How to Turn Fear of the Unknown Into Your Biggest Growth Superpower with Scott Stirrett

Scott Stirrett left a prestigious career at Goldman Sachs to build something from nothing — and it changed everything he understood about growth. In this episode, Scott (founder of Venture for Canada, author of The Uncertainty Advantage) breaks down why comfort is actually the biggest threat to your growth, and how uncertainty — the thing most of us run from — is a skill you can systematically build. Connect with Scott www.scottstirrett.com Take the Quiz: Discover Your Uncertainty Advantage Buy the book: The Uncertainty Advantage Connect with Kwame: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Request A Customized Workshop For Your Company⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Kwame Christian on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠negotiateanything.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click here to buy your copy of Finding Confidence in Conflict: How to Negotiate Anything and Live Your Best Life!⁠⁠⁠⁠⁠⁠ @kwamenegotiates across all social platforms

• 0:00Speaker 00

  I just had Scott Sturrit on the podcast and this man is utterly brilliant. He is the founder of Venture for Canada and he's helped over 10,000 entrepreneurs find success in their relative businesses. He's the author of The Uncertainty Advantage and he talks about how you can use uncertainty as a learnable skill. Because I don't know if you've noticed, there's a lot of change happening and I've got news for you, that is not going to change. So that means we have to change from the inside out. And he walks us through how you can build that uncertainty muscle. But here's the thing, he's not just looking at this academically, he's lived this himself. He had a really promising career going into Goldman Sachs and then he decided to leave

• 0:42Speaker 00

  it all to chase this dream, helping all of these entrepreneurs around Canada to live their dream as well. If you are a person who wants to take their life to the next level, if there is a big swing in your mind, but you're afraid of the uncertainty and you're not sure how to navigate the ambiguity, this episode is for you. This is the story of Scott Sturrit. Welcome to Big Swings Only.

• 1:07Speaker 00

  If you listen to this show, you're probably one of two people. You're someone who's trying to improve their communication skills and learn how to resolve conflict, or you're a dealmaker who's trying to learn how to get an edge in their next negotiation so you could either make more or save more. The American Negotiation Institute is built for both. We have keynotes for conferences, workshops for teams and courses for everyone because the best things in life are on the other side of difficult conversations.

• 1:34Speaker 01

  The biggest opportunities in life come from the biggest risks. And what is risk-taking? It is making a decision in a highly uncertain environment. So if you're going to take really big swings in your life, you're going to have to become really comfortable with embracing the unknown.

• 1:53Speaker 00

  Yes, I agree. And it's one of those things about life where we might not want it to be true, but it certainly is true. The, what's really interesting psychologically is that, yes, we might be afraid of a specific thing, but a lot of times we are more, we're more afraid of that unspecified fear where we're saying, okay, I don't even know what's coming. I don't know if I have what it takes. I don't know if I can handle it. But one of the things that I think is really interesting about your approach to uncertainty that you highlight in the book is that you actually approach it as a skill, right?

• 2:30Speaker 01

  The ability to thrive with uncertainty is a teachable skill that you can get better at over time. And what I talk about in the Uncertainty Advantage is that there are six core pillars of how to build your uncertainty muscles. That includes self-compassion, adaptability, anti-pregility, entrepreneurial mindset, generalist skills, and a network building. And it's all of these things combined together that help you become more comfortable with embracing the unknown. And it's to say, in my experience, I have found that there are far more people who are afraid of uncertainty than those who seek it out. I've spoken at audiences across Canada, US, UK, and I've had around a thousand people fill out a quiz about their relationship with uncertainty.

• 3:14Speaker 01

  And what I found is that there are around four to five people who dislike uncertainty for every person who likes uncertainty. And to go to your question of, of why is it that people fear the unknown? Part of it is because for much of our history, we were hunter-gatherers and unknown situations were matters of life and death. So if we're walking by a cave and we don't know if there's a bear inside of it, and the bear is inside of it, and the bear eats us, like our story is done. Luckily today, we live in an era that's very different where we don't need to go to worst case possible scenarios in our head in order to survive. But out of that survival instinct, our brains tend to fear the unknown, which is why a

• 3:59Speaker 01

  lot of studies show that people tend to prefer to know a really bad outcome than to know an uncertain outcome. Because uncertainty is something that most of us are hardwired to dislike. That's to say, all of us need to be intentional about constantly building our uncertainty muscles, because our default as a species is often to dislike the unknown. And the good news is that whether you love uncertainty today, or you're really afraid of uncertainty, you can apply those six pillars to build up your capacity to not just tolerate uncertainty, but to thrive with it.

• 4:34Speaker 00

  Yes, oh, that's so good, Scott. And I'm wondering, tell us your story, because somebody doesn't just wake up and say, you know what, I'm going to write The Uncertainty Advantage. There has to be something in your personal narrative that got you to this point. So can you tell us about your relationship with uncertainty?

• 4:53Speaker 01

  In my life, I have loved uncertainty at some points and I have really been afraid of it. And I'll mention a few different snapshots of when I both embraced uncertainty and when I recoiled from it. When I was 22, I graduated from Georgetown University in Washington DC and then I went to go work at Goldman Sachs in New York City. And in many ways, it was the dream job, prestigious, high-paid, especially in the context of that age range. And it wasn't the right fit for me. I studied international relations, I'm an entrepreneur at my core, and being a part of a 35,000-person institution was not a good fit for my skillset.

