they’re doing with their lives. They’re sticking what they have to do every day ahead of who they want to be. The two don’t have to be separate, but you can make sure that you’re being the person you want to be as you finish the things that you have to do every day.

Because when you don’t, eventually you don’t get to answer the question why do I matter because you don’t have any evidence. And if you do, but if you don’t give yourself evidence, that impacts how you feel about yourself and how you treat others.

Pete Mockaitis
Yeah, I dig it. I think it’s so true. I remember one of my happiest thoughts – I think Einstein has a happiest thought – but I recall I was right in front of my childhood home. I was 18 years old, going to graduate high school pretty soon. I was just sort of chilling in my car, a 1989 Chevrolet Celebrity.

I was licking some ice cream and just thinking, “Why do I feel so amazing right now?” Then I was like, “And why at other times do I feel really just yucky even though the circumstances around me are somewhat similar in terms of family and friends and school and whatever.”

Then I sort of came up with the same kind of conclusion, kind of like, “Oh, your baseline level of satisfaction with life and yourself is determined by the extent to which you are living in accordance with your values.” I thought I was really a brilliant guy for figuring that out, but then I realized that no, that’s very well kind of established in sort of the human condition and philosophers throughout the millennium.

But it was cool to arrive at and say, “No, yes, this is true. I buy it and I can kind of see how in the last few weeks I’d been on sort of a hot streak. Hey, how about I do that more deliberately rather than just get lucky.”

I’m right with you. It is powerful and well worth prioritizing. I like how you’ve put it there in terms of getting systematic about making it a practice and say, “Well, did I do that this – today and this week?” I want to kind of rewind a little bit to the starting line in terms of what is the step-by-step process by which you reflect upon your experiences and come out with your true values on the other side?

Drew Dudley
Well, I think it’s one of those questions I gave an example of a little bit earlier, a little earlier. One of those questions that people learn something when you ask them, for me, it’s the edge of the bed advice. The edge of the bed advice happened on that train trip. It came out of when I started speaking to people after that young girl, her name was Alison, sort of made me realize that I wasn’t living the life I wanted.

The edge of the bed advice says this – I started to ask people on the train. I learned a lot.

If it was the last night your son or daughter was living in your house and you’re walking by their room, and they call you in and you sit on the edge of the bed and they say, “Mom, dad, what do I need to know? What do I need to know to be happy and healthy and successful in this world? What insights have most contributed to your happiness? Give me 30 of them. Bring them back tomorrow when you wake up.”

See, because what happens is if you ask people for one piece of advice, they think it has to be some sort of Dalai Lama-esque, Confucius says, massive insight. You give people 30 and they actually start to realize, “Man, I know a lot and I never thought about that phrase, the things that have most contributed to my happiness.”

What it does is you start to reflect as you go through these 30, “What do I know to be true about,” fill in that blank. What do I know to be true about love? What do I know to be true about business? What do I know to be true about happiness/sadness/friendship?

When you think about that, ‘what do I know to be true,’ and you start to write down these 30 pieces of edge of the bed advice, what they do is they emerge from your wisdom.

Now your wisdom comes from experience. Wisdom – you can’t just sit and come up with wisdom. You earn wisdom through what you do, what you’re successful at, what you fail at, what makes you happy/sad, other people happy and sad.

As you write down these 30 pieces of advice, what you’re ultimately doing is reflecting on what you have done and writing down what you learned from it, which means those 30 pieces of advice are born from your lived experience, not from some idealized version of what you think sounds good about your life. This is actually what you did.

Now, the next step, I actually can’t give away, not because I want people to run out and buy the book, because if you know what the next step is, it influences how you create the list, if that makes some sense. Because you need to do step one first in order to – and not know what the next step is because otherwise it starts to – you don’t get an honest assessment of what your values are.

The reason I say it is that you need to surface your values is what my work has taught me. You can’t just ask someone. You actually have to put them through a reflective process on their experiences that help them surface it.

I don’t want that to be a cop out. It’s one of the challenges of trying to give practical advice through podcasts or on the radio is that you can’t actually surface your values if you know step two when you do step one. But that’s where you start.

