SPP: So I guess we’ll just start it off I was hoping to first learn a little bit more about what you do. I’ve watched many of your videos, Jon has as well read up on you, but obviously some people might not know. So wanted to talk about what you do and then after that I guess we’ll get into how you got there.

Drew: Sure. You know what I do is changing every day. I guess the best way of describing what I do is I just get to do what I love. I accidently stumbled into the fact that apparently I can say things that people felt were worth listening to And I often joked that I was 27-years-old before I discovered the thing that I was born to do. Because I think I was 16-years-old I went on stage to do something or another in high school and totally froze up, like just the most mortifying freeze up of all time. And I don’t think I went and did something formal on stage for quite awhile after that.

And eventually I was asked to come back and do something when I was a professional fundraiser for my old university. They asked me to come out and talk about a few projects I started back at the university. And I said yes because I was into a girl. Like all of the things that change so many men’s lives it was a woman. And I was totally crazy about this girl at my old school who was still out there.

And so I decided when they called and say “Hey, would you like to come and talk about some of the leadership ideas that came out of” – I worked a lot with fundraisers. I did some things with the Canadian Cancer Society. We lost a friend of our to cancer and we started a project for him. We lost a roommate to a car accident we started a scholarship fund for her. For years at that point I’d been involved with a charity here in Canada called a Shinaramus Students Fighting Cystic Fibrosis. And they asked me if I’d come back and talk about the initiatives we started as fundraisers. And honestly all I could think of was sweet I can go to dinner with this girl.

So I said “Yeah of course free flight, who’d say no to that?” And as soon as I hung up the phone I thought oh my God I actually have to give a speech. You have absolutely no idea what you’re talking about. You should have though this through. And I ended up going out there and talking about a few ideas that popped into my head as a result of listening to the music of some of my friends because of the musical project we created in honor of our friend Jason was a compilation CD of university music.

And so I started talking about how some of the lyrics connected me to ideas about leadership. And I was so nervous and so terrified. And I stepped out on the stage and it was being hit by lightning. And I said “I have to do this for the rest of my life, it’s amazing.” And a friend of mine ran backstage afterwards and got this really long standing ovation. And a friend of mine ran backwards and said “Hey I didn’t” know you could do that” And I said “Neither did I but I need to do it consistently from now.” And he said “I just have one tip for you.” And I said “What?” And he said “You’re going to make it shorter.” And I said “Well I have like an hour and fifteen minutes. How long did I talk?” And he said “Two hours and forty-one minutes.”

SPP: What?

Drew: Yes. And he goes nobody went to the bathroom my friend, it was the most amazing thing I’ve ever seen but never do it again. And that was it was just a realization that I love doing this. And apparently some of these ideas most of what I talked about were things that I’d screwed up. Ideas that I wish I’d known as opposed to here’s what got me here. It was more like here’s all the things I’ve tripped over on the way here, and if I had a chance to walk through this minefield again here’s where I wouldn’t step. And it seemed to resonate with people.

So that made me realize I wanted to move from professional fundraising at the university into leadership development. And I started to build the program at the University of Toronto Scarborough. And that got larger and larger and eventually on the side I kept doing this presentation. These workshops that’s facilitating. And I got to develop new ones through running the program at the university along with working with these really extraordinary people. And the next thing I knew I was making more money and having more fun on the weekends than I was at work. And so eventually it just became let’s do this. Let’s take the plunge.

And I was so poor when I left. I hadn’t save up any money really and I moved out back out of the east coast in Canada, which I was in love with, and no money at all. And I remember because I was doing presentations but universities pay you like six weeks later. So for one week of every month for the first two months someone had to buy me food. And when I ended up going to speak at TEDxToronto, which eventually became the talk that ended up on TED.com, my shoes are stapled together during that presentation. I was having the time of my life, I had no money, I had no idea if it was going to work out but I never felt more free, never felt happier.

And I’m up there with these stapled together shoes and I gave that talk. And so many people had a chance to see it. And the next thing you know it became a reality that I get to do this for a living. I get to talk with individuals and organizations, schools, colleges, universities, high school students, to come in and talk about redefining leadership. I think leadership development is important, but I think the first concept we have to work on is that the reason that most of us start at a step back where we have to develop into leaders the reason we say that is because our definition of leadership says that we’re not a leader right now. And so much of the work I do with Nuance first it was just me and now what we’ve done is we’ve created a roster of speakers and facilitators who can help organizations sort of foster that idea amongst whether it’s their students, whether it’s their employees, their upper management that the most successful organizations are going to be the ones who create what Robin Sharman calls Leaders Without a Title at every level.

