The Learning Leader Show With Ryan Hawk - 432: Sukhinder Singh Cassidy - How To Take Risks & Thrive (Even When You Fail)

Episode Date: August 15, 2021

Text LEARNERS to 44222 for more... Full show notes at www. LearningLeader.com Twitter/IG: @RyanHawk12  https://twitter.com/RyanHawk12 Sukhinder Singh Cassidy is a leading digital CEO and entrepreneur... with more than 25 years of leadership experience founding, scaling, and advising companies including Google, Amazon, StubHub, Yodlee, and more. Most recently, Sukhinder served as the leader of StubHub, the premier global consumer ticketing marketplace for live entertainment, which she and her team sold for $4 billion in February 2020. Earlier in her career, Sukhinder built Google's business throughout Asia Pacific and Latin America. Notes: "Nothing will ever be attempted if all possible objections must first be overcome." - Samuel Johnson "We think when we do nothing there is no cost." That's not true. There's a cost to standing still. Proximity to opportunity benefits us even more than planning. Sukhinder moved to Silicon Valley in 1997. She rode the tailwind of the Internet and being at the epicenter of it all. Prioritize the WHO before the WHAT. As a leader, watch what you validate with your words and actions. Reward the behavior that you want. If you want to promote taking risks, then reward the people who do that. "You get what you create and what you allow." At one point, Sukhinder went to her boss at Google (who worked with Eric Schmidt) and said, "I'm pregnant, I want to keep running international at Google. I need for you to pay for me and my nanny to travel the world business-class. And they said yes." BIG ASK.  She did the calculus and realized it was a reasonable ask. And they said yes. Career path - "My career is not linear, it's cyclical. It has ups and downs. I've made 13 different meaningful choices along the way." The myth that there is a linear relationship between risk and reward. Not all choices have an equal amount of upside and downside... Sukhinder sas been on the board of Urban Outfitters with Scott Galloway: Should you move to a big city? Should you move to your company's headquarters? Being at the center of the action matters... It helps if you can understand the pulse of HQ How to become a smart risk taker? What are our goals, passions, and values? What are we great at? Look for headwinds and tailwinds - (Join a growing company that has momentum) With that said, Sukhinder went to StubHub and there were significant challenges Over-prioritize the WHO over the WHAT Why did Sukhinder take the StubHub leadership role? It was a calculated risk She missed running a company of scale They needed entrepreneurial and executive energy How do you create an environment for people to take risks? You want people who are "truth-tellers, truth seekers, and authors" Make it safe to take risks -- Reward that behavior. Watch what you validate by your words and actions. Understand the magnitude and the weight of your words. People are always watching how the leader responds, who they commend, what they say... How to go for a job that you aren't qualified for? "The next level of learning is going for something you don't know..." To be a CEO, you need depth AND breadth. You need to expand your skillset. This is the path to accelerated learning. How do you know when you should leave a job? "I like 3-5 year sprints. Are you having fun? Are you making an impact? If you aren't having fun or making an impact, you'll want to leave." Think about: "Who am I doing this with? Are our values aligned?" Why did Sukhinder want to be a CEO? "A little bit of ego" "I was built to lead" "I enjoy being on the hook" People who sustain excellence: They surround themselves with other great people. They don't let their ego get in the way. They don't feel threatened by great people. Career/Life Advice: "We tend to assume that everything is zero-sum. It's not. Choice is a multiplier of opportunity and we get to control it. Make a choice and get in motion."

Transcript
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Starting point is 00:00:01 I think you want to create an environment in which people can be truth tellers, truth seekers, and authors. Most people wake up every day wondering if their leaders really want them to speak up. Do they really want them to ask questions? Do they really want a debate in the conversation? Do they really want a new idea to be presented and interrupt the flow of how the organization works? You have to create a construct in which people feel very comfortable doing those things. And I'd say the best way I know you to do that as a leader is you have to make it safe in little ways. Welcome to The Learning Leaders Show, presented by Insight Global.
Starting point is 00:00:44 I am your host, Ryan Hawk. Thank you so much for being here. Text learners to 4422 to become part of Mindful Monday. You along with tens of thousands of other learning leaders from all over the world will receive a carefully curated email from me each Monday morning to help you start your week off right. You'll also receive details about how my book, Welcome to Management, will help you become a more effective leader. Text learners to 44222.
Starting point is 00:01:19 Now on tonight's featured leader, a great one. It's Secinder Singh Cassidy, an executive and entrepreneur with experience, building, scaling, and leading businesses for more than 20 years, including, Stubhub, Google, and Amazon. She's also the author of a great book titled Choose Possibility, Take Risk and Thrive, Even When You Fail. A few of the topics we discuss the myth that there is a linear relationship between risk and reward. And then why don't we have to be specifically qualified for a job before going for it?
Starting point is 00:02:02 she tells some great stories about that one. And then how to build a culture that rewards smart risk-taking. Ladies and gentlemen, you're going to love it. It's Secinder Singh Cassidy. All right, Secender, I want to start at a specific moment in your career. And this may surprise you, but I know you've heard you talk about this on a stage before. So there was a time when you were working at Google and you walked into Eric Schmidt's office. And you said, quote, I'm pregnant, but I want to keep running our international business at Google. I need for you to pay for me and my nanny to travel the world business class. And they said yes.
