Young Professional? Here’s How to Get Hired in 2026

About the Episode

In this episode of the Career Warrior Podcast, Scott talks about navigating the uncertainty around these challenges using some of the key pillars from his bestselling book, The Uncertainty Advantage, including strengthening your risk-taking muscles, the Regret Minimization Framework, and the RULER Method.

Scott is the founder of a national nonprofit that has raised more than $80 million and supported 10,000 young professionals. His book, The Uncertainty Advantage, has been endorsed by Andrew Yang and Eric Ries, author of The Lean Startup, and hit #1 on Amazon Canada.

Learn more about Scott at scottstirrett.com, or connect with him on LinkedIn.

Listen on Your Favorite Podcast Platform

Young Professional? Here’s How to Get Hired in 2026 | Scott Stirrett

[Episode Transcript]

Chris Villanueva (00:00.076)

Today’s episode is for our young career warriors who may be struggling with their job search in 2026. We’re going to be covering some heavy hitters today: uncertainty, getting past the rejections, risk taking, and making career decisions. But first, a quick story. It was four o’clock in the morning, and Scott Sturrett was pacing empty streets, Googling his own symptoms. In his early 20s, Scott was grappling with OCD flare-ups while facing several other life-altering decisions.

That required him to embrace uncertainty, founding a nonprofit, moving countries, and coming out of the closet. This ambiguity ultimately led him towards a greater mission, which is helping young professionals navigate career uncertainty. And it is no surprise that he is my guest on today’s Career Warrior Podcast episode. And in this episode, Scott’s going to be talking about navigating the uncertainty around challenges.

Using some key pillars from his best selling book, The Uncertainty Advantage. This is going to include strengthening your risk taking muscles and something called the regret minimization framework and the ruler method. Scott is the founder of a national nonprofit that has raised more than $80 million and supported 10,000 young professionals. In his book, The Uncertainty Advantage, this has been endorsed by Andrew Yang and Eric Rees, author of the Lean Startup.

And this is a hit, a number one hit on Amazon Canada. You can learn more about Scott on ScottStirrett.com and we’ll include that link within the description of this episode or connect with him on LinkedIn. So this is going to be a really special episode, especially for you young folks who might be struggling with your job search. I don’t care what part of life you are, what position you’ve been in. I hope that you can tune into this episode and relax with some confidence because we’re here for you. You’re not alone and

Chris Villanueva (02:18.749)
there are some good things coming for you in the future, I promise. So without further ado, this is episode four three of the Career Warrior Podcast. Scott, welcome to the show, man.

Scott Stirrett (02:32.424)
Thanks so much for having me on.

Chris Villanueva (02:34.413)
I am so excited. ’cause I know we had a really cool conversation before this. you were all about dealing, I think, with these things that young people are struggling with, uncertainty, making career decisions and in a time that’s really difficult. So my opener question to you is young people now are facing job search issues now more than ever. why now in twenty twenty six? What’s going on?

Scott Stirrett (03:01.286)
It’s not an easy time for a recent grad or young person to start their career. And that’s because of many different reasons. I’m going to highlight some of the most significant. The first is that AI is having, I think, an impact on the job market, in particular for a lot of entry-level folks. And while there are a lot of debates amongst economists about the extent to which this is purely caused by AI, I think that.

It doesn’t take rocket scientists to see that AI automates some of the more manual kind of tasks that people do as an intern or as an early stage employee, summarizing reports, filing things. And a lot of that work is no longer being done by humans, it’s being done by AI. And that means that it’s really challenging for a lot of young people to get their their first job, because a lot of those first jobs

unfortunately no longer exist. I’d say a second major challenge for a lot of young people in getting their foot in their door is that the nature of how folks apply for jobs has changed. Because of the advent of AI and the advent of online job applications, there’s more people who are applying for a given job than ever before. A company can post an online job application, get a thousand applicants. And what does that mean in practice is that

Companies are bombarded with job applicants, and it means that they’re using AI or their personal networks to determine who gets in an interview. So if you have a more sparse resume or you don’t have the same kind of professional network, it’s a lot harder to get your foot in the door. And I’d say the third kind of final thing that makes it a little bit more tricky for young people entering into the workforce today is that.

There is an increase in just like cost of living pressure on a lot of young people, which means that there’s more pressure to get a job that pays a certain amount, and means that more people are are kind of fighting for a certain kind of of job, which means that the economy is more competitive than ever before. And that cost of living is driven by increased housing costs, which obviously varies across the US, but has become significantly more expensive since COVID.

Chris Villanueva (05:12.865)
Yeah.

Chris Villanueva (05:20.951)
Yeah.

Scott Stirrett (05:27.156)
but everything from food, transportation, gas, it’s not cheap to to live. it never was, but it certainly become more expensive.

Chris Villanueva (05:33.26)
Yeah.

Yeah, it’s funny. It’s like I these are all things that I’ve seen in the news and just seen posted on social media. But I think it’s it’s so telling that you’ve been like on the field talking, like giving these talks, like connecting with young people and like really seeing this firsthand. So

yeah, if you’re listening to this right now and any of that stuff sounds familiar, like you were not alone for sure. it reminds me I like a I remember I was scrolling Instagram and I saw somebody giving a commencement speech a few months ago. And in that commencement speech, she was like, and now AI is here, something like AI is here and it is here to do amazing things. And like all of those graduates just booed like so loud and she was like so taken aback.

