Turning Uncertainty into an Advantage

In this episode of The Impostor Syndrome Files, we explore why uncertainty feels so uncomfortable for so many of us and how we can build a healthier, more productive relationship with it. My guest this week is Scott Stirrett, author of The Uncertainty Advantage.

Scott shares how his own experiences navigating major career risks, leading a national nonprofit and managing anxiety during the pandemic shaped his thinking about uncertainty. He explains why our brains are wired to fear the unknown, why many people would rather know a bad outcome than face uncertainty and how building “risk-taking muscles” helps us become more resilient over time.

In our conversation, we discuss the concept of anti-fragility, the hidden risks of staying too comfortable and why action is often the best antidote to anxiety. Scott also shares practical strategies for strengthening confidence, including creating a “hype document” to track wins and reconnect those successes to moments of uncertainty and growth. Finally, we explore the impact of AI on the future of work, why learning to learn is becoming one of the most important professional skills and how self-compassion helps us navigate change more effectively.

About My Guest

Scott Stirrett is an entrepreneur, author, and advocate for young people. As Founder and CEO of Venture for Canada, he's raised $80M+ to support entrepreneurial talent, backed by RBC, TD, Scotiabank, and the Government of Canada. His work has been featured in Forbes, The Washington Post, The Globe and Mail, CBC, and BNN Bloomberg. He is also an Ashoka Fellow, former Goldman Sachs analyst, and committed to helping people navigate uncertainty with clarity and compassion.

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Connect with Scott:

Book: https://www.amazon.com/Uncertainty-Advantage-Launching-Career-Change/dp/1459753224

LinkedIn: https://www.linkedin.com/in/scottstirrett/

Websites: https://www.scottstirrett.com/ and https://ventureforcanada.ca/

Past podcast appearances: https://open.spotify.com/playlist/1xarZbEJGnncpUs3AlPE4e?si=umdVGEaeRBu_DOrek3ma-A&pi=hqkWxSVGQHyeE

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Websites: https://kimmeninger.com

Transcript

Kim Meninger

Welcome, Scott. It's great to meet you and have you here today. I would love to start by inviting you to tell us a little bit about yourself.

Scott Stirrett

My name is Scott Sturt, and I am the author of The Uncertainty Advantage, which is a research-backed guide on how to turn all of the uncertainty that is out there in the world into an advantage in your life and career. The book is informed by my own personal experiences navigating uncertainty, founding a national charity that ended up raising over $80 million and supporting 10,000 young people across the country. And I've loved uncertainty at some points in my life, like when I quit my job at Goldman Sachs at 22 to co-found a not-for-profit, but I've also struggled with uncertainty, like many during COVID. I dealt with very high levels of anxiety and really found it hard to see uncertainty as a positive, and my lived experiences motivate me to provide a guide and resource for people on how to learn to turn uncertainty into an advantage in their lives and careers.

Kim Meninger

So, I love that you mentioned the fact that we have mixed feelings or a kind of a mixed relationship with uncertain uncertainty. There are certain aspects of it that might be motivating, or it feels almost like a bit of an adrenaline rush, but then there are others that can be really overwhelming. How do you think about humans and uncertainty? Like, what is it about uncertainty that we resist or don't like?

Scott Stirrett

For most of human history, matters of uncertainty often related to like life and death, when we were cave people wandering around, and there was a cave, and we didn't know what was in it, there could be a bear that comes out and eats us, and as a result, our brains tend to go to the worst case possible scenario when confronted with an uncertain situation, and that was important for keeping us alive, but in the real world it's often not matters of life and death when it comes to uncertainty, and it's evidence and research shows that often people prefer to know a bad outcome rather than an uncertain outcome. That being said, there are some people who love uncertainty, and even if you are one of those people, everyone needs to learn to continue to work to develop their uncertainty muscles, because in a world that is more uncertain every year, all of us need to build a regular ongoing uncertainty practice.

Kim Meninger

So, I'm glad you described it as a muscle, because I often use that term to describe different things as well, and I wonder what you think about practically speaking, and doing that, you touched on the fact that we are in a rapidly changing world, uncertainty is kind of the, the only certainty, and so for people who are feeling uncomfortable with it, and you know, not sure how to, how to navigate it more confidently. What do you recommend?