Starting point is 00:02:50 And I love this story because it's a big ask, but you have to know at that point that you've earned it. Can you take us inside that room what you were thinking and how you had the guts to make that big ask? Sure. Well, first of all, I want to make sure these stories entirely accurate and sometimes get translated. I actually asked Omid Kortostani, my boss, who also talked to Eric. But Eric was aware. My boss was the chief business officer. And obviously, I had a lot of exposure to Eric Schmidt, our CEO. He was kind of to do the endorsement for my book. But it was Eric and Omead. I was who I asked. And Eric was definitely aware and supportive. So what's going through my head at that moment, and many of you know this, as we, um, have the good fortune to, you know, ascend in our careers if we do good work. Well, I've been married a year. I'm 24 years old, 35 years old. And I'm pregnant. And I've just been in this job. I, you know, I came to Google to run local and maps and be the first kind of leader there. But I'd move over to run international. And my territories were from China all the way to Brazil. So we used to call that rest of world. And then I changed the name to Asia Pacific and Latin America. So what's going to
Starting point is 00:04:02 my mind is like I don't want to give up this job. I mean, you're into this job. But like my God, like I don't want to leave a baby at home. What am I going to do? And so you're right. I could not think of a way to make it work that was good to work for my family. And by the way, even then at home, I'm negotiating with my husband to be like, this one I'm going to ask for at work. But that means that you have to be okay, that we're disappearing for two, two and a half weeks at a time. I'm going to take our daughter with me, which he wasn't particularly happy about, but he supported it. If I can get Google to say yes. And I went into that room, I wouldn't say trepidacious, but I went to that room knowing two things. Number one, by the way, this is a huge ask. To go in there and be arrogant about it
Starting point is 00:04:41 would be a sin. I'm like, nobody needs to say yes to this. But at the same time, I'm doing the calculus that I've been working hard. I think I'm well thought of. I realize that for me to switch out and quit the job is also really painful for Google because I'm just getting going here. Like we're a year into, you know, building this business. And so that calculus has. like what do I have to lose by asking? And again, I definitely give a lot of kudos to Google to saying yes. They did the calculus too and decided that, you know, maybe my work and having me in that lead ship goal was worth it. And that's how that's how we rolled. How to go then once you actually did it? I would say it went. I'll tell you the things that overall it went well. Overall went well. I mean,
Starting point is 00:05:25 don't remember wrong. It was very binary. I mean, we were on or off and my daughter, I think, became an amazing traveler. She doesn't remember it now. She went to every country, like China, Korea. We lived in Hong Kong for two and a half months. And my family came to visit, India, like Brazil. She did all of it. Wow. So I think she's quite flexible as a result, though she doesn't remember that like she was
Starting point is 00:05:43 literally on a plane for the first two and a half years of her life. But interestingly, I'll tell you, the thing that people say to me the most in hindsight and I appreciate this now is that like my daughter showed up with me everywhere, sales conferences, you know, like everywhere. People chuckled because we had a sales conference in China when I was five and a half months pregnant and I hiked up the Great Wall. And people always like, Sukhinder, I remember that you walked at the Great Wall when you were five and a half months pregnant. And I'm like, I don't really, I didn't think that that was that big a deal at the time. But people were like, the fact that you showed up and you did it, like we were impressed. But then like everywhere I showed up,
Starting point is 00:06:21 I think that my organization understood that like it's okay to show up as your full self at work. Like, if that's what it takes to make it work, so be it. So I think I achieved some degree of notoriety, but I hope more importantly, some degree of respect for being transparent about my desire to be both like a mom and just trying to do my best to figure out a situation and like a full-fledged leader. Like, I am not giving up my ambition on this role and I'm going to find a way to make it work. And so I think it ended up having maybe an appreciable difference in more than I realized. at the time and signaling to other people what's possible.
Starting point is 00:07:00 Not that everybody needs to want that. Sure, sure. Yeah. The point that, you know, maybe that it's possible for themselves. Yeah. I just like the thought that you didn't set a limitation, right? You thought like, okay, I'm going to make a big ask, but there's a, I'm going to have a justifiable reason for this ask.
Starting point is 00:07:18 And then you had the guts and you went and did it. And I think that's really hard. You go to Merrill Lynch. You moved to London, right? Then at one point, you're in, within, startups, you're starting businesses, you're getting acquired, you get acquired, your business gets acquired by Amazon. So then you go work at Amazon in the earlier days, right? You work at Google, you become president at Stubhub, and there's other things amidst all this happening to other parts
Starting point is 00:07:40 that I've skipped. A wild career arc and trajectory, can you kind of summarize that? I'd just be curious to hear how you viewed it, the choices you made, like the decisions is why you've made from place to place, because it's a pretty cool, pretty cool linear path. at least it seems like that on paper, but you're the one who lived it. I'd be curious to hear your story of your career there. Sure. So first and foremost, the most important thing is it's not linear. You know what the problem is?
Starting point is 00:08:09 People look at my career or maybe the career of people they consider successful. And it looks linear because you see the points in time that everybody lives, right? Exactly. And I'm the first person to tell you it was cyclical. And I think that's a really key point when we make choices. when we believe it's linear, we actually potentially don't take the risk we should because we perceive other people are peak jumping. One big choice, another big choice, another big choice.
Starting point is 00:08:35 Wow, these guys must be the riskiest people in the world and the best risk takers because they just move from like strength, the strength of strength. And often what we're missing because this is just the way the hero's journey works. And everybody remembers it in hindsight is the big choice. But in between what's going on as big and little choices, some of which deliver and some of which do not. And I think that's such. And so the arc of my career has been cyclical, not linear. And I think that's really an important thing for people to remember. What does that mean? What does cyclical mean? It means that ups and downs. In fact, I mapped in the book. I made 13 different meaningful choices
Starting point is 00:09:09 over the last 25 years. And some were little choices that produced big outcomes. Some were big outcomes, big choices that produced complete failures. Some were big choices that I, that produced little outcomes. I mean, like, if I would have mapped it for you, what you would see is it's big and little choices. The correlation between any single choice and the size of the outcome is not what you would expect. But strung together cumulatively, there is an up into the right pattern. So when you say cyclical, I mean, like if you caught any single choice, I would tell you, the correlation between the risk and the reward was completely unobvious, completely. And that's part of the myth we have in our heads, right? So when I say my career cyclical, well, you can think of it as roughly I've been
Starting point is 00:09:54 everywhere I've been, and that gives me joy. Roughly, I've made decisions and choices based on taking risks not just to an achieve and ambition, but to learn or to, the learning has been a big theme of one I've taken risks. And then there have been to them other kind of things that are important, but I've taken risks to build, to build small companies from scratch or to help, you know, companies that were small get bigger, disproportionately fast, right? So Google, you know, I got to join a company and learn. And like,
Starting point is 00:10:26 and I basically bet on the fact that I thought Google had tailwinds to its business. And then starting completely from scratch businesses where you have to create all the momentum yourself. And you're looking around the world and say, well, I think this is a good idea because what I perceive is that I'm making it up. People are going to want more control of their financial wealth. Oh, this company comes along, you know,
Starting point is 00:10:44 called Yotelie, one of my first startups if it does that. So my career could be summarized as cyclical. Single risk, single reward, hard to find the correlation. You will see the correlation is in the frequency of risk and reward, meaning many choices to unlock a reward. And sometimes the reward was what I thought and sometimes it wasn't. And always building. Always building.
Starting point is 00:11:06 Okay, because building is like, that's what lights you up. That's what fulfills you. It gives me joy. It's a great use of my energy. Of those 13, could you share an example or two? Sure. So let me share one big example to the positive and one big example to the negative. So you talked about the fact that I went to, you know, I was at Merrill Lynch. I was in New York and then in London as an investment banker and I really wanted to be an entrepreneur. My dad always was like be an entrepreneur. I didn't know what. I didn't know how. And I'm in London and I'm restless. I've been there two and a half years. I'm getting lonely. I want to be an entrepreneur. I don't know how. So I quit my job and I went skiing at Whistler for about a month because I wanted to. to learn how to ski. So I went from zero to here. I was a skier. And then I moved to California.