But I think like there’s this air of uncertainty and not knowing what’s going on and it’s it’s a struggle. I think it’s definitely a struggle now, especially now in here in twenty twenty six. So I don’t know if you have anything to add to that, Scott, but

Scott Stirrett (06:37.819)
No, no nothing kind of key to add, but I I’d say one point beyond diagnosing the problem is how can young people cope with all the challenging circumstances. And the first pillar of my book, The Uncertainty Advantage, is about the importance of of self-compassion. And there are three core aspects of self-compassion, according to Dr. Kristina Neff. the first is the importance of

Chris Villanueva (06:48.801)
Yeah.

Scott Stirrett (07:04.399)
Recognizing your shared humanity with other people. The second is the importance of being mindful of how you’re feeling. And the third is the importance of talking to yourself like you would talk to a good friend when they’re going through a challenging circumstance. So if you’re a young person out there and you’re applying to a lot of jobs and you’re getting a lot of rejections, I really encourage you to foster a self-compassion practice because self-compassion is not for the weak. It’s not this woo-woo thing. And sometimes it’s become almost trite to say, be kind to yourself.

Chris Villanueva (07:17.324)
Yeah.

Scott Stirrett (07:34.567)
But I think that in an era where it is really hard to get your first job, being kind to yourself is one of the most important things you can do to be more resilient and ultimately to be more successful.

Chris Villanueva (07:46.061)
Yeah, I love that. In this episode, for you listeners, we are gonna delve into some specific job search techniques and some tips that we have for you as somebody who’s sending out their applications. But to me, what is more interesting and something that we cannot forget is dealing with uncertainty and some of those more call like quote like soft skills and more of those soft things that we have to develop.

So that’s why like I wanted to dive into this as our first topic here, which is dealing with uncertainty. You know, we talked about uncertainty is dealing with it can be like a learned skill. So how is that possible, Scott? And how can people learn to deal with uncertainty as something that they can train themselves on?

Scott Stirrett (08:29.531)
Uncertainty is definitely a teachable skill. And in my book, The Uncertainty Advantage, I go through six core pillars that are research-backed on how you can learn to develop a better relationship with the unknown. And those six pillars include self-compassion, but also adaptability, anti-fragility, entrepreneurial mindset, generalist skills, and network building. And it’s important to note that many people talk about all these things. But I think what is a little bit unique about my framing is that.

Chris Villanueva (08:33.75)
Okay.

Scott Stirrett (08:59.555)
It’s these things, things taken together that reinforce your relationship with uncertainty. And that everyone needs to have an uncertainty practice. That even if you have a really healthy relationship with uncertainty today, you need to be intentional. Just in the way that if let’s say you’re someone who is in great shape, you still need to go to the gym to stay in good shape. I I think it is really important that everyone be mindful of building their capacity to cope with uncertainty.

Chris Villanueva (09:04.993)
Okay.

Scott Stirrett (09:28.955)
Because the more that you let uncertainty control you, the more, or the more that you run from uncertainty, the more that you let uncertainty control you. And one of the most important things you can do is just to view uncertainty as a good thing in your life, and in some cases to actually try to seek it out.

Chris Villanueva (09:46.831)
Yeah. I’m remembering back when I was about to graduate college, and that was something I really struggled with was my gosh, I don’t know what’s coming next. Like that was that was I think my first real taste of uncertainty is like not knowing that next job and what it was gonna be. And you know, I I like to say I have no regrets, and this is certainly not a regret at all because I think everything happens for a reason. But

I felt rushed and I think I rushed myself into making a decision on what that next job would be because I just wanted something fast and I just had to have it because I couldn’t deal with that uncertainty. so I wish I had that framework like that all those years back to deal with it because it it is one of the biggest, greatest skills that I think that we can have to deal with so much. So I’m glad that you called that out. I think that makes sense.

Scott Stirrett (10:39.791)
In the context of careers, I think it’s a big mistake a lot of people make as they rush to immediately the the next thing, the next opportunity, the first thing that comes their their way, particularly at the beginning of your career. And I’ll reflect in terms of this even specific moment right now for me. I led Venture for Canada for 12 years, an off-a profit I founded. I then chose to leave the organization and I went traveling for a couple months. And I’ve been doing consulting work for the last six months. And it took me a couple months of

Chris Villanueva (10:48.194)
Yeah.

Scott Stirrett (11:09.199)
Around six months of reflecting and trying out a bunch of different things. And I decided to dive into a full-time search to acquire a business. And it took me a lot of time to realize that that was the path that I wanted to to do. All to say

Chris Villanueva (11:25.282)
How long did it take you? What was like the the time on like the process and like deciding it?

Scott Stirrett (11:31.331)
It took me so I wrapped up at VFC at the end of this year. sorry, end of 2020 five. And then now it is August 20 and 26. And I made the decision in May to kind of embrace this path. So for me it took around five months for me to figure out Yeah, and it f you know, five months is still a pretty long time. And it was uncomfortable because I see my friends getting promoted, I see

Chris Villanueva (11:50.064)
okay. Yeah. It’s carefully thought though, yeah.

Chris Villanueva (11:57.699)
Yeah. Yeah.

Scott Stirrett (12:00.976)
People advancing it, and I’m just like kind of figuring out what I want to do. And especially when you’ve been used to running something for 12 years, it can hurt your ego and your identity a little bit. But I thought to myself, you know what? No, I’m going to not rush in and just like make a decision and sit in this uncertainty and explore a bunch of different ideas. And I’m so glad that I did, because rushing into a decision just to minimize uncertainty.