• 5:35Speaker 01

  So as soon as I started Goldman Sachs, I began thinking of this idea of a not-for-profit in Canada called Venture for Canada. And around a year into my time at Goldman Sachs, I quit and I moved to Toronto, Canada, where I never lived before and I had virtually zero social connections to start to build a not-for-profit from scratch. And that was an example of me embracing uncertainty and it was really risky. But it was also the moment that created the most opportunity for myself and for others in my life. At over 12 years, we built Venture for Canada from a little idea to a national entrepreneurship institution where we've raised over $80 million of funding and supported over 10,000 young people across Canada.

• 6:17Speaker 01

  Likewise, on the flip side, in COVID, I really struggled with uncertainty. I was diagnosed with obsessive-compulsive disorder. I struggled really to tolerate a lot of things, like even in-person kind of social engagements. And I felt I became a shell of myself. And through therapy, as well as working to build up my capacity to tolerate uncertainty, because that's what, for context, the core OCD is a fear of the unknown, is trying to control the unknown through compulsive behaviors and avoidance. And it was through that experience that it motivated me to want to write a book and to help others learn to navigate uncertainty.

• 7:00Speaker 01

  Because it's not just me, and it's not just people who have OCD. I've seen in the context of my work at Venture for Canada, where we support thousands of people to launch their careers, that fear of uncertainty holds so many people back in terms of their ability to take risks and capitalize upon opportunities. And I believe that one of the most critical ways that we can unlock more human potential in this world is to help more people to learn to embrace uncertainty, to not view it as an enemy, but to actually view uncertainty as the place where opportunity comes from in our lives. And I've seen that firsthand, that whether it's launching Venture for Canada or writing this book, or a variety of other risks that I've taken, it's in those moments where I

• 7:45Speaker 01

  have sat with uncertainty, where I have befriended uncertainty, that I have been able to create the most value for myself and for others.

• 7:53Speaker 00

  Wow, kudos, kudos. It's really impressive and thank you for sharing that because the, I think a lot of people could look at your success from the outside looking in and not understand the difficulty that you had to go through in order to get to where you are. And I'd be interested to explore just internally, when you think about your, yourself, who you are, your identity, there's going to be part of it that is natural. So we have nature versus nurture and there's part of your identity that's going to be shaped by the big swings that you have taken. So let's, let's do a little thought experiment here, Scott. So hypothetically, let's assume there's another dimension where there's another Scott, the

• 8:34Speaker 00

  exact same age, but he decided to do what society might say was the right thing, just stay on that career path, just go to Goldman Sachs, stay in that, in that realm and continue to rise through the corporate ladder. What do you think would be the key differences between those two versions of yourself? The version of yourself today that's been built by your big swings and the version of yourself who decided to play safe and stay on the path that society might have suggested?

• 9:04Speaker 01

  It's a great question. It's sometimes something I've thought about in moments that have been more challenging of during my journey at Venture for Canada, where I've thought, why did I turn down this opportunity? What would it have been like if I had stayed at Goldman Sachs? I remember having a series of dreams about this in the kind of early days of Venture for Canada, which I share in the context, this clearly something in my psyche was really kind of grappling with that, with that kind of question. So in terms of, to answer your question of how I would be different if I had stayed at Goldman Sachs and I was still there 13 years later, I think that I would probably still have an interesting kind of career. I would have learned different things.

• 9:48Speaker 01

  I would probably be, you know, quite well off financially. But I'd say that some of the skills that I would learn in the Goldman Sachs setting, which are different than the skills I learned over the last 13 years, are first off, an interesting ability to navigate or learn to navigate and kind of play the corporate game. I think that when you're in a corporate setting, that is one of the main things that you have to learn to do in order to, to, to rise up. And I think that I would also be a lot less entrepreneurial because I think inherently, when you're in a large financial institution, there are so many constraints and it it limits your ability to navigate things with as much can it ambiguity versus if you're an entrepreneur

• 10:33Speaker 01

  in a really highly ambiguous environment. When I reflect on my experiences at Venture for Canada and other entrepreneurial experiences, I think some of the things I ended up learning were the ability to wear multiple hats. Because when you're an entrepreneur, and you probably relate to this, is that you have to, you know, learn a lot of different things. I learned, I managed a team around thirty five people. And it's like, I learned everything from IT for small business. I learned to wear the hat of marketing. I learned to be in like, the finances of the organization. I learned a lot about a variety of different things. And in doing so, I think that that taught me that perfect is enemy of the good and just

• 11:14Speaker 01

  how to navigate highly ambiguous environments and learn a lot about a variety of different things. And I think what also I learned a lot about Venture for Canada is learning how to build. There's a great book by Andrew Yang, who founded Venture for America and endorsed the uncertainty advantage, is an acquaintance of mine. And he writes in how how how to build things is that the way you learn to build things is by building things. And I think maybe the one major difference between Venture for Canada Goldman Sachs is I think in the Goldman Sachs context, I would probably be more of a manager, a risk manager to some extent. Versus, I think when you're an entrepreneur or you're building something from scratch,

• 11:59Speaker 01

  you're learning how to build something. And that's something that can carry you forward in so many other different domains in in your life. And I think that that in a nutshell, that that's the main difference in terms of the skill set trajectories of the two different paths.