And the Number 1 way to do that is to make people realize that they really don’t have that far to go to be a leader. In many cases they don’t have to go anywhere they simply have to realize they’re already there. The idea of leadership isn’t about getting better it’s about realizing there’s nothing wrong with you. And changing the way you think and how you perceive yourself so that you remind yourself of that more often. That’s really where leadership starts and what I do. I mean this is a long answer I’m so sorry.

SPP: No, no.

Drew: Really what I do is I try to create through my own work and through the work of other brilliant people I’ve met is I try to help connect people with others who can open their minds to ideas of leadership they may not have considered before because we have such a narrow focus on it if we can create more ideas of what leadership means it’s more likely that one of those ideas is going to connect with an individual and make them embrace the idea that they are actually a leader.

SPP: Actually that’s good that we kind of transitioned into the topic of leadership, because without really thinking about it on a day-to-day basis leadership is something that I think we take as this abstract idea or just not even abstract. It’s just you don’t dive into the subject too much. Like a leader is the general on the battlefield or the CEO of a company, or something like that. And you have a little bit different take which is when you think about is really enlightening. Could you kind of talk about what you think a leader is and how they come about I guess?

Drew: Sure. I think that over a long period of time, obviously you can’t do this job and not have somebody say “What is leadership?” And that’s tough because it is a constantly evolving concept. And right there things differ from the way people traditionally think of it because it is positional and it often has been positional and it often has been where it fits in a management or bureaucratic structure.

I think that leadership is striving to act every day in a way that makes it more likely. You’ll have a positive impact on your own life and on the lives of other people. And I say striving to act every day because we will fail sometimes. Even with the best of intentions sometimes what we try to do won’t work out, but I think if you strive to act every day in a certain way more days than not you’ll succeed. And I say makes it more likely you’ll have a positive impact on your own life and on the lives of others. Because there are times that even when you do everything right it doesn’t work out.

So for me that’s the definition of leadership is if you aspire to be better you inspire the people be around you to do the same. That’s a very broad definition. I’ve actually sat in meetings with senior academics who say “Well Drew if you define leadership that way everyone can be a leader. And anyone who’s responsible for knowledge generation is a leader.” And they say it in such a dismissive tone as if it’s ridiculous.

I don’t get why that’s a ridiculous concept that everybody can be a leader. I think that we all are because I think that as long as we see leadership as these positional things we’re saying very few people can do it. And that’s unlike any number of things in our society. For whatever reason we have agreed to live by rules and by definitions that say “A very small number of people are valuable.” And that boggles my mind. The whole education system does it. We start ranking and grading people because why would we do that if it wasn’t to give people the top something people at the bottom didn’t get?

So Ken Robinson will say in his phenomenal TED Talk we’re rewarding one type of intelligence in education and only people who can write tests and essays well are seen as valuable in the education system but they’re a relative minority. And yet everyone in the system, kids from every age and the teachers too, seem to accept that okay that makes sense. We look at a world where let’s say we strip away jobs and money, and I know that’s a crazy idea, but let’s say that hypothetically we strip away money and jobs, that you couldn’t use those to evaluate people. If that was your reality, who would you look up to? And those people are leaders. And that’s it. Like who lives the life in a way that you would look up to if money and jobs were not part of the equation.

And my argument is that those people influence us so positively every day, but for whatever reason we agree to live by these rules that say “Well they’re not as valuable as people who are tall, who are good looking, who make a lot of money, who are straight, who are white”, any number of things we agree to these rules that say this small number of people are valuable. How on earth the majority has agreed to a set of rules that say they’re not valuable boggles me?

So for me leadership is recognizing that every single individual whenever they make something positive happen for their own life or the lives of other people. And when I say their own life I mean in a way that isn’t self-centered, but they take steps to live the best life that they can. I think that that’s leadership. And I realize that it’s positional and it’s not traditional, but positional and traditional has gotten us into a place where very few people are seen as valuable, not only by society but by themselves. To me that makes no sense and as long as it makes no sense I think we should change things. Lily Tomlin I remember said – I don’t remember it but I remember reading it – said that “I always wonder why somebody didn’t do something about that”, and then I realized I’m somebody. And for me I took a look around and said “Look traditional led to so many people feeling like they’re nothing, so many people feeling like they don’t matter, and so many people treating each other like they can be stratified based on these ridiculously arbitrary measurements.” Well that makes no sense. So what’s a better solution because I don’t think you can just whine about something without thinking of a better solution?