That’s how you end up pursuing a career path or a a type of field that that ends up not actually being a good fit for you or your skills or your interests.

Chris Villanueva (12:39.106)
Yeah. So look you kind of using that example, I don’t know if this is the perfect segue. I think it might be, but like the risk taking muscles. I imagine that you had to evaluate the risk that it took, at least from a perspective oppor of opportunity cost in your own time, but in making that decision. So what does it mean to strengthen your quote risk taking muscles and how can someone actually practice doing that to deal with the uncertainty?

Scott Stirrett (13:09.176)
Each week think about what is one thing that you can do to push yourself out of your comfort zone in the context of your socioeconomic situation or reality. That can be as little as eating a kind of food that you’ve never had before. That could be going to travel to yeah. That could be going to tra

Chris Villanueva (13:23.798)
Down. It’s cool. My wife, not so much. She hates eating new foods, but I’m like, I’m gonna try to encourage her.

Scott Stirrett (13:32.035)
It’s good and it’s important for building uncertainty practice. Like before we started recording, I mentioned going to Ithaca, where you went to college, and I hadn’t been there. But it’s great for building your comfort with uncertainty to go to places that you’ve never been to before. And I love the novelty. And as I reflect on all these things I’ve done to build up my uncertainty practice over five years, today I’m more comfortable and in some ways I thrive.

with uncertainty than when I think about in COVID when I was so afraid of the unknown. Five years ago, I would never have pictured myself leaving Venture for Canada to pursue a more high-risk thing, like going to to buy a business. All to say is that I was able to get to that path of being able to take this kind of entrepreneurial risk through a lot of

Chris Villanueva (14:16.388)
Yeah.

Scott Stirrett (14:27.696)
gradual steps that I took to build up my risk-taking muscle over time. That’s to say there’s no panacea or one thing that builds up your capacity to take risks. It’s a lot of smaller risk taking over time that gradually increases your capabilities.

Chris Villanueva (14:38.169)
Yeah.

Chris Villanueva (14:42.169)
Think that would be like a misconception is somebody like, okay, I’m gonna listen to this podcast episode and you know, Scott and Chris change my perspective. I’m brave, I’m ready to make some big moves. Heck, if that comes to you, then great. You know, if you have something that came from a higher calling, you know, whatever that may be, I think that’s great. But a lot of the times it comes as a like progression in life. Like, let’s start with smaller things and just make it like a regular habit. Every week, like you said, trying something new. So

I don’t know what it’ll be for me this week, but I I’m I’m encouraged to try something new, to get out of my comfort zone, which I have. So in the book you talk about something called the regret minimization framework. I thought that that was fascinating. Can you talk more about it at a high level?

Scott Stirrett (15:29.252)
Regret minimization is thinking about your eight-year-old self and reflecting back on what would your eight-year-old self most regret and then minimizing that regret. So I’ll take an example is that when I was 22, I quit my job at Goldman Sachs in New York City to go found a not-for-profit called Venture for Canada. And that was a really audacious bet. I moved to Toronto where I knew no one. I ended up

Chris Villanueva (15:55.919)
Mm-hmm.

Scott Stirrett (15:57.117)
going and building this organization. And I gave up a really prestigious, high-paid job in New York City that had a lot of perks and a lot of social prestige to go follow my instinct, which was that I wanted to build this this organization. And I’m really glad I did. Venture for Canada’s ended up raising over $80 million of funding, it’s thriving today. And

That was through minimizing regret in my life. I I also use that framework very directly in making the decision to buy a business because you only have one life and I think one of the most difficult emotions for people, at least for me, to process is regret. Like when I think back, I don’t have too many regrets, but the regrets that I do have, they are very painful to to process. And I don’t wanna ha live a life where I have a ton of regrets of would have, could’ve.

Chris Villanueva (16:26.255)
Okay.

Chris Villanueva (16:31.822)
Yeah.

Chris Villanueva (16:46.691)
Yeah.

Chris Villanueva (16:52.887)
Yeah. I think that’s very trippy. So like you’re you’re going into the future as your eighty year old self, correct? So as you’re imagining yourself as an old man looking back decades before on what you would regret. I’ve never thought about that. I think that’s like super super interesting. So like how do you even get in that mindset of like knowing like what you would think as an as an eighty year old? Is it just like something that’s like so deep and personal to you?

Or how would that work?

Scott Stirrett (17:25.126)
I think it’s deep and personal to you. And I think on how you figure out kind of regret, there’s a couple different ways, or or what you would regret it in the future. I think the the first framework that maybe is helpful is to listen to your instincts to some extent. Like like what are your instincts telling you to kind of do? And your like if you’re in in a

pursuing a path that you just know is gonna make you miserable for 30 years. Like you know that deeply and intuitively. and you know I think it’s important to listen to those instincts in many cases. I think one maybe tip on thinking about your eight year old self is to actually like write a letter to yourself. Like like think about, okay, I’m an eight year old and go like take a pen and paper and write like advice from your eight year old self.

Chris Villanueva (18:02.435)
Yeah.

Chris Villanueva (18:14.039)
I love it, yeah.

Scott Stirrett (18:24.634)
to you. And I think that that’s like a good way to get into that eighty year old mindset of helping you not make big mistakes that you’re gonna end up regretting forty, fifty, sixty years later.