• 12:16Speaker 00

  Such a great answer. And there's so much to explore because the and it would be interesting to almost psychoanalyze this too, because it's a window into the way that you think. Because it sounds like, based on the way that you describe this, a major part of your identity is built, not born, and focusing on the skills. So the skills that are required to do what it is that you're trying to do. So with the the pathway of staying with Goldman Sachs and building that that reputation and building that career, you would have been a risk manager. Here, as an entrepreneur, you had to be more of a risk taker. And as a builder, you had to learn different skills in order to build the the business of Venture

• 13:00Speaker 00

  for Canada. And what's what's so fascinating, too, is that we often don't think about the the modifying effect that the that skills have on us. We literally have to change our brain in order to acquire skills and achieve mastery. When you think about it through the lens of neuroplasticity, neurons that fire together, wire together, we're creating those neural connections. And if you were to literally take a scan of your brain, like in these two dimensions, the Scott you are now versus the Scott on that other path, you would have had to wire your brain very differently in order to be effective. And it's really fascinating to look at identity through that lens, through a skills based lens. That's, I think, I thought that was a really fascinating nuance.

• 13:45Speaker 01

  To paraphrase what you just said there, we are what we do. And our daily actions fundamentally shape and shift us in really significant ways. Likewise, Andrew Yang in his book talks about his experience being a corporate lawyer for, I think it was like eight months, and how that experience of being a lawyer in some ways trains you how not to be an entrepreneur, because it's so different from that path. It trains you to be a risk manager, to be really risk averse. And in the same way that entrepreneurship can be taught through building, I think there's some paths that teach you how not to build,

• 14:23Speaker 01

  how to be really cautious. And even if you're a builder now, you can't just rest on your laurels. You need to constantly work at developing that skill set over time, pushing yourself out of your comfort zone, developing anti fragility, which is the ability to not just tolerate disorder, but to benefit from it.

• 14:45Speaker 00

  Yes. Oh, that's so good. And you're speaking to me. Now this feels like a therapy session because I am a lawyer. And what's funny is that a lot of folks don't know that because I made an intentional identity and brand shift because I recognize that we are risk averse by nature. My job as a lawyer is to point out the the risks and make sure you don't get in trouble. And the it is a mindset that is fundamentally antithetical to the entrepreneurial mindset, too, which is so interesting. And I didn't, I didn't know Andrew Yang was a lawyer either. So it's really funny to see how when people have that foundation of law, we can recognize, yes, problem solving skills are great, being able to issue spot is fantastic and everything like that. But then we realize, wait a second,

• 15:30Speaker 00

  for us to become the builders that we need to be, we really need to make a fundamental identity shift. It's that's, that was, that really resonated with me. When you, when you think about the the shift that you had to make, were there any things where you said just explicitly to yourself, hey, I used to be this way, but now I need to be another way, where you're making a specific shift to say, this skill or this identity, I need to close the door on that? Or were you always thinking about it in terms of building and evolving from this same foundation? Every year, I swear that I'm going to get ahead of holiday shopping. This year,

• 16:11Speaker 00

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• 16:52Speaker 00

  and 365 day returns, now available in Canada and the UK too. And when Quince asks where you heard about them, let them know it was Kwame with big swings only. That's the best way to support the show. If you were going to take a big swing this holiday season and start a business, what would you build? Maybe it's that one idea that you can't stop thinking about. I've built a business from the ground up, and I can tell you that the hard part isn't the idea, it's getting it live. That's where Shopify comes in. You can sell everywhere people shop, online, in person, across social media, even in AI chats. And Shopify checkout with shop pay converts up to 36% higher than the competition. So more of the people who

• 17:35Speaker 00

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• 17:58Speaker 01

  I'll zoom in actually to the present day because that is the example that pops into my current head. I wrapped up my time at Venture for Canada just the end of last year. I led the organization for 12 years. It was an amazing journey. But I didn't want to be involved in the not for profit sector for my entire career. And I've always wanted to be a business owner. So I am about to start a full time search to acquire a business in in Canada. And to answer your question, I'm going to link it to some of the skills that I'm currently having to to build or rebuild. And even though Venture for Canada was a builder, by the time I left, the team was around 35 employees. So I had this big

• 18:43Speaker 01

  support system. I could just, a lot of my job was getting people to do stuff for me and dealing with HR issues and coaching people and managing and leading. And now I am doing this search. I am a full time team of one. And I'm having to leverage AI, AI maybe as my like assistant, but I don't have this like big team that I can lean on. So Kwame, one of the things that I am beginning to to learn is that getting my hands dirty and getting in the weeds and figuring out, okay, how do I build a list of 350 target companies? How do I work with freelancers to pull information on the corporate ownership

• 19:24Speaker 01

  of obscure companies across Canada through corporate registries? These would be things that I would have just delegated kind of in the past. And it's, I can feel the skill building up. I can feel that skill of being in the weeds and getting technical with a problem. And then perhaps at Venture for Canada, I got two out of the weeds. And I think that I can feel that it's uncomfortable for me to to do some of these things that are a little bit more manual, a little bit more specific. But it's also so valuable because I feel my ability to problem solve at that more tactical level is a lot stronger today than it was three or four months ago.