Starting point is 00:11:52 I hung out in L.A. for two weeks thinking like, hey, two to three weeks thinking maybe I want to be in television because I was at, you know, I was at B-Sky B right before. But I ultimately had fallen love with the Bay Area because I saw all these entrepreneurial people. I saw this great lifestyle. I saw great weather. And so I drive my car up the coast from L.A. to San Francisco and I find a job at a startup. And so what are the lessons in that? Number one, I chose to be proximate to entrepreneurship when I didn't know what it meant. So I just was like, I'm going to move here and figure it out. Okay. So people would be that. And by the way, you say, well, it's a big risk because you quit a job and you moved to continents. And I would say that was actually relatively small
Starting point is 00:12:32 risk because I was responsible only for myself. I had some savings. I had 10 grand in the bank. And I knew I was employable. And I knew if I wasn't employable, I had the benefit of having parents who would, you know, support me if I needed. Were you scared? I wasn't really scared. No. But that's because, but that's because to me, to me, it was judged as a little risk. And in hindsight, it was.
Starting point is 00:12:53 I wasn't responsible for family, responsible for myself. And like I said, I had my backup plan was like my parents, if I had to go move home for six months, I can do it. Right. So I always think of that as a little risk. So people would say, well, that was a big career risk because you left a job and you went to nothing. And I would say, well, if you know you're employable and you know that you have financial security
Starting point is 00:13:11 from your parents or something else, a place to live and a roof over your head and food, I'd say that's not a big risk. But other people would say it was. But that risk turned out to the positive for two reasons. Number one, I chose to get proximate to entrepreneurship to learn about entrepreneurship. And that's how I got my own first startup opportunity. To your point, I joined a company, got sold to Amazon as a startup. And I met the founders of that company went on to become angel investors.
Starting point is 00:13:36 And I got the opportunity to co-bound my own company as a result. That's one to the positive. But the second reason that that decision was successful had nothing to do with me. And people think that when we take risks, it's all about us. And I'm like, I moved to Silicon Valley in 1997. If I showed you the graph of internet usage as a chart and what happened, you know, starting in about 1997, is internet usage globally started to accelerate. So I just rode one of those most macro tailwinds of all time.
Starting point is 00:14:06 So people were like, well, you know, you had an explosive crew. And I'm like, hmm, guess what? It's like Nemo on a current, you know, on his way to Australia and has no idea what he's getting caught up in. That was me in moving year in 1997. So we tend to think the career risks we take are all about us. Like I might, it must have been such an Oracle. I was not an Oracle. I wanted to figure out how to be an entrepreneur.
Starting point is 00:14:27 I didn't know that I timed it well. Like, come on. So sometimes what I got right was the internet. Did I get the magnitude of it right? No, I underestimated it by a factor of like a hundred or a thousand or, and so I ended up in a place where there was so many abundant choices that if I failed at one, there was going to be another and another and another. You know, I just was, I had a root, I had so much room to fail and so much room to win because I was just riding a macro trend. So that's it, that's one choice
Starting point is 00:14:55 I talk about. And I think it's really important when we try and find great risks to take. I'm not saying to be uncalculated. I'm saying, hey, take into account not just your passions and what you like to do, step back here, my friends and figure out what tailwinds you want to ride because riding tailwind is actually one of the best ways for us to assess what a good and bad risk to take. Okay. Do you want to share another one? Or is that the reason I ask this, I've had Scott Galloway, a very polarizing guy. He's been on the show and he said one of the pieces of advice he gave to a young person is get to a big city or get to HQ.
Starting point is 00:15:33 What do you think about that advice as of this moment today, getting to a big city or getting to HQ headquarters? Well, first of all, Scott and I sat on the Urban Outfitters board together. Really? He just rolled off. So I know Scott. Oh, wow. I didn't, I didn't realize it. I will say this to Scott.
Starting point is 00:15:49 Scott introduced me to when I have the idea for writing the book. I've had the idea of the book for a while. But a year ago, when I wanted to write the book and I didn't know where to get started, I reached out to Scott because as I said, we sat on the board of Urban Outfit and it finished together. I'm like, Scott, I know you're an amazing author. Like, I want to write a book. And Scott literally introduced me to his agent.
Starting point is 00:16:09 Jim Levine. Mine too. Jim's my agent. Wow. What a small world. I will email him after this. I'm going to record with Jim at the time my next book comes out. But that is, what a small world?
Starting point is 00:16:22 First of all, he's like such a gem of a human being. The best. He is the best human being. Such a good dude. And he happens to be the best agent also. But actually, so Galloway introduced me to Jim. Sorry, that's my aside on Galloway. But coming all the way back, what do I think to, and by the way, Scott's very smart.
Starting point is 00:16:38 Oh, yeah. I will tell you what I believe is right about Scott's wisdom and wrong. In the world post-COVID, the action used to be in big cities. It's not clear if it will again be in big cities. You know what I mean? Like people literally were moving into big cities. I think that post-COVID, what we're seeing is a reverse and all the suburbs are starting to get, you know, people on mass as they decide for
Starting point is 00:17:04 themselves that hybrid work is likely to be a reality. So whether the action is still in big cities, I'm not so sure. So that's my, that's a place I would disagree with Scott. I think it may be for the first time in our careers that not being in a big city may actually be more than okay for our career ambitions. Does that make sense before like all the action is in big cities? So on the big city front, I'm not sure. But let's come to the HQ comment that, that Scott made.
Starting point is 00:17:33 Like it or not, I think being at the center of the action, matters. So what do I mean by that? In a world that's virtual, it's kind of hard for all of us, right? Because I don't even know where the center of the action is anymore. But what I do know is that they're understanding the pulse of what matters to an organization is everything. So I'm going to take Scott's comment and I'm going to extrapolate it a little bit. And let's like, let's talk about that idea of like being the virtual IQ. They're like understanding what the pulses of the virtual HQ, I think is everything. Because I think when leaders in some ways go awry, in execution or what have you.
Starting point is 00:18:08 It's because they are so busy focused on their execution that they don't understand a macro environment in tailwinds and headwinds of what's important to an organization. Does that make sense? Yeah. They're very heads down. So what's the value of being kind of connected to HQ? If you're in like a far office,
Starting point is 00:18:25 if you're in a hybrid work environment, if you're three levels down in an organization, you always want to understand, like, what's the environment and that macro headwinds and tailwinds in your own organization. so that you understand what the agenda and priorities are, and you can fit yourself in that. That's what I call being heads up.
Starting point is 00:18:42 So where I agree with Scott is, regardless of where we find ourselves physically in the world, the importance of being heads up to really what is the pulse, the heartbeat, the importance, the priorities of HQ is really important. And too often people go awry when they're overly focused on their own execution, but they literally cannot fit what they're doing in the context of what is important to the organization. interesting i just thought of that question based on your when you as a way you phrased it as moving to silicon valley being kind of in the midst and surrounded by those people because
Starting point is 00:19:19 i'm a big believer in your who you know you rise and fall to a level of your peer group and whether it's your friends right your boss bosses mentors people in your life so when you put yourself and kind of force that to happen it seems like it increases your odds of good things happening when you do that. Absolutely. So you were probably taking a different place. And you're right. I always say put yourself in, you know, prioritize the who over the what.