Chris Villanueva (18:38.061)
Yeah. Think about as an exercise how impactful that could possibly be. Like, imagine just because I I I know I don’t take enough time to introspect or like think about like those deep career decisions. I’m la I am admittedly like a chicken with my head cut off half the time. Cause I’m always like, I have to do this and this and this. I have my checklist of short-term things to do so I can feel like I’m surviving. But I really encourage

listeners who are going through especially young people who are going through a period of transition to take the time to do things like this because you never know if you’re gonna make like one of the best decisions of your entire life. Like don’t just take this as an as like just some trivial exercise, but do this because it could change your life. So I think that’s awesome, Scott. Thank you for sharing.

Scott Stirrett (19:24.794)
My yeah, my pleasure.

Chris Villanueva (19:27.085)
So kinda going through this and then I wanna transition on to like practical hiring tips you have in twenty twenty six, but what is the ruler method?

Scott Stirrett (19:38.033)
The ruler method is a evidence-backed method from Yale University on how to regulate your emotions. And there are a couple different steps. the first is the important kind of step just to kind of understand of like how are you feeling kind of in the the moment. So just reflecting. Then it’s about understanding.

Like so if you’re anxious to say, okay, why am I anxious? Maybe it’s that I have a big test the next day. Maybe it’s that I am, you know, have a surgery. Or there’s a lot of ways, but to understand our anxiety is really important. Then to say the next stage is actually labeling, okay, I am feeling anxious. And sometimes that can be saying that to a friend. Sometimes that can be writing that down. and then it’s about expressing it. as I mentioned, that can be what just what I said.

Chris Villanueva (20:09.112)
Mm-hmm.

Scott Stirrett (20:34.65)
And then the the final part is this regulation, which is that the more that you label how you’re feeling in the moment, the more that you can begin to gradually control the emotions. There’s the famous line from the psychologist Carl Jung, where he said, What resists persists. And when I think about my struggles in with anxiety during COVID, a lot of it was because I was being hard on myself and I said,

I don’t want to be anxious. I want this emotion done. I want this out of my head. And the more that I find that I tend to resist difficult feelings, whether it’s anger or it is sadness or anything, the more that those emotions begin to control me. And I think the ruler method is really effective because when you’re it’s actually moving beyond even saying that those are difficult emotions, ideally. It’s almost this more Buddhist kind of concept eventually of.

Chris Villanueva (21:07.299)
Yeah.

Chris Villanueva (21:28.258)
Yeah.

Scott Stirrett (21:32.322)
acceptance of all feelings, of of saying there is nothing good or or bad in terms of feeling. There they are thoughts and that we observe them and everything is allowed in and and out. And I think that as a result, it’s not about not ha feeling sadness or anxiety. We’re all gonna feel that. It’s about trying to move towards a path of accepting those difficult feelings. And I think one of the biggest challenges that often people can fall into is when they

Chris Villanueva (21:50.916)
Yeah.

Chris Villanueva (21:55.151)
Yes.

Scott Stirrett (22:01.283)
try to blunt or avoid those feelings. And those feelings are part of life. And the ruler method, what I love about it is it’s not about hiding from those feelings. It’s about sitting with them and and ultimately accepting.

Chris Villanueva (22:14.158)
Yeah, exactly. I think early on in this podcast, I talked about labeling and it is such a powerful thing to label your emotions, to know it as something you’re going through temporarily and something that is not a part of your identity and your core of who you are, and something that changes with time. So I think that’s one of the most powerful techniques out there for dealing with anxiety and certainty and all those types of things.

Another thing that I would do, this is an interesting perspective exercise, but whatever you might be grappling with right now, say like you’re just so plagued and so bothered by the fact that you don’t have a job right now and that’s all you’re thinking about, that too will pass, believe it or not. You might be so wrapped as a young job seeker, like consumed with the idea that holy crap, I don’t have a job. Like this is the worst thing in the world. I’m, you know, I’m consumed by it.

But ask yourself, what was something that gave you anxiety and uncertainty five, ten years ago? You’d be surprised how you might just laugh it off, or you might be like, holy crap, I can’t believe I was so worried about that. But that’s something that was in the past. Like I know for me, something that I really struggled with five, 10 years ago, I’m just like kind of like pulling a random point in time. But yes, I was like dealing with my own,

you know, issues trying to like work my way up in my own career. And I remember I had like one very specific relationship that was like botched and it just like it bothered me so much and I was like worried about like all the things that came with it. Now, ten years later I look back on that and I’m like, I have a whole different set of un uncertainties and anxieties to deal with. And it’s it’s learning to deal with it and knowing that it it changes over time and and and it’s gonna be okay. So

I hope this reaches like someone who’s like might be really struggling with that and knowing that you’re you’re normal to deal with this and it is okay to feel anxious or uncertain and it it changes. It’s gonna be okay.

Chris Villanueva (24:25.57)
So any other thoughts on that, Scott, as we move on towards some tips on AI, ATS, all those fun words and things then that we’re dealing with.

Scott Stirrett (24:37.249)
yeah, I’m good to to move on.

Chris Villanueva (24:38.704)
Yeah. So how is AI changing the white collar job market and what should young how should young people be responding because of some of these changes that you mentioned at the very beginning of this episode?