Honestly, my friends, if you’re listening, just do that assignment. Do it for yourself. Sit down over the next two weeks and think that question, ‘what do I know to be true about.’ If you have kids, give it to them.

If you are a manager, get the people in your office to do it. Bring them in or take them and then put together a list of your favorites, take the names off of them, hand it out anonymously because what you’re doing is you’re saying to people “This is the brilliance of the people who surround you,” because if you come up with 30, there will be at least 3 on your list that you are proud of, that you say, “Man, I want to Tweet that because that’s really smart.”

Do that assignment. That starts to get you thinking about what has made you happiest, what has made you wisest. You can start to pull from there. But in terms of actually identifying the values, it’s step two. But that’s where you start. Your values come from what you’ve done, not from what you say.

Pete Mockaitis
Yeah, that’s intriguing. Wheels are spinning. I guess turning has a more positive connotation, so they’re turning as opposed to spinning.

But that’s – so you say, ‘What do I know to be true about,” and so you had a few things there in terms of love, happiness, so is it just kind of any big piece of life, like money, business, fitness, relationships, friendship. Is it kind of like how you think about how you fill in the blank there is just sort of the big buckets of stuff?

Drew Dudley
Yeah, really it comes down to the idea that some people get stuck. They’re like, “I don’t even know where to begin,” so you can sit back and just reflect on your wisdom. Some people can come up with 30 like that.

What I discovered however, is that people really sometimes need a little bit of “Okay, well, where do I start?” Ultimately that really helps is you sort of write down a list of things that are obviously a challenge that someone’s going to face: love, family, friendship, work. What do I know to be true about failure or stress or fear? Ultimately that little phrase, that can really get you thinking about it.

Pete Mockaitis
Neither borrower nor a lender be.

Drew Dudley

Pete Mockaitis
I’m just thinking about all of the – that whole speech. Is it Polonius and Laertes? He really goes on. But I guess that’s helpful for those Shakespearean folk. Well, cool. That’s awesome. Drew-

Drew Dudley
You know what’s funny my friend?

Pete Mockaitis
Let’s hear it.

Drew Dudley
You mention that, one of my – because I put together my list there. One of them is number – what was it? Number 14, I would have told my kids there are more Rosaline’s out there than Juliet’s.

There are more people – there are more things that you think you desperately want and you can’t live without them and then all of the sudden, you realize that you didn’t really want them, that there was something else out there for you. That’s something wise to keep in mind when you lose something you thought you really wanted is that that was probably a Rosaline, not a Juliet.

The next piece of advice is that both Romeo and Juliet end up dead at the end of that story. Love does not conquer all, but love has an incredible winning percentage. Love is LeBron James and you should adjust your expectations accordingly.

Pete Mockaitis
Well, that’s fun. Drew tell me, lots of good stuff here, is there anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Drew Dudley
Mostly folks, if we can start to recognize that we get educated out of leadership by using these big giants as our examples, for those of you out there who are parents, you can start to shift this. We can start to widen the definition of leadership.

Most of the leadership on the planet is coming from people who don’t see themselves as leaders because we were taught to think of leaders as these giants. That divided or that put a wedge between our identity and what leadership actually was.

When you start to talk about leaders to your kids, to your coworkers, let’s start to realize that all of our biggest leadership heroes should be people that you know personally because you get to see how they make decisions every single day.

When we look at famous people, when we look at the RFKs and the Martin Luther King’s, I’m not trying to diminish that. What I am saying, however, is that we only see the outcomes of their decisions, we don’t see how they made them. Most of the leadership heroes you know should be people that you’ve seen how they make decisions.

I do not argue that everyone should be a CEO or everyone has the capacity to be a senior manager, but there is a form of leadership to which we all can and should aspire. We’re ignoring people who consistently behave in ways that make their lives and the lives of people around them better.

If we can recognize these moments of compassion and generosity and kindness and we recognize them as leadership, what we’re doing is we’re doing a better job recognizing the leadership that’s being ignored. Leadership recognized is leadership created.