Starting point is 00:19:45 Meaning put yourself in the, you know, amidst great people and do great work for great people. It's a very simple philosophy. But it's like do great work for great people. People from whom you can learn, who admire, who accelerate your own capabilities. And quite frankly, they themselves are talent magnets and, you know, are great to apprentice under. So I think that sometimes, by the way, sometimes that happens at headquarters, sometimes it doesn't. So I think the headquarters point for me is an adjacent but different point, but both are true.
Starting point is 00:20:12 Number one, putting like, you know, when I say take a good calculated risk, I think calculated risks that are all about the who are great risks to take. Like if you say, I don't know what's going to happen in this situation, but I'm going to work with somebody amazing, you know, who is the best of their field, who can teach me a ton. There's almost no scenario where that's not a great. risk to take if that makes sense. And like I said, the headquarters point is more about having the pulse of what's going on around you. And sometimes that happens best literally at headquarters, though we're all living in the world today where that may or may not be possible. Yeah. You mentioned single choice. What is the, and this is something you write about in your book, choose possibility. What's the myth of single choice? What's that myth I talked about
Starting point is 00:20:57 earlier, like, you know, just how we want to see, I think there are two myths that dominate our life when it comes to risk taking. One is that myth of risk and reward. If I take a big risk, I'm going to get a big reward. If I take a little risk, it's not worth taking. I might as well go home because like little risk, little reward. And so we never take the little risks because we think it's all or nothing. And we tend to think of as quite binary, you know, small risk, small reward, big risk, big reward. And it's all going to like work out magically. That's one myth. The other myth is is an associated myth, what you call them, and I call the myth of the single choice, which is the world has trained us to believe that the world's biggest risk takers
Starting point is 00:21:31 must have made one mighty choice that is responsible for their success. And the corollary of that is, if it's one mighty choice to success, if I fail, it's going to be an abysmal failure. I'm going to be made or broken by one single perfect decision I make. Does that make sense? And that defines me. when it turns out that almost any journey I know is not only nonlinear in the risk reward relationship, it's about 10, 20, 50 choices before you unlock a reward or the reward you saw.
Starting point is 00:22:01 So we tend to overweight this first choice and we make it so big that we never make it because we think it needs to be perfect. When I'm like, what I understand about risk and reward is, you know, the first move is like one among 10 or 100 or 1,000 or 1,000 you need to make to unlock success. and it's all about being in a feedback loop of choices. So forget this idea of a single choice and embrace the idea that the journey starts with one choice, but quite frankly,
Starting point is 00:22:28 you still have 99 at least more moves to make, you know, to get to where you want to go. So, you know, the myth of the single choice makes us feel like risk is inaccessible because it's one mighty choice and then nothing could be further from the truth. It makes me think of a quote you wrote in your book. It's from Samuel Johnson, quote,
Starting point is 00:22:47 nothing will ever be attempted if all possible and objections must first be overcome. This is, I think, I feel like this is about being decisive and making a choice and not having to have, I mean, Cole and Powell talked about like basically you're at maximum you're going to have 70% of the information prior needing to make a decision, make a call. This is for those people who are always about to do something or, hey, I'm going to do this, or I'm thinking about this, but that they never actually do. do it because there will always be objections. I would love for you to speak to those. We're all that person probably from time to time. Speak to that person who has this big thing they want to do
Starting point is 00:23:28 or even a little thing they want to do, but there's an objection or there are objections that they can't fully answer so they just do nothing. What advice to that person? Well, yeah, a couple of things. Well, first of all, I think we think that when we do nothing, there's no cost. And we think like we can be static and the opportunity will be there tomorrow. Well, what we've learned, you know, what I've learned in a number of business negotiations, including deals that I was waiting to make happen and they never happened because by the time I was ready to do the deal, the partner had moved on or found a competitor or quite frankly, their own business circumstances had changed and now the deal they wanted to do was not one I could afford, right?
Starting point is 00:24:04 I've lived the world of biz-dav negotiations where you think if I do the deal tomorrow, it'll still be here and often that same deal is not available to you. But in our life, it's the same. We think that if we wait, the same choice will be available to us tomorrow. And every condition around us is changing. So there's an absolute cost to staying still, right? There's just an absolute cost. So to somebody who says, I'm not going to make a choice today because I can make it tomorrow, that may well not be true. And to the person who says, I'm not going to make a choice today that's small because I could make a bigger one tomorrow. I'd say like, okay, well, if you're not good at making small choices, what makes you think you're going to be great at making big choices? I'm like, hey, exercise that muscle,
Starting point is 00:24:43 get good at making small choices, practice taking little risks, to deal with little, uncertainties because me, that's the best way you train for the day the big choice comes. You know, you just have more experience and data and pattern recognition. So I feel like when people kick the can down the curb, to your point, it's not because they fear the upside. They know the upside, right? They fear the downside. And I'm like, okay, well, what if I told you the downside of stasis is worse?
Starting point is 00:25:09 And the downside of, you know, the downside of waiting for the big decision is like, you're actually going to be a poorer risk taker than somebody who practice. is taking little risks every day. So I, you know, I'm, I'm quite convinced that the way we get good about choice making is we practice like anything else. You've written about becoming a smart risk taker. And I want to think about this, seconder from two angles. One, for an individual within a business, maybe they're in a leadership role for themselves and their own career and then separately for someone who's leading a large team of people of creating. I know there's two big kind of separate questions, but I know you can tackle both.
Starting point is 00:25:52 But for that second person, it's they're leading a big organization. Maybe they're an SVP or in that role. They have hundreds of people that roll up to them and they want to build a culture of risk taking, of innovation, of making something happening, of not standing still. So let's start with the individual first and maybe tackle the leadership position one, second, when people report to them because I think this is a big key for you is how to become a smart risk taker. Absolutely. And I think you noted that's so important. And by the way, if you want to know what kind of a risk take you are naturally, you can go to the website for the book, Choose Possibility.
Starting point is 00:26:28 And there's a simple risk quiz you can take that helps you sort of identify what kind of are maybe your natural style of choice making. So that's a fun thing for you to do if you'd ever like to figure that out about yourself. Choosepossibility.com, right? And there's a risk quiz on. Risk quiz. Yeah, which would be really good. So for the individual, I think, who is sort of thinking about that becoming a calculated risk taker, right? Not a rash risk taker, but a calculated one. I always say there are four big things that we need to know to be smart risk takers. Number one, clearly, what are our, you know, what are our goals, passions, and values, right? And so, of course, you, you know, we can identify our goals, my goals to become a CEO, my goal.
Starting point is 00:27:07 That's one piece of it, right? But the other things we need to know about ourselves are what are we uniquely great at because when we align our choices with what we're uniquely gifted at, right, we increase our probability to success. And that third part of what I call that self-awareness sandwich is like, what are our values? Because again, when we go to environments where we align our values with the organization that we're part of, so, you know, we bring complementary strengths to that organization or to that company, but our values are aligned, we feel safe to contribute, right?