• 20:06Speaker 00

  Yeah. Well, let's, let's actually explore this because it sounds like there is a tension between who you want to be and also who you have to be from time to time, right? Because there are certain times where I recognize as an entrepreneur, I say, okay, well, I'm good, I guess I'm tech support today. So in the early stages, you might be, might not be able to outsource all of it. So you have to learn these skills. I didn't want to do it, but I have to do it. And even though I've graduated to a point where most of it is outsourced, some this morning, we had a situation where we had to make a crucial update to the website. So it's, we started this at 10am. And already this morning, I was a

• 20:46Speaker 00

  team manager, a an IT support person, a course director, and then a a podcaster. And I would tell you, none of those things were things I expected to be 15 years ago. And so it's really interesting to recognize that sometimes on this journey, we have to become someone maybe but for a time in order to to achieve the outcome we want to. And that requires a lot of mental dexterity and a different form of resilience where you say, all right, I might not enjoy this particular part of the process, but I recognize that it is an important part of the process for this journey.

• 21:27Speaker 01

  Absolutely. And to go back to the earlier point, the, as an entrepreneur or, or someone working in a smaller organization, that ability to wear multiple hats is so critical. And to have that dexterity to be able to move between different things. And I think even if you're not an entrepreneur, it's increasingly important for everybody to have that ability to adjust, to be adaptable, to be nimble. The second pillar of my book, The Insecurity Advantage, is all about adaptability. And in a world where things move so quickly, it is really, really important that people be able to adjust their plans. But likewise, it's important to not be too adaptable. Because when you're too adaptable, you can be like a ship in the

• 22:10Speaker 01

  wind and get pulled in random directions. So, one of the tips I've mentioned in my book is the importance of really being clear about what is your life mission statement, which can maybe sound cheesy, but when I have done sessions with all of these people across dozens of institutions, and I get people to raise their hand about whether they have a life mission statement that they can clearly articulate, there's probably five to 10% of people who can do it. And it is such an important thing. For me, my life mission statement is to help others achieve their full potential. It's quite broad. And it might sound counterintuitive to say a

• 22:51Speaker 01

  key part of adaptability is being really clear about what is your purpose. But I think it's so important, because once you're clear about what is your true north, what are the values that direct you, it helps you be very adaptive, while at the same time not being too adaptive, of advancing with a degree of purpose, and of aligning your activities, your time, your resources, to the highest value-added activities.

• 23:20Speaker 00

  Brilliant, brilliant. Yeah, because that, it can be really confusing. Because we talk about the, the need to be agile. We talk about the need to adapt, but adapt to what? For what purpose? And it really can be a little bit disorienting. When you say, okay, well, this isn't working, I have to adapt. But what, to where? But yeah, it's true. We do have to have that true north, but most of us don't. And it's funny, our missions are very similar. I, I think about mine as being the bridge between where somebody is and where they want to go. And so you could see, even though from the outside looking in, the transition from negotiate anything is very different from the, what Big Swings Only is, is meant to be. But when you say, okay, I recognize that the great, the best things in life are

• 24:05Speaker 00

  on the other side of difficult conversations. So I want to help people to make their lives better, one difficult conversation at a time. And that was the purpose with negotiate anything. We wanted to create the, the largest free library of negotiation content on the planet. And we, we did that. So, mission accomplished, we can move on. And now I see, okay, with Big Swings Only, it's still that same goal, to be the gap between where you are and where you want to be. But now we recognize, in the past, when negotiate anything, it was negotiating and having tough conversations. But here, it's, that's this big swing mentality, being willing to, to take these risks. And like you're saying, adaptation agility is going to be part of that. I, I love this so much. And what, what's cool about you, Scott, is

• 24:48Speaker 00

  that you've already built something for yourself. You're looking to acquire another company and then build that again. Now, you also, though, have helped, how, how many entrepreneurs at this point have, have you helped through your programs?

• 25:01Speaker 01

  10,000.

• 25:02Speaker 00

  That's absurd. That's so cool. So, so you are better positioned than most people to, to answer this question. When you think about the entrepreneurs who have succeeded versus the ones who have failed, what are the patterns that you're seeing?

• 25:19Speaker 01

  I would say that the first defining difference between those who succeed and those who don't is taking kind of complete accountability for oneself. I think, when you're in a bigger organization or environment, you can have more of a tendency to blame others, or it's easier to be less accountable. I think really successful entrepreneurs, the buck stops with them, and they take complete accountability for everything that works or, or doesn't. And I think that that accountability links to drive, that when you're an entrepreneur, no one's going to do your work for you. So, a lot of entrepreneurs, I think, are incredibly

• 26:03Speaker 01

  self-driven, and they wake up every day, and it's not work for them, for, in many cases. It's about constantly moving the, the ball forward, and being accountable with every minute of their time to achieve their goals and objectives. So that's one defining aspect between those who are more successful and those who aren't. I would say a second key of aspect, in terms of entrepreneurial success, I think is just resilience, and the ability to overcome challenges and setbacks. I think a lot of really successful entrepreneurs are actually good at balance. That the Elon Musk version of just like working yourself like