Scott Stirrett (24:52.357)
I think AI is not necessarily going to replace like all jobs. I think it’s going to impact and change the nature of jobs significantly, but it’s not going to cause necessarily mass, mass, mass removal of jobs. I think what we are seeing though is that the way that we work is changing a lot. I think about my own use of AI and I must be asking like hundreds of prompts a day. I’m using it all the time. So

What I would encourage listeners to do is even if you don’t love AI, you need to learn to develop a relationship with it. You can’t boycott it because it is here. And I think that the the best way to learn how to effectively use AI is not taking some course, it’s just playing around with it all the time. Figuring out what works, what doesn’t. So the first thing I would say is just like be curious. It’s one of the things I talk about in the Uncertainty Advantage.

Chris Villanueva (25:45.456)
Mm-hmm.

Scott Stirrett (25:50.746)
I think curiosity is one of the things that is so important in an era of rapid change. And those who have curiosity about the world around them have a huge advantage compared to other people. And I would really encourage you to embrace your curiosity, in particular as it relates to how AI can help you in your life and career. Second tip that I would have for job seekers in terms of how to kind of stand out in a changing kind of job market.

I think this is the importance of building a degree of like taste and judgment. That’s generally developed kind of over time, but I think we’re living in a time where there’s now so much AI slot, and having really good taste and discernment and judgment is in some ways more important than ever before. So don’t while I say I’m

Chris Villanueva (26:41.528)
Mm-hmm.

Interesting. I never thought of that. Yeah. That’s a good point.

Scott Stirrett (26:47.833)
Well y you don’t want to well, you want to embrace AI, you also want to be someone who is very discerning and who is questioning and not over leveraging kind of AI. So that would be my second kind of tip.

Chris Villanueva (26:59.055)
Yeah.

Chris Villanueva (27:02.394)
What if I I because I know these people are out there and there’s tons of them. What if I genuinely am not going to embrace AI, no matter how much you tell me or anyone else does? Are there any compromises you might make to that or any other insights that you would have? Like, say you’re just like the next thing close to disgusted by the by it and you you really don’t want to touch it. Like I know I I know like just for me being a musician, it’s a tough one because there’s apps like Suno out there who

they make music and they generate it, but there’s so many different levels of AI use. There’s using AI to create an entire thing or using it as like a small tool. but curious what thoughts you may have for someone who’s like averse to it.

Scott Stirrett (27:48.273)
I think to say that you can hold the two things at the same time. You can be both averse to A AI and you can recognize that it’s a part of s you know succeeding in most kind of modern careers. And it’s about having guardrails about not overusing it as well. I mean and I think increasingly saying that you’re gonna boycott AI is going to s be like saying you boycott the internet, you boycott phones, you boycott cars.

Chris Villanueva (28:00.346)
Mm-hmm.

Chris Villanueva (28:04.538)
Yeah.

Chris Villanueva (28:17.967)
Yeah.

Scott Stirrett (28:18.158)
All to say is that you can do that, but you’re going to live like a very different kind of life, right? Like if in this way the Amish choose to do that, and that’s why they have a great life, but it’s a different life than most of the other people. So if you’re going yeah, if you’re going to just completely have zero AI usage in the future, you’re probably going to be opting into a different curve type of career or different life than most people. With pros and cons.

Chris Villanueva (28:29.754)
Good point. Great metaphor. Yeah.

Chris Villanueva (28:44.026)
Hm. But there are l so I that’s a paradox and I love that. So like how you can be averse to it and like hate certain aspects of it and reject it, yet at the same time make it a part of your life if you choose to live like with that. And I think that’s a that’s something that people are going to be like dealing with a lot, like over these next few years is like how to do that. So

I will kind of circle back to that ’cause I think like with the job search itself, it’s like where do we draw that line now on using AI to like for like resume generation, for example, or to reach out to people and like tools like that. Cause I think it’s a very interesting time, I think, for the job search with so many of these things still changing.

Scott Stirrett (29:30.843)
Yeah, I totally agree. And I think it’s a time that will require people to be constantly like adapting and and we don’t know where AI is gonna go. Like there may be I think we’re already beginning to see like a huge AI backlash. I think that AI backlash is going to probably grow substantially over the next couple of years. And we’re already seeing that in terms of

Chris Villanueva (29:47.087)
Right.

Chris Villanueva (29:56.368)
Mm-hmm.

Scott Stirrett (30:00.57)
disputes about data centers and other things. I mean AI is if you look at the public polling in the United States about support for AI, it’s going like way downhill. Like AI is not very popular. So all to say is I may eat my words, but I think that for many, many people, I think there’s going to be this interesting balance where they use AI all the time for their work, but they also loathe AI and

Chris Villanueva (30:28.656)
Yeah.

Scott Stirrett (30:30.928)
Figuring out a healthy balance, I don’t necessarily have the the answer for for those people. I have sometimes challenges in terms of my own views of the way that AI is is changing things. But but I think that

Chris Villanueva (30:35.514)
Yeah.

Chris Villanueva (30:41.745)
Yeah, me too.

Scott Stirrett (30:46.138)
The answer to it I d I don’t think is just ignoring AI and saying it doesn’t it doesn’t exist.

Chris Villanueva (30:52.367)
Yeah. I appreciate that. And I I didn’t mean to like get so into that, but it’s such an interesting discussion. And I think like listeners are it’s something at the back of their minds just like constantly right now. So I think that was that was fabulous insight. So AI or not, my next question for you is how to a very common question, how do I get through the applicant tracking systems? how do I get through those initial filters so I can just start getting noticed? what have you noticed is working?

