The Uncertainty Advantage with Scott Stirrett, Founder of Venture for Canada

0:00On Builders, I interview CEOs, leaders, leaders, and entrepreneurs about building their businesses and careers. Scott Stirrett is my guest today. He's the author of The Uncertainty Advantage, which is about launching your career in a time of rapid change. And the inspiration for the book comes from his experience as founder of Venture for Canada, which has helped more than 20 ,000 young professionals throughout Canada with their career. It was really cool because I actually spoke with Scott on his last day as he hands the organization over to his successor. I think you're going to really like this episode.

0:38Hi, Scott. How are you? Good to see you. I am doing great, John. And yeah, it's great to see you as well. So we're going to talk today a lot about careers, the job market, and what young workers should do. In preparing for this, I kind of reflected on my early career. I actually started my career in college doing internships for businesses during the dot-com boom. And there was so much disruption at that time to work. Businesses were sending emails for the first time, scheduling meetings, using online calendaring, etc. And so there's a ton of disruption to work. For folks like me, though, really early in my career, there was so much opportunity.

1:22And it felt like there were tons of jobs, too. You've written a book about the uncertainty and disruption facing young workers today. What about today's market and then your own experience inspired you to write the book? And what's the book called? Where can people get it? The book is called The Uncertainty Advantage, and it is a guide for early career professionals to learn to develop a better relationship with uncertainty. And I'm so passionate about this topic for two reasons. The first is that I founded a charity called Venture for Canada that has helped now close to 15 ,000 young people across Canada launch their careers.

1:59And I've seen that fear of uncertainty is arguably the most significant thing that holds people back in their lives and limits risk-taking and really limits the development of human potential. And I've also seen in my own life where I've loved uncertainty at some points, like when I quit a job at Goldman Sachs to go work and found Venture for Canada. I was only 22. It was one of the moments where I dove into uncertainty the most. But then during COVID, I was diagnosed with obsessive compulsive disorder and really struggled in coping with uncertainty. And one of the things I've learned is that our relationship with uncertainty ebbs and flows over time.

2:38And that learning to thrive with uncertainty is a skill that we can all learn. And that equally important is that we all need to constantly work on developing our uncertainty muscles, especially in an era that is defined by rapid change. I'd love to know some of the things that you characterize as rapid change going on in today's market. I mean, there's macro uncertainty. I'm in the US, you're in Canada. There have been tariff situations that have occurred over the last year that's caused disruption. There's the advent of AI. What else is you've seen facing young workers in particular? According to the World Uncertainty Index, the world today is four times more uncertain than it was in early 2010.

3:27And that's being driven by so many different things, geopolitical uncertainty, climate change, and I'd also say just the rapidly changing nature of our technological world. The rise of AI has transformed so many different jobs and is likely to create even more changes. in the future. And the world has always had geopolitical uncertainty. Since the dawn of humanity, there has been violence and kings deposed and wars. But what makes this time really different, I think, is the rate of the change. Because we have geopolitical uncertainty compounded by the fact that we have so many new technologies that are emerging at such a rapid pace.

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4:59Check it out at business.com slash plus that's business.com slash P L U S. I try to think about, in the context of someone beginning their career. And I guess I don't feel old, but you wouldn't call me early career anymore. And what I might have done in a quote unquote traditional career playbook where I try my best to get into a good school and then I major in something that's relevant to business or money making. And then I get my foot in the door at a big company. like what's potentially ineffective or wrong about that and then you know what would you call like like a playbook what would you encourage younger workers to do to come up with their own playbook there are risks in not taking risks and I think it's really important for recent grads to think about that I remember there's someone I know who started his career in like 2005-2006 he had a job offered to go to Lehman Brothers and he turned it down to go work in a startup.

6:04And a lot of people probably don't even know what Lehman Brothers is today, but it was one of the largest investment banks in the world. And in the global financial crisis, it went bankrupt. At the time, people would have thought Lehman Brothers was not a risk to go work at. And then two years later, it ceases to exist. I think in our current world, one of the most important things that you can do is bet on yourself. For some people, working in a big corporation is a great path. But I think for many, I would encourage you to think about the risks that you can take. And what are the risks in not taking risks?

