80. Scott Stirrett and The Uncertainty Advantage

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You're listening to the entrepreneur podcast from the Western Morrissette Institute for Entrepreneurship, powered by Ivey. Scott Stirrett is the founder and CEO of Venture for Canada, a national charity that fosters entrepreneurial skills in young Canadians by recruiting, training and supporting them to work for innovative Canadian small businesses and startups. After running the venture for a decade, Stirrett has collated many of his learnings into a book titled The Uncertainty Advantage: Launching Your Career in an Era of Rapid Change. In this episode, Stirrett speaks with Ivey faculty member Eric Janssen about turning down a job at Goldman Sachs, launching and growing Venture for Canada, and some of the Six Pillars cited in his book for building our "uncertainty muscle" for a world that is looking more and more volatile.

Eric Janssen  
Scott, excited to have you here. Thanks for coming in. You've got a new book The Uncertainty Advantage that we're going to talk about. But I want to rewind back, because we're about to walk into a classroom with a bunch of 22 year old, 20-somethings that are ready to take on the world. And I just wanted to rewind back to where you were at when you were in their shoes. Where were you at 22?

Scott Stirrett  
When I was 22 I was in a period of a lot of uncertainty in soul searching in my life, for a variety of reasons. One was that I was really figuring out what I wanted to do with my career. I had, at 22, accepted a job to go work at Goldman Sachs, and that was based on having interned there between summer of third and fourth year of university, but I knew that that was not the right fit for me. So when I was thinking of this exact moment is, in the first semester of my final year of university, I had a signed offer to go back to Goldman Sachs, but I had this gnawing in myself that this was not the right fit for me for a variety of reasons, I like more entrepreneurial type of environments. It was also a period of time that was a complicated one, just in general, for identity formation. I hadn't actually come out of the closet yet then, it was in February of my senior year of university, and I was agonizing about coming out the closet, and it was a really stressful period of time. And then the other thing that made it kind of stressful was my strength is more in the liberal arts academically, but I had to take a stats class through the School of Foreign Service at Georgetown where I graduated, and I was not very good at stats, and I ended up going to, every single office hours. I got like a D on the midterm, and then I literally ended up spending so much time with the TA that I feel like the TA basically gave me a C plus, and passed me out of pity. But at times I was stressed. I'm like, “Oh, my God, am I going to graduate?” So to answer your question, I was to zoom in to where the students are right now. It was a time that was stressful for a variety of reasons. And candidly, when I even think back of like how did I feel, somatically in my body, then it was very stressed out.

Eric Janssen  
It's not uncommon. I think at this age, people will say often that these are the good old days, right? It only gets more. The demands will only get more. You'll feel the demands more as you get older. In some ways, that might be right. You know, there are other responsibilities. Maybe you become less focused on you. There are maybe children, there are pets, there are family demands, or work demands, other things. But I actually don't remember my 20s as being totally stress-free. It actually is a pretty overwhelming time, and I found at least not a lot of resources to support that. There's the "get the degree from your school", and they're progressing you through the steps to be able to get the degree. Some courses are useful in setting you up for your career, but there's not, like, a "how do I navigate this actually very stressful time to figure out what the next chapter looks like?" We don't really have those supports.

Scott Stirrett  
I agree, I think a lot of the time there's a lot of focus, a lot of pressure on young people to be like, "successful," but there's not necessarily a huge amount of investment in career readiness. And to acknowledge another thing you said is that I think your 20s are a really stressful period of time for a lot of people. It's stressful because it's a period of identity formation. It's in your 20s that you're really figuring out, for most people, their strong sense of self -- what do they like? What do they not like? For most people, it's where they meet their long term romantic partner, they move to a new city. There's a lot of uncertainty when you're starting out. And it's also a decade that carries a lot of consequence for later on in your life. I think sometimes there's this false sense that, oh, your 20s don't really matter. And Meg Jay has a great book called "The Defining Decade," where she makes the case that what you do in your 20s really can shape the rest of your life, and it sets a pretty strong foundation for what is to come in your 30s and 40s, etc. And the final thing I share is that when you look at life happiness, it often actually dips in one's 30s and 40s with the pressure of young kids and things. But it's often people in their 80s that are the happiest. And I think there's a degree, because when you're in your 80s, you've kind of, you know who you are, you've lived kind of your life. You know a lot, most of your experiences are behind you, versus when you're in your 20s, it's really easy to be anxious because you have so much of your life ahead of you. There's so much unknown -- your story is just getting written. And the final thing to end more on a positive note, is that, yes, that's really an anxious time, but it also is a time that is full of so much possibility. And I think that the importance for career education is how to get people to harness those anxious feelings, which are valid, into seeing the positive, the possibility that's ahead in life.

Eric Janssen  
I love that, and I think it dovetails nicely into probably the reason why you wanted to write a book like this. But before we get into the nuances or the details of the book, in the book and a critical part of your story is that decision that you made to not go full time back to investment banking and leaning into starting this venture, Venture for Canada, the stories and the lessons learned throughout founding that, I mean, it's an organization that's really held in really high regard in Canada. Everyone knows of it. That's in the startup or tech space. You raised a ton of money and got tons of support and supported 10,000 plus students in finding jobs in these ventures and leveling them up. And so I want to spend a few minutes on that, because at the time, maybe there was an inkling of an idea, but to turn down a job at Goldman Sachs, which is, like, the job that all of these business school students want. Could you just talk us through that? Where were you at? Where were you? Where was your head at, when you were making that call?