Starting point is 00:27:36 we feel safe to take more risk. So that's one piece of it. As an individual, the second thing I often say to people, if you want to be a smart risk takers, look for those headwinds and tailwinds. And you find opportunities in both, right? But you want to align yourself with, in the case of tailwinds, let's say companies or divisions or industries where there's momentum because there's a lot of room to succeed. Does that make sense? By the way, there's also room to fail. Because if you're getting something big right, you can afford to make a lot of mistakes and, you know, the overall trajectory will still be up into the right. see that though that it's see like looking back yeah it's like wow what a brilliant choice you made to
Starting point is 00:28:12 move where you did when you did with the rise of the internet there's as you already mentioned there's there's there's definitely a luck component for like how do is there a way to to become better at kind of getting in front of that like what do you think let's let's the best thing for a risk taker is there's somebody wants to get it be better at risk taking is I'm not saying you need to be an oracle I'm not saying predict the trend I'm just saying identify it and you can easy. Like if you're thinking about joining a company, what rate are they growing at? Ask them why. If your boss is trying to convince you, you know, to go to a smaller division and you're like, oh, that really sucks. I'm in this big, stable job. But your division's growing at 1% and that
Starting point is 00:28:51 thing's growing at 50%. Ask yourself why. Like maybe they're not trying to demote you, but give you an opportunity to ride a tailwind. You know, so and Sethia Patel, Sethia Nadella did that at Microsoft. Like he took an old state division and he became CEO because you figured out the cloud, the cloud division, which he had under him and people were afraid of because he was going to cannibalize Microsoft's big business. He was the guy figured out, like, while I have a whole business, I'm going to take this part that can cannibalize the rest, and I'm going to grow it faster and give it resources and not worry about the other part of the business that is stable, the server business. Guess what? That became Microsoft Azure, and Microsoft has were put
Starting point is 00:29:29 Sefia Nadella in the CEOC that Microsoft. It was like his earmark, right? And he took a small division that nobody else wanted to take because it was risky and he put more resources into it as opposed to fearing that it was cannibalizing the big slower growing business. So that's an example. That's a good news is. Yeah, I want to pause for a second because that's big. This is something I didn't think of earlier in my career. Probably I just wasn't smart enough to really think or I didn't think at all. But this is an important point to make like keep your eyes open, whether it's within your own business or a different one of understanding growth and momentum. putting putting yourself in a position of opportunity to be because I know people say like oh yeah you
Starting point is 00:30:10 worked there when it was easier because it was just growing like this my dad always told me like I worked at this business when we would roll out of bed and it would grow 25 percent those are the good old days but to credit to him that he found the place in the right industry and he did it right it's not I think I mean we call that being lucky I would say okay guys like if there's external momentum and you want to make a calculate a choice. Don't you think going somewhere where there's momentum? And that your job naturally rises. You have maybe more cash flow to experiment. Like, is there anything wrong with that? Like, you know, you usually don't cut jobs at places like that, right? You don't have to, the, the October cuts where I've worked at a place where that happened before because we were growing like 1%.
Starting point is 00:30:52 And I was like, God, this is not fun. All my friends are getting laid off. And I'll say be attuned to both. Because when you say, can I ride, can I win in a tail, in a situation with headwinds, The answer is yes, if you understand what winning means. So often if you'll, let's say you're in a headwind situation where a company is not growing fast, whatever, I went to Stubhub. Stubbub was not growing very fast when I went. But my opportunity to change, pivot, try new things. I had licensed to do that because we were trying to figure it out, right?
Starting point is 00:31:23 So I had an opportunity to learn because, you know, we needed to do that. By the way, in sometimes in headwind situations, you don't have the luxury being able to hire who you want. So guess what? You ask for more responsibility. You know, those are the situations in which, quite frankly, learn to deal with adversity, you know, which by the way is the number one skill that recruiters want to recruit for on LinkedIn. Think about that. Agility and adversity. They want people who know how to be agile and deal with adversity. So it actually weirdly, even in headwind situations, we find opportunity. But the point is read the tea leaves and go to where the opportunity is. In headwind situations, it's disproportionate learning. Do you know what I mean?
Starting point is 00:32:03 Somebody may give you a shot because nobody else will take the shot. In the tailwind situation, it's like momentum, just pure momentum and your ability to have license to, you know, try more in that environment. So that's a big one. Like I say to individuals all the time, you have to be reading the macro environment. It's not actually all about you. Yeah. Okay.
Starting point is 00:32:24 How about for the leader? Maybe you even did this when you were at Stubhub. You're the president of Stubhubb, correct? Yes. So I am kind of curious about. like how that all came about, how they came and got you, why you said yes. And then maybe how you built or tried to build a culture where people were willing to take risk to try to innovate or to take smart risk within the environment with which you led. That's happy, happy to go there.
Starting point is 00:32:49 One last thing on just for individuals, we talked about knowing who you are and finding alignment with who you are, right, and your goals. Number two, we talked about headwinds and tailwinds. The third one that's really important is what we talked about before. Over-prioritized the who versus the what in your choices. When we go to environments where we can apprentice and learn and get proximate to people who give us learning faster, they also often expose us to opportunities faster than we would see them ourselves. So that was the one on the individual side. So coming to the Stubhub, part of my journey, first of all, I went to Stubhub, it was a calculated risk for me. I went to Stubhubhub for two reasons. Number one, I had spent the last 10 years as an e-commerce
Starting point is 00:33:31 entrepreneur. I left Google in 2010 and I, you know, started a company called Joyus. I was CEO of the company called Polywar, which is like an early version of Pinterest that Yahoo bought. And I, and I become an e-commerce board member and investor and immersed myself in e-commerce. So after doing that for seven years, I really missed running a company of pretty significant scale. I missed, you know, the complexity, the leadership challenges. And so after we sold my small company, Joyas, I really said to myself, I'm going to go back to finding a leadership opportunity at a platform that's big where I can impact millions of customers, you know, lead a large organization, you know, enjoy that side of my brain. And I think I got the nod at StubHub
Starting point is 00:34:12 because it needed the combination of entrepreneurial energy and executive energy I had to expand, right? So eBay had held it for 10 years. Stubhub, have great brand, but an increasingly, increasingly competitive ticketing environment, you know, Live Nation Ticket Master, the Behemoth. StubHub had a bunch of competitors that had grown from nowhere to half its size. So feeling competitive heat everywhere, an organization had been within eBay. So, you know, eBay really wanted somebody, I think, who could be innovative and entrepreneurial, but understood, like, you're dealing with a large-scale operation.
