Comfort: When Cozy Becomes a Cage

Matt Gilhooly (00:00)
Most of us think comfort with uncertainty is just a personality trait. You either have it or you don't. But Scott had it at twenty-two, then watched it quietly disappear over the next decade, and then he had to rebuild it from scratch. And that rebuilding, that moment of realizing how small his life had gotten, changed everything. Today Scott shares what it actually takes to stop fearing the unknown and start seeing it as a thing that makes life worth living.

Scott Stirrett (00:27)
say it was during COVID when I was having kind of challenges coping with all of the uncertainty out there in the world and in talking with the therapist, really realized that I was being extremely hard on myself, that I was trying to be obsessively productive all the time.

Matt Gilhooly (01:18)
Hello everyone, welcome to the Life Shift Podcast. I am here with Scott. Hello, Scott.

Scott Stirrett (01:23)
Hey Matt, great to be here.

Matt Gilhooly (01:24)
Well, it is great to to talk to you finally, 'cause we've been trying to do this for s nine months, something something a really long time in which your life has probably changed since that moment as well.

Scott Stirrett (01:36)
Yeah, it's great that we're have the opportunity to to meet and yeah, it's amazing. The world changes a lot in nine months.

Matt Gilhooly (01:43)
It's it's so true. What's what's interesting though, and I think it's probably true for a lot of people. Typically I talk to people about these life shift moments that have probably happened longer than say a year ago. Like they've had time to reflect on these moments. And so sometimes I'm worried that if it takes six months for the episode to like come out, that their life is gonna be completely different. But I so far, so good. We're pretty safe. Maybe the early episodes life has changed a lot, but but I think, you know.

Pretty current.

Scott Stirrett (02:15)
Yeah, d totally. I mean, I think that it's you know, life changes, but also some things always remain constant.

Matt Gilhooly (02:23)
You know it. Yeah. Well, I appreciate you wanting to be a part of the Life Shift podcast. You know, here in my mid-40s, getting to talk to people all over the world about sometimes very personal moments, sometimes very inspirational moments, sometimes a mix of both, maybe even add some trauma into that, has been really weirdly healing for this version of me as someone who lost his mother as when I was eight and then struggled through grief for twenty plus years.

Now being able to have the conversations that I wish I felt comfortable enough having and asking questions that maybe I was wrong about or I make wrong assumptions about. It's really nice to have that. Whereas growing up, it was like I only asked the questions that I already knew the answer to. So I didn't feel like I got it wrong or did something wrong. So I'm just I'm so grateful that people like yourself want to share your story in this way and wherever the conversation ends up taking us.

Scott Stirrett (03:23)
Yeah, it's important for people to, you know, be authentic and I think also to have candid stories about their life. And I think ultimately we learn more from people sharing stories than often from like specific frameworks.

Matt Gilhooly (03:39)
I agree. I agree. And and there's so many people out there that will resonate with your story, whatever parts of it they connect with. And it just helps them feel less alone or it helps them feel validated in certain ways that they thought about things. So I I I'm looking forward to this. So but before we get into your actual story, maybe you can just tell us who Scott is in 2026. Like how do you show up in the world? How do you identify these days?

Scott Stirrett (04:05)
I am Canadian. I grew up in Nova Scotia. I am an entrepreneur. I founded a charity called Venture for Canada that helps young Canadians be entrepreneurial across the country. For a long time, that was a big part of my identity. I led it for 12 years and founded the organization and probably still is a part of who I am. I am married. I have a lovely husband named David. We've been together for almost 11 years.

I have a cat named Luna and I wrote a book called The Uncertainty Advantage, which is a guide for young professionals on how to embrace all of the uncertainty that is out there in the world today. And I'm really passionate about helping people learn to see all the opportunities and uncertainty rather than to fear it.

Matt Gilhooly (04:51)
Yeah, well I would venture to say that there's probably more uncertainty than there is certainty these days.

Scott Stirrett (04:57)
Yeah. I mean, I think in some ways we live in one of the most like uncertain times. And it's because the amount of rapid change that's going on in the world.

Matt Gilhooly (05:04)
Right. Yeah.

And then you could flip it on its head and and like you have, I'm assuming, that it's like a positive too, because it gives us this opportunity to create what we want next, how we can move through the world next, how we can show up differently. At least for me, that's how I see before it was like I don't know what tomorrow is gonna bring and now I can like look at it and go, well tomorrow is gonna bring whatever I want it to, because I can create that. So I guess if we look at it with rose colored glasses, we can

Feel good about it.

Scott Stirrett (05:34)
Yeah, it's often I think in moments of the greatest uncertainty where we have the greatest opportunity in our lives. You know, if you're in the midst of a career rut and you have the resources, like take a couple months off, like reflect, think about what you want to do. And I think there's so much opportunity when you s are comfortable sitting in uncertainty.

Matt Gilhooly (05:53)
Yeah. Do when you talk to people, this before we get into your story, curious if there is a level of too much uncertainty at which it it stifles people. I feel like there's a comfortable level of uncertainty, but if it's like way like blank slate, that could be more detrimental to some folks. Do you see that?