Scott Stirrett (31:24.484)
I think in many cases it’s actually to sidestep the ATSs and it’s to build your professional networks to be able to get coffee chats and kind of skip over the ATS kind of system. The sixth pillar of the uncertainty advantage I talk about network building. And one piece of advice that I talk about is the importance of being mindful of building both weak ties and strong ties.

Strong ties are people who are your really good friends, your family members. They can be your personal advisors, your mentors. They’re really important to to to build those relationships with people. So when I’m launching my search to buy a business, I have like seven advisors. And they are really helpful. And they’re people who they’re formally advisors to my holding company as I do this search. But then there’s a network of many, many weak ties that I have. So I send out a newsletter which

Chris Villanueva (32:04.251)
Yeah.

Scott Stirrett (32:22.448)
Goes out to strong ties as well. And there’s 2200 people that I send that to. And that’s an efficient way that I maintain relationship with thousands of weak ties. many of whom are people who I have spoken to in an event once, or they’re they’re I just received a really great email from someone who I interned with 15 years ago in Washington, D.C. and I haven’t spoken to since.

Chris Villanueva (32:48.539)
Mm-hmm.

Scott Stirrett (32:48.75)
And she’s been getting my newsletter for a year and a half, and it was this lovely kind of note and email. All to say is to link back to your question, is that.

Chris Villanueva (32:51.269)
Yeah.

Chris Villanueva (32:56.655)
Which can feel kinda funny ’cause it’s like they they know they see into your world, but you won’t necessarily see back until they reconnect with you. Yeah.

Scott Stirrett (33:05.06)
I I totally. I it’d be interesting. There’d all these people that I don’t really talk to regularly, but they have like regular updates in terms of what’s happening. And you know, I also try to share articles and and things that I think are of of interest. And all to say is that so many job opportunities or opportunities in life come through your weak ties that one of the most cited papers in

Chris Villanueva (33:09.967)
Right.

Scott Stirrett (33:32.25)
sociology over the last 60 years is called the strength of weak ties. And in it, Mark Randter found that most people get hired through their weak ties. So my advice for a listener on how do you build get you know, a system to get through the applicant tracking system, it’s to have as many weak ties as possible. And how do you build systems to maintain relationships with these weak ties? Because weak ties are going to be people who refer you for jobs. They’re going to reach out. I had someone just reach out to me and actually

Chris Villanueva (33:50.521)
Okay. That’s fair.

Scott Stirrett (34:02.393)
Kind of pseudo-offered me a job, which I politely declined because I want to do this business acquisition. And it was someone I hadn’t talked to for like 12 years. And he just reached out, hey, I’m kind of interested in doing this thing. And I think how I partly maintained a connection with him is just through posting on LinkedIn regularly. So so the now, lots of people talk about the weak ties. I think the thing that I’m sharing it that maybe is a little bit different is it’s important to create a system.

for maintaining contact with the weak ties. For me, it’s the email newsletter. Think about for you as a listener, like how can you build that kind of system so that you’re not just talking with someone once and then losing contact with them and not never being in touch with them for the rest of your life.

Chris Villanueva (34:48.142)
I love that. And I I think it actually and I’ve never thought about this or given this as advice, but I could see that as a viable option for a young professional. not as like even a short term move because a newsletter is a commitment. I’ve been running newsletters, I’ve done I’ve had one for, you know, twelve years. It’s it’s it’s a it’s a relationship, you know, it’s it takes time and it’s it’s endurance, but it

possibly could be one of the most fruitful things. And do people read emails? Yes, they do. Emails are still the number one way of engaging with people. better than social media, I think, because people open those emails. I don’t even get, you know, posts from my followers anymore, people that I I follow. it’s just the algorithm sends me whatever the algorithm thinks I want. but I think email is just really powerful and maybe putting that up as an idea for somebody

is start a newsletter. It could be fruitful. any other practical do you have any like practical tips on top of short ties for getting noticed, getting more interviews?

Scott Stirrett (35:55.334)
Another tip that I would recommend I think is setting a goal of beyond just how do you create a system for nurturing weak ties is how do you grow your weak ties. So one thing I talk about in the Uncertainty Advantage is setting a goal of like every week getting coffee with like some new person or having a conversation with them over the phone. And over time that really compounds. And what I would encourage people to do is to build their social network constantly.

Chris Villanueva (36:24.955)
Yeah.

Scott Stirrett (36:24.995)
Like every week talking to new people, every week getting out there. And I’m way more of an introverted person than I’m an extroverted person. But twelve years of pretty much every week I have talked to people who I’ve never spoken to before. And when you do that over and over again, it makes you much more comfortable talking with with strangers. And just getting comfortable with cold outreach, cold email, talking to people. That that if there’s one tip, that’s what I would have. Because I think for a lot of young people,

Chris Villanueva (36:45.018)
Yeah.

Scott Stirrett (36:55.107)
And all people, how you get jobs is who you know. And you n I would encourage people not waste too much time on just applying to jobs through applicant tracking systems. Rather try to get jobs through coffee chats and the the hidden door that is increasingly the way that most people get hired.

Chris Villanueva (37:16.495)
Yeah. Especially in this day and age, this year. And, you know, I I’m not shooting myself in the foot here. I know I own a resume service in which the ATS is an important thing to get past. But even I will say that like Scott, you’re exactly like point on and it’s something that I would encourage is like go through that side door, you know, figure out

What is another way that I can get these opportunities other than just seeing a job posting online in posting? And my personal stance on that is to use both, is to use the the networking and the people aspect and also on to post online or to apply online. certain people have different opinions on what mix you should have for that. I don’t know if you have one or thoughts on, you know, just deciding for yourself. but I think it’s that’s an interesting question, is like how.

much time should I spend on networking versus applying online. Do you have any thoughts there?