6:35And I say this from someone who has actually done it, that I worked at Goldman Sachs for around a year full time. And I decided to quit to go found something because I realized that for me, Goldman Sachs would be a dead end job, that I wasn't particularly good at what I was doing. I wasn't passionate about it. And it wasn't a fit for my skill set. So ultimately, I realized that the greater risk was staying in an environment where I was going to stagnate. And that the lower risk in some ways was betting on myself. And I'm so glad that I did. We raised over$80 million of funding at Venture for Canada.

7:11I've had an 11 and a half year amazing journey. This is actually my last day at Venture for Canada after 11 and a half years. So it's kind of fitting to do this podcast now. and taking that risk was one of the most important things that I've done. So if you're a recent grad, I encourage you to take smart risks and to think about the risk and not taking a risk. Yeah. I also think that it's really hard to know what you're going to like. Like I imagine that you went to Goldman Sachs thinking either I'm going to make a lot of money or I'm going to love what I do or finance seems exciting or this role seems to fit my skill set for whatever reason, then you find you found it, it didn't.

7:50And that can be the same thing, like working for a startup, working for a big company, you know, working, working with your hands, you know, working on a computer. It's, it's, I think that that kids I have, I have kids in high school right now, like, I'm sure they don't know what's going to make them happy later in life, the more experiences you have, the much more likely I think you can you can stumble onto that thing. I totally agree. And I think that follow your passion is actually like bad advice for a bunch of reasons. And the first being is that we don't have one life-defining passion. Our passion changes over times.

8:22And more important is also to focus on what skills that you have, because a lot of people don't know their passion. And that's totally okay. As Cal Newport talks about in So Good They Can't Ignore You, I would encourage folks to think about how do they make themselves useful in the world? And in doing so, you develop the skills. In the context of founding Venture for Canada, yes, I was motivated by the mission and I had passion for it. But candidly, what I was more interested in is I thought it was a great way to learn how to fundraise, learn how to build an organization, learn just how to build things.

8:55Yes, I was passionate about the mission, but initially I wasn't necessarily that passionate about it. I was more passionate about learning. And for recent grads who are looking at next steps in their careers, I would encourage you to think about where can you learn the most? Where can you develop skills that make you useful in this world? And then go out and seek out and pursue those opportunities. As you're seeking these things out, some things you can do consciously, you can go out and build a skill, seek out a certain experience, etc. But then also you have to learn how to become adaptable because things are thrown your way that you can't anticipate.

9:36We all know that change is rapidly happening, but it's very difficult to predict exactly how it's going to impact you, I think. And so how do you achieve adaptability? And then also in your mind, how do you prove that you're adaptable to a hiring manager or a coworker that might need to take a risk to give you an opportunity to do something different? In an era of rapid change, being adaptable is one of the most important things that you can do. And I hear that from so many different employers. And one of the ways that you can learn to be more adaptable is not holding true to really rigid plans for yourself.

10:15I think one of the most common mistakes that smart people make is they try to control uncertainty by creating a rigid plan. And often this is in the context of rigid career plans. And what's really important is, yes, really long term ambitious goals for yourself. Create like a life mission statement. I talked about that in The Uncertainty Advantage. but then be really flexible in terms of what are the ways that you're going to get there. And one of the main ways I think you can foster adaptability is simply like not being too dogmatic and just focusing on one plan and saying, I'm just going to execute this no matter what.

10:53I'd say other ways that you can foster adaptability is being in environments that require you to be adaptable. That's environments that are ambiguous, complex. And I'd say a third is actually traveling. Like just being in an environment culturally or geographically different than where you're from. I'm on Monday about to go on a trip for nine weeks to Japan and Australia. That will teach me adaptability because I'm going to be in environments, especially in Japan, where I am not familiar with at all. And I think that's one of the great ways you can like build your adaptability muscles. And I think one of the ways that you can demonstrate that to employers is, A, I think when you've worked in startups or small environments, it shows that you're comfortable with adaptability if you've thrived there and you've worked there for a while.