Scott Stirrett

In my book, I go through six core pillars of advice, but I'm going to focus on one core one in regards to this question, and that's the importance of fostering anti-fragility. Anti-fragility is the ability to not just benefit from chaos, but to actually emerge stronger from it. And one practical tip that I recommend people to do is think about every day, every week, what's one thing you can do to build up your risk-taking muscles, because what is risk-taking? It is making a decision in an highly uncertain environment, and in a world where there's more uncertainty, there's more risk, and everyone has different socioeconomic realities in terms of their ability to make risks, but we can all do one thing every day to build up our risk-taking capacity, that could be if you're in the workplace signing up to give a presentation, if you're afraid of public speaking, that could be if you're searching for a job, applying for a job that is you think of reach. We can all do different things to build up our risk-taking muscles, and even if you're comfortable with risk-taking today, it's important to not let those skills atrophy and to be intentional about continuing to make smart risks and build your risk-taking capacity.

Kim Meninger

I'm glad that you brought up different ways of doing that, because I also think when we think about risk there, and for people who work within organizations, for example, there are different levels of psychological safety that allow for risk taking, right? So I think that there, whether it's our own personal wiring, some people are like you said more natural risk takers than others, and for some people they may fear the consequences of getting it wrong because of the environment that they work in, right, so having different types of, of examples of risks, and the thinking about how it applies to your particular situation is helpful.

Scott Stirrett

Yeah, totally. And it's - we all face different risks at different points in our life, you know. Bringing a child into the world, there's a risk in that. Aging parents, there's a risk in that. Starting your career, there's lots of risks. Risk and uncertainty is not something that impacts us at one stage of our life. It's something that is a should be viewed as a friend that follows us at every stage of our life and career.

Kim Meninger

So, you describe it as uncertainty as an advantage. So, can we talk about how to shift from it's not just not bad, it's actually good.

Scott Stirrett

The number one determinant of whether you have a positive relationship with uncertainty is if you view uncertainty as positive, and it's important for people who are afraid of uncertainty to sometimes think about everything positive in their life, and all of those things, whether it is bringing a child into the world, whether it's founding a business, whether it is creating a piece of art, there is uncertainty in everything, and joy comes from uncertain moments and situations, and I think the more that we start to see the positive that can come from uncertainty, the more that we can learn to develop a healthier relationship with it and be less afraid of uncertainty.

Kim Meninger

I think a lot about the fact that when we are making a risk calculation, oftentimes we are really focused on the unknown, the thing that we're thinking about doing, and so we may decide, oh, that's too risky, or I'm too afraid to do that, or we make all kinds of rationalizations about why it's not the right move at the right time, but we often don't think about what we lose by staying in place and maintaining the status quo, and I think that that is a risk too, that people just don't tend to look at it that way. So, do you have any thoughts on how we can balance the scales a little bit?

Scott Stirrett

Totally, one of the most important lines in my book, The Uncertainty Advantage, is that there are risks in not taking risks. When I was 22 I was at Goldman Sachs, but it wasn't a good fit for my skills or interests, and there's probably a good chance that eventually I would have gotten like laid off, and I realized there was a risk in me leaving to go found the not for profit, but there was also a risk in me staying in potentially like a dead end job where I wasn't going to advance, and a lot of the time people just think of the risk of taking a risk, but there are also so many risks in not taking risks in life, and you have to weigh both the risk of decision, but also the risk of indecision.

Kim Meninger

Yes, and I think, too, that just because of the way our brains are wired, we're always focused on the negative, and you mentioned the fact that joy often comes from risk, right? So, it do you have suggestions on how we even.. I'm trying to think of the right word, but essentially even notice some of the, some of the benefits that come from our risk-taking, because I feel like we're much more inclined to notice what went wrong than we are to notice what went right.

Scott Stirrett

One piece of advice I talk about in the book is the importance of creating a hype document, which is a list of all of your wins that you've had in your life or your major wins, and what I talk about is like, write them down, take screenshots of people's compliments, and I think it's good for fostering self-confidence, but it's also good to sometimes link that back to moments of uncertainty, and then when you look at these wins in your hype document, think back to how these wins ultimately associated with you choosing to make a decision in an unknown environment, in essence, in choosing to embrace risk, and I think that that can be a helpful practice to begin to see the joy, the amazing things that can come from embracing uncertainty.