That’s one thing that I want to say is that we’re teaching kids to not see themselves as leaders because they’re not yet in charge. I think we can start to change that if we start to give different examples of what leaders actually are.

Pete Mockaitis
I dig that a lot. There’s one more thing I’ve got to get before we hear your favorite things that is you talk about those moments of kindness or compassion and whatnot and how often following your values sucks in terms of – it’s unpleasant or uncomfortable in terms of the consequences.

Do you have any pro tips for when you’re in the thick of it and either you just don’t feel like it or it’s like, “Oh, this is going to hurt,” any pro tips for following through and being consistent with those values when you sure don’t want to?

Drew Dudley
One, imagine yourself explaining the decision to a group of people you respect five years from now. Imagine that every single decision you make in your life, five years from that day you have to stand up and in front of a group of people that you love and respect, you have to explain the decision that you made.

That – when you do that a lot of the noise surrounding our decision falls away. When you don’t know what to do, what would the person I want to be do, and then do that.

Second, you’ve got to practice. You have to practice. Yeah, that’s part of what the book is about is how do you create this habit of making decisions based on your values. That’s really, really important is that you have to do it regularly because what it does is it makes you so aware of the fact that you are capable of handling the consequences.

So much of how you handle those extra tough days are determined by the behaviors that you engage in on the days that aren’t tough. We need to prove to ourselves that we have courage and resilience. I can make tough decisions not because I am a better person than other people, but because I made it a habit to make decisions consistent with my values, which meant a lot of times bad crap happened.

But what you become aware of is that you can make it through bad crap. Only when you become confident in your ability to do that are you more willing to take those chances.

Your brain’s job is to keep you from harm. When you can prove to your brain that you can get over those consequences, it will be more likely to say, “Okay, then let’s do it.” But if you don’t practice and if you don’t get used to it, then you’re always going to shy away from the consequences because you haven’t yet proven to yourself that you can handle them.

Pete Mockaitis
Awesome. Thank you. Now can you share with us a favorite quote, something you find inspiring?

Drew Dudley
I shouldn’t tell so many stories, I know. Here’s a quick one from the book though about the word favorite.

Two World War II veterans told me you should never use the word favorite, best or greatest because it diminishes everything else in your life that isn’t the best. They said draw what they call the great line and all you ask yourself, it’s not where does that rank in terms of all the things in my life, best meal, favorite quote, greatest sunset, just say to yourself, that’s above the great line.

Because there’s an unlimited amount of things that can go above the great line. There is only one greatest. He said to me “Drew, greatest is the enemy of great because when we focus on the greatest, we diminish all the great.”

I will probably give you more than one answer for these favorites. I’ll try to limit it to two. When it comes to my favorite – you asked for quote, right?

Pete Mockaitis

Drew Dudley
Two. The last thing my girlfriend ever wrote to me was “I want to build a better life for myself and a better self for my life.” She passed away just a couple of days later. That – it’s so odd when the greatest summation of what you try to teach in the world is summarized by somebody else. “I want to build a better life for myself and a better self for my life.”

The other one is one that she and I shared. I actually have – well, I actually have hers tattooed on my arm and I have this one tattooed on my leg. It’s from Hamilton by Lin-Manuel Miranda, “Look around, look around at how lucky we are to be alive right now.”

Pete Mockaitis
Awesome, thank you. How about a favorite study or experiment or bit of research?

Drew Dudley
That’s going to be Jim Kouzes and Barry Posner work in the book The Leadership Challenge, specifically around personal value clarity because what they found was – they identified five exemplary practices of leaders. I highly recommend the book. But what they really showed is that individuals who are clear on their personal values have higher levels of commitment, pride, and happiness at work.

That’s much more co-related than clarity on organizational values. If you want to be happy at work, proud of the job that you do and a better overall work experience, get personal value clarity in. The book The Leadership Challenge talks about how those things are linked.

Pete Mockaitis
Thank you. While we’re at it, how about a favorite book?