11:40And then I'd say the second is just the way that you talk about your career, the way you talk about your planning, that life isn't this linear process where you go from A to B to C, but rather it's a zigzag. And I'd encourage you in interviews to emphasize this zigzag, that you're not just an adaptable person, but you recognize that adaptability is essential for thriving in our modern world. I want to dive deep into this in so many different tendrils. So just a personal anecdote about long-term goal setting is many years before I turned 40, I wrote a list of 40 things that I wanted to achieve before I turned 40.

12:2040 things I wanted to do, not necessarily achieve. when I got to 40, I'd done some of those things. I hadn't done some of those things. But what was interesting was such a high percentage of those things I actually didn't care about anymore. And so it just it just shows like, like knowing exactly where you want to be or what you want to do or what boxes you want to check five years from now or seven years from now is not is not honestly a great prediction of where where you'll be. I'm excited about you going to Japan and Australia, like you were saying, maybe I don't know if you have any anecdotes about traveling and experiencing a different way that someone does business or a different way that a culture experiences life in such a way that's helped you in Canada.

13:03So I was born in Canada, raised in Canada, but when I was 18, I actually moved to the United States to go to university. I did my undergrad at Georgetown and I lived five years in the US. And while Canada and the US are quite similar, having lived in both countries and spent a fair amount of time in both, they're also very very, very different places. And there's a lot of different cultural subtext and differences. I'd say one broad thing is I think Canadians just tend to be a lot more, less direct. So often if you're in meetings with Canadians, there's like a whole subtext to the conversation that's sometimes not said, but that is really important and that a lot of people know is being said, but it's not being said like explicitly.

13:46Versus Americans, I think, generally have a little bit more of a tendency to say what they think. That was something that I learned a lot in the US. It was actually about being a little bit more kind of like direct and also just navigating American context where people are a little bit more forward. And how do you navigate that as like a Canadian? I think that my experience being in the US, I would never have found Adventure Canada if I hadn't lived in the United States. It pushed me on my comfort zone. When I was 18, I had to navigate all these things. I was living Washington, D.C. I grew up in a small town in Nova Scotia.

14:18Like it was a huge cultural shift. And also for context, within the first like two weeks of going to Georgetown, I had major complications from wisdom teeth surgery and actually was hospitalized for like four days. I had to stay overnight in the hospital. I had all this two major surgeries over the course of a couple of months. So then I had to navigate the American health care system, which is also completely different than Canada's. And I've been in the kind of I've grown up in a quite nurturing, tight knit kind of environment. And all of a sudden, I had to spend for myself and navigate. And in short, it was these experiences that taught me to be adaptable to deal with different contexts, to deal with different environments, policies, ways that people operate.

15:01And it not only made me more adaptable, I think it made me more confident to take risks to plunge into the unknown that if I had just stayed in a in my same environment my entire life, I probably wouldn't have had that same kind of comfort or risk taking. In your writing, especially your your sub stack, and we'll we'll put that in the show notes for for folks listening. You write about self doubt, and also overcoming, like you mentioned earlier, being diagnosed with OCD, things like anxiety, or mental health. And I have someone very close to me, who's diagnosed with OCD, and he learned how to face his fears and ride the wave.

15:38I'm curious how your journey about being open has helped you because not everybody feels comfortable talking about these things. What would you encourage to folks that feel cautious about being open about this? The first point that I would say is it's really that when you're open about mental health challenges, I think it lets you move forward with the experience rather than just trying to put it in a box and forgetting about it. I went through a really tough six month period because of OCD. In some ways, two years that were challenging, but there were six months that were really challenging. And that was brutal.

16:11In some ways, I look back on that now, five years later, and it feels like it was like a bad dream. Like I couldn't sleep. I was really struggling to talk to people, to function. And it was brutal. Like it really does feel like a nightmare when I look back on that. And the way that you move forward with traumatic things, and it was traumatic. I think it's important for people to know OCD is not just like washing your hands a lot. Like at extreme cases, it is extremely debilitating. It's actually one of the top 10 causes of disability in the world. So OCD is a very serious thing in some cases. And it was for me.