Starting point is 00:34:47 And so for them, I think the combination of my Google experience and executive experience fit. And I went there because it was a chance for me, lead, you know, a well-recognized consumer brand, give people delight, which gives me a lot of joy as a company to build, you know, give people live experiences. It's a pretty fun business to run. And for me, it was my path back as a calculated risk to being in a larger corporate environment, yet still getting to be a CEO of an independent business. So it was a good calculated risk for me to take, right, on that dimension. So that's why I took the job. In terms of what I
Starting point is 00:35:20 was trying to do with stuff, have to create an environment in which people can take risk. which I think is particularly relevant to this conversation because stuff had not been an independently owned company and startup for 10 years. It had been a part of eBay, right? And part of the eBay culture. I think there are two or three things that I focused on doing that I think that leaders in general
Starting point is 00:35:40 can think about for their own organization. First and foremost is, you know, I think you want to create an environment in which people can be truth tellers, truth seekers, and authors. So what do I mean more that? If we want people to take risk, what is every CEO want or every founder want? They wish everybody woke up obsessing about the business the same way they do and willing,
Starting point is 00:36:02 and in the case of a founder, which I've been, willing to take as many risks as they would take to make their baby successful. Yet most people wake up every day wondering if their leaders really want them to speak up. Do they really want them to ask questions? Do they really want a debate in the conversation? Do they really want a new idea to be presented and interrupt the flow of how the organization? works, you have to create a construct in which people feel very comfortable, right, doing those things. And I'd say the best way I know to do that, know to do that as a leader is you have to make it safe in little ways. Like if you just say to an organization that never
Starting point is 00:36:37 takes risk, take big risk, it's the same thing. Who's going to do that? It feels very risky. But if you say to an organization, I'm going to demonstrate to you every day that when people take little risks in anything, in a meeting, in anything, that I'm going to start rewarding that behavior. Because what everybody does is they, watch to see what's rewarded in an organization. So I'll give you a really little example at StubHub, two examples of things I did. Number one, when I got there, you know, most companies run planning processes and they only want to run them with the top part of the organization. Yet one thing you shouldn't recognize when you're leader of any organization is the real work and the real ideas
Starting point is 00:37:13 might be happening two levels beneath your VP level, right? It's not the person who's telling people, like, who's managing. It's the person who's doing. So, you know, if you look at the business, like they were probably, if I looked below the VP and director level, or even the VP level at stuff. There were probably 100 people that were running key parts of the organization that could impact what we do next. So I set up our OKR process from the very beginning. I was like, I want to meet with all 100.
Starting point is 00:37:38 I'm going to get rid of like, so our planning process ended up invoking about 100 people because I wanted to go to the two levels deep in the organization where the ideas were happening. And I wanted to see them in the room directly presenting their ideas. I would get to learn them better. They would get that. They're the people who are the authors, right? Like, they probably know best what we should do to reinvent our customer to customer
Starting point is 00:37:59 selling part of the country. Like a frontline obsession. Chris Zook said that on this show. Right. Who's the product lead? Who's the person owning like the five to seven engineers that are containing, you know, working this part of the business? They're going to know the answer on maybe have the best ideas of what to do.
Starting point is 00:38:15 So in our planning process, we literally expanded the number of people we bought into quarterly planning. you know, I was like, I'm not going by hierarchy. I want to go by who's leading the teams that touch every part of the key flows to the company. And so we expanded to 100 and we invited all 100 into the room in our quarterly planning process. And I'm like, and I wanted, and a big portion of those people would present their ideas directly. It wasn't like their leader was presenting the idea because I wanted everybody to watch the debate and be part of the debate, right? So not every, all 100%, but if you're in the room watching the dynamic and debate and seeing that the person
Starting point is 00:38:49 who authored the idea gets a chance to present it, maybe you feel like you can author too. So that's one example of what we did. And then another one that I think is really important in the leader in any dimension, whether you have 100 people in there and whether you have five people in the room, is watch what you validate by your actions. So I remember one of our quarterly planning sessions, we had this really smart woman who was new and was presenting how the numbers were going on one new business we were trying because we had a, you know, we created an area of the business where we're just incubating new services. And she was probably three or four months into the organization. And so she was presenting the numbers in her business plan for the next quarter.
Starting point is 00:39:29 And our CFO, who was a pretty extroverted character like me. And, you know, I'd say, you know, the two of us were always joking in meetings or whatever. Lots of people would divert to us, obviously. He starts asking her, like, really pointed questions and just firing off at her. Well, what about this? What about this? And she stands her ground. And she, and, you know, she answers him with confidence and assertion and sort of, you know, just keeps ticking through, like, isn't it's way that just keeps ticking through her data and gives him a rebuttal for every one of his questions. Very well done. So that finishes. And you'd say, okay, well, that's the interaction. But then I'm thinking, like, I'm the CEO. So I just chuckle in that moment and in the whole room. And it's not like I'm so perfect. But in the whole room, I was like, I was like, you go, girl. Way to give it to Greg. Like, look at that, Greg. And everybody in the room starts laughing. But in that moment, what I'm doing. is validating. Like, good for you. Like, yeah, you go tell our CEO. You had a reason. So you were in the moment thinking you did this for a purpose. You were intentional with your action. Yeah, I'm intentional in that I understand that when I'm the leader in the room, everybody's looking to see how I react.
Starting point is 00:40:33 And what I want to do is validate that activity. That's the way I wish every young person would stand up and like defend their ideas. And it doesn't matter if you're talking to the CFO of the company. Like, that's validating that you can meet him as a peer and have conviction in your idea. and your data and your capabilities and that that action is what we want to see more of, right? So I think that in our little actions, people take away what is acceptable or not. So I always say, like, honor the truth tellers, honor the questioners, honor the authors. In every little way you see it happen, call it out. It doesn't have to be a big speech.
Starting point is 00:41:07 It's just like a funny joke or, you know, or, hey, that's awesome. Like, and move on. But people are reading from our actions what we actually value. And I think that's really important. And you kind of prove that this is a type of culture we're building. It's safe to do this. There's a lot written out there on psychological safety. This is the leader proving that, yes, you can do that here.
Starting point is 00:41:31 And to be clear, she was proving it was doing all. She proved it. You validated it. All I'm trying to do is a leader is validate the behaviors that let other people know it's safe to do this. And not only is it safe, we're going to celebrate when you do this. How about, um, let's talk about for an individual going for a job. And I think this may be a male-female thing.