Scott Stirrett (06:15)
I think everyone has a different relationship or comfort level with uncertainty. and it's to say what is too much uncertainty differs by the person. and also that someone's relationship with uncertainty can change and evolve over time. So it that person's relationship with uncertainty is is temporal. But I would also say that the

You know, our our relationship with uncertainty is is so critical because it's when we're you know, our the more that we can embrace the unknown, the more that we can take risks like launching businesses or traveling to new places or building new friendships. And I'd encourage folks to just think about like what's all the opportunity in their lives that they can unlock and their careers as well.

when they become more comfortable sitting with the unknown.

Matt Gilhooly (07:08)
Well, that's a very nice way of saying, Matt, you're crazy. because you're there's a certain level of uncertainty that I'm comfortable with and then there's parts where I'm like, Well, this is too much too many opportunities. Can't take it off.

Scott Stirrett (07:20)
Well,

I all to say too is I think that there's like a Goldilocks like for uncertainty in many ways. What I mean by that is that if there is so much uncertainty in everything in your life, for a lot of people that can cause challenges at a certain point. And you know, a lot of there's a great book called The Upside of Uncertainty. And one of the main points in that book is that it's important that a lot of successful entrepreneurs are really comfortable.

with the unknown, but then they have a lot of stability in their personal life, whether that's a spouse or routines. And for me that's really important. like for instance, trying to like exercise six times a week, there might be a lot of uncertainty in my life, but that can be like a constant that like helps me. My relationship with my spouse helps provide stability when there's a lot of instability. But I think for people, you know, if you're dealing with a lot of business stress, let's say, and

then you have a home stress and you have parent stress and like the list goes on and then there's a pandemic. Then then that can push people to the the brink. and yeah there I think there are there is a line of only so much uncertainty that people can reasonably you know handle. And and then I'd say when you're pushed to that limit, it's lore it's impossible to have like compassion for yourself, which is

Matt Gilhooly (08:23)
Hm.

Scott Stirrett (08:41)
one of the core pillars of the uncertainty advantage. And I put that as the six the first of the six pillars, because I think it's really your your ability to be kind to yourself, to to say what I'm dealing with is really challenging right now is what allows you to cope and and ultimately thrive in the moments that are the most uncertain, that can be the most challenging.

Matt Gilhooly (09:04)
Right. No, that's a really good point. And we could talk about this part all day, but I wanna hear your your personal story. So perhaps you could paint the picture of the previous version of Scott or a version of Scott leading up to a main pivotal moment that we're gonna talk about today. Like who was Scott before?

Scott Stirrett (09:24)
Yeah, I'm gonna talk about my experience actually in university. And I didn't come out of the closet till I was twenty one and almost twenty two. And I think the closeted version of myself was a lot different, a lot less comfortable embracing kind of who I am or taking risks. And I think I was a lot more fearful of what other people thought or about yeah, about judgment.

And coming out is a gradual process over time. But one of the things I talk about an uncertainty advantage is I don't think it's a coincidence that within a year of coming out of the closet, I found a venture for Canada and then made huge bets on myself. All all that's to say is that I think when you lean into authenticity, when you're true to who you are, it is way easier to take risks. and for me, I think really helped.

put me on more of a path of creating a lot more impact, a lot more fulfillment, and not trying to live someone else's life, but doing things that actually aligned with with me. And yeah, I think that me today, as you know, Scott in 2026 is a lot more confident, a lot more comfortable with uncertainty, a lot more of a risk taker in a good way than the Scott of 2012, who was a lot more timid.

and a lot more afraid of of the you know external environment and and the unknown.

Matt Gilhooly (10:53)
So if we go back to your growing up and childhood, did you feel like you had to perform or mask or whatever it might have been to be what you thought other people wanted to see in you, or were you free to be who you were and at some point you assumed this role that maybe wasn't allowing you to be your full authentic self?

Scott Stirrett (11:17)
My parents were always very supportive, but I didn't grow up in a broader environment that was very supportive of like gay or queer people. Like I grew up in Durban, Nova Scotia in the 1990s. when I was growing up, I knew pretty much no one else that was publicly out. And the even idea of being gay was like so far removed from what I thought was was possible. And

In same in high school, gay was often a slur. in university, things I would say started to change just with the broader discourse. I I w first attended university in 2009. And I think that was a moment where there was a watershed and a a lot of evolution in terms of how people thought, particularly in the United States, which is where I went to university. So all to say is that, you know, I think the trauma that you have as a kid in terms of not feeling comfortable or feeling stigmatized.

can take a lot of time to process. And certainly that that was my case. And and I think it often made me less comfortable with the unknown. That, you know, if you're afraid of what's around you or you're afraid of being your authentic self, it makes you more afraid of uncertainty as well. And when I reflect on some of the people I know who are most comfortable with uncertainty, they're often the people who are also the most comfortable with who they are.

And are comfortable in their own skin.

Matt Gilhooly (12:43)
Yeah, 'cause they they've learned to trust themselves fully, I guess, in that way. Would you say that growing up you were you like a good student? Were you very dedicated to your studies or?

Scott Stirrett (12:56)
Yeah, I was a good student. And you know, the there's another podcast that I once did an interview on. It was about perfectionism and kind of gay men. And there's lots of studies that show that often marginalized people can feel a need to be you know, perf to be perfect all the time. and there's a great op-ed that was published in the New York Times right around when I came out and it's called like the best little boy in the world and it talks about how you know, a lot of gay men feel this strong

desire to be perfect all the time. And sometimes I can be still very perfectionistic. In my book, The Uncertainty Advantage, I talk about how to overcome perfectionism. And one of the most important mindsets to have is that it is impossible to be perfect. That when you just accept that perfection is unattainable, you can learn to develop a better relationship with failure. And just

I if you struggle with perfectionism, I really encourage you just to like say that over to your and over to yourself. Like perfectionism is is illogical and it is an impossible goal.