Scott Stirrett (38:14.733)
Yeah, I I to your point, I still think you need to apply online sometimes. Certainly most people, even if you have a conversation with them, they’re gonna recommend that you apply because they want you in their system. so you’re gonna need to to apply, you know, regardless. But and even if you get a good coffee chat, you’re gonna need to have a professional resume and like a good profile within their system because that sheet of paper is what they’re gonna share internally to the bunch of people who who interview you. So

Chris Villanueva (38:40.785)
Yeah.

Scott Stirrett (38:43.119)
Just to be clear to listeners, I’m not saying 100% just do coffee chats. But it in my view, I I think, especially because AI can automate a lot of the work that is being done to apply to jobs. I think that that shifting it more and more to the coffee chat. Like I think spending 70% of time on coffee chats, 30% applying to jobs online is probably a good balance. Versus I the the issue I think I see a lot of people ha have is that sometimes they spend like

Chris Villanueva (39:05.936)
Yeah.

Scott Stirrett (39:12.811)
80 or 90% of their time applying online and only 10 or 20% of their time actually doing these coffee chats.

Chris Villanueva (39:22.566)
when the opportunity is like imagine if you like switch that up and allocated more time towards those coffee chats. Yeah. I was on Reddit yesterday and somebody commented, like, do you have any recommendations for like cheap resume services? And I’m definitely not cheap by any means. So my comment was it’s like save your money, use ChatGPT instead, because that’s probably what most of those cheap resume services are doing. Like take that hundred dollars and use it to

buy lunch for somebody who’s like one step ahead of you. like that will take you so much further. because it’s that that is the way to move through. That is some, you know, what other people are just not doing in this day and age. So I’m all for it. I think it makes perfect sense.

Scott Stirrett (40:10.755)
Yeah, and I used a resume service when I was in university. I don’t think I would have gotten my job at Goldman Sachs, maybe. I might might not have gotten the interview at least if I hadn’t done the resume service. Because there’s so much strategy, as you know, that goes into kind of a resume. And yeah, I’m really grateful that I that that I did that. A lot of my fellow students didn’t necessarily. And you know, a lot of people were surprised when I got an internship at Goldman Sachs, but partially it’s ’cause I was creative and

Chris Villanueva (40:24.272)
Yeah.

Chris Villanueva (40:30.098)
Cool.

Chris Villanueva (40:38.576)
Nice.

Scott Stirrett (40:40.911)
The resume in terms of the the way things there’s an art to it.

Chris Villanueva (40:42.234)
Nice.

Chris Villanueva (40:46.704)
Maybe I should have used one. I remember getting rejected by Goldman Sachs back in the day. So I should that’s just really cool. awesome. I want to talk about your book, The Uncertainty Advantage. That just it to me it’s it’s a beautiful name. It sounds like an almost like a pseudo oxymoron or something like that. But why why did you name it the Uncertainty Advantage? Like why is how is it an advantage to have uncertainty? I just want to kind of go into the name for a second.

Scott Stirrett (41:16.729)
A lot of people have this opposition to uncertainty, and it’s because our brains are often hardwired to dislike the unknown. And that’s because for most of human history.

Chris Villanueva (41:28.134)
Mm-hmm.

Scott Stirrett (41:33.039)
The unknown could result in situations that were life and death. We could walk by a cave and we don’t know a bear is there, and the bear could come and eat us. So our brains tend to go to like the worst case possible scenario when we’re presented with a threat. At this point, I have talked to many, many people. I’ve done maybe 70 interactive sessions about comfort with uncertainty. And I’ve had around a thousand people fill up my uncertainty quiz, which I’ll give more context at the end. And

What I found is that there’s probably four to five times the number of people who dislike uncertainty for every person who does like uncertainty. All to say, you may be listening to this and be in that minority, but most people do not like the unknown. So to link back to your question, the uncertainty advantage challenges that to say that we we need to see uncertainty as a positive in our lives. That

Chris Villanueva (42:21.314)
Mm.

Scott Stirrett (42:30.796)
It is in moments of uncertainty, like when I left Venture for Canada and went traveling and did some consulting work and said, What do I want to do? It’s in those moments that there is the most possibility. Likewise, when I graduated from Georgetown, I had a couple months before I started Goldman Sachs, couldn’t leave the United States, and all my family lives in Canada because of immigration rules, and I just had all this free time on my hands, and I just thought up of all these ideas, and that’s where the idea for Venture for Canada first came in my head. So

I would encourage people to see moments of uncertainty as not things to minimize or to run away from, but rather that uncertainty is something to seek out and to embrace in your life and career.

Chris Villanueva (43:13.67)
Cool, I love that. what was your favorite chapter in the book? Like as an as an author, what would which chapter would you say you enjoyed writing the most if you could pick one?

Scott Stirrett (43:26.212)
It’s a great question. I no one’s asked me that. I would say that.

Scott Stirrett (43:36.581)
Probably the anti fragility chapter was the most cathartic for me in some ways. in it at the beginning I talk about coming out of the closet. And there was a much more detailed version of the coming out of the closet story that included in an earlier draft. But just even writing that down, like way back in the day that was such I I found it such a challenging moment to kind of come out of the closet. now I’m married and and you know

Chris Villanueva (43:37.658)
Okay.