• 26:48Speaker 01

  120 hours a week, that clearly works for Elon Musk in the context, he is the world's richest man. But I think for most entrepreneurs, that is not the most sustainable path. Most people aren't built like Elon Musk. And I think a lot of successful entrepreneurs invest a lot of time in their family, in their fitness, in their mental health. Because that is good for overall wellbeing, but it also helps you in the long run, be more sustainable as an entrepreneur. Because entrepreneurship is a marathon, not a sprint, although sometimes it's a marathon punctuated by sprints. And I think it's really important to, to think in the long run, when you're an entrepreneur. And I think a lot of successful entrepreneurs

• 27:31Speaker 01

  invest in fitness, they invest in eating well, they invest in family and, and relationships. And I'd say a third aspect that I think is defining of a lot of successful entrepreneurs is the ability to focus and prioritize and make the most important thing, the most important thing. We can all spend a huge amount of time every day doing work. You know, we could all work for 20 hours a day. And I think a lot of entrepreneurs, they don't necessarily have these really complex systems for prioritization. I actually find that, that people who often have really complex prioritization systems are those who struggle with prioritization.

• 28:14Speaker 01

  I think that a lot of really successful entrepreneurs have almost this innate ability to wake up in the morning and think, these are the two or three things that I need to accomplish today in order to move my objective forward. They don't have these really long to-do lists. They can almost like intuit, like what is the thing that I really need to focus on? And the ability to prioritize is so important as an entrepreneur, because strategy is what you say no to. And I think that people who just say yes to everything end up failing as entrepreneurs. The most successful entrepreneurs make big bets on a few things. They don't make big bets on everything.

• 28:58Speaker 00

  Hmm. Oh, this is so good and validating. Thank you. Because there, there were, there were a few parts that were idiosyncrasies that I just, that I developed, that I said, man, am I, am I broken? Am I doing this wrong? But you, you're helping me to recognize that there, there is a lot of intentionality behind it. So let me just run through these and add to it without duplicating. So when you talk about complete accountability, it's can, it can be really scary. Because we love to own our successes, but we like to outsource our failures to something else. And the other thing that's interesting is that folks who are not on this entrepreneurial journey with you, who are beside you, who care about you, they can almost push back to this. So here's what I mean. So, very loving, well-meaning

• 29:42Speaker 00

  people can try to help you to feel better by saying, oh, it's not your fault. And I tell them, I say, listen, I, I know you're trying to help, and I appreciate the, the love, but I need to believe that this is my fault. Because if it's my fault, then, then I am responsible for a solution. I can, I can solve this too. So, yep, this happened, and, and it's on me. Even if it wasn't out, even if it was outside of my control, I need to still feel like I am in control of that solution. And then the drive, resilience, balance element. I believe one thing that's really interesting about this is that some folks struggle because they say, I don't know if I can make it. But the, the greatest entrepreneurs I've seen, they, they already have the end in mind. They say, I will make it. Now the

• 30:27Speaker 00

  only question is how. So no matter what is the, what bumps and bruises they get along the way, they just say, this is part of the journey. I might not have wanted this to be part of the journey, whatever difficulty it has to be. But it's almost as if they are starting their journey already reading the final chapter of the book. So they say, I, I know I'm going to get there. I am 100% certain that, that I will. I just don't know how. And then you, you develop this, this playful curiosity where you run into a, a problem. Oh, interesting. I'm really excited to see how I get through this. It's not, will I get through this? I know I will. Let's see how. And then focus and prioritization.

• 31:08Speaker 00

  Because you see, there are some of these very, very complex systems for keeping track of your to-do list and things like that. And I recognize that a lot of those productivity matrices and things like that are more optimized for people who are working in a business versus people who are building the business. We just have two to three major priorities. And I call it strategic disappointment. There are hundreds of things I could potentially do. And then there are other things that other people might want me to do. And it's my job to figure out, okay, let me focus on what my true north is, and let me say three things. As long as I get these three things that are completely within my control done, then today is going to win, to be a win. I might have wanted to get some more,

• 31:52Speaker 00

  but I didn't. That's okay. People have, might have wanted me to do other things, and they'll be disappointed, as am I. And that, that's okay. That's just part of the game. And once you just understand that that is completely normal, then you don't create this emotional tax on yourself, where even though you had a successful day, you handled the things that were within your control, but now you give this emotional penalty for yourself where you feel bad, which depletes your energy that you could use for the next day to keep on going. And so it circles back to one of the things that you said at the beginning that I thought was really interesting, self-compassion as a key to success. And a lot of times you hear entrepreneurs where they say self-flagellation is the key to success. So, could you help us

• 32:37Speaker 00

  to distinguish between this perspective that you have about self-compassion being really important versus the people who frequently beat themselves up in, for not accomplishing what they thought they could?

• 32:48Speaker 01

  It's important to find this balance between self compassion on one end and pushing yourself out of your comfort zone on the other. And to me, self compassion is not about just loafing around and stagnating. It's actually about being more ambitious. And I think it's important to define what exactly is self compassion. To me, self compassion is not just lying on the beach and drinking margaritas all day and being kind to myself. To me, self compassion is a bunch of things. But to quote Dr. Kristin Neff, who popularized a lot of the concept of self compassion, there's three core aspects.