Matt Gilhooly (14:05)
Yeah, easier said than done. I think. Like for me, it was very much I became a perfectionist after my mom died because I thought if I wasn't perfect, then my dad was also going to leave. And so that becomes a self-fulfilling prophecy in which it just builds and builds and builds. And then it just becomes part of my nature to become a perfectionist. And it took like probably to like 40.

Scott Stirrett (14:07)
Yeah, totally.

Matt Gilhooly (14:34)
To be like, okay, like to your point, not it's not attainable, it's not realistic, it's not anything. But it's really hard to break those patterns, I guess, if if that's all like I was just chasing good grades or was chasing whatever it was, the next thing, so that I could show my dad, which he didn't need it, of course, but we just didn't have that com conversation. And I would just, you know, that was

My perfectionism was just embedded in me in the fear that other people were gonna leave because I wasn't perfect. And so it's a it comes from a different place, but at the same time it's like it's there and it's really hard to shed as much as we want to.

Scott Stirrett (15:16)
Yeah.

It's so hard to shed. And one of the other things I talk about in the uncertainty advantage is the importance of focusing on the journey rather than the destination because we don't control outcomes. We influence outcomes with our decisions, but there's a lot of luck that happens in the world. And the more that you focus on just making high quality decisions and the less you focus on what you can't control, I think the more that you can

develop a better relationship with success and with with failure. Another thing I talk about in the Uncertainty Advantage is the importance of just recognizing that failure is an important part of life, that you learn things from failure. And that if you're not failing, you're not pushing yourself out of your comfort zone. So learning to develop a better relationship with failure is also really important, I think, to learning to overcome perfectionistic impulses.

Matt Gilhooly (16:11)
When did you I mean, I'm assuming part of your life journey taught you some of these things to put in the book? Like or were you always focusing on like what is your what is your life shift moment? Is it what you told us, like as far as coming out or like trying to figure out how you got to this place? Were you always this way? Were you always focused on the journey? Were you I mean, you said you were perf perfectionist and that shouldn't be something that we focus on? So curious of like how that

where you shifted into this different mindset.

Scott Stirrett (16:44)
Yeah, on the perfectionistic piece, in terms of life shift moment, I would say it was during COVID when I was having kind of challenges coping with all of the uncertainty out there in the world and in talking with the therapist, really realized that I was being extremely hard on myself, that I was trying to be obsessively productive all the time. So when I think on that that aspect of a life shift, that was something that

Matt Gilhooly (16:50)
Mm.

Scott Stirrett (17:10)
just naming it and having someone help me identify that in myself was really helpful. And I look back at other times like in university of just like pushing myself so hard and having like an anxiety attack because of like exam or sleeping two, three hours a night for like a week, like things that were just like completely unsustainable. And the expectations I had in myself were just way too much. And that's to say I the antidote to perfectionism is not not being ambitious.

continue to be an ambitious person today. but I think ultimately those who have more self-compassion for themselves, those who recognize that failure is a part of life, are in the end more impactful, more ambitious, because they keep on going. They're they're put themselves in the arena. And that's so much of life, is it's your willingness to put yourself in arena and try. And if you're afraid of being perfect all the time.

It's really hard to embrace the the unknown because uncertainty means that you're making decisions in a potentially more risky environment where things aren't going to work out, both because you made the bad decision, but also sometimes because of just bad luck. And in the context of my, you know, life experience, those that experience really in COVID changed my view of of per of what is, you know, I went probably in twenty fifteen, I would say perfectionism is a superpower. In twenty twenty five, I

I think perfectionism is actually really, really bad for you. And that people who are perfectionists need to try to unlearn those kinds of habits.

Matt Gilhooly (18:43)
Yeah. W was there like a watershed moment from one second to the next you were like, this is how I'm moving through life differently now or was it like was it a line in the sand, like no more this version of me, now this version of me, or was it something that was maybe more gradual, less of a

Scott Stirrett (19:00)
Yeah, there was one moment in COVID where there was a kind of a a coach that I worked with, not not a therapist, different person. But she really helped me. we did a sign of session together where she got me to think through kind of all the perfectionistic pressure that I've put on myself at various points and just like to kind of let go of it. And it it really it sounds cheesy, but in that moment, like five years ago, I was a member of virtual because it was during COVID.

It really helps me release that like desire to be like a perfectionist, which I'm not generally a woo-woo person. It's one of the few moments of my life where I really did feel like I released some of the pressure that I was putting on myself. And I still put a lot of pressure on myself sometimes. I'm not like cured of it. But I I think like so many things in life, none of us are perfectly self-aware, but just being able to name and label.

And understand our weaknesses a big part of being able to manage them. And that that COVID experience really helped me kind of realize. And I still sometimes like, my God, I'm getting pulling back into that perfectionistic impulse. It's something I'll have to manage my entire life. But if you're not aware of the tendency, then it's really hard to manage it.

Matt Gilhooly (20:19)
yeah.

Well, you're not going to manage it because you're not aware of it. You're not really paying attention to that specifics. Do you how did you start showing up in the world differently for yourself after that? Because I think that's something we see people or we see like 10 years ago you and this version of you now, and we think, well, that was it this long journey? Was it an overnight switch? Like what do you recall like what you started to do differently, or was it all just mental like gymnastics for yourself?