Scott Stirrett  
One paradigm, I think that influenced my thinking a lot in that time period was the question of, like, regret, and what am I going to regret doing? And I think at that age, I knew that I would regret staying at Goldman Sachs a long time, that I would regret, at 22, not making the leap to go build something that I thought is more aligned to my interests and could genuinely help people and be a more interesting kind of experience. So regret minimization, I think, was one thing that was part of it. I would say that a second thing that I was thinking about in the context of that age, well, a little bit, was the risk of not taking risks. I worked at Goldman Sachs, but I didn't work in investment banking. I was in more of a communications type role, which makes sense, because I didn't study finance. And the job of Goldman Sachs did not necessarily align with my skills, my interests, my passion, and I'm not believe of follow your passion, but I think if you're in a role that's misaligned with what you're interested in, but also what you're good at, you're not setting yourself up long term. And part of what I was also thinking in that context is that, does that make sense? Thing on like, a dead end job that's, like, a lot riskier than, like, taking the risk of betting on myself and launch something new. And the final thing I'd say is just kind of build on that, is that I think it's always good to bet on yourself. Like, the things that have turned out the best in life for me have generally been when I've taken things, you know, under my own control, and said, I'm betting on myself and going all in, and I'm going to work hard to try to achieve that. And I'd rather bet on myself than be in a big corporate setting where there's so much out of my control. Now I probably have, as I talked about in the book, perhaps I ended up having maladaptive control issues which I think a lot of entrepreneurial people have, but those are some of the things that influenced me at that age to want to leave Goldman Sachs.

Eric Janssen  
So the book, which I would say is a must read for the 20 somethings who are trying to navigate this. Why did you choose? What was the motivation to write it?

Scott Stirrett  
Two things: the first is that in my experience with Venture for Canada, where I've worked closely with, like hundreds of people, I've known thousands of people who've launched their careers, I've seen firsthand that fear of uncertainty is the most prevalent blocker that holds people back in launching their careers. And especially in the context of COVID and post-COVID, the level of anxiety that a lot of young people are feeling is extremely high, and I wrote this book to help young people thrive more in their careers and in their lives. On a second level, I've also personally experienced the fear of uncertainty firsthand. During covid, I was diagnosed with Obsessive Compulsive Disorder, and I really struggled with coping with uncertainty for a period of time. And like most people, I still have my moments where uncertainty can be really overwhelming to me. And there's a degree of writing this book that was sort of therapeutic for myself, of processing really challenging experiences, because just to dive a little bit deeper into the OCD part, I think unless someone has a sort of direct connection with OCD through themself or a close loved one, it can sound like a less significant than perhaps it was. But there was a period of time where I almost felt like I couldn't work, like I was not sleeping. It was a I would describe, now in retrospect, almost like a traumatic part of my life that was extremely dark. And it was one of those things I never thought that I would have a severe mental health challenge like that acute in a period of time. I would say that in some ways, there was a Scott before that happened, and then there was a Scott after that happened. And I emphasize that because I think that my OCD experience is a core motivator for me to write this book. Because while a smaller percentage of people, 2% or 3% of the world's population, is OCD, fear of uncertainty is a much broader thing that most people challenge with, or have challenges with. And I think when you go through a really challenging moment, you can kind of look at that moment and just say, “that was horrible, that was a really bad experience,” or you can try to find meaning. And as humans, we are meaning makers. And I think there's a degree of me writing this book that was meaning making for myself in terms of processing and ultimately trying to create a resource that would help me moving forward, but would also potentially help other young people as they cope with uncertainty in a rapidly changing world.

Eric Janssen  
A term I want to pick up on there, you said, "cope with," and I think that's probably the way that we think about uncertainty, right? It's this thing that's happening and like, "Oh, it's a bad thing," and like, how do we, what are the mechanisms that we can use to deal with uncertainty, to manage the uncertainty? And I think the way that I read your positioning of it is actually almost an analog to antifragility. It's like we actually want to embrace it, to lean into the uncertainty.

Scott Stirrett  
I totally agree. It's funny. I had another conversation recently about the book, and similarly, the person kind of pointed out like, oh, this seems like it's more kind of talking about the negative of uncertainty. In “cope with,” which I recognize does have more negative connotations, I think it's emphasized that the more someone sees the possibility in uncertainty, kind of what we were talking about earlier, the more that I think someone is going to benefit from the uncertainty in the world that it is important to acknowledge in conversations, that these can be, like anxiety inducing times we're doing this interview, and like Charlie Kirk was assassinated yesterday, it feels like a lot is going on in the world, like at the moment. And yes, it's important to acknowledge that anxiety, and at the same time, it's important to see that there are, with the rise of AI and massive technological breakthroughs, so much opportunity out there, and I think sometimes with uncertainty, our minds go to the negative for a variety of reasons. But for young people, it's important to see the possibility, and the more that you see the possibility and uncertainty, I think the more that you can ultimately learn to thrive. Because as this therapist that I worked with when I had OCD said to me, and is a core part of the book. The only way out is through. The more that you actually try to control the uncertainty in the world, the more that the uncertainty begins to control you, the more that you go and face the uncertainty head on and embrace it, the more you actually develop a healthy relationship. And I think unfortunately, a lot of people who have a tendency to fear uncertainty go more the direction of trying to control the unknown, which just makes them more and more vulnerable. So to your point, if we're going to embrace the chaos of the world, we need to be anti-fragile. We actually need to think about not just tolerating disorder, but how can we gain from chaos?

Eric Janssen  
Yeah, I spent a lot of time in the go-to-market and sales space, and it seems like an area that's changing. Everything in the world is changing quickly, but it's the world that I live in, so I see it changing in more nuanced details that I see other parts of the world changing. And yeah, it's easy to look at, like, oh my gosh, like, literally, the way that I would teach this or execute this a year ago is totally different than the way that I would do it. Now the students that are going to be entering entry-level go-to-market or sales roles or even startup roles like you've prepped tens of thousands of folks for those roles are changing really quickly. And I think it's easy to look at that and say, “damn, that's a challenging thing to work through.” But I like your frame on it, which is good, like what a neat opportunity that everything is changing. These young people have more in front of them than behind them. Let's lean into it totally.

Scott Stirrett  
And the core of being entrepreneurial is to identify and act upon opportunities to create value for others that I did not create that term. It comes from this framework called EntreComp, that stands for the entrepreneurial competency framework that was widely used throughout the European Union. And to zoom into that, it's to identify and in a world that is moving really quickly, there are more opportunities coming up than ever before. It was one of the reasons why I'm leaving Venture for Canada now is, I think this is actually, like, a really exciting time to launch new things. It's sort of, I often as a kid had sometimes jealousy of, like, oh, it would have been interesting to have been 20 in 1994, when the internet was starting. And I think in some ways it's kind of like that. Now there's this new opportunity because of AI, which I think in some ways can be overhyped in the short term, but probably in the long term, the potential is very significant. And yet for young people, we live in a time where opportunities are going to emerge at a quicker pace than ever before. Sometimes for me, I find FOMO can be the hardest thing, because the world's moving so fast that there's almost so many different directions that you can go in that it can be challenging to pick one thing to sort of focus on. Before we were recording, something we were talking a little bit about, is like, just that importance of focus and yeah, so we live in an exciting time, there's so many opportunities out there, but it's also important to be really clear on, what is the one or two things that you're really going to like focus on in your life?