16:48It was by far the hardest thing that I've ever had to deal with in my entire life. And it was really brutal. So what's the benefit of me talking about it? One is that you move forward with traumatic things by acknowledging that they happened to you and looking them in the face and saying, this happened to me. It was really bad. And I can't run from that experience, but I'm going to move forward with it. That it's part of me. And it was part of my life experience. And lots of research on dealing with challenging circumstances talk about the importance of moving forward with it. Like a lot of PTSD training, I'm not saying PTSD, but it's around often visualizing what the experience was that you went through that was really difficult and being able to face it and to process it.

17:36And even if you haven't gone through extreme traumatic thing, and I wouldn't say mine was extreme trauma, but it was, as Gabo Ramate would say, you know, trauma with a not capital T is what I went through. So the first is it's important for processing. I remember when I first talked about these publicly more like a couple of years ago, it was so hard for me to talk about it. Now it's way easier. The second thing that I think is really important when you are open about it is it reduces like your own shame. That when you have shame about something, shame is one of the worst emotions, one of the most powerful ones.

18:13The worst, no doubt. The worst. And I think when you're just acknowledge something, you talk about it publicly, it gives you power over it and the shame kind of goes away. So that's been something that I think that's really important is it reduces the shame. I'd say the third is it helps give you meaning, because for me and part of the reason I wrote the book, The Uncertainty Advantage, was I went through this really tough time in my life, a time that like it shattered my world. I never thought I was somebody who was going to have an extreme mental health issue that came up and emerged. It's hard to describe the extent to which you have a worldview of your life.

18:51And then something like blows up your world. Like I was shocked. I'm like, how did this happen to me? But ultimately, you know, why I wrote this book and why I talk about uncertainty is one of the things that I have tried to do from that experience is how do you find meaning from pain and suffering? I think it is one of the most important things we can do in this world. Viktor Frankl talks about a man's search for meaning is how do you take a really difficult experience and ideally learn from it and find meaning. And for me, talking about uncertainty, like I feel like that traumatic thing I've gone through, I've now been able to help all tons of other people hopefully navigate uncertainty.

19:28So it was meaning making for me. And maybe the final point is just the benefit of being open and talking about mental health and getting other people to be open and talking about mental health, that half of all people in America and Canada go through an acute mental health issue in their lifetime. Very few people talk about it openly. The more that people do it, including people who've had a degree of career success on things, the more that it normalizes being candid and open. And part of the reason why I realized I had OCD and ended up getting clinical treatment and actually getting diagnosed by it, is that I listened to a podcast with Brad Feld, where it's on Tim Ferriss.

20:05This was around a a year before I was diagnosed. And in that podcast, Brad Feld talks about his getting diagnosed with OCD, him going through that experience. And I am so grateful for Brad Feld. And I've emailed a little bit with him about how he impacted my journey. And I hope that myself in being open and talking about OCD, that it helps other people who maybe have OCD to realize it because in particular, it relates to OCD. It's often very underdiagnosed illness. and there's a lot of misunderstanding about it. And I think it's important that people understand what OCD is because it impacts like two or 3 % of the world's population.

20:44And the more that people are open about their experiences, the more that hopefully it helps other people. Well, Scott, thanks so much for sharing that. And I totally agree with everything you said. I want to loop back to Venture for Canada. So it's your last day today. what's the next stage for for venture for canada is it is it continuing with a new leader what's the next chapter for venture for canada and then i don't know if you if you can share or will share not what's the next chapter for you yeah so on vfc we have hired a great new ceo stephen wang who is a amazing person graduate of harvard law school road scholar uh he started actually six weeks ago but i've been kind of overlapping with him until today in supporting his transition and i'm so confident about the future of VFC.

21:31And we went through a very competitive process to hire the new CEO. And yeah, he's now officially enrolled and I'm excited to see what he accomplishes. And then for me, I'm doing a couple of things. One is in February, I'm starting in a new role that has not been announced yet. So I can't share it publicly just because there'll be more of an announcement. But it'd be a consultative role that is in how do you build kind of a better Canada grounded in communities that are thriving. And I will be like half of my time and excited to that. And the other half of my time, there's a few entrepreneurial projects that I'm kind of working on.