• 33:33Speaker 01

  The first is the importance of recognizing your shared humanity, that if you're going through something that's really tough, there's likewise probably millions of other people in the world who are going through something similar at the exact same time. And sitting with that shared humanity is really important for reducing your anxiety and for being kinder to yourself. The second core aspect is the importance of being mindful of just like, how are you feeling in the moment? Are you anxious? Are you stressed? Are you happy? And if you're going into that self critical mindset of just like labeling it and accepting it, and it's not trying to resist the, those feelings, it's about accepting those feelings ultimately.

• 34:16Speaker 01

  And the third core aspect of self compassion is talking to yourself like you would talk to a good friend when they're going through a tough time. So if, for instance, so yeah, say you're a listener and you're going through divorce. That's a really tough, challenging circumstance. Don't beat yourself up and say, woulda, coulda, I made all these mistakes. Why did I destroy this relationship? Think about if your best friend called you and said that he was getting divorced. How would you talk to your best friend? You wouldn't say that a hundred percent unless you're trying to end that relationship. You would say, I'm so sorry. That sounds like it's really tough. How are you doing? And you would talk to that person in a kinder compassionate way.

• 34:59Speaker 01

  And that's what self compassion is. It's not about loafing. It's about being kinder to yourself and it's about recognizing that failure is a part of life, that we learn from experiences. And that self compassion helps us keep on getting up, keeping on making more big swings and trying to do bigger and better things. And in my view, some of the most impactful people out there are those who are really self compassionate. Because that's what enables them to make big swings and take risks in their lives. And the people who lack self compassion are the ones who tend to be perfectionists.

• 35:42Speaker 01

  And they just stay in their small little bubble where it's safe. But they're not doing the risks, they're not making the bets that will make them stand out in their lives and careers.

• 35:56Speaker 00

  I love it. I love this. This is great. Cause um, in my first book, I talked a lot about self compassion too. And I was really interested to see who you cited and we cited the same person, which is really, really cool. And also, I wish there were more people talking about this. So I wish, I'm so glad that you're bringing this, especially into the entrepreneurial space. Because when it comes to the self caught, the, the self talk, the, the metacognition that we engage in, not just thinking, but thinking about thinking, that deeper level, this is the key to introspection. And if we are too aggressive and mean with ourselves when we are talking to ourselves, then we are going to stop the process of introspection short.

• 36:38Speaker 00

  And we're not going to be willing to, to have these deep internal conversations to figure out who we are, who we need to be, what we want, et cetera. So it really is a, a great pathway to deeper self reflection. And growing up, I used to play tennis. And one thing that's interesting about tennis is that tennis players, we, we all would struggle with bad attitudes. You see people throwing their rackets, yelling, it's a, it's a very lonely sport. You don't have a team, you're not even allowed to talk to your coach. And so people start to melt down. But you take those same people and put them on a doubles court. So they're not playing singles by themselves. Now they're playing doubles with a partner. You never see that same person talk to their doubles partner that way.

• 37:21Speaker 00

  And so the way that I, I would describe it is you want to talk to yourself like a doubles partner. You want to be kind. You wouldn't try to break down your teammates. But we often try to break down ourselves and try to use this negative energy in, in order to propel us forward. And when we think about energy too, this is something in your work that I think is really interesting. Because we always hear in, in entrepreneurship, follow your passions, follow your passions. But you have an interesting take on that. Can you tell us about that? Every year, I swear that I'm going to get ahead of holiday shopping. This year, it started with a Quince cashmere sweater that I bought for myself. It was so soft, so well made, and my first thought was, who else on my list needs one?

• 38:03Speaker 00

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• 38:47Speaker 00

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• 39:30Speaker 00

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• 39:50Speaker 01

  First, to double click a little bit on the tennis side, that is a great tip that I am going to apply. Cause I am a recreational tennis player and I recently was at the quarterfinals of the National Bank Open in Toronto. And I saw Naomi Osaka play and as well against Elena Long, Russian last name, but she's the number two in the world.

• 40:13Speaker 00

  Spitalina? Oh, Osadinka.

• 40:16Speaker 01

  Uh, it starts with, it was like, yeah, it might be that she was number two when we, uh, so I, I couldn't pronounce her last name. But she technically plays for Kazakhstan, but I think is Russian. Um, and uh, one of the things that I, uh, you know, saw was that at one point Osaka like threw the tennis racket uh, on, not in the air, but in, on the ground, which is, I think, not super common in, uh, at kind of high. I mean, I've seen it, but it's the first time that I've watched a tennis match where I saw it live, where the tennis match, the tennis. And I, I just felt bad for her because I could tell she was being so hard on herself in that moment. She ended up losing the game, but she had a kind of a lead.

• 41:00Speaker 01

  All to say is that, uh, yeah, to your point, sometimes just being in a team can really help you kind of be more self compassionate. And, uh, you know, I think that it's something that, uh, it's important for us, like whether you're building a business or even you're doing something like tennis, is just to be, have that kind of like kindness. Like self compassion is something that we all kind of develop, uh, over, over time. And it's, it can be in, in hobbies, like we don't just develop self compassion in the, the context of, uh, of, of our work. Um, and can you repeat the question again?