Kim Meninger

I love that strategy. I recommend it myself for confidence reasons. I think that it's so important to be able to recognize what we're doing well, and if we don't intentionally document it, we aren't as likely to notice it. I love the idea of linking it back to risk as well, because I think that even risk feels sometimes like a negative word for some people, like we talk about risk management, and risk feels sometimes irresponsible or reckless, right? So I think even just the our relationship to the concept of risk is, is warped by a lot of things in our experience, and just being able. Able to recognize where we're already doing it, and it's going well, can help reshape that.

Scott Stirrett

Yeah, totally. It so much is shaped on whether you view uncertainty and risk-taking as positive or negative.

Kim Meninger

Yeah, so what else do you think about, and maybe you can tell us a little bit too about your own experience, because I'm curious, you know, a lot of people have been through transitions as you've described and have had the discomfort of being with uncertainty, but they haven't gone out and written a research-backed book about it. So, how did it, how did it emerge for you in such a way that you decided I'm actually going to study this, and I'm actually going to, going to think more, you know, in a more focused way about this?

Scott Stirrett

In my work adventure for Canada, where we help over 10,000 young people launch their careers across Canada. I saw that fear of uncertainty was arguably the most prevalent thing that holds people back at the beginning of their career, it prevents people from applying to jobs, it prevents people from taking risks, it prevents people on realizing their full potential. And I knew I wanted to write a book, and I did some work to understand what's the book that A, I'm really passionate about, and then I have the lived experience to speak about, and B, where there was like a gap in terms of no other book that has been written. There are many books that have been written about uncertainty, but there's no book that to date really had been written on how to develop a positive relationship with uncertainty in the context of the earlier stages of your career, in your 20s and 30s, and what's interesting is the uncertainty advantage also appeals to people at older ages as well, but it's really written for people in their early career in terms of a target kind of demographic, and you know, when you're writing a book, it's thinking about what's a niche that is underserved, there's lots of books out there. The Uncertainty Advantage is the only book in its specific niche about uncertainty and developing a better relationship with it, with a focus on people in their 20s and 30s, and it.. I saw the market opportunity for it, and then likewise I thought that hey, this is a book that I'm actually qualified to write, because I've lived this in my own personal life, and I have supported 1000s of people to live through navigating uncertainty as well.

Kim Meninger

So, because you're so steeped in this, right, and when you write a book about something and you think about it a lot, it obviously becomes part of the way you see the world. Do you still practice your own risk-building muscles? Like, what does it look like for you at this point?

Scott Stirrett

Yeah, totally. I still practice risk-taking all the time. I ended up leaving Venture for Canada organization that I founded after 11 and a half years, and I did this. It took me about a year to leave the organization, because when you found something, especially sometimes when it's a not-for-profit, it can be hard to disentangle yourself. But we ended up having a great new CEO that we hired and played an important role through the transition, and I decided to leave Venture for Canada, because I was seeing myself beaming to atrophy, that I felt I could do more. I had done the same thing for almost my entire career, and I could have easily stated that for decades, but I realized that it was important to take a risk, and this was something I just left Venture for Canada like four and a half months ago, so it's very fresh, and I'm actually in the process of launching a new business that will start in September, so all to say is that I am continuing to embrace uncertainty in my life, and the uncertainty advantage was actually a catalyst for me in choosing to make that decision to leave Venture for Canada, because I've done so many talks, I've thought really deeply about uncertainty, and there's a great line that resonates with me, which is, teach what you most need to learn, and the uncertainty advantage genuinely has had a huge impact on my own life and my own willingness to take risks and embrace the unknown.

Kim Meninger

Well, congratulations, I know that was not sure an easy decision, but I think that is a really good way of looking at it, too. I often think about myself as somebody who's a very highly anxious person, as kind of part of my physiological makeup. I, when I start to get too comfortable, I start to realize I'm probably not challenging myself, I'm probably not taking enough risks, and so I use that as almost a barometer for, do I need to step outside my comfort zone? Is there, is there like a new, new challenge that I need to take on right now?