Scott Stirrett (20:48)
Yeah, I think one thing that I started to do differently was like even being more flexible about about what I ate. Like I still eat pretty healthy, but not being as like obsessive about healthy kind of eating. I'd say maybe another thing that was like very tangible at the time was just like less a focus on just being productive all the time, although I can still get into that. but just being okay, like, hey, you know what, I'm going to go read for a little bit, or hey, I'm going to go watch some TV and

Not to say I didn't do that in COVID, but I think I was really getting pulled into this constant productivity cycle. And yeah, those were a few instances where I think that they were really like tangible, like not checking my email as much. yeah, th yeah, it is. And sometimes I as I say that, it's like, okay, I need to be a little bit more careful because that that that that's someone that can pull me back in.

Matt Gilhooly (21:31)
Could be hard.

Yeah.

Do you remember or I mean, maybe you could compare the risk that you might have taken before to a risk that you took after that? Like it was there a notable difference when you faced something that would the old version of you would have been like, I'm not even gonna take that chance. Was there a big risk that you took or?

Scott Stirrett (22:00)
Yeah, so

y y years later, this is kind of so in COVID, I had this awareness, I did Venture for Canada for 12 years. And at the end of 2024, I realized that I was ready to move on and go do something else. Now, when you found a charity that is also a community and has 30 employees and 14 million dollar annual budget, and it's really tied to you personally, that is not an easy thing to exit.

So it took around a year. We we hi were able to hire a great new CEO. but it was a very complex complex and quite lengthy process. I don't think I would have ever had the courage to leave Venture for Canada if it was not for my increased comfort with uncertainty. And there's new thing that I'm launching in a couple of months that and I some ambitious things that I don't think I would have ever done. I wouldn't have written a book about uncertainty and have it published by a major canadian publisher and

talked about it all over the world. And all to say is that the, you know, my like I'm so passionate about talking about uncertainty because I saw in COVID my life become smaller and smaller because of my fear of the unknown. And I think that it's like there's a famous N an Nai Sanin kind of quote that like life expands or shrinks based on your courage. And that is so true to my own experience. Like,

The more that I have courage to take on things, to to have difficult conversations, to take risks, the more that my life becomes even, you know, more beautiful. And I think that there's so much beauty out there, but there's also so much in some ways.

unharness beauty or un untap beauty. Like the everyone one of my my life mission statement is to help others achieve their full potential. And I think one of the most yeah, what one of the most including my own self, one of the main things I think that you can do to unlock potential in your life is just to view uncertainty as an amazing gift. That sometimes, you know, to think if we knew everything going forward in our lives,

Matt Gilhooly (23:43)
It's a big ask.

Scott Stirrett (24:02)
Our bore lives would be boring as heck. We would not like that. And or at least I wouldn't. And that that uncertainty is like I think is while it can be really challenging, it is what one of the things I think makes life so beautiful, so interesting. And I think that it's important more people kind of see that and understand that.

Matt Gilhooly (24:24)
Yeah. Would you do you look back or do you look back with any regrets of the version of you that didn't take the risks or was a little too measured or any of those things? Or are you someone that's like, That's the past, we carry on?

Scott Stirrett (24:38)
Yeah, I think a little bit. I mean, I probably wish that I would have come out of the closet earlier in university. I think that that would have been something that would have just made my life easier and created less turmoil. I would have said that certainly in COVID that I hadn't shrunken so much to myself and become afraid of the unknown. and I that was a long time coming through my twenties, then my uns fear of uncertainty kind of got built up.

I'd say that that's a big part of it. But but I and it but I think that it's when you go through, I mean, and you can probably relate to this more than me, Matt, is like when you have some bad things that happen to you. you know, I was bullied a lot as a kid, and my childhood wasn't always the happiest for variety of of reasons. And you know, when bad things happen, it can make you more afraid of uncertainty because you've seen the bad things happen.

And you know, in some ways I think that it was sort of in moving through my childhood experience and kind of becoming an adult, it it it sort of took me, it took time to to train my brain to not see uncertainty in terms of the worst case possible situation. And when you've seen really bad situations, it's easy for your brain to go there. I mean, one thing I'll share is is a lot of researchers show that people

often prefer to know a bad outcome than to know an uncertain outcome. And it's because our brains are often hardwired for survival. So when we have an uncertain situation, our brain goes to the worst case possible scenario. I had something recently where there was something and I thought, this person just trying to do like like I was assuming negative intent. And I was like reflecting on it. I was like, my I am in a bad head space there. Like this is not rational of what I am thinking in this situation.

And yeah, it's it's really important that our brains don't like we label when we go to worst case possible scenario, but we understand that often it is quite irrational. And and that's why many of us don't like uncertainty. Like I and for context, I've done now probably 50 in-person talks about the uncertainty advantage. And in those talks, I ask people to raise their hands like whether they like uncertainty or whether they dislike. If you're a listener, you might you might be like, well, a lot of people like it. There are there's a minority who like it.

I would say consistently, there's probably one person who really likes uncertainty for every five to six who dislike uncertainty. And I do think sometimes really bad or challenging life experiences can at least temporarily make someone fear the unknown in a way that is more significant than for others.