• 41:36Speaker 00

  Also, he's talking about energy.

• 41:40Speaker 00

  Versus passions.

• 41:41Speaker 01

  Oh, yeah. So to go back to the, the, uh, in, in terms of, I think, follow your passion is some of the worst career advice out there. And the reason being is that often we don't know our passions. They shift and change over time and that's okay. And I'd say the second kind of aspect is that a lot of our passions aren't necessarily monetizable. Like you could have a, a passion, but you're not going to make any money, uh, uh, out of it. And the reality, we live in a world where you, you know, unless you come from like generational wealth,

• 42:22Speaker 01

  you're going to need to find a, a passion that is, uh, that can earn you an income. If you're going to do that as your kind of full-time, uh, job. And I'd say the third is that a lot of the times people don't know what their passion is and that that is, uh, okay. And Kyle Newport in an amazing book called So Good They Can't Ignore You. He talks about that rather than focusing on following your passion, people should focus instead on how do you develop skills that actually make you, you look useful, uh, in this world. And that's what I am even, that book has impacted me a lot in my career trajectory that I, as I leave venture for Ken, I didn't have like a set business idea or thing that I wanted,

• 43:07Speaker 01

  but I knew that I want to take an existing business. I want to grow it. I want to add value and, and expand on the business owner's legacy. And I want to be useful in the world and learn valuable, uh, skills. And I think a lot of young people fixate so much on that. Let's find, figure out our passion that they end up making career decisions that are ill thought out or that don't put them into the place where they, they really want to be. So if you're a listener and you're, don't know what your passion is, or you're feeling the pressure to quote unquote, follow your passion.

• 43:44Speaker 01

  Label it, but recognize that in many cases, the better path is thinking about what are the career decisions I can make that put me in a situation where I can learn as much in as short a period of time and develop skills that are really valuable for myself and for the world.

• 44:03Speaker 00

  Brilliant. Oh, that's so good. I like that, especially focusing on skills, because this feeds back into what we were talking about with the agility and adaptability. Because once you see a threat, you can use those skills to avoid the threat. Once you see an opportunity, you can use those skills to navigate toward that opportunity. But if you're busy chasing your passions, you might be jazzed up about what it is that you're doing, but you might not have the skills to actually make the moves you need to make in the moment. Oh, that's great. Um, but before we wrap, let's make sure we bring Simone in here. He's always listening patiently and has something insightful to say or a great question to ask.

• 44:42Speaker 02

  You were talking, Callum, about what people should be afraid of and they are not afraid. And I think it was, yeah, because of my life experience, people should be afraid of, uh, getting used to comfort. Because then a black swan comes and you have to start over. And that hap- has happened to me many times in my life. I'll tell you, um, uh, when I went to Argentina, uh, I, I was living in Venezuela. I, I was born in Venezuela, then I went to Argentina, then I came to Canada. Venezuela, uh, is, it was a society that, um, wanted to make people feel certainty. Argentina is the opposite.

• 45:27Speaker 02

  So people from Argentina change quickly. People from Venezuela are more stable, but more fragile at the same time. So, um, when I went to Argentina, um, I had to start as, I was nobody. In Venezuela, I was a designer. People came to say, hey, Simone, do you want to work with me? And then in Argentina, no one was going to look for me. So, uh, at some point I had to become, I, I had to start selling things, you know, selling everything. And I had to become the person I always hated, which was a sales rep. And I loved it, but I didn't know I was going to love it.

• 46:12Speaker 02

  It was just through going through that experience that I, I understood I, I, I was okay with selling things. Um, so I think that one of the biggest skills that you have to develop,

• 46:28Speaker 02

  to become anti-fragile is to be willing to change your morals. Because, uh, you think that all your morals are okay until you learn new things and you can understand that you were wrong in the past. And, but it's the, oh, it's so difficult to change your mind in that, in that point, because you cannot believe that you're wrong. It's something really difficult to understand. So I think that comfort makes you think that you're right, because you, you just feel that you're in a, in the, in your comfort zone. And it turns out that a black swan can change everything and you had to start over.

• 47:07Speaker 00

  Brilliant. That's so interesting too, because that the, when you think about comfort, one thing about comfort is that you don't want to let it go. And so you say, okay, I'm comfortable right now. I don't want to be uncomfortable again. And then I think about the circumstances that I'm in right now that have led to the comfort. Now I don't want those circumstances to change. And then when you think about that through the lens of Stoic philosophy, you are then by definition, not thinking stoically, because you are really putting your, your identity, your hopes into something that is outside of your control. Because circumstances will certainly change. And it makes it harder for you to change if you are unwilling to accept the fact that circumstances must change.