Scott Stirrett

Yeah, it is true. I think if you aren't doing something, thing to push yourself out of your comfort zone every week, you do begin to atrophy. I recently saw this, like, TikTok video of the CEO of Harvey, which is one of the kind of most successful legal tech AI companies. I think it's worth, like, $10 billion and he's like, you know, in his, like, like late 20s, early 30s, and he was talking about trying to do something in his own life every week that like scared him like so much, and that in doing so he knows that he's pushing himself like out of his comfort zone, and I was thinking about it because I'm definitely pushing myself out of my comfort zone a lot, but maybe not every week I have like some really big thing that I'm like, wow, this is way out of my comfort zone, but I think his point is a good one to think about. Like, often we can push ourselves a lot more than we realize in terms of our ability to embrace uncertainty and the unknown, and if you're just coasting, or if you're just staying in the same spot, I do think not only are you not moving forward, but you're potentially going behind. Like, momentum is really powerful in life, and momentum works both ways.

Kim Meninger

So, can we talk a little bit about AI? Because it's obviously the big hot topic right now, and it is going to change the world, and it already is, and it's affecting our present as much as it will affect our future, that is a big source of anxiety for a lot of people, and I wonder, I mean, there's a lot of different angles to this, but I wonder how it fits into your own thinking around uncertainty, and if there's anything more specific that you would invite us to think about when it comes to AI.

Scott Stirrett

Yeah, it's interesting. The book, The Journey of Writing, had started in September 2023 when I'd say AI was just becoming more well-known. ChatGPT launched in like November 2022 so it was in the early, early-ish days of AI kind of adoption, and it's been interesting as I have been promoting the book over the last year to see how AI has influenced the relevance of the conversation in some ways. I think that AI makes the key message of the book about embracing uncertainty more important than ever before, because there's different, somewhat cheesy tips and tricks on how to be AI first, for a long time it was prompt engineer, or how to design AI agents, et cetera, et cetera, but to me the most important skill actually of learning to thrive in an AI-driven world is actually learning to embrace uncertainty, because AI creates a lot of uncertainty, creates a lot of change, and I would say, relatedly, also learning to learn, like just learning on how to continue to keep up with all of the changes in AI, is a really important skill, and I think if you're good at those meta skills, comfort with uncertainty, learning to learn, you're well, you're better poised to thrive in an AI world, and I would rather recommend focusing on those meta skills than some of the more niche technical skills, like learning to prompt engineer, which can quickly become less relevant because of changes in the technology.

Kim Meninger

Yeah, that's a really good point, and I have done a lot of thinking and speaking about leading through change, which you know, obviously, AI is the big conversation around change. Not long ago, it was the pandemic, and what that was doing to our lives, and there is this way in which fear takes hold, and it starts, it starts making us think about all the bad things that could happen. I might lose my job. What if AI replaces me and my skills, and, and things like that? And that's a possibility. We can't guarantee that that won't happen, but what I like about your lens, and what's similar to how I think about it, is if we always try to think about what's the opportunity here, right, because there is a way in which, if we don't, if we let fear hold us back, we sit on the sidelines and we let somebody else write the future for us, as opposed to saying, How can I embrace this opportunity and be part of whatever the design of the future becomes, and we can all do that in different ways. I mean, people with a lot of power are going to have a different effect than, than you know, those of us who don't have that, but it's a more empowering way of looking at a world that feels very out of our control right now.

Scott Stirrett

Focusing on your locus of control, what can you do in this situation in a uncertain, you know, somewhat anxiety-inducing world is really important. And I think about a lot of my life, there were, you know, when there's frustrating situations that happen, it's important. To sit in that frustration, and that's okay, but what I found often is, how do you channel that frustration into something productive, which is often within your locus of control. So, don't be doom scrolling or trying to get as much information as possible on all of the uncertainty out there in the world, rather focus on action, and I think that acting is one of the best ways to reduce anxiety, because it is something in your control that you're doing, and it's a tangible step, rather than just kind of spinning in your head.

Kim Meninger

I'm glad you said that, too. That is kind of my, my mantra, or my way of operating, too, because it is so easy for me to spin in my head, and I know that's true for a lot of people listening. We can spin up a really dark story, what's going to happen, but like you said earlier, we would rather know a bad outcome than an uncertain outcome. For me, that's the benefit of action as well, because I'd rather do it and find out what's going to happen, and then I can adjust accordingly than I am to sit in my own, you know, worse fears and wonder what's gonna happen. Totally, is there anything else that you think about, or that is in your book, that we haven't covered, that you think is important for people to be thinking about right now?