Eric Janssen  
In the book, talk about six pillars, and I think if you're okay with it, we can double click on a few of them, but a few that really stood out for me were, the first one was self compassion. And you had mentioned your diagnosis with OCD, but before that, I think in the book you talk about your there's a perfectionism, panic attack, I think that you had in college. So on the topic of self compassion, you had a really interesting learning around that time in your life, can you maybe bring us back to that panic attack that you had when you were in college?

Scott Stirrett  
When I was in college, I went to Georgetown, and I, for context, grew up in Nova Scotia, and I went to a high school that had like 50 people in the graduating class. It was very small, so there weren't that many opportunities. I mean, there were, I did a lot of competitive debating, but the choices were limited in the context of there being, like, 50 people a year in this school. And then I went to Georgetown, and there were so many opportunities, like in terms of clubs and student organizations, and you're in Washington, DC, so a lot of students do interesting internships while taking classes. So by the second, By the second year of university, the first semester, I was taking full course load. I was interning 15 hours a week at a political consulting firm. I was involved in all the, like, a bunch of student organizations in a very significant way. And when I added it up, I was working like 110 hours a week between because I was like, you know, 40-50 hours a week on school, like 20 hours a week working, and then, like, probably 30 to 40 hours a week doing these student clubs. And I remember I just couldn't sleep, like I ended up sleeping like three or four hours night, and I had so much work I was part of this, in retrospect, kind of silly student organization at Georgetown where we were very basically a bureaucratic agency that approved funding for student clubs, and we would have meetings from like 9 AM to one in the morning. These are, like formal, like Georgetown, like student meetings, which, in retrospect, was also just really unhealthy to have meetings from 9am - 1pm also, there was a staff member with us to like, I'm like, in retrospect, like, what was this guy doing to one in the morning? Like, that's not reasonable work expectation for him. And I remember after one of those sack meetings ended at like, one in the morning, I ended up having something due the next day that I hadn't had any time to do. So I ended up basically going to the library and then, like, working on it, and I just, I reached a point where it was like, Oh my God. Like, I basically had a panic attack because I was like, I'm gonna sleep like 30 minutes tonight. Then I have to do all this internship work the next day, I have literally no break time. And kind of, what I resolved then was okay, I can't cut all these things, so I'm just going to push through, and then I'm going to gradually not do the things the next semester, and then it got better. But I think in my life, and I've had other points- not as extreme as that, even right now is a pretty busy time, but I think I’m being careful. I have a tendency to push myself to the limit, and I think an important part of the conversation on antifragility is you want to build your muscles of risk taking and pushing, putting yourself out of your comfort zone. But there becomes a certain point when too much is too much, and that was my experience in the second year of Georgetown.

Eric Janssen  
You can push beyond, I think that was one of your points on this is, I like that you called it out to say that there are things in life that, when you're really into it, are worth putting probably an unhealthy amount of work into for periods of time. I'm paraphrasing, so feel free to change my read of it, but it was like when you're building a Venture for Canada, when you're launching a new book, there are going to be sprint times. And even during those sprint times, it's healthy for you to maintain whatever it is that keeps you a good whole human. Maybe it's your sleep, maybe it's your exercise, maybe it's your diet, maybe it's your time outside, maybe you call your mom, I don't know. But I like that you balanced like, “look, there's always going to be these busy times, but you've got to intersperse it with these.” You called it periods of renewal.

Scott Stirrett  
Yeah, there's a line I think I quoted in the book that I had seen on X a long time ago where this person said, "Life is a marathon punctuated by sprints," and sometimes you do have to work really, really hard for periods of time. I think part of the challenge with the soft life discourse and like, the excessive work life balance, I think, is that people think, like, I don't necessarily buy, like, the four hour work week, that you can just do that and like, be really successful. I think sometimes you have to grind it out and you have to work really hard, but also that it's important then to have periods of time of reflection, of pausing, even when you look in history. And by the way, actually, I think I might have read deep work now by kind of important. I think about it. Because I think in his book, if I recall, he talks about how in history, there were certain people who they would work really hard, and then they would go on like a three month long voyage. And there was more built into, like creative lives that you would have these, like, long sojourns. And I, after leaving Venture for Canada, I'm going on a nine week trip and doing that, and I'm working really hard now, but I know that I have this, like nine week restorative experience anyway. All to say is I completely agree. I think it's, it's thinking about trying to do both in life, and sometimes you do have to work really hard. But I think for most people, it's tough to have that, that sprint pace for an excessive period of time. The body does keep score on that; eventually it comes back to bite you.

Eric Janssen  
Another element you talked about in self-compassion was the comparison game. We're all guilty of it. I think I'm guilty of it, but I've realized over time that's particularly triggering for me to see other people that I think are further ahead of where I should be. And I think you had some really interesting insights into how to stay out of playing the comparison game as I stare at my cell phone jail lock here on my desk so that I keep my phone away from me. So maybe talk about the comparison game and how you're able to filter that out a little bit.