And I thought well look at these people I look up to. And if you stripped away money and jobs I’d want to live like that. The only reason I don’t say “Oh I wish I was them right now”, is because well they don’t have all that much money. A janitor at my high school named Mr. Kiff and he was this remarkable man. And he smiled at everybody and he knew everybody’s name. He knew which kids were being bullied and he’d be friends with them. When people would lose a family member he’d anonymously leave these calls at their locker. And I just remember thinking this is such a remarkable guy.

And I went back and I was there because I’m speaking there at my old high school in a week or so, and I went back and I saw him and he gives me this big hug, and he says “Drew.” And I said “Man I can’t believe you remember me.” And when I said “I think of you so fondly all the time, you really are an amazing man.” And he said “Ah I’m just a janitor who knew you guys before you made it to the big time.”

And I thought man just a janitor. If I could strip away money and jobs I’d want to be like Mr. Kiff because he’s got all these amazing people he’s been friend with over the years, these students who’ve gone onto all the things that we value in society, doctors and lawyers and architects and CEOs. And when his name gets mentioned, if his name was mentioned in one of their offices 20 years after they last saw him, people would smile.

And I think that’s a great measurement of leadership is how many people would smile if your name was mentioned in a room you’re not even in 20 years after somebody met you? And that man that’s what he has. And I don’t see how that’s not a leader. And the only reason that I don’t say “Wow that’s the life I want”, is because somewhere along the way we said “Well what he does for a living isn’t as valuable as what I do.”

So what I did is I said the traditional definition of leader doesn’t work for me. It excludes too many people, it makes too many people feel like they’re less than they are, and there are too many things in our society that lead people to feel like they’re less than they are and I don’t understand why somebody doesn’t do something about it. All I know is that I’m somebody who wants to do at least my part about it.

SPP: Absolutely. And what kind of response do you get when you go and you speak at these schools, whether it be middle school, high school, college, university level? Are you surprised by the response and reaction that you get after people hear you talk? I guess what is the thing that kind of blows you away after you give these talks and then talk to these students?

Drew: Wow that’s a great question. The whole idea that we get to do it or that I get to do it blows me away to be honest. And the fact that so many people are eager to hear it. And I don’t mean before I say it but afterwards it seem like they were eager to hear it all along but might not have realized it. I guess the biggest thing that blew me away is this. When I started to speak I figured that the most powerful things that you could get an audience to say to themselves was, wow I didn’t know that.

I realize now that the most powerful thing you can get an audience to think to themselves is oh my God I thought I was the only one. And I didn’t realize how powerful this idea that we are being taught lessons. They’re never explicitly taught but they are learned in our education system that says this is what’s valuable and the rest of you aren’t. And there’s a tremendous impact on how people feel about themselves as a result.

And there’s a very small number of people who put up their hand when I say “How many of you are comfortable calling yourself a leader?” And it amazes me how big a difference there is from beginning of presentation to end on the number of people who are willing to put up their hand just because somebody said it was okay to think what they already thought. I’m not telling anybody stuff that most of them don’t already think. What I’m telling them that I think is that I hope I’m letting people hear somebody else with a microphone who has lived within schools, and who has been some modicum of what is traditionally considered successful. They’re getting to hear somebody else say what they always thought.

And that’s what blows me away is how many people actually already think this. And for whatever reason have sort of pushed it off to the side and thought well that makes me kind of crazy. And how easy they respond when they’re like, oh my gosh somebody else thinks it too. And my question that still baffles me to be completely honest is if this many people think it why is nothing changing? And that’s something that what I love about my job is exploring with people. 1) Why that is, and 2) what we can do to change that.

SPP: So do you think that oftentimes you’ll speak with like you said high schoolers, college students, things like that. And at that point people haven’t necessarily been out in the real world been exposed to a lot of, I don’t want to say difficulties because everyone has, but just real world experience per se. Do you think that by saying everybody you’re leader is a little too feel good almost like maybe they aren’t a leader? And I’m just asking to see the other side of it maybe they don’t live their life in this way that is so giving or motivational, or things like that. Do you at all say “You have to work hard for this to be true to you?”