Scott Stirrett

The first pillar of the uncertainty advantage is the importance of self-compassion, and I care a lot about this, because during the COVID pandemic I was diagnosed with obsessive-compulsive disorder and went through exposure and ritual prevention therapy, and in doing so I really learned the importance of self-compassion, that I can be extremely perfectionistic, extremely hard on myself to this day, and being kind to yourself, and that involves three things, the first is recognizing and talking to yourself in a way that you would talk to a good friend, two is recognizing your shared humanity with other people, and that there are millions of other people going through a similar challenging situation, and three is just being mindful of your emotions and how you're feeling, and I think self-compassion can be really helpful, whether you've just been laid off from a job or you're struggling with a family member, the list kind of goes on, but we often have a lot more compassion for friends or family members than we do for ourselves, and in an uncertain world where there can be a lot of havoc, but also a lot of opportunity, learning to be kind to yourself is really, really important.

Kim Meninger

That's a really important point, and I think a lot about the inner critic and the pressure that we put on ourselves, the expectations often unrealistic that we hold ourselves to, and many people listening to this podcast who struggle with imposter syndrome and other confidence challenges struggle with perfectionism as well, and I think that one of the challenges of the moment, and this is maybe true to some extent in lots of other transitional periods in our lives, but this is the one that's most salient to us now, is that we are living in a world where we are going to have to experiment, where we don't have all of the answers yet, and I think many of us have built our confidence on feeling like we have precise answers that we've adequately prepared, right, that we, we know what we're doing, and we're pretty, pretty sure how it's going to land, and now we don't have that kind of predictability as we're talking about with uncertainty, and so to be willing to experiment to try new things and not beat ourselves up on the other side of that, right?

Scott Stirrett

Yeah, it's so important, and, and perfect is the enemy of the good. We're all going to fail all the time. Some failures are better than others, but it's to recognize that failure is like a part of life, and if you're not failing, you're not learning. And a part of embracing of uncertainty is accepting and being okay that sometimes things are not going to work out. Actually, often they're not going to work out, and that is okay. And I think it's when you accept that bad things will happen and do happen, even if you made the right decision. Then I think you can learn to develop a better relationship with the unknown, because what is the root of a lot of anxiety? It's that fear of bad things happen thing, and if you just accept that those bad things will happen, I think it can make you a lot less anxious. Certainly, for me, it has made me a lot less anxious in my own life.

Kim Meninger

I agree with you, and I think there's something about what you said with learning to learn that's really important here, because we all grew up learning, and very, most of us grew up. Learning in formal school environments, right, that were very structured, and there were certain expectations of us, and for better or worse, we learned how to learn in those environments, but for those of us who haven't been in school for a while, structured learning isn't a constant in our lives anymore, and we are not, we don't really know or think about how to do that effectively, and it does become a thing where it's like I should have already mastered this, or I don't know what I'm doing and don't belong in this role, right, as opposed to just accepting, as you said, learning means we're going to make mistakes, and that's okay. That's just part of practicing something new, and I just don't think that many of us are there yet.

Scott Stirrett

Yeah, and it's a practice we have to all constantly need to work on. As we said at the beginning, this conversation, it's a muscle that needs to be developed.

Kim Meninger

Exactly, exactly. This has been such a fascinating conversation, Scott. I really appreciate your bringing your insights to this podcast, in particular, because I think that there's a lot of relevance to those of us who struggle with imposter syndrome. For people who want your book, who you know, want to follow your work. Where can they find you?

Scott Stirrett

The first thing I recommend is that you check out a short quiz that gives you a score out of 48 in terms of what is your current relationship with uncertainty, and I think the first step of learning to develop a better relationship with uncertainty is learning what is your current relationship with uncertainty. The quiz just takes like two minutes. You can access it by going to Scott Stirrett, S-C-O-T-T-S-T-I-two Rs-E-two Ts dot com slash quiz and then you can fill up the quiz and get your score and use that as a jumping off platform for learning to develop a better relationship with the unknown. If you're interested in checking out The Uncertainty Advantage in general, it's available at Amazon, Barnes and Noble, or wherever you buy your books. And yeah, I really appreciate the opportunity for being a guest on the podcast today. And I wish all listeners the best as you look to turn uncertainty into an advantage in your lives and careers.