Scott Stirrett  
Yeah, and I can still fall victim of the comparison game. I think we are very comparative creatures. I think in some ways it's about how to mitigate the comparison game. I think for most people, the comparison game doesn't disappear. But I'll just share a quick story, and then to give the advice part is, I remember in university, just like, fixating on this, like, and while I was at Goldman Sachs, this one person who I thought had it all together. Like, had founded this company, you know, raised all this money, had all these employees, and, like, built this, like, really successful thing. And then, like, in retrospect, I realized that this person's life fell apart. This person had significant mental health issues, got divorced, the company, kind of like, collapsed. And it was a good example of, you never know what's actually going on in someone's life. And I think the second point is that it's also really important to acknowledge that we're all playing like our own game. And I think one thing that's helpful for me is to not get in a comparison with another person, but to think about, okay, if I'm competing against myself, how am I doing this year relative to the other year? The final piece of advice, though, I'd have for a listener, is a lot of it is just, I think, being mindful and being aware of when you fall into that comparison trap. So just labeling it and saying, "Hey, I'm getting into a comparison trap, this doesn't really make sense." I had something recently where I was looking at my book relative to another book and how the sales were doing, and then I was like, oh, no, I'm going into the comparison trap. I was like, stop that. I was like, you know, let's compete against myself again. And that final piece, I'd say that I also talked about in the book just limiting social media time. It's something I found challenging recently, because a big part of promoting a book is social media. I feel like I have a love-hate relationship with social media now, because I kind of need to engage with it. But I do think social media can be a really bad driver of the comparison trap. And I think learning to develop like a healthy relationship with social media. I think for a lot of careers, you can't just completely disconnect from social media. But I think thinking about social media in an authentic way, and it's not getting into that kind of comparative trap that can be really challenging. The final thing I share on the Social Media front is it's funny, for a lot of my life, I would be the kind of like, not recently, but I'd say before 2019, 2020, I'd be the kind of person who would like, share, like, things like picture on vacation, on Instagram and stuff like that, which I don't do anymore. But I found that the things I've shared on social media that have had the most resonance are actually when I'm like, very like, vulnerable, and not saying, "Oh, look at me," it's being authentic. And as a broader point to this kind of comparison trap is, I would encourage more people to, like, lean into like, talking about, like, the challenging moments too, that that happen. And I think in doing so, we can make it like, where social media can be so powerful is when I think it's authentic, when I think of things I would maybe regret, of how I've used social media in the past. It's more in that, I think when I'm in more of that “look at me,” where I'm on “vacation mode,” I'm implicitly kind of falling more into that comparison trap.

Eric Janssen  
I'm guilty, we're all guilty of it. I think the difference now is how I've evolved with it, is I do exactly what you do, which is like, I can label it. I can say, this person just posted about a new toy that they got, whatever, boat, cottage, car, a thing. And I see it, and I go, I feel the pang of like I, you know, they're the same agent. Why don't I have those? Why don't I have that thing? Maybe I should, I think, and I'm able to step back and go, Wait, is that actually what I want? Or do I just see it? And I'm playing the comparison game. So I think I'm better able to pull myself out of it, almost view that feeling from a higher level and say, like, Huh, that's interesting that I'm feeling that right now. I wonder, why do I actually feel that way? Or is this just like an instinctual response?

Scott Stirrett  
And I think it's, you know, as one gets older. But I think same, what this conversation also relates to young people is, I think it's easy to, in particular, with like possessions, or kind of like money, to get into this comparison trap. And I think the thing that has been sometimes helpful is to recognize, even if someone's like, a billionaire, or they're really rich. I think a certain level of financial wealth is important for freedom, and that's not immaterial. But I think sometimes, when people are like, okay, like, if someone's driving like, does that material like, when you get into that material trap, I think it can make you you just want more and more that there's a and you just end up keeping on chasing those things, and you end up not actually being kind of happy. And the reason being is because there ends up being more an extrinsic driver. Clayton Christensen, in his book "How To Measure Your Life," which I think I referenced in this book, he talks a lot about “you need to focus more on, like, what are your intrinsic drivers?” Because you can control the intrinsic, the extrinsic someone can take away at any different point. And it's a useful message for me, and it's something for me to reflect on too, is to not get stuck in that kind of extrinsic, kind of competition, of just wanting more and more. I remember, I love the books by Robert Caro, in particular, the ones on Lyndon Johnson, and there's a line from that that always resonated where, yeah, I forget the context of it, but he says that "the appetite grows by what it feeds on". And I think it's a useful thing for a lot of people to think about is once you want more of it, you people just want more and more and more. And I think a lot of the feel like a lot of the traps of like, really successful people who sometimes are unhappy that, and Clayton Christensen talks about this from his like Harvard business school class, and how so many of the people end up being divorced or like alcoholics or Enron and going to like prison, is that they get stuck in this extrinsic kind of competition track where they just want more and more and more, and they're not focusing, kind of going back earlier on, like, the pillars of life, family, health, friends. Ultimately, those are the things that really matter. Not to say, I mean, I think it's, there's a degree of socio economic privilege to be like money doesn't matter. Money does matter. And I think it in particular matters because it buys freedom. It buys choice. It reduces stress, but I think beyond, at a certain point, people end up just doing it for the extrinsic driver, rather than then, kind of, what is? What are things that are likely to provide more happiness and fulfillment long term? By the way, in an earlier version of the book, I talked a lot more about this subject. So my book goes through a lot of iterations. Some of this content is making me think back to an earlier draft of the uncertainty advantage.

Eric Janssen  
So you do touch on this, actually, in the second pillar on adaptability, you talk about the value of coming up with your list of personal values, as well as your mission statement, which maybe can act as a bit of a rudder or a guide in navigating the next chapter. So how can you develop those things and then take actions or live a life that's in alignment with your mission and your values you talk a little bit about, we talk about this from a company perspective, but maybe not for a person. So what is the role of mission statement and personal values, and how should people think about coming up with those?