22:09So one thing that I think I had a misconception of when I was thinking about next steps in my career was that I had to pick one thing and say the one thing that I'm going to do. And what's become is I'm going to do two or three things in the next part of my career. And I share this because I think it was a mistake I made. I thought, oh, I have to pick one thing, one thing that's going to dominate. And it's a false dichotomy. You don't need to necessarily always pick one thing. You can sometimes do two or three things. And yeah, I'm excited to kind of explore a couple of different projects, especially after one all-consuming chapter of my life over 11 and a half years where I've devoted it to principally one thing, venture for Canada.

22:50What you say dovetails with some advice I saw in a talk this week by Rashad Tabakawala. He's a longtime advertising exec in the C-suite of Publicis Group. And he was talking about how workers today, everybody's a company of one. And your actual main job is maybe the side gig of something that you want to do. And that's similar to if people are going to have, you know, I can't think of the right word, primacy over their career or something like that. then then you know you should be doing multiple things and figuring out everything that you like to do over the next five or ten years i think is really really smart you've probably in venture for canada gotten to travel throughout canada and see all these pockets of of industry i'd kind of be curious to if you wouldn't mind closing out here by giving both a recommendation of a part of Canada's that's really thriving that this audience might not know about.

23:54You know, it could be in tech, it could be non-tech. And then also an off-the-beaten-path vacation recommendation for those of us like me. I would say I went to the Okanagan for the first time three or four years ago. Totally mind-blowing. Gorgeous. So I'm curious your take on those two topics. Yeah, and I love this question. I've never been asked it before, but it's a very insightful one because I have traveled a lot of Canada. I've been to 10 provinces, two territories. And luckily, I'm really grateful for the opportunity to travel Canada way more than the vast, vast majority of Canadians and gone to a lot of places most people don't visit.

24:34So on the topic of a place that I think is really thriving and doing interesting work. So one community that I think is really interesting that for Americans or other people to learn a little bit more about is Fogo Island in Newfoundland and Labrador. Small island north of Newfoundland. And it is a very isolated location. But there's an amazing woman named Zita Cobb who is from that island. And she ended up making a fortune in the tech sector. And around 20 years ago, she had this idea to create the Shorefast Foundation. foundation and in it she created this very high-end hotel called the foco island inn this inn is often rated by kind of nest as like one of the best hotels in the world in canada the new york times has called her the most interesting woman in travel okay she's built this this inn is very expensive and very high quality experience but it really leverages the local assets of uh of newfoundland the foco island newfoundland in general is just a really interesting place to visit as well.

25:38But the foundation has worked that's much broader. There's a fishery, there's a furniture business, ice cream store, employ hundreds of people on this island. And the island has kind of rejuvenated economically and it's a great example of like place-based economic development of leveraging the assets and really of an entrepreneurial story and of community kind of success. So I share that the Pogo Island has become an increasingly well-known island in Canada, but it is not, you know, I think to an American audience, it's important to emphasize it's such a unique kind of place. And I think a place that's thriving that a lot of people on a global stage should know more about.

26:21I'd say a second in terms of your part, a question of like a place in Canada that I think is really kind of interesting to visit, that is a little bit off the beaten path. I would recommend Whitehorse Yukon in general, the Yukon Territory, which I have been to. And again, not, I mean, it's a little bit off the beaten path, but it's become better known. But the Yukon is an amazing place to visit. Whitehorse is a quite great city, only around 30 ,000 people. And Kluwani National Park is not very visited. There's not even that many hotels there, but it has the tallest mountains in Canada. There's Alaska, so you can get there from Anchorage, not that far.

27:01There's the Alaska Highway actually goes through Canada. The U.S. government actually pays for a lot of the Alaska Highway. Oh, I did not know that. It's in Canada because the U.S. military uses it to transport a fair amount of stuff to Alaska through Canada. Yeah, the Yukon has a beautiful kind of nature. And if you like hunting, there's tons of Americans, from what I saw, go there for moose hunting and various things. And yeah, just an amazing... And I went there last year, around a year ago, for the first time for around eight or nine days. And it's an amazing place. And maybe I'll add one final place that's a unique one in Canada.