Drew: No and it’s a really valid point. Like I want to be very clear I’m not all sunshine, lollipops and rainbows. I mean people call me motivational speaker and I wince, probably for two reasons. 1) I grew up in a generation Matt Foley and Chris Farley playing Matt Foley. The whole idea of motivational speaker then down by the river, God help me if I’m ever that.

The second is this I find that motivational speakers they go after the emotions first. Like what they’re focusing on is how people feel. And I think that’s phenomenal > but what I try to get is to get at how people think. And I hope that I appeal to people’s minds first and then what we get them thinking affects how they feel. So there’s an extra step in there you want to go through the brain first down into the emotions, as opposed to just appeal to the emotions, so not all sunshine, lollipops and rainbows.

I hope people feel good and recognize but I also want to – I do acknowledge this is a real world out there and you can’t just go around and think that as long as I try to make little lollipop moments happen my life will be okay. Although I will tell you that the more you focus on it the more likely your life is going to be okay. But I did have a student come up to me. And business students man they’re a special breed business students, and I spoke once and he came up to me at the end of it.

And he said “Drew I’ve seen you speak three times.” And I said “Oh great.” And he said “I really like some of your stories.” And I said “Wonderful.” And then he drew a complete curveball and he said “Do you want to know what’s wrong with you?” And I mean who wants to turn down the chance to hear a complete stranger tell you what’s wrong with your right.

SPP: Yes.

Drew: And so I said “Fire away man.” And he goes “You never tell anybody how to win.” And I wasn’t sure what it meant. So he said “Look this is a competition”, this is a game and we all know it. And we’ve known it from the first time we were graded. If we’re getting ranked why else would we be? And he said “This is a game and there’s only so much money, and there’s only so many jobs, and if I don’t get it somebody else will. So you’re not doing anybody a favor by telling them that the little things matter. You’re not doing anybody a favor by telling them that it’s who they are and not what they do that matters. All you’re doing then is making sure they get run over in the game.” And so stop telling people something that’s going to get them hurt and tell them how to win the game. And I mean that was kind of a shot right.

So I thought about it because the last thing I want to do is hurt people, but I honestly think that he’s right in that he’s right in that I never told anyone how to win that game. But I think that’s because I think the only way to win that game is not to play it. And I talk about what I call an Economy is Scarcity. And I think that looking at the world as if it’s a game leads us to believe that it is a world of scarcity. There’s only so much but if we look at it as being an economy of abundance. And I think what you’re asking it’s a really valid question is that, look people do have to live, and they do have to get jobs, and they do have to work hard, and I don’t deny any of that.

But my point is that what we do is we say that working hard means that you make a certain amount of money or you get a certain job. And what I’ve discovered is that money and titles make lousy goals because you’re not in charge of any of them. And this is what I want to tell students. I don’t just say “Do nice things.” But my point is that what I want them to do is re-shift what it is they’re chasing because I think if they re-shift their goals or if they shift their goals what they’re going to do is the pursuit of their goals will become much more productive financially and emotionally, psychologically, and intellectually.

Money and jobs and titles are lousy goals because ultimately you’re not in charge of any of them. As long as you work for somebody else how much money you make is going to be somebody else’s decision. How hard you work and how well you work is going to play a role in how much money you make. But if you think about it ultimately how much money you make is somebody else’s call. And whether you’re promoted or you’re given more responsibility that is because someone else is in a position to decide that for you. And I think that as long as we tie our live goals to somebody else’s whims it’s tremendously disempowering.

Like I went and I realized that when I worked for somebody else that what I was doing was going to work every day to try to please somebody that I worked for so that they could give me my life goals, money and titles. Like somebody else had to give me my life goals.

SPP: Right.

Drew: And what I realize now is that we will never feel like leaders in our lives when we feel like everything that we really want has to come from somebody else, so my point that I try to tell individuals is that I’m not trying to tell you a different way of living than getting a job, working incredibly hard, and trying to do well. I’m saying make your goal in life to add tremendous value. This idea that leadership is adding value, if you add value in interpersonal interaction you’re going to make more money, you’re going to get better jobs.

And the thing is adding value, the ability of giving something somebody they didn’t even know they needed or something they didn’t even know they wanted every time you interact with them, if you do that everyone can do it, not just people who can write essays well, not people who can write tests well, not people who just people who went to Ivy League schools. Everybody can add value in interpersonal interactions. My point is that when you do that, when you make that one goal to add value as opposed to money and jobs, if you treat adding value as your goal which everyone can do, which isn’t the case with graduating Harvard not everyone can do that, but every can add value. So let’s make that the goal and let’s treat money and jobs as an a natural byproduct that will come from adding value. So work hard, do as well as you can, and I’m not saying that as a soft way, do as well as you possibly can as you get ready for the world, and work at jobs. But don’t make money the goal make adding value the goal.