Scott Stirrett  
On a mission statement? It's, it's thinking at a really broad level, like, what's the purpose of your life? And think about, I mean, I use, like a guy kind of concept of, "What is it that you like? What is it that you're good at what is it the world needs? What is it that you can get paid for?" I think that that's a helpful framework a little bit to think about as you create this, this mission statement, then just start writing down a bunch of different mission statements, look at company mission statements well, and then eventually, kind of whittle it down to something that resonates for you. I remember it took me, like, a couple months. I workshopped it with a bunch of people. But for me, my life mission statement is to help others achieve their full potential. And I see a real through line through most things that I do as it relates to this mission statement, from Venture for Canada, to writing The Uncertainty Advantage, to I'm pretty involved in promoting access to competitive debate for high school students in Canada. And, yeah, I think it's, it's also reflecting on those experiences and thinking about, like, what is the mission statement that most of the lines to you, and I think it's valuable that it's actually pretty broad. Like it, you know, I could say my mission statement is to, like, help 18 to 24 year olds in Canada become more entrepreneurial. One could say that that has been a focus. But is that the focus of my entire life? Probably not. That's where I think creating a pretty broad mission statement is helpful. Then in terms of values, similarly, I would recommend, think of like, 20, 30, 40, values, and then start to bucket them into different areas, and then think about, what are the values that show up to you most when you're challenged or you're facing a moral dilemma? And for me, my core four values are integrity, inclusiveness, curiosity and ambition. And those are things I reflect on when I am in challenging moments. But in a world where things change really fast and your life can shift, I think thinking through the mission statement and then your values as a core guide, as I believe, Venture for Canada, I was considering a bunch of different opportunities and things, and I found the life mission statement in this specific point in my life has been really helpful For evaluating opportunities and ultimately being like, "What is mission statement aligned? And what's not mission statement-aligned?" And to the point, strategy is what you say no to. I think I'm trying to be more ruthless in trying to focus on my core life mission statement and aligning the activities of my life to support that mission statement.

Eric Janssen  
So I've done versions of this, and sometimes it takes saying it out loud a few times to like, how did that feel, saying that in front of a room of people and like that felt okay, but like, there's some tweaks that I need to make. Reading your book reminded my partner and I to go through and we actually did it for our family. So we had four young kids, and I think we kids actually want rule almost like rules or frameworks for how to behave. So if we've found that if we have clear criteria for what we expect in our family, what do we all value? What do we want out of this experience together as a family, and we actually included them in the process. And then we reward, we celebrate as a family when someone acts in alignment with those and then there's consequences, if you don't super simple one, we're all a team, like, how would you treat someone that's on the same team? Some of them play sports. Would you do that to someone on your hockey team? So anyway, I don't think we've got, we haven't gone far enough to do it for us. Personally, I've always seen the value in doing it for our company, but also as a parent, laying that out for our family,

Scott Stirrett  
I love that, and it's funny. We're in the process of having a child via surrogacy, and I actually thought a little bit about this in the context of raising kids, is that I think it's a great idea. At Venture for Canada, we've interacted a modest amount with the family business space, because of some of the programs that we do. And there's a guy University of Ottawa, Peter Jaskiewicz, who runs this center on family business, and that's what he talks a lot about his, like, the really enduring family businesses and enterprising families, I think is the term, because, you know, it's there's the business, but then it anyways, in a lot of these situations, it's a constellation of businesses. Is that there's really clear, articulated values for the family, that there's a constitution for the family that governs the rules of behavior that is quite detailed, especially on some families, like the larger the family, the sort of more net worth, the more complicated these rules of engagement can become. But anyway, all to say is that I think it's, it's something that, you know, someone doesn't need to be that like, I think it's something that a lot of families should consider more, not necessarily a formal constitutional though I could imagine, even for some things, having really clear rules of engagement can actually be helpful. But I think thinking through kids, and you know, to your point, from what I've read, is kids want stability. They want clarity. And I think to sometimes, if someone acts out to be like, "Is this values-aligned behavior?" Even sometimes with different situations of people closer to my life, sometimes I’ve thought, is that person behaving in a values-aligned way? And I've started kind of thinking that a little bit more, but it's really useful for family members, because then it's not saying, Oh, that's not good, but it's saying, like, "this is the code for the family." So anyway, I love that, Eric, I think that the context, like, it's really helpful for a person, but also for the family unit. And ultimately, the family is the basis of society, and I think families thinking about family mission statements also, I'd say the freedom that people have, you know, individual mission statements within that. But I really love that idea and something I'll carry forward as I think about things in my life.

Eric Janssen  
Last thing on values, then we're going to jump to the next pillar. I find it helpful as a constraint to help young people make decisions. So something that I think I forgot for a bunch of my 20s and 30s was fun and adventure. Not that I didn't have any fun, but I was pretty focused on work. And when you think back to the times that I was most joy-filled or happy or reflect positively on it's like travel was a big part of that. Sometimes having no plan for the day, and like going to the park, going to the water park, that actually is, when you look at the defining moments in the year, those often came up. So, as students think about making career decisions, if you were clear about a thing that's important to me is fun and adventure, or to your values ambition, you can actually start to make decisions, career decisions, partnering decisions based on the values that you've articulated. So I find it a good reference point as you're trying to navigate this next chapter.

Scott Stirrett  
100%, yeah, I think it's and even reflecting on me, on the values, it's like doing this nine week trip. It links to curiosity, like, I love learning about the world. I'm going to places that I have not spent very much time. And yeah, it really will fill my cup. And to also point on regret minimization, like, I think for a lot of people, if you look back at the end of your life, you'll regret not doing those kinds of adventures. And I also mean to relate to other parts of the book is adventure is how you build your risk taking muscles. It's how you foster more entrepreneurial thinking. I talk a little bit in the book about travel and the importance of it, and early versions of the book were actually even a much bigger chunk of it. But I actually think, you know, if recognizing there can be so many different socio economic realities, there's still thrifty ways to travel too. I think going and traveling the world and just getting out of your comfort zone is like a really important thing to do in your 20s, particularly if you have had less exposure to it, kind of earlier in life. I think it's even more important to go. The world's a really big place, and sometimes in Canada, we can be a little, perhaps too insular.

Eric Janssen  
I love that travel keeps coming up as a recommendation from folks who have come speak to this group of people. So that's another good reference I want to talk about, so you reference antifragility, which maybe might be worth spending just a minute on, for people that aren't familiar with the term. But what I wanted to narrow in on with it was two pieces: The first is the idea of it being similar to a muscle. I think sometimes people think that resilience or antifragility is something that you're either born with or not, and you talk about it, I think more like a muscle, which I want to spend some time on, and then also how you build it being around other people who also exhibit those characteristics. So maybe start with what is antifragility?