Starting point is 00:41:52 I think the science would back this up that guys tend to not worry about going for a big job that they're not qualified for, but women seem to be more concerned about that. Again, I don't have the research also top of my head, but I have read about that. Women tend to think they're underqualified and men to be overqualified. Right. So speaking to both guys and girls here, what are your thoughts on? going for a big job that you may not be specifically qualified for. Well, I think that this is one of the risks worth taking, to your point, because I say,
Starting point is 00:42:27 and there's research to support this, which will come to a moment, we think that we have the most impact when we stick with what we know. And to some degree, by the way, if you look at Malcolm Gladwell, you know, be an expert. There's lots to suggest that as you keep building competency at something and keep doing the same thing, you grow, right? And you have more impact, right? get more skills. So it's not that I don't believe that you shouldn't go after things that you're specialized in or qualify for. But there's this breakpoint when the next level of impact you can have and the next level of learning is engaging the thing you don't know. It's getting breadth of experience, not just death, right? So de facto, let's just think about that for more. De facto, for you to learn,
Starting point is 00:43:05 it means you don't know something. So when somebody offers you a job for which you're not qualified, they're offering you the opportunity to accelerate your learning, right? To accelerate your learning. And while we go into those environments and think, like, I'm not qualified. The reality is we typically will learn at an accelerated rate. And the impact we unlock, and this is really important is LinkedIn and others have done a story. There's a New York Times article that I quote in the book that the path to the CEO's job is a winding one. There is research to support that today what's valued by companies is depth of experience, but breadth of functional experience. Because if you want to be a CEO, you can't just be good at one thing, right? You have to prove that you're capable of understanding five parts of an organization. You have to prove that if you ran engineering, you're capable of understanding product enough to be a leader of it. So how do you ever acquire all the skills necessary to be a great leader if you don't expand your skill set to the things you don't know? So coming all the way back, when people say, like somebody's offered me a job I'm not qualified for, I'm like, okay, first of all, that's
Starting point is 00:44:07 your path to accelerated learning. Number two, research would suggest that if you actually want to get into the top job, you need not only depth of experience, but breadth of experience. And the best job, the best path is the New York Times says to the CEO job is a winding one where people literally have experimented and tried different functions, right, adjacent to what they know to expand their capabilities and their learning. And it turns out that will expand your ability to have impact too. So mostly what I say is like the best risk worth taking or the risk to learn. Because not only, you know, do you kind of get more satisfaction and improve your own growth? Turns out that that breath is actually what people are seeking when they're looking for
Starting point is 00:44:48 people who can ascend all the way at the top. What about leaving a job? There's someone right now working out in the morning thinking, I want to leave my job. But this is a risk. I'm not sure if I should leave, right? And you've certainly done this. How do you know when it's the right time to leave a job? Well, for me, I actually try and measure my, measure any situation in my own career in, like, call it three to five, three to five years sprints.
Starting point is 00:45:18 I know there's some people who don't measure them or measure them in 20. I take three to five because in three to five years at anything, I want to, A, achieve some ambition. Maybe it's a title. Maybe it's wealth. Maybe it's, you know, maybe it's learning. I want to have enough time at something to know that I can have an impact, right? And that impact will unlock a future opportunity. So it's very hard to have impact if you want to be at something for six months.
Starting point is 00:45:41 Like, good luck with that. I don't know any careers that are built by like six months of impact because you can't really learn enough to deliver enough, right? But let's just agree that in three to five years sprints of history, you would suggest that, you know, you can achieve some meaningful ambition in those in those needs. So first of all, I'd say to you, where are you in that cycle? And if you're thinking about leaving, you're either thinking about leaving because you're not having fun or you're not having impact or likely both.
Starting point is 00:46:04 And so I think first of all, before you leave, diagnose. why are you not having the impact you want? And sometimes when we're not having the impact that we want, we can go back to all that criteria I mentioned, right? Who are you with? Are your values aligned? Are you in a macro situation that will allow you to be successful at your job or thrive at your job, right?
Starting point is 00:46:24 And then lastly, you know, if you're, if you can, you have to evaluate those macro conditions and say, am I not having fun for these reasons? And then lastly, what is your contribution to that situation, which is a pretty big, you know, pretty big deal, as you know. So you want to evaluate the conditions you're, you've put yourself in. Who are you with? How do they align with your values and strengths, the job that you're doing? And like, is the macro condition conducive to your success? If not, what would you pivot within your
Starting point is 00:46:51 job to try and find more ability to contribute and have success? Which of those conditions would change? Last of the most important of which is your own contribution, right? So that's like, what are the things you're doing every day to maximize your impact? So I would say to people, Is it time to leave? The first question is, why are you not having impact that you're in your current situation? Because usually when we have impact, we have fun. Or why you're not having fun but impact? Like what's missing for you?
Starting point is 00:47:15 Maybe it's passion. Maybe it's like you just don't enjoy the job even if you're good at it, which comes back to who you are and what you value. And then number two, if you're not having fun and impact, you know, the question is, like, have you topped out? In the organization you're in, have you topped out? And I would say we've often topped out if we're fundamental. in an organization that doesn't fit with our values and doesn't have any room for our strengths
Starting point is 00:47:40 or value our strengths. But if you're in a place where your values and strengths fit, the question is like, could you be doing more? You know, does the environment, like, is there no more to learn? Sometimes we just talked out because there's just no more to learn. You know, and that may be a chance to move on. But I always look at that where you are in that five, three to five year cycle, why are you not having a diagnose, use the choice in the framework I gave you to diagnose. Is it the environment, is it the people, is it you, is it you in the context of your values and strengths? And then like, what could you be doing to have more impact? If the answer is you've done it all and nothing, like you've diagnosed and there's nothing
Starting point is 00:48:13 more, then you may be at a natural ending point. But so many people want to jump without diagnosing. And I think that we could cut short our impact in an organization. Other places, by the way, it's just done. I mean, I was the founder and co-founder and, you know, SVP of Yodley for five years. The company took 15 years to get public. I left it year five. I feel very good about that decision.
Starting point is 00:48:35 Like, I had done every job, but the CEO's job, every single job. The company was not growing fast enough for it to produce new learning opportunity for me. And the CEO job was filled. By the way, with the guy who was very happy with who stayed there for the next 10 years. There was no more for me to learn. Like, it wasn't growing fast enough to be spawning new learning opportunities. And I left. So sometimes we are just topped out.
Starting point is 00:48:58 I topped out of five years in that organization. By the way, Google, I could have stayed for another 10 and probably had five more careers of Google. I wanted to achieve a new ambition to be a CEO. That ambition was not available at Google. I was not going to be Google CEO. By the way, neither one of my peers. We were all business people, and it was going to be led by a technologist or a product leader, and that's what I end up happening. So there was one ambition Google could never give me, which was being a CEO.
Starting point is 00:49:24 How was that an ambition of yours? Probably half ego, you know, this notion of like, am I just lucky to be here or am I capable of, you know, of leading and building an organization that can achieve impact. So one could call that ego. The other half of that is purpose. Like I am built to drive and lead. And I guess I always get joy from challenging myself at the next leadership level. Sometimes for some people that's about scale, for some people that's about complexity. For some people, it's about being the ultimately accountable person. And for me, it's probably all three. I get enjoyed scale. I enjoy complexity. I also just enjoy being
Starting point is 00:50:00 on the hook. Like there's a leadership pressure and challenge that said for good or for bad, the buck stops with me. And I guess that was something that I wanted and thrived in. And not just for ego reasons, but just like it's what drives me. It gives me purpose and meaning. Yeah. You, you, you love the responsibility that comes with that leadership role, I sense. I do. I do. And don't get wrong. Sometimes it sucks and it's scary. And when you fail, like every other looks to you and it's you. But there's also. like I said, I also thrive in feeling like I wake up every day and I understand exactly what my purpose is. And I feel like I'm maximizing my leadership capacity and capability. And maybe that's
Starting point is 00:50:39 the gift I want to maximize. I just really, I personally, Secundra, I identify with that. I played quarterback when I played football. And the reason I chose that and continue to play it and even transferred to continue playing that position when they tried to move me at the first place I went is because I love that part of it. I love the fact that if I, I play well, we're probably going to win. And if I play bad, we're probably going to lose. I just think that's a, I love that responsibility, even though there are moments when it's the worst. You throw in a game losing interception. They return it for a touchdown and you lose. And you're like, that's because of me. Yeah, yeah. No, it's all true, right? I mean, yeah, it's brutal.