If you’re great at that money and jobs will be the natural byproducts that come from adding value. And as a result when I talk to students my point is this, you should work incredibly hard to make your grades extraordinary. Report cards and transcripts students are obsessed with these things. They’ve been obsessed with them since they were little. What I try to tell them is that you should work incredibly hard to make your grades extraordinary, but the part that I wish was in 10 foot letters on the wall of every school is I wish I would say “Work incredibly hard to make your grades extraordinary and then work twice as hard to make them the least impressive thing about you.” And if you do that I think that leadership and success will follow you all the days of your life.

And so I don’t tell people that it’s all light and fluffy and that just be nice and it will all work out. Being nice it’s a responsive thing, adding value in work, in play, in relationships, being conscious about that and figuring out the skills and the education necessary to add the most value in whatever way you can, that is hard work and that is what education is about. So that’s what I tell people because I think if you add value, what I am telling them is that that’s still how to make money, and that’s still how to get great jobs, and most importantly that’s still how to be happy.

SPP: Right. See and I really like that description, I like the way you went about it even if starting talking about the game, because I think even in my life I started in my professional career started off thinking it was a game. Let’s go the route of just trying to make as much money as blah, blah, blah. And t hen struggled with that. And people said “That’s not what it is.” Do you what you want to do like life is good. And so then I went the complete opposite end of the spectrum and I was like fine I’m going to do what I want to do and I’m going to sleep in and life’s going to be great. And then I realized okay I’m on the right mental track but now I’m not putting in the effort.

And I think it finally took the realization that it’s both. It’s like you said “Don’t play into others games like really know yourself.” Which God how cliché is that? And then work hard as hell towards what you want to be not what other people tell you or things like that. So it’s kind of, maybe it is a game but your own game you made up.

Drew: And yeah and the rules are different. And I think the big one is that that’s what I think some people think when you say “Oh well don’t play the game.” I’ve often said the only difference between a cubicle and a cage is that a cubicle doesn’t have a roof and a door that locks. And most of the reason is because you haven’t shown the company that you deserve it yet. Like the idea that the only real difference between an office and a zoo is that in a zoo they never let the animals out at the end of the night, expect them to feed themselves, and then come back the next day.

So I don’t go around saying “Oh just like screw off. Do whatever the heck you want and sleep in all day and play freaking Xbox or go live in a mountain.” Okay because you know what, that doesn’t add a lot of value.

SPP: Right.

Drew: That’s the big difference between saying don’t play the game. Well if you’re not going to play the game what I’m saying is that the way to win the game is not to play by someone else’s rules but in fact to change what your goals are, which is become someone who wants to add tremendous value. Now you just screw off and play Xbox all day you might be adding value to your life, but you’re not adding a whole lot of value to the world.

So my idea is let’s identify what it is that you can add the most value at. And what I found the education does is it keeps telling people if you just work hard enough it will all pay off in the end right. But we don’t tell them how hard is hard enough and we don’t help them with what they want the payoff in their life to be. We don’t tell them when the end will come. We just say keep working hard and it’ll all pay off in the end. And they believe that the payoff is a job, that’s the ultimate thing.

Now the problem is that school grades you on a certain type of intelligence again and it tells certain people that what you are good at isn’t really a gift. It says the role of education is to figure out what the market values so you can learn it and then offer it back to the market. And we don’t care whether or not it’s something that you are good at, something that you love, something that you’re passionate about or something you’re gifted at. And what I like to say is the worst thing of all is that it tells people who are musicians and who are artists and entrepreneurs, and change agents, it tells everybody who’s brilliance cannot be measured on essays and on tests it says to them, well you know what your gifts aren’t gifts at all.