Scott Stirrett  
Antifragility well, and first to kind of give context on how the term kind of got created, comes from Nassim Taleb, and he wrote a book called antifragile around 15 years ago. I think now that is a best seller, great book, lot about more investing and essentially, what Taleb argues is that antifragile are things that don't just tolerate disorder, but they benefit from disorder. So if I have a glass cup and I throw it on the ground and it doesn't break, then it's resilient. But if I throw a glass cup on the ground and it turns into 20 glass cups that are nicer, then that's an antifragile thing. And when you think in society, there are certain things that are very fragile to disorder. He talks of a lot of big systems and sometimes like government processes, for instance, they are not that adaptable. So when something really big changes, there can be a lot of consequences. But then, what are the things that can benefit from disorder? Often, it's startups. It's very agile people. It's entrepreneurial people. Those are the general entrepreneurial people and organizations are, I think, he would argue, generally, the people in institutions that benefit the most from chaos, because they see the opportunities and they move quickly and they capitalize on them. So that's what antifragility is. In terms of spending time with antifragile people. I think it's a really core part the class I took at Georgetown. I remember the professor, he hammered this home so much is that you are the average of the five people that you spend the most time with. I remember that Jim Rohn quote still to this day, and I think it's really true, like it's something that always stuck with me, and it applies to antifragility, like the more that you're with people who are pushing themselves out of their comfort zone and that are benefiting from disorder, the more you yourself will become antifragile. I have a really good friend from high school who has done really well, runs a hedge fund in Bermuda, very smart person, and just his risk taking propensity and his entrepreneurial kind of mindset is very, he left a very lucrative role, and then at a significantly kind of later period, ended up launching a fund that has done really well, you know. And, yeah, this person, you know, I think, is a good inspiration for me, in a in a great way, because he and there's other people in my life like that too. But I think in particular, when it's someone you've known so long, you know, I think likewise, I think if you're with people who fear uncertainty, it becomes more the norm. So I would, you know, be careful who you spend your time with. And I think a core part of being antifragile is being around antifragile people.

Eric Janssen  
Yeah, it's great advice, because I think some people maybe grow up in an environment where there's not a lot of risk taking. You've mentioned a few times, like a lot of I think there's some privilege with that, right? If you come from a socio economic background that is ridden with uncertainty. Maybe you actually want to get away from that, or maybe you've grown up with in an environment where that isn't valued, and, in fact, is dangerous. So you actually want safety, but I think leaning into finding people that pursue it or exhibit it, and the positive sides of it, the safer you know, ways that you can test it out in an environment that feels safe to you, you should pursue that. But how do you reconcile those two like, what would you say to someone who maybe grew up in an environment that they feel like they want to run away from that fragility?

Scott Stirrett  
I think it's the only way out is through and I get it. I mean, there are times in I get if you've had childhood experiences that make you fear the fragility. But I think that the more that you try to seek order, especially in a world that is not ordered, the more that you're going to become vulnerable to chaos. It's interesting. I find in my anecdotal experience that people who have had the more fragile, challenging kind of upbringings, sometimes it can be extreme, like some of those people they lean into the risk taking. And then there's the people who then, like, go the inverse. I think, I mean, there might, I'm sure, scientific research on that, but I do find that sometimes those situations cause like, the like, sort of extreme and in kind of personality type, like you look at someone like an Elon Musk, like very challenging childhood father from all you know, reports quite abusive. And then like, super intense characteristic. And then there's others who end up, you know, developing more like anxiety disorders, and then, like, kind of, you know, really almost being kind of shut ins from that level of traumatic experience. So it's interesting, just the how people kind of respond to that. But yeah, we, you know, I'd say that my main point, though, is that I think regardless of of your experiences earlier in life, the only way out is through like, you need to embrace the chaos of the world to to thrive and to ultimately be able to capitalize on all the opportunities that are out there.

Eric Janssen  
Last one I want to mention is generalist skills. I'm lying. I may actually go into professional relationships as well, but generalist skills, so I love this, because we've historically thought of these as soft skills, and I've liked a movement to rebrand them as power skills, like really important skills, actually, that are going to differentiate you from the pack. And so you mentioned a few of them in the book, and feel free we can double click on any of these. But the ones that stood out to me were communication, actually listening and then being reliable. So any or all of those are interesting to me. But which one would you like to spend

Scott Stirrett  
some time on? I think on the reliability piece, because I think that that's perhaps the most important for, like, a young kind of audience. The Financial Times recently had this article that was about the decrease in conscientiousness in young people. Essentially, there was a study done in the US that it was on personality traits. And there's the big five personality traits and they're the personality traits that are widely thought to exist across almost every culture. So, like, people have done all these studies, like, if I'm like hill tribe people to like people in Japan, to like New York City, you can measure agreeableness, like, as a thing. Conscientiousness is another one. What? What I mean by conscientiousness is essentially like, are you conscientious about how your actions impact other people? Part of that is reliability, like, there's a strong link. Highly conscientious people are much more likely to be super reliable and follow through on what's what they're going to do, because they know that if they don't follow through, they're negatively impacting the person, and they're conscientious, so they don't they don't do that. Essentially, this study has shown that there is a significant decrease in conscientiousness amongst young people. According to this there's some debates, and there's been it's not they're somewhat contested, but it's something from my own anecdotal experience that I have observed, perhaps, in people just enter into the workforce, a little bit of a decrease in conscientious behavior. But I think even started with, like millennials, I think there's a lot kind of driving the perhaps, I think perhaps a society that is more individualistic, and there's a lot of perhaps, like, I wouldn't blame, I think in in this kind of conversation, this tends to be blame young people for being lacking conscientiousness. But I think it's definitely a thing, and it's emblematic and everything from like ghosting job interviews, like this trend of people just like not showing up, but also a lot of other broader things, I think, sometimes in the workforce. So this question, then to go back on kind of reliability. And reason why I kind of give all that context is, I think if you're a reliable person today, it is a huge advantage, because there it's a really hard thing to find like, to find someone who is just like, super like they say they're going to do what they like. If they say they're going to do something they do. It is like, a rare, like, commodity. And when I see it in someone, I'm like, oh my god, this is like, a great, you know, thing to look at. And it's funny, even just, I would say, like, we've only gotten to know each other more recently. But I was like, I My instinct is I feel you're very conscientious. Like, I feel like, if you're somebody who you know, in all of our interactions, I've seen like, you say you're gonna do something you like, follow like, through on it. And I think for young people, like on a more practical way, like, how do you be reliable? And I actually don't think it's that complicated. It's like, if you say, if you make a commitment you like, follow through on it. And there's a framework I've talked about in the book, the pillars of helpfulness, which I think is also helpful. But essentially, in this it's, don't just come with like, problems. Like, I think a lot of times people will entry level employees will say, Oh, well, this is a problem, and they just overwhelms the manager. It's just like, you're coming it's like, find the problem, create the solution, fix the problem, and then, like, tell your manager you fixed like the problem. Like, that's how you're. Are like a really top notch kind of person. So in a world that is really uncertain, where there, in some ways, there's a need for some stability, I think really reliable people who do what they say that they're going to do are going to be at a huge advantage compared to others. And candidly, I mean, I think I'm not the smartest person. There's a lot of people who are way smarter than me on a lot of things. But I think one thing that I tried to be like, really good at is to try to be conscientious. Is like, just following because it's like, you know, I can't choose how smart I am, but I can choose how conscientious that I am. And I also think the final part is on a point of values is just, it's just respectful, like I think from a beyond the fact that I think it puts you at a career advantage, I also think it's just the morally right thing to do, to be conscientious and to follow through like, on your like, perhaps It's a little bit moralistic, but, I, yeah, I think it's, it's, it's, you know, as I reflect on it, I also think it's like values aligned, like, to me, being reliable is really important to me because it aligns to some of my core values, such as integrity.