Matt Gilhooly (27:12)
Yeah. Definitely understand that. I I also was thinking, you know, those of us, which probably everyone, let's be honest, the bad times we've I'm sure everyone's had a bad time in their life. But going through those, I think it also, and this is so cliche, but I think it helps us see the other side so much brighter and so much more worthwhile.

Like I think if we were all at this steady state and we made an incremental change, it's like you don't even notice it. It's not but since we've been in the depths or we've been somewhere that we definitely needed to get out of, now we see this other side of like, why wasn't I doing this? This is so much better, all the all the pieces that come along with it. So it's like that that comparison and crappy as it is, you can't trade what you went through.

If you're gonna continue enjoying these things up here.

Scott Stirrett (28:09)
Yeah, totally. And I do think I've one of the things I've also heard from these sessions is I've asked people to reflect on how their relationship with the un with uncertainty has evolved over time. And what I often hear is it's going through really challenging things like it, including like raising kids and dealing with business stresses. Like it can result in a temporary decrease in your comfort with uncertainty. But then in the long run, it can actually make you like more comfortable with the the unknown because like you've dealt with it. And

I think it can go both ways. Like in there's post-traumatic stress, but then there's also post-traumatic growth that can exist. And I certainly have seen people who go through really challenging things. And even I think of my own life in challenging moments, often it can make me maybe more temporarily sensitive. But then I think over the long term, it can build more resilience. And and I think part of it that is really important, and I talked about this a little bit in the book, is that it's important

Matt Gilhooly (28:40)
That's true.

Scott Stirrett (29:08)
I if you you know, view these challenging s moments as situations that made you stronger, that taught you different things. Essentially, in the word way of like Victor Frankel and Man's Search for Meaning, if you can try to find meaning and pain, I think that that's really important in terms of moving forward with grief. I I remember reading an article once and talked about it criticized this concept of like

This the five stages of grief or like graduating from grief. And it resonated a lot with me, which is to say is that I think often you don't graduate from grief or you don't graduate from traumatic things. It rather you move forward with those experiences. and you know, one of the I think the challenges is is if you go through a challenging thing and you try to box it away, that situation begins to try to control you.

And I and that's where I think ultimately learning to like move forward with that experience, to be open about it. even if I mean I'm not a psychologist, but if you look at how PTSD is treated, it's it's often about getting those people to picture the really traumatic situation in their head and to try to be less anxious in terms of their body, and to be more comfortable like sitting and picturing that that that experience. and I I you know, I'm I'm I giving a very high basic or high level kind of description of it.

But but I think that you know the a lot of learning to develop a better relationship with uncertainty is to accept bad things happen. They will happen, they have happened to you and or to most pretty much everyone. And and accepting that and still moving forward and embracing all the unknown is really important.

Matt Gilhooly (30:42)
Yeah.

Yeah, I think it it just goes back to what you were saying before and I always think about is that self-awareness. I think if you have that awareness, it allows you to reflect on those things and process them in a way that is healthy. If you don't have that self awareness, sometimes when you look back on those I know from personal experience, looking back on those things, they become a crutch. They become

a reason why things happened. And as soon as I gained the ability to acknowledge how I was, who I was, why I was that way, and be fully in tune with myself, I was then able to process the dumb things I did because I was pushing down grief and it just manifested in all sorts of ways and and forgive that part. So I think for me a lot of it was just

finding a space of like true, authentic self-awareness, of of like, okay, this is really what's happening and not the previous version in which I was filling in some blanks that were there with whether it was true or not.

Scott Stirrett (31:55)
Yeah, and thanks for sharing your experience. And I resonates a a lot. And I think it's to the point like self-awareness, self-reflection is something that's like so critical. And I think one of the things that I is really important when you go through these experiences or like anything in life is to make that time to like reflect. and in the Uncertainty Advantage, one of the things I talk about as like a specific piece of advice is like diary. I diary, not every night.

Like around once a month. but I have detailed diaries going back like 15 years. And it's so helpful for reflection of just and I re and it's not just diarying. To me, it what one of the things that's really important is also it's about reflecting back on the diary entries years later, seeing patterns of behavior, seeing how I view the that. I think in our more digital world, diary diary writing is maybe like less common.

I I would say maybe particularly less common amongst men. I feel like more women I know diary, but I think it's quite rare. Journaling, yeah. There's not that many men that I know that that journal. And I think it's really important.

Matt Gilhooly (32:50)
Mm. Yeah. Men call it journaling.

Yeah.

Yeah. It i I mean it is. It especially I always think that the things in my head are much scarier when they're in my head. And when I get them on paper or I say them out loud, I'm like, that's not so bad. You know, I can move through it. I just talked to someone who her entire apartment or house burnt down and the only thing that survived was like three hundred of her diaries that she had from growing up. And so she she was like

Well, I guess this means something. And she went back and she read everything and she learned so much about herself and about her journey. Because I think when we're in the moments, they're quite different than when we can read them in a in a span of of time. And so to your point, I think one, get your thoughts out of your head, put them down, mark what's happening, but also then later on read it, reflect on it, see what's happened in your life and learn a lot about ourselves. But

I think the hurdle for a lot of people and probably a lot of people you've met is is the first step is being willing to reflect, to look back on it with honesty and and and ownership, maybe.