Starting point is 00:51:16 But it's like, but the highs are so, I don't know, like it's hard to. Yeah, the highs are high and that, you know, the lows are incredibly low. And so we're all built differently and for different purposes. And yeah, for good or for bad. So, my point is like I have left journeys that have been amazing even though that for me what I wanted next was not achievable there. But that's different from leaving when we have failed to have the impact we are capable of having. Yeah. By the way, the only frustrating times to leave or when you really leave because you can fail. Like even if you fail with the goal, if you fail to have impact, it's a particularly heartbreaking type of departure.
Starting point is 00:51:52 And I've had that happen too. You spent time around some amazing leaders who have impacted the, the world. You're also one of those people. What have you found to be some of the common characteristics of leaders who sustain excellence over an extended period of time? I think that is a great question. I think leaders who sustain excellence over a long period of time do one thing particularly well. They surround themselves with other great people. and they never let their ego get in the way of finding, you know, recruiting, retaining the best talent to meet the goal and exceed the goal. And leaders who fail to sustain are leaders who, and there's other things that fail too, but leaders who I admire the most, you know,
Starting point is 00:52:47 are leaders who never feel threatened by the level of talent and excellence around them. They realize that the entire game improves and they improve. they just move on to their next goal or ambition because they're able to, you know, surround themselves with other great talent, including peers. I mean, I know leaders who have recruited people who have done multiple times better than that, by the way. I've recruited people who, you know, gone on to have more success than I have. And I don't look at that as a badge of failure. I look at that as like, wow, like, first of all, how lucky that I was able to work with this person. And number two, like, that allowed me to go on and do new great things because I was able to work with them.
Starting point is 00:53:23 So that means that requires a level of humility and understanding that it isn't all about us. And when we, we don't look great because of who we control. I would say we look great because of the people we enable and empower. Yeah. You become more. Yeah. I love it. One more.
Starting point is 00:53:44 You got time for one more question? One more. Yeah. Go for it. For someone who has recently graduated college, maybe. Yeah. earlier in their career, not 100% sure what they want to do yet, but they definitely want to leave a dent, right? They want to impact people in a positive way. They want to be a person who does well in the world, right?
Starting point is 00:54:04 Leaves an impact, as you said. What are some general pieces of career slash life advice for that person? So a couple of things. First of all, we tend to assume that everything is. a zero sum game. You know, we talked about this. Like, if I make a great choice, that means you make a poor choice. If I have more, you have less. And I will tell you, and I think this is so important. One of things you're going to find is that possibility, choice, power, these things are abundant. So I know you think if somebody else, if your classmate gets more, you get less. We've been set up to think that there's like scarcity. And one of things I want to tell you is there's abundance. Like, you will find that whatever choice you make, it doesn't mean that the
Starting point is 00:54:51 person beside you need to make a losing choice for you to make a winning choice. If somebody besides you makes a winning choice, it doesn't mean you're left with the leftovers. That's just not how the world works. The good news is, is when we make choices for ourselves and generate any kind of impact, we get the opportunity to make more choices. And so we find that we can regenerate our own opportunities quite quickly if we're focused on this continuum of make a choice, whatever it is, focus on impact. Whether you fail or succeed, focus on impact. Then you get to make another choice and another one and another one and learn from everyone. And learn from choice. And it's a, like, choice is a multiplier of opportunity and you control it. Nobody else does.
Starting point is 00:55:27 That's probably the singular most important thing because we've been trained to think, if you get it, I don't. If you get the job, I don't get the job. If you win, I fail. It's just not like that. The good news is you can generate choices for yourself by just continuing to focus on impact. That's one. Number two is like you think the first move matters most. The thing that matters is make a choice and get in motion. Because as we talked about in this podcast, choosing possibility is not about one great choice. It's about every choice we get data, learning, maybe success. And in any event, it leads to the next choice. So what you want to do is just get yourself on that path by staying aligned to some of those first principles we talked about
Starting point is 00:56:04 of making good choices. But it doesn't need to be a perfect choice. Just get on the continuum of choice, make a, you know, do your best to make a first good one, and then recognize you, you have a hundred, a thousand more choices to make. And that should be freeing rather than paralyzing. I love it. Have a bias for action. So good. So, So Kendra, the book is called Choose Possibility, take risk and thrive, even when you fail. Where else would you send my viewers and listeners to learn more about you online? Well, I hang out most on LinkedIn. So you can always find me on LinkedIn and follow me there. And that's why I post most actively. I'm on Twitter too. And as I often say, I'm on Instagram, but I hide. It's just one more channel to manage.
Starting point is 00:56:50 And mostly I'd rather look at other people's photos. So, but LinkedIn and Twitter are always great places to find me. Awesome. Well, love the book. Love what you stand for. And certainly would love to continue our dialogue as we both progress. I loved it too. Thanks so much for having me. Thank you. What an awesome combination of intelligence, kindness, curiosity, thoughtfulness, and a willingness to share so much wisdom. Love that conversation with Secinder. A few of my notes. The Samuel Johnson, quote, nothing will ever be attempted if all possible objections must first be overcome. And Secinder said, we think when we do nothing, there's no cost. And that's not true.
Starting point is 00:57:40 there's still a cost to standing still. So when in doubt, I think, takes some sort of action. You really learn who you are in practice more so than in theory, so the only way to do it is to do it. So take action. And then she told the story about moving to Silicon Valley in 1997, and she said, proximity to opportunity benefited her more than any type of plan. So really what this comes down to is who before what, who before why, who before anything else.
Starting point is 00:58:17 The single greatest determining factor in your long-term success or failure will be based upon your who. Think about this for you and your career and who you're choosing to surround yourself with. And then as a leader, watch what you validate with your words and actions. She told the story of how she responded to people. in meetings, knowing the weight of her words, knowing the weight of her actions. As leaders, we need to know this. This is important that you understand how to reward the behavior that you want. So if you want to promote taking risk, then reward the people who do that. Just like Dr. Henry Kyle told me you get what you create and what you allow. Once again, I want to say thank you so
Starting point is 00:59:07 much for continuing to spread the word telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Secender Singh Cassidy. She'll help you become a much more effective leader. And because you continue to do that, and because you continue to write reviews on Apple Podcast and rate the show, hopefully five stars, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so much. Talking soon. Can't wait.

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