Eric Janssen  
I think about some of the student businesses, even that I've backed or invested in, some of the best interactions I've had with students are, you'll have a meeting. They'll say, at the end of the meeting, they'll say, Well, that was really interesting. You know what I'm taking away is, here's a couple things, and then they'll go, do them or not do them, right? Maybe I'll say, give them some advice, or give them some options. They think about it. They consider it. And if they ask for a follow up meeting, starting with like, hey, last time we spoke, you mentioned these three things. Two of them, they wouldn't say this, but like, kind of nonsense. I didn't really follow that. Appreciate your insight, but like, not going to pursue it. But this one was really interesting. So here's what I did, and I have some follow up questions based on that thing. I love those meetings. I feel like that's conscientiousness. And those are the I think about the businesses that I've actually ended up investing in that started from in this building. It was those students who just consistently there. They clearly they got value out of the interaction, they articulated what they were going to do, they did or did not do all the things that they at the end of the meeting. And then they had a follow up, and that's kind of where things picked off again. What a healthy what a healthy interaction. And then I even think, as a manager, to know that someone's consistently you're going to talk about stuff, they're going to take those things away. They're going to do things and then come back to you and follow up. You now don't have to keep track of all of these conversations and tasks that you've assigned or had conversations about with your employees. So I see it reflected in the it's sort of a leading indicator of future success that I see young entrepreneurs.

Scott Stirrett  
I love that. And I think it also relates to one of the other kind of generalist skills that you mentioned, which is active listening. Like, it's them saying, like, okay, these are the things that we heard from you, and then it's then mentioning them back to you. And it's like, closing, like, the loop. I think that that's really important meetings, but it's also, like, really important, important in life, like I think listening like, I always need to work on my own listening skills as well. And I just think one of the things I try to be mindful of is to, for my own learning, but also to signal to the other person, is to repeat back like, what you heard from them, not in like, a robotic way, but, I think that. But I think it signals respect. It signals listening. It's like evidence that you actually weren't just like distracted. And in a world where there's so much distraction, in some ways, I think that there's like less like real, like listening something I've been my journey a lot is I did a lot of competitive debate in high school. I was on National High School debating team. I participate in like 12 or 13 debating tournaments a year all across Canada. Each one of these debating tournaments just like three days long. So it's like a huge amount of time. And when you do that much of an activity, it shapes you. And when you debate, it's you're debating to win. You're debating to prove people wrong. And that carries some negative habits that I still need to work on, where sometimes I listen to like, okay, how can I win? How can I listen to prove that person wrong? Versus I think in life, what is more important in almost all cases is actually listening to like, deeply understand like, even if you don't agree with the person, it's like, well, how did they come to that kind of conclusion? And I think that if fostering that ability to like and to sort of catch yourself like, am I listening to just try to win, to prove my point, or are you listening to in a more deeply, like profound way,

Eric Janssen  
I love that in Charles duhigg's book, super communicators. Have you read that one? Yet? I have.

Scott Stirrett  
Not actually I have read, but not like more skimmed, not I wouldn't say I read it super extensively.

Eric Janssen  
Have it devoured so similar to your book, I read it like a hawk hunting for prey. I It's an amazing book. And in it, he talks about a concept called looping for understanding. And it's the same thing. It's like, here's what I heard. Do I Are we on the same page about what that we just had that conversation about? And it's a really important part of making people feel heard. It's also a really valuable sales tool to be able to read back to someone like, here's what I'm understanding your pains and problems to be and how we might be able to help.

Scott Stirrett  
Yeah, I agree. And to sell is human, right? Like it's sales is such an important- we're all selling kind of all the time, and it's such an important skill that people don't do the sort of the looping back. What is it? Looping? Looping for understanding. I love that as a the other point too, that it makes me think of that's somewhat different, but I think some people who can have challenges in the workplace, it's like, they go into meetings with some like and their decision is made, and then be sometimes, some people will be like, Okay, how is this one person on a completely different page than all the other like people, and it's and that's where, like, the lack of listening can create real issues. Like, I, you know, I've had situations where you're in workplaces and then you're kind of like, people are like, well, we agreed on this in a meeting, and then you're, I'm not even in the meeting, but I'm kind of like, I'm like, Well, it seems like there's like, what? But a certain point, four people will say that, you know, certain thing, have a meeting, and one person didn't then that that's issue for that one person anyway. All to say is that being really clear on next steps, it's good for both, like signaling respect and relationships, but it's also just good for, like, organizational clarity on decision making, a great thing with now more zoom note takers and things, is that there's even more clearly documented decisions and discussions than perhaps ever before.