Scott Stirrett (34:10)
Yeah, I mean I think the ownership piece is is important. It relates to acceptance. Yeah, it is. And it's accept that like everything, good or bad, mediocre, is all part of our life. And there are good things in our lives, there are bad things in our lives, there are mediocre things in our lives. Going forward, there will be good things, bad things, and mediocre things. And accepting that that is just all part of the human condition, I think is is really important. It makes uncertainty and risk taking less scary because

Matt Gilhooly (34:14)
Heart.

Scott Stirrett (34:40)
When you accept that, bad outcomes can happen. They do happen. You can learn, I think, to be more comfortable with risk taking.

Matt Gilhooly (34:49)
So like what would if if we were having this conversation the week before you were meeting with that coach and you had a little woo-woo moment in your life? Like how would what were how are you looking at life at that point? 'Cause you had accomplished a lot of things and so you had taken risks and whatnot, but how different is that version of you to now?

Scott Stirrett (35:14)
I think I just in that time I was way more afraid of everything. I think that that is I mean, like pre the pre-the situation. Yeah, I mean I I I all to say at different points, like when I left Goldman Sachs at 22 to go find Metro for Canada, I was comfortable with uncertainty. Then my uncertainty muscles atrophied over a decade. And then I have took some time to build them back up. all to say is I think our relationship with uncertainty ebbs and flows. So when I say like pre and post,

Matt Gilhooly (35:18)
Okay. More calculated risks, maybe?

Yeah.

Okay.

Interesting.

Okay.

Yeah.

Scott Stirrett (35:43)
I

think that when I was like 22, I actually was pretty comfortable with uncertainty. And then I I was 22. yeah, it's a little mood, so so naive on a lot of things. but you know, then I think I you know, became more comfortable with uncertainty in in recent kind of years. So, you know.

Matt Gilhooly (35:48)
'Cause you're twenty two though. Right. Everyone at twenty two is a little not so.

Scott Stirrett (36:04)
All to say too is for me, it's not necessarily like a switch where you just go from being comfortable with uncertainty to not. It is this, it is like going to the gym. I think like all these things. Like it's a gradual, ongoing, habit-based process, which is really what the uncertainty advantage is all about. It's that there's not just like one unlock that like helps you build a relationship with uncertainty. It's yeah, exactly. There's no Zempic for uncertainty. you know, I think at the end of the day, you

Matt Gilhooly (36:25)
That's what Americans want.

Scott Stirrett (36:32)
have to learn to develop a better relationship with the unknown like one of the things I talked about in the book is like gradual risk taking. Like what's like one risk you can take every day, every week that pushes you out of your comfort zone. And I think it's so important because it's like if you just do that, you you are intentional but building your risk taking capacity, it compounds like anything in life.

Matt Gilhooly (36:56)
Yeah, I would think you would need some wins at first from those risk taking.

Scott Stirrett (37:01)
Yeah.

total, which is where that, you know, it's not just blanket and that's one of the things I talk about in the book too, is that it's not and it's also it's different from people's socioeconomic realities. Like it's easier to take risks if you have more social safety net. It's it also winning makes you comfortable kind of taking risks. All to say is I didn't win all the time venture for Canada, but the fact that I raised 80 million dollars and supported fifteen thousand people and and did all of these things.

Gives me the self-confidence to then go do other stuff. I also had a ton of failures along the way. So many things didn't work out. and in uncertainty advantage, I cite the research of Amy Edmondson, the famous Harvard Business School professor, and she talks about the difference between intelligent failures and unintelligent failures. And that's where I think it's important is that this to think about is that not all failure is created equal. An intelligent failure is the

an instance where you're not wiped out by the failure, where you learn something from the mistake, and where you it wasn't something easily avoidable. So I think a lot of times people if it's just like a silly error, then that's not a good learning experience. And I think sometimes we're like, all failure is equal. It's not. Failure is painful. And she talks about that in that book. It's no one likes failure. It is part of life. We have to accept it.

But we have to recognize that we want to get seek the right times types of failure and we want to avoid the unintelligent failures that can be really damaging.

Matt Gilhooly (38:30)
Yeah. But that also comes with the same thing is like you have to be willing to really look at that failure and determine where you could learn from it. Right. Like I feel like sometimes people that aren't ready for that, they might take a big swing, they might take a big risk, they fail, and it becomes this see, shouldn't have done it. Now you should never, you know, like and and not really pick it apart as to why maybe it you failed at that because of

Scott Stirrett (38:41)
Yeah.

Matt Gilhooly (38:59)
whatever variables that were part of that decision that you made. But some people it's just easier. It's just easier to fall into the trap of, see, I told you so. Wasn't gonna work to begin with. I'll never try anything again. It's very easy to fall on that.

Scott Stirrett (39:14)
And Amy Duke, who is the champion poker player in thinking and bets, I cite this in the Uncertainty Advantage. She talks about how often we equate good outcomes with good decisions. But sometimes we can make a really good decision and has a really bad outcome because of bad luck. Likewise on the flip side. So all to say is that being kind to ourselves that sometimes like you actually make it Yeah, you pillar one, you can make a really good decision. but

Matt Gilhooly (39:29)
Mm-hmm.

Pillar one.

Scott Stirrett (39:43)
Life is random. There there's a lot of randomness in luck. And that's that's not to say that life choices don't matter. They do, but there is way more luck in life than most people I think are willing to recognize.

Matt Gilhooly (39:45)
Yeah.