You see they’re only gifts if one day they can monetized, otherwise they should just be hobbies. And many of the people in our education system the students that I work with, the greatest value they can add to the world is through some sort of activity that isn’t what’s marked in elementary and high school. Whether music is the first thing cut, drama is the first thing cut. What are you going to do with those things? That question what are you going to do with that it just makes me want to tear my hair out. What are you going to do with a philosophy degree? I don’t know you happy. If philosophy is the way that you enter the world, if philosophy is the way that you’re going to be able to change an impact on most people that’s adding value. And if philosophy is the avenue that gives you the way to add the most value my argument is that you should try to do that as much as you can. Now you may not get paid for that your whole life, but as Seth Godin said “Your art is anything that you put into the world that changes people. And even if it’s not what you get paid for make sure you keep sending it out into the world because one day someone will pay you for it.”

And that’s what I did and I honestly think that’s true. The problem is so many people give up on what they’re passionate about and what they’re gifted at because early on in life they’re told well you won’t make much money at that. And so they shove themselves into these places where they’re extremely unhappy. And an unhappy life is never a successful life.

Leadership to me you can’t lead other people until you lead yourself right. And I think a big part of leadership is asking yourself honestly in what part of my life am I settling? Am I settling for my relationships? Am I settling for my job? Am I settling in my health, whatever it is and then not being willing to settle. I don’t try to tell people to not strive, achieve everything they can. I’m just saying to make sure that whatever list they’re trying to fill out of the things they need, they think their life has to be to be a success, I’m just saying please make sure that you wrote the list. Because if you spend your life chasing a list of other people’s goals you’re always going to fill unfilled.

And leadership to me before we can start running companies and leading troops into battle, which is a form of leadership, I mean before we can do any of those things I think we have to be willing to lead ourselves in a direction that will allow us to give the most to the world. And I’m not doing that in a cheesy charity way I just mean we are what value we add, and value isn’t just profit. Profit is only one type of value.

SPP: Right.

Drew: But along the way we teach people that it’s all about profit and I want to try to let people know that the key to getting the most profit, financial or otherwise, is adding the most value. And people right now are told that sacrificing whatever they’re best at in order to do whatever they think is going to make the most money is how they chase value, and that’s not the right path.

SPP: Yes and this is one of the themes that we have on our podcast where a lot of the guests that we have on here have chased after their dream and their passion and started working around that. But one of the questions that we don’t really ask that often is, what advice would you have for our listeners who want to take that similar road that you have where you’ve chased after your passion and you’ve created work around it? What advice would you have for them to just going ahead and taking that plunge and doing it; a million dollar question.

Drew: Well I think you hit it right there the whole idea of do it. I guess my advice first of all don’t take advice from people who are really eager to give it, I guess is a cool way of doing it. I guess a couple of things. One you’re not going to starve to death. I think that is something that I realized that you have people who care about you and if you have people who care about you do not be afraid to try it. If you’re alone, if you’re truly alone you need a support system to go out and take a shot at things. Because as long as you have a support system, as long as you have friends, as long as you have family who care about you, you will not starve to death. You can’t do it.

I mean I knew I wasn’t going to be homeless. I knew that I wasn’t going to starve. I realize that the only thing keeping me from going after what I wanted to see if I could make a living doing what I love. And I think if you’re good at something and you love it you owe it to yourself at least one in your life to see if you can do it full time. I realize the only thing that was keeping me from doing it was not a real fear that I was going to starve, it was not a fear I was going to become homeless, which are really the only real threats physically right.

SPP: Yep.

Drew: I realized the only thing keeping me from doing it was a feeling that I might end up looking in the mirror in six months and say, “I expected more from you by now.” The only thing that I was afraid of is me looking at myself and saying “I expected more from you. That’s all that it was.” And I had to realize that that means that I was the only thing that could hurt me. And I realized that if I looked at myself in six months and I was still doing a job that made me miserable then really would that not be the reason to look and say “I expected more from you?” I don’t know the secret to happiness guys but I swear to God the secret to sadness is when there’s a gap between the person you envision yourself to be and the way you’re actually behaving.

And I never saw myself as somebody who would accept less. I never saw myself as somebody who would settle, and I knew that if I looked in the mirror in six months in a job I hated I would say to myself “I expected more from you.” And I realize the only reason I wasn’t taking the plunge was because that was the only thing that could hurt me. Because as long as you’ve got a support system you’re not going to starve and you’re not going to be homeless. All that you might end up is feeling like you’re not where you’re supposed to be. And if you can make yourself okay with that then go for it. And you realize that you’re going to feel just as bad if you don’t go for what you care about. The other one is this is that I think in every piece of success there are 5 Steps. And right now I know I feel terrifyingly like a motivational speaker with the 5 Steps, so bear in mind that’s not what I’m trying to do. But somebody asked me in an interview the other day like what are the 5 Steps that you think you would tell people to take? And I am giving such a bad interview that I was desperate to come up with something even remotely useful.