Eric Janssen  
They're great tools. I find that actually I can be more present in the conversation with those recorders, because the notes are being taken. I actually don't need to write stuff down. I can just be present. I agree. Last one I want to mention is professional relationships and two things, because I'm the Sales prof here, you've mentioned or talked about the value of cold calling and then the value of weak ties. Let's talk about cold calling and maybe sales. It's something that's not really taught at a lot of business schools. Thankfully, Ivey's embraced it. What role has sales broadly or initiating conversations with people that you don't know. Ie cold calling played in the success of

Scott Stirrett  
your career. I'd say it's been a really important part. I'm a very active cold emailer of people, and I still am constantly and sometimes it works, sometimes it doesn't, but I feel like I've done it. Whenever I'm starting something new, I am doing it, so I'll share some specific highlights from my life where I've done this, starting Venture for Canada. I grew up in Nova Scotia. I was living in the US. I've been there for almost five years. I started Venture for Canada when I was, 22, 23. I had, like, no professional network in Canada, because I had been away from my, like, formative years, and I essentially just had to, like cold email, like a ton of people about this idea of Venture for Canada, like hundreds and hundreds, and I just was, like a machine sending out cold emails. And then gradually that helped me get, like, an advisory board, and then you start to kind of gradually build more and more awareness. But pretty much everyone who I know through Venture for Canada comes in some way, indirectly, through cold emails, which is kind of remarkable. The board chair who ended up being board chair for like 10 years, who's still there, like, through basically a cold email. And it has been pretty kind of remarkable, some donors who've given Venture for Canada hundreds of thousands of dollars of their own money, like significant individual donors through cold email, literally, that I just kind of went into this person's office somebody. A lot of times it did not work out. But even with my book, it's been I'm doing an event in the UK, and I'm trying to build like, do speaking in the UK. And right now, like, one of my current cold email is, like, I've never lived in the UK. I don't really know very many people in the UK, but I'm like, on this, like, cold email tear of just like, contacting all these career centers. And, you know, I'm getting a lot of rejections, but I got one recently where they're like, Oh yeah, we're submit this, like, little application and and all it takes, you know, is just like one, but you just have to. So anyway, I share those concrete examples to say cold emails have been really important. Oh, the other part is on the the entrepreneurship through acquisition, lower middle market, kind of business buying program, Venture for Canada did initially, we had, like, no background or context on that. I have a list of my like, eta people, entrepreneurship through acquisition, people I've spoken with. There's like 120 people on the spreadsheet where I just have like, relentlessly. So there's like, all these points in my life where, again, to the point I don't I don't share this. I think sometimes people say, like, I don't think I'm an unintelligent person, but I don't think there's a lot of people I met in my life, who are much more academically, like gifted than myself. I think what I do have, though, is just a willingness to sort of shamelessness of just contacting people and not being afraid of rejection, and being somewhat relentless too and contacting people. The final thing I'd share is just, I think if there's like, tips for someone on how to embrace the cold emailing, is, I think one is, just like, all it takes is, like a few people to reply. So it's okay to get like rejections. Like, you're probably gonna get way more rejections than not. And that's like the other one is, is, think about like, just like, this is probably somewhat, this is not like novel, but it just like, really test out, like, the wording of like the emails that you're sending, and it's amazing, just like the like, well written kind of cold outbound can have, like, a significant, like, difference versus not, well, well run, Yeah, just, I think for young people, like embrace, like cold contacting, in in your career and life like it, it can open so many like doors to you. And I think it also perhaps requires a degree of humility, like, I think, I think maybe for me, it's like, there's a little bit where I'm like, I'm okay to, like, do grunt work and just stuff like that. And I think some people maybe think that they're like, above doing it, because some of it can be like, a little manual or like, maybe not the most like, again, maybe not feel the most intellectually challenging, but it's actually really important, I think, for your like, life and career and on. Beyond the fact that it's helped me advance in a lot of things, it's also just like, I've met so many amazing people through cold emails. So you'd be amazed who will respond to a cold email, as I'm sure you probably teach, and you've talked about, in your course.

Eric Janssen  
It's shocking, the connections and the high level people that you can reach through, well rifted, well drafted, not I'm not talking one to many. We're not talking about pumping, creating an engine to send out 10,000 cold emails. It's like actually doing your homework, legitimately reaching out to someone in a one on one manner. It can, it can make your career. It can kick start your business. It can kickstart a relationship.

Scott Stirrett  
Totally, yeah. And I think as you get older too, it's not so cold emailing, but also how to meet people through your broader network. It's also, how do you get more introductions to people too, which is powerful.

Eric Janssen  
For those that are interested, where can they find the book? Where can they learn more about you and the concepts?

Scott Stirrett  
They can learn more about the book on Amazon. So it's on amazon.ca, amazon.com, they can also, in Canada, buy it at Indigo. They can buy it at independent bookstores across Canada. And to learn more about me, you can check out my website, stirrett.com, a benefit of a having unique last name, and yeah, and on my website, there's a quiz where you can get your uncertainty score. Because I think one of the first steps of learning to develop a better relationship with uncertainty is learning what is your current relationship with uncertainty. And I encourage you to check it out if you're interested in learning a little bit more about your current relationship with uncertainty. And the final plug that I'll make is I'm also on Substack where I send out an email once a month that is about navigating uncertainty. And as I've done this book marketing, it's actually working on the newsletter that has been one of the most fulfilling, and it's been a great way to also build and foster relationships with a large number of people. And yeah, I share personal stories, tips, resources, articles, all the sort of best things about navigating uncertainty that I've seen from the past month. 
Eric Janssen  
Amazing. If you are working through the process of whether we're managing or embracing uncertainty, you're starting your career, mid-career, looking for a change. I think it's required reading for anybody in that situation right now. So thanks for sharing some of the concepts. Highly endorse it. You can see my copy here, dog-eared, marked-up, highlighted to the moon, so a ton of value, and I appreciate you having you here.

Scott Stirrett  
Thank you so much. I really enjoyed it.

Introduction/Outro  
The Entrepreneur Podcast is sponsored by QuantumShift 2008 alum and founder of Closing the Gap Healthcare Group, Dr. Connie Clerici. To ensure you never miss an episode, subscribe to the show on your favorite podcast player or visit entrepreneurship.uwo.ca/podcast. Thank you so much for listening until next time.