Yeah. I come at it with such like a and I I wouldn't classify myself as a cynic, but also a very like cautioned individual. I don't know if it's because of early trauma as a you know, with kid and and and losing what I lost and then trying to figure it all out. But I'm always like bless you. I always feel that like I feel sometimes I feel like I'm so far down the path of where I was and then sometimes like, well see, it's easier to fall in that pattern.

Scott Stirrett (40:21)
Thanks.

Matt Gilhooly (40:30)
Because comfort is just like so compelling. And I just want to like grasp onto it. For instance, if I'm feeling depressed, say that like a period of my life, I'm feeling down, it's so much easier to put on sad music and like sit in the dark and watch sad movies than it is to be like, all right, let's carry on. Let's move through this. You know how to do it. It's just so much easier to stay in the comfort zone. So, you know, I think through all these things. I'm like, yeah. You know, all these things are great ideas and great

processes and habits that we should build. And that's the key word probably habits. But it's just so much easier to stay in a comfort zone. So I understand why some people don't move through.

Scott Stirrett (41:10)
And

and yeah, I think one of the things that's important is that emphasis on it's a muscle. It's about doing small things, the compound, like atomic habits, you know, and various books talk about, but in the context of uncertainty, it's the same. It's like how do you gradually build that capacity over time where you become more comfortable with embracing the unknown? And it's not easy. Like, like I think that that's an the important point is

Matt Gilhooly (41:34)
Yeah.

Scott Stirrett (41:37)
Learning to develop a better relationship with uncertainty, in some ways, relearning my comfort with uncertainty is one of the hardest things that I've ever done in my life. And it's still something I work on. Like leaving Venture for Canada was part of, you know, I was cozy there. I could have stayed there for like my entire career. I founded that whole organization and built it. But I realized that that's just being cozy is not good for my personal growth and development. And there's risks in not taking risks.

And I was like, this is the time to leave and take a big risk and go do something. And hopefully, if I live a long time, like I'll do that multiple times where I decide to shake things up. But that decision to leave Venture for Canada was only through years of hard work of building my uncertainty capacity. and I can share mean so many differences of doing that, of just like you know, the putting myself out there, or even I think of in the context of the uncertainty advantage.

I did public speaking before, but you know, I've done I've spoken fifty plus events. I've I'm in Toronto, but I've like done events in the UK. I've done in the US. Like I like all of these things, I think, of even this experience of promoting this book has pushed me out of the comfort zone and got me to do a lot of things that I previously had never done. And, you know, I think if you can try to do something novel, like it can be really hard for people, I think, to like, okay, well.

you know, I think if you think of it as this binary, comfort with uncertainty, not comfortable with uncertainty, then it's harder to learn to develop a better relationship with it. Versus it's like the hard work of like it's like learning to run a marathon. How do you gradually, you know, build that up over time?

Matt Gilhooly (43:20)
I don't.

I did a half, that was enough.

Scott Stirrett (43:24)
I know I I just did a half marathon, actually in Buffalo.

And you know, one of the things that yeah, I was like, I I like half marathons. I'm not sure I'm that into doing a full marathon.

Matt Gilhooly (43:34)
Yeah, I don't

even want to drive 26 miles. So I mean, I'll do the half, and that was enough. Yeah, no, I get I I I think that's really important to think about, you know, like there is not a in this instance, like you said before, it's a journey. It's there is no destiny. You're not gonna like, okay, I'm here. I'm a hundred percent comfortable with every uncertain thing that's ever gonna face me. Right. Like this is something that is a

perpetual journey that you're on to practice or work out that particular muscle and be comfortable in reasonable uncertainty. Yeah.

Scott Stirrett (44:13)
Yeah, totally.

It and it is. It's about building an uncertainty practice.

Matt Gilhooly (44:18)
Yeah. I guess it's like meditation, it's like all the other things. It's like you're not gonna do it once. You're not gonna do something once and then all of a sudden you're like, I got it, like nirvana. Here we are.

Scott Stirrett (44:30)
in the book I go through six pillars where it's around self-compassion, adaptability, anti-fragility, generalist skills, entrepreneurial mindset, and network building. And it's to say it's like all of those six pillars together is what helps you learn to develop that better relationship.

Matt Gilhooly (44:43)
Yeah.

Did you ever have a moment where you're like, everything kind of cli like everything makes sense now in this new version of my life and this is and maybe that was the impetus to write the book, but like we're putting all these practices together where you were like, I got something here. Something feels different.

Scott Stirrett (45:01)
I think it was my own challenges in COVID with uncertainty made me passionate to like help others. and and I think it it you know where I've seen it is in moments of where I embrace uncertainty the most, whether that's leaving venture for Canada or founding venture for Canada, that I often am in I feel the most energized and excited and where there's the most opportunity in front of me. And I think that that's maybe one thing that has been helpful.

For me of a kind of an unlock of like

Scott Stirrett (45:32)
I mean I think at the at the end of the day, it it's about all of these six kind of core pillars of the book kind of working together of how you build a better uncertainty practice.

Matt Gilhooly (45:43)
Would you say that the book is your story just put in not your story, but like your experience put in framework based on research? Or would you say that you had to pull from things that maybe you you personally didn't experience?

Scott Stirrett (45:58)
I'd say it's more using research and then having my stories be expository that help kind of gr bring it to life. I I mention other people's stories, but the book is quite personal. It kinda goes through a lot of my own experiences.