Drew Dudley
Oh gosh, The Five Dysfunctions of a Team by Patrick Lencioni. Also Silos, Politics and Turf Wars. Good to Great is the best business book of all time.

Hey, there’s one I’ll recommend to everybody, which is Why We Sleep: The Power of Sleep and Dreams. You will get eight hours of sleep a night when you read that book. The number one resource that will make us better that we’re ignoring is sleep. We all know it, but when you read this book, you realize you’re not going to deny it anymore. It’s scary for individuals who get four hours of sleep a night.

Pete Mockaitis
It’s funny, when I tell people “Oh what do you do?” “I have a company called How to Be Awesome at Your Job and a podcast.” “Oh yeah, so what’s your top tip?” “It’s like well, it’s hard to condense over 300 interviews into a top tip for you, but since you’ve asked, it’s sleep.” Yeah, I’m right with you there. How about a favorite tool?

Drew Dudley
Tool? What do you mean by tool?

Pete Mockaitis
Like you’re a tool Drew.

Drew Dudley
Well that’s got to be like – I love a hammer, a good quality hammer. Actually those little multi-tools or did you mean favorite tool to use for success in life.

Pete Mockaitis
Well, yeah, something that helps you be awesome at your job.

Drew Dudley
Exercise. The endorphins – your body is the greatest tool. I used to be 300 pounds. I lost 100 pounds. I had a good job and liked what I did before that, but I am 1,000 times better when I realize that the greatest tool you were ever given is your body.

Look, do not hate your body, but do not lie to yourself when it’s unhealthy. I lied to myself for a lot of years that my body was unhealthy. The greatest tool that I have is my body. It’s one that we all have. Exercise is a profoundly good tool.

Pete Mockaitis
Is there a particular nugget you share that really seems to connect and resonate with folks?

Drew Dudley
Two things. When you don’t know what to do in a situation, ask yourself what would the person I want to be do and do that.

Three words—these saved my career—elevate don’t escalate. When you’re getting trolled, when you get an email that pisses you off, three words, elevate don’t escalate. Leaders elevate situations. They never escalate them. Elevate means trying to succeed and escalate means trying to win.

Those three words over and over again, elevate don’t escalate, elevate don’t escalate, I repeat them on a loop and it’s gotten me out of some trouble because we’re the only creatures on the planet with a gap between stimulus and response. Your career and your relationships and your life is in large part determined by how you use the gift of that gap.

Pete Mockaitis
If folks want to learn more or get in touch, where would you point them?

Drew Dudley
DrewDudley.com. D-R-E-W-D-U-D-L-E-Y.com. You will notice that all of the words on that webpage have u’s in them though. Humor has a u ladies and gentleman. Come on, stop I don’t know why you Americans are so exclusionary sometimes. Embrace the u. Embrace the u.

Pete Mockaitis
Colour me embracing. I couldn’t resist.

Drew Dudley
That’s not really cool there, eh? Don’t be doing that.

Pete Mockaitis
Do you have a final challenge or call to action for folks seeking to be awesome at their jobs?

Drew Dudley
I do, number one, by the end of today make sure you have an answer to this question. What have I done today to recognize someone else’s leadership? That question you answer for 30 days, you journal how you answer it. Your job’s going to get better. Your relationships will get better. Your career will get better and your life with get better. Leadership recognized is leadership created.

One of the best things we can do to make our lives better and our jobs better is to start to recognize all those moments of kindness and compassion, that person at the coffee shop who knows your name and smiles at you every day, the custodian at your workplace that keeps the place spotless every single night, the receptionist, who thinks she’s just a receptionist, all of those people make your life, your job, better.

Take a moment and recognize that as leadership because we continually do the things that make us feel good. When somebody tells you that when you do this it’s having an impact, you’re going to do it more often. Be the catalyst for making that happen. What have you done today to recognize someone else’s leadership?

Pete Mockaitis
Awesome. Drew, this has been a ton of fun. I wish you all the best of luck with Day One Leadership and all you’re up to.

Drew Dudley
Oh, my friend, thank you so much. It’s been a blast.

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