• 47:51Speaker 00

  I think about it for me as an entrepreneur, Simone, you, you, you'll know this story. I mean, we had a, we had a, a major client that we worked with. We had a, it was a major media deal and it was great for us. It was, um, the easiest money we ever made. And I was just saying, this would be great. Give it last forever, a multi-six figure deal that was just fun and easy to deliver. And we shifted our business with the assumption that it would never change. And then when we were at the peak of our powers, it all changed and, um, and we, we had to adapt. And I recognize now, looking back, that if going into it now with this mentality,

• 48:33Speaker 00

  when I have these good times, when things start to get easier, just recognize that's not what entrepreneurship is. It will, it will change. You need to be ready for the change. So enjoy the moment for sure, but also plan and be ready to be agile. And then mud, but not just resilient, because I love the fact that you're bringing anti-fragility in here. Just saying, okay, when something bad happens, how can I use this as an opportunity to get stronger, to, to make my systems more robust and make the company better than before, even though circumstances change in a way that I, I wasn't expecting or hoping for.

• 49:05Speaker 02

  Sometimes we, we are afraid of losing the comfort, because, uh, we, we, we are like just rolling the dice of life. So sometimes we have a double six. And then we, a black swan comes and we have to roll the dice again. But we don't know that, that life has more than six phases. So we can, we can roll the dice again and, and have a double 10 or double, double one million. But we just know that we are okay with the double six, you know?

• 49:36Speaker 01

  Yeah, what Simone was saying on,

• 49:39Speaker 01

  there are comfortable situations that can kind of lure people into this illusion of control or illusion of, of certainty. And I think it actually makes people a lot more vulnerable to the vagaries of, of the world. That, that resonated a lot, I think, particularly as a, as a Canadian. Uh, like Simone, uh, you might relate to this in the context of some of the people you meet in Canada. But I grew up in Canada, I was born in Canada. I did live in the US for five years. But I find Canada is a pretty like comfortable place, uh, to, to live. Uh, and things generally like work. Uh, it's a pretty safe place generally. And one of the reasons I was interested in writing my book, uh, The Uncertainty Advantage,

• 50:21Speaker 01

  is because I think that the message is really important for Canadians, because we live in a more tumultuous world. And it's important for Canadians to push themselves out of their comfort zone and to build anti-fragility and the ability to see all of this chaos and all these changes is actually an opportunity to build a stronger country. Uh, I gave a talk related to my book, uh, I've given a couple of talks related to this. Two for Global Affairs Canada, which is the equivalent of the Canadian State Department for, uh, Canadian diplomats on how do they build anti-fragility in their work? And how do they represent Canada in a way that, uh,

• 51:04Speaker 01

  seize the opportunities and the uncertainty rather than, uh, the setbacks? I gave another talk at, uh, an event called the Banff Forum, which is one of Canada's kind of leading uh, public policy conferences, kind of like a world economic forum, but for Canada. And one of the things that I sort of shifted the talk was, was really thinking about the uncertainty advantage for Canada as a country. The book is, and our conversation today is framed in the context of

• 51:32Speaker 01

  people, but I also think the uncertainty advantage applies to businesses, applies to countries, that when you're kind of lulled into this sense of comfort, that is when you are the most vulnerable for disruption. And I think the people who are often the most resilient in life, they are constantly, when they're too comfortable, they're like, hey, nope, I'm going to change it up. And I'm going to make myself uncomfortable. And that's, I've been a state of venture for Canada for like 30 years. I realized I'd been doing this for 12 years. I was getting too comfortable. And I need to change things up and I need to push myself out of my comfort zone. Otherwise I'm at more, more risk of being disrupted. And I'd say the final thing I'd say to wrap up this question is,

• 52:15Speaker 01

  I remember someone who's a really successful entrepreneur in Canada, said this line is that there are risks in not taking risks in life. And that resonates with me a lot when I'm afraid to do something. Because I think on the counterfactual, and I think of, for instance, that decision to leave Goldman Sachs. There was a risk in me staying at Goldman Sachs, because Goldman Sachs was not the right fit for me necessarily. I probably would not have been super motivated and a really hard worker at Goldman Sachs. Maybe potentially I would have been let go, uh, eventually. And, uh, I was in a type of the bank, an area that too was more vulnerable to kind of automation. And all to say is that, it, to link back to that question on comfort,

• 52:58Speaker 01

  I think the, the ability to push yourself out of your comfort zone and to recognize that there are risks in not taking risks is so critical for individuals, for countries, for companies.

• 53:09Speaker 00

  Love it. No, this so right. This, you're so right. And Scott, I, I really appreciate you coming on the show today, because your insights are more timely than ever. And I feel as though every year that goes, goes by, your book will increase in value, because we all need to embrace uncertainty. So thank you, my friend, for coming on the podcast. And before you go, just let, give one last, uh, final shout out for the book and how people can get in touch.

• 53:35Speaker 01

  To get in touch with me, I recommend that you fill out a short quiz. Uh, and you can access the quiz by going to Scott Sturd, S C O T T S T I, two R's, E two T's, dot com slash quiz. The quiz will give you a score from zero to 48 on how good are you today in navigating, uh, uncertainty? And the first step of learning to develop a better relationship with the unknown is learning what is your current relationship with uncertainty. The quiz takes three minutes to fill out. And I really recommend that you do that as a next step from this interview, uh, as you look to improve and build up your uncertainty muscles.

• 54:16Speaker 00

  Amazing. Scott, thank you so much for joining us. Really appreciate it.

• 54:20Speaker 01

  Thanks so much for having me on.