Matt Gilhooly (46:10)
Yeah. Does

it like what I'm I guess what I'm saying is the framework that you have in there or the pillars and all those, those are also embraced by you. And okay.

Scott Stirrett (46:20)
Yeah, totally. That

and I also say is that sometimes I think back to the book a lot of you know, Pillar Six, relationship building. we did organize, you know, spent my husband and I spent a bunch of time organizing a big birthday party. and it was great, connected with a lot of different people. And I think back to network building, maintaining relationships. I mean, that was one big change in COVID too, is that by being more comfortable with uncertainty, I just started becoming a lot more

bold in just like inviting people over for for dinner, building friendships, like putting myself out there. And I reflect to like my I had my 35th birthday just recently. And you know, obviously five years ago I had my 30th birthday. And I feel like I have so many more social relationships in my life today than I did five years ago. Like you know I w it it it's like a sea change in terms of the number of relationships. And

That was through hard work too. And that was, you know, I think being bullied as a kid, I sometimes was afraid to put myself out there. And being more comfortable with who I am, way more bold of just like, hey, want to come to dinner? And if someone rejects me, that's fine. But I've made, you know, through those dinner invites, there's a ton of people who become really, really good friends. And there's a the benefit to putting yourself out there.

Matt Gilhooly (47:42)
Yeah, I think the more you can show up as like fully you too and and comfortable with who you are, you're attracting the people that are also feeling that way. And you kind of we avoid that that bully stuff that happened to most people, you know, growing up. So I I'm it seems like this is working out for you. And it seems like you're not that you were ever, I would from your story, the way you tell it, it doesn't seem like you were ever in a really bad situation, but you've only improved

improved your life through this way. Like it wasn't desirable, maybe, looking back, but would you say that's true?

Scott Stirrett (48:14)
Yeah.

Yeah,

I I mean that's one of the the reasons not to say my life is perfect or that I'm perfect in navigating uncertainty, but I think that leveraging these six core pillars in my own life have been super helpful at improving my happiness, my career, like absolutely. and that's why I'm actually like genuinely passionate about this, is that there is a I have a very different life today than I did five years ago, and that is

because I chose to embrace uncertainty and sit in an uncertainty. And it's really hard, not easy, but it's worth it.

Matt Gilhooly (48:54)
Yeah, and you gotta keep doing it. It's not like a one and done thing. If if this version of you, if you could only say one sentence to the twenty one year old version of Scott, like what would you tell him? You had just one sentence, if maybe it would help him.

Scott Stirrett (49:11)
Coming out of the closet.

Will have virtually no negative repercussions on you.

Matt Gilhooly (49:20)
And he was afraid at that time, would you say? Yeah. Yeah.

Scott Stirrett (49:22)
Yeah, yeah, especially at twenty one.

And I think just like saying that, you know, you you can build these big to the point of worst case scenarios. You can build these worst case scenarios in your head, but it's like wasn't a it was all in my head. And that's to say bad things can happen and they do happen, but I also think that like you just have to sometimes put yourself out there. And you know, I

Matt Gilhooly (49:38)
Yeah.

Scott Stirrett (49:48)
had so much psychic suffering because of that for a couple of years that yeah, the Scott if Scott went ahead of in time by fourteen years, I think you'd be very surprised.

Matt Gilhooly (50:00)
Yeah. Well, in a good way. Yeah. That's awesome. So if people listen to your story and they want to learn more about your book or they want to like connect with you, tell you their story, maybe say something that that you said that resonated with them, like what's the best way to find you and connect with you if they're allowed?

Scott Stirrett (50:02)
In a good way. Yeah.

The first step of learning to develop a better relationship with uncertainty is to understand your current relationship with uncertainty. So I recommend you take my short quiz that takes like two minutes, and you can find it by visiting ScottStir.com slash quiz. You can spell that by S-C-O-T-T, S-T-I-2R-E2Ts.com slash quiz. And when you fill out the survey, you'll get your results out of from zero to forty-eight.

in terms of what is your current relationship with uncertainty. And I really recommend that as a first step for listeners, because you can't learn to develop a better relationship with uncertainty until you know your current relationship with uncertainty.

Matt Gilhooly (51:03)
Cool. So they can can they find you and reach out to you too if they take the quiz and they're like, I want to learn more. Awesome.

Scott Stirrett (51:10)
Absolutely. And to contact me personally, you can add me on LinkedIn.

and yeah, contact me there.

Matt Gilhooly (51:16)
I I the reason I asked that is I think there's there I know there's so much power in storytelling. And sometimes by listening to other people's stories, we hear permission, we hear validation, we hear something that we needed to hear. And some people haven't shared that with other people. And so if something that you said resonated with someone, I encourage them to reach out and at least share what that drew from them, you know, and and maybe there's some power in them letting that out of their head.

and sharing it with someone else. So hopefully you are good with that.

Scott Stirrett (51:47)
Totally.

Yep. I look forward to hearing from people.

Matt Gilhooly (51:52)
Awesome. Well, I appreciate you coming on this journey and letting me ask all random wild questions and inserting my own personal experience into them.

Scott Stirrett (52:00)
Well, it w thanks so much for having me on and it was great meeting you.

Matt Gilhooly (52:04)
It was nice to meet you as well. Thank you all for listening. with that I'm gonna say goodbye and I'll be back probably in a couple of days with a brand new episode. Thanks again, Scott.

Scott Stirrett (52:13)
Thanks, Matt.