SPP: It’s torment.

Drew: And so I said 5 Steps. And this is what I tell people too. The 5 Steps of everything I’ve ever cared about went like this. The first step which is the tough one, you like to start down the path when you don’t know where it’s going to go. So Step 1 the most important step in everything that you ever care about is going to go through this process.

Step 1 Starting So Hard. Aaron Sorkin was one of my heroes and says “I love to write but I hate to start, because there’s nothing scarier than a blank sheet of paper.”

SPP: Yes.

Drew: So Step 1. Then there’s the Second Step, which is also terrifying because you want to go back because now you’re out there. And the second step is the one that you take when there’s no going back. You feel like you’re cut off and this is it. Then there’s the wrong step, which is the one that goes down the wrong path. And that’s the one where you recognize that wow this isn’t the way to go. And then there’s the step backwards.

And it’s hard to take that step because we equate change with failure. And we think that adjusting is failure. And it’s with this political crap where we say somebody flip flopped. Well sometimes people change their opinion so they can get elected. That’s one thing. Sometimes people change their opinion because they learn the more. And this idea that we treat people who adjust midstream or who do one thing and then choose to do another, we treat them as if they screwed up the first time.

Well a lot of reasons we don’t change our lives is because we think that we have to admit to ourselves and everybody watching we screw up. If we change what school we go to, if we change who we’re dating or we marry, we get out of a marriage, we change jobs, we think that means we have to admit everyone watching we screwed up the first time.

The Fourth Step is the step back. It’s being willing to say there’s nothing wrong with recognizing when you went down a wrong path you can just back it up.

And then the Fifth Step is that difficult step that you take when you know that you already took a misstep so that there’s a possibility that you’ll end up taking another one but you do it anyway.

Those are the five steps. The first one, the second one, the wrong one, the step back, and then the step into the unknown knowing you’ve already screwed up once. Those are the ones everybody makes. And somebody said to me once like “What’s your biggest regret?” And it’s one of those questions that we’re so sure we know the answer to we’ve never actually answered it. And I thought about it and it came down to this we can’t screw up.

Jessica Holmes a successful comedian said “That a funny thing happens when you reach your goals. You become terrified of making a mistake.” And I think that this idea that we equate change with failure not failure with failure. And I’m not going to give some speech about how failure teaches you a million things everyone knows that, but I what I found interesting is that we equate change with failure. This idea that if we decide to do something different, that what we’re actually admitting is that we failed the first time. And I think as long as we equate change with failure we’re never going to make it a big part of our life, if that make any sense.

SPP: No it does.

Drew: So it becomes like the thing where we lock into everything. And the reason that we don’t decide to go for it is because inherently starting something new means that you screwed up something before. Very rarely do we look at periods in our lives as being completed. We look at periods in our lives as being missteps. That relationship wasn’t over that relationship was a mistake. And I wonder if many of the mistakes that we make aren’t really mistakes at all they’re just things running their course.

To go back to the point that I realized now is that somebody asked me what is your biggest regret? And I thought about it and I kept coming up with all these things that I really regretted. And then I realized though that now that I’m thinking of them for the first time in a while I’m actually really glad they happened because they led to x or y. Right before I left the University of Toronto I wanted a job somewhere else. And I really wanted it. And I didn’t get it. And I was really upset and it was a really big regret, but if I’d gotten it I wouldn’t have done this.

SPP: Right.

Drew: And I realized if I listed all the things I regret, and I encourage you guys to do it and all your listeners to do it too, start listing all the biggest regrets. The moment at when they happened you were really upset list them all and then look and tell me how many of them you’re still sorry it happened. You wish that you hadn’t been hurt or disappointed, but right now you’re still sorry it happened. For me I did it 80% of the stuff I regretted in my life I was now glad it happened because it led to a new person or a new experience or a new opportunity. And if we look at it like that isn’t it crazy, if 80% of the things I’ve ever regretted in my life now I don’t regret every time something new happens that sucks I can just tell myself well it’s one of the 80%.

If 8 out of 10 are usually something you eventually are happy about well isn’t that enough of a sample size to be like, well there’s an 80% chance everything that doesn’t turn out for me now will end up to be something good. That changes everything right.