Chris Villanueva (43:51.922)
Mm-hmm.

Scott Stirrett (44:05.442)
I’ve been out of the closet for like thir thirteen years. So if the the emotions fade. But when I think back to that time it was like I felt like my like world was ending. And

Chris Villanueva (44:16.122)
It’s like everything, like we talked about perspective earlier. But yeah, that that was it for you.

Scott Stirrett (44:20.782)
That was for me. It was it was one of those things that was really tough for me to to process. And what I would say is that writing that chapter is really important because in it I talk about how it was coming out of the closet a couple months after that I went to go found venture for Canada. And and that wasn’t a coincidence. That it’s when you like lean and pushing yourself out of your comfort zone that you become more.

confident in doing that. Likewise, if I flash forward 13 years later, me leaving Venture for Canada and then taking some time to travel and kind of pause and then saying, hey, I’m gonna do this bold thing to go buy a business in a sector that I potentially have no previous knowledge in and move to a completely new place, that that also is I can I feel like I can only do that because I’ve done things to build up my risk taking muscles over many many years.

And I think that sometimes we live in a society where people think what doesn’t kill you makes you weaker. And sometimes we use the word trauma in like an extremely broad sense. And that’s like there is very real trauma that people deal with. But I think also that anti-fragility is something that’s really important and that the only way out is through. We we all need to, in some ways, build up our ability to cope in a world that

Chris Villanueva (45:45.553)
Yes.

Scott Stirrett (45:47.417)
We don’t control the level of turbulence and volatility. so we need to prepare ourselves for potentially challenging times through building up our our risk taking capacity.

Chris Villanueva (45:59.742)
That was so beautifully said. I that is a message I hope everyone in the world gets at some point. Like it’s it it is so necessary right now, I think, to move through that. Everyone deals with uncertainty. Everyone has you know, things that they personally deal with and then things that they might struggle with together, things like the pandemic, you know. And I think like yeah.

That’s a really cool answer to like what chapter you enjoy writing the most. Cause yeah, I think that is that is really cool. and so for listeners, if you’re listening, you know what I do? If you do want to get Scott’s book, I will include that within the description of this podcast episode, or if you’re subscribed to our newsletter, I’ll make sure to link that. so Amazon, correct? Or do you have like a website that you’re also selling at?

Scott Stirrett (46:54.103)
Amazon works the best.

Chris Villanueva (46:55.589)
Okay. And tell us about this quiz that you have for listeners as well.

Scott Stirrett (47:01.334)
One of the best ways to learn to develop a better relationship with uncertainty is to understand your current relationship with uncertainty. So on my website, there’s a short five-minute quiz that will give you a score of zero to forty-eight, with zero being you’re not comfortable with uncertainty, and forty-eight you’re being you’re very comfortable with uncertainty. You can visit it by going to Scotster, that’s s-o-t-t, s-ti two ts.com slash quiz. To fill out

Chris Villanueva (47:18.727)
Okay.

Scott Stirrett (47:29.294)
the quiz and get your results. And if you’re curious about your relationship with uncertainty or you’re looking to build your uncertainty muscles, I really recommend that you take a couple minutes and fill up this short quiz.

Chris Villanueva (47:41.652)
Cool. That sounds like a quiz that I would take. So I might take that right after this. That’s really good. That’s neat. perfect, Scott. You’ve been an awesome guest. and I really enjoyed this conversation. I got wrapped, I didn’t realize how long we were going. but I just want to hear if you have any last final words for the struggling young job seeker out there. So if this is my world right now and something that I’m having a hard time, even pausing, pausing, thinking about for a second, what advice?

Or words of encouragement would you have?

Scott Stirrett (48:14.19)
Job seeking can be very demoralizing and is not easy to process. And to go back to the very beginning of this interview, I just think it’s important to like be kind to yourself and to acknowledge like it is not easy doing the job searching and practice some of the self-compassion tools that I mentioned earlier. In particular, if you’re going through a tough time, think about.

How you would talk to a friend going through a tough time and channel that to yourself. And I think that that is something that is so important. And self compassion isn’t about weakening your goals or being less ambitious. It’s just about recognizing that perfection is impossible, that mistakes happen, that failure is a part of life, and that it is okay to do go through hardship.

And that perhaps more most importantly, you can do difficult things.

Chris Villanueva (49:16.561)
Yeah. Awesome way to conclude this episode, Scott. Thank you so much for joining us. I just I really enjoyed the conversation and something that hits home for me. and so I make it a mission on this podcast to make sure to you know, visit this topic and help people who are who are dealing with that. So I think this episode was marvelous and I appreciate you coming on the show.

Scott Stirrett (49:38.446)
Thank you for having me on.

Chris Villanueva (49:39.731)
Cool. All right, listeners, this wraps up the 403rd episode of the Career Warrior Podcast. I really enjoyed this one. do me a favor, if you got something out of this episode, share it with your network. I always encourage you because somebody may be struggling with this, possibly even more than you. Somebody could possibly have something that they’re going through that you had no clue. So share this on LinkedIn, share this with a friend who you think might need it, and

While you’re at it, feel free to connect with both me and Scott and let us know in the personalized message that you are a listener of this up this episode. Those are always my favorite connection requests to get, and I encourage you to reach out. So this wraps up today’s episode. Thank you so much for tuning in and we’ll see you next time.