SPP: Yes. And it’s funny because I’ve actually gone back and forth on this. You hear that a lot you can learn from your mistakes and things you regret, but then sometimes I wonder what if it’s just a fact that we’re resilient as humans and regardless we’re going to be okay. Because sometimes I go man I’m really glad I didn’t take that job because now I’m at this job which I like for once. And then I’ll go, but what if I took it and on my way to work I bought a lottery ticket and I hit the lottery. So I don’t know if I look at it at just we will get pass these things or if I just go we’re resilient. And so regardless of what happen as long as you approach it with the right attitude you’ll be okay.

Drew: Yes that’s a big one. People love to say “Stuff happens for a reason.” And I don’t know I’ve never gotten next to that in that it seems to me that when we say – because I think you’re right we are resilient. Absolutely the things that bring us closest to breaking I think are the things that will keep us from breaking in the end. And this idea that everything happens for a reason it seems to take like our own credit away from us.

And I’m not saying that if there is a higher power or whatever, they don’t deserve some credit, but everything happens for a reason. So if there’s a big plan and it doesn’t pay enough respect to our resiliency, just like you said I love that word because I don’t think everything happens for a reason. But I think that if you’re patient and you’re resilient enough, everything that happens to you can turn out to have a positive. Now if we say it all happens for a reason well then we’re not giving credit to the fact that we were patient and we were resilient, because it was all planned anyway right.

SPP: Right.

Drew: I think that’s the key is that we are in fact resilient. And I think it’s really important that people give themselves credit for this. Absolutely every problem you’ve ever faced you’ve dealt with. Because you’re still here right, we’re talking right now.

SPP: No that’s a good point.

Drew: Every problem we’ve ever faced you’ve dealt with. You might not be happy with how you dealt with it but you did deal with it. We have beaten every problem that has ever come our way. And why don’t we give ourselves credit for that? And seeing as how we’ve dealt with 100% of our problems why on earth do we not say “Well you know what I’m going to deal with whatever the heck comes next.” Because I have a 1000% batting average, but if we’re not happy with how we dealt with them, we’re not happy with the fact that we got hurt in dealing with them, we somehow act as if somehow we failed in dealing with them.

No everything that we’ve ever been faced with we’ve beaten. We’ve moved through. I’m not saying we moved through with the same person, I’m not saying we’ve moved through and a little piece of us didn’t get left behind, but man we made it through everything we’ve ever faced. So why don’t we give ourselves credit for that?

SPP: That’s awesome. And that’s definitely a good positive thing to leave our listeners here with. Drew I know I asked for 30 minutes of your time and we’ve definitely gone over. We really appreciate that. I had a great talk with you. Are there any Web sites or do you want to plug your Twitter? I mean now’s a chance just to get the word out where everybody can find you anywhere on the web.

Drew: Oh that’ll be amazing. Thanks guys. Yes I’m getting a little crazy about Twitter I’m at @NuanceDrew. And my Web site is www.nuanceleadership.ca and there’s all kinds of information there. And you can link from the Web site to all of my various TED Talks. There’s one that’s obviously been on www.ted.com “Redefining Leadership or Leading with Lollipops”. There’s one that honestly I love even more than that and it’s called “The List” TEDxUWO.

And there’s another one there’s something I care a great deal about now at TEDxQueenView and its hiding out in some obscured corner of the internet with less than 1000 views and that was probably the toughest talk I ever gave because I was talking about how all of this the role that bipolar disorder, because I’m bipolar, and didn’t know it until just a few years ago. The role that all of this played in being a part of my life, for good and for bad. So yeah if anyone wants to share those, those are sort of the things I’m proudest of the opportunity to have gotten on stage and take 60 minutes and cram it down. Because as you guys can probably guess unless you put a hard cap on I don’t shut up.

SPP: No that’s never a bad thing.

Drew: Yes. And www.nuanceleadership.ca, @NuanceDrew on Twitter, and you know what I try to answer every tweet and every Facebook message, www.facebook.com/drewdudley, that I possibly can. It might take a little while but I’m so grateful that people share this idea. That something I said matters. And what I really want to share with people is that you have something to say that matters too. And the thing that keeps us from saying the things we believe in is this belief that somehow we don’t have the right to say it. And the leadership is recognizing that man you do matter. So do it and let’s stop playing by rules that say that so many of us aren’t valuable. And the only reason we can do it is because all of us are like well I’m not enough. Well you know 7 billion personal revolutions who knows what will change in the world right.

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