6 Out of 10 People Regret Their Career Choice. Here's What to Do Differently in the AI Era | Bill Gurley on the Future of Work

Bill Gurley spent 25 years watching careers get made and destroyed. He just wrote "Runnin' Down a Dream" and his take on AI is the opposite of what most people are telling you right now. He backed companies worth over $50B. The people he watched lose everything weren't the ones who took risks. They were the ones who played it safe. In this episode: how AI is changing your job, which careers disappear first, and one move you can make this week if your role is already shrinking. This is for anyone who suspects stability is no longer safe. 🎧 Episode with Linked CEO Ryan Roslansky about the future of work:⁠⁠https://open.spotify.com/episode/5sa1EeC262QyyZow3bfwYY?si=55maoBEITMWE02O8rV78nQ⁠⁠ https://open.spotify.com/episode/5sa1EeC262QyyZow3bfwYY?si=55maoBEITMWE02O8rV78nQ More from the Silicon Valley Girl: Newsletter:⁠⁠⁠⁠⁠ https://siliconvalleygirl.beehiiv.com/⁠⁠⁠⁠ https://siliconvalleygirl.beehiiv.com/ Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/siliconvalleygirl/ ⁠⁠⁠⁠⁠⁠⁠⁠ https://www.instagram.com/siliconvalleygirl/ YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@SiliconValleyGirl⁠⁠⁠⁠⁠⁠⁠⁠ https://www.youtube.com/@SiliconValleyGirl LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠linkedin.com/in/marinamogilko⁠⁠⁠⁠⁠ https://www.linkedin.com/in/marinamogilko/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.

• 0:31Speaker 01

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• 0:59Speaker 02

  The thing to do right now is to run as fast as you can.

• 1:04Marina Mogilko?

  This is Bill Gurley, the legend who backed Uber and Zillow, who's lived through every major tech cycle for over 25 years, and he says this one is different.

• 1:14Speaker 02

  There is so much disruption coming from this new technology that if you don't take control of your own career path, you're likely at risk. We did a survey where we asked people, if you could go back in time and start your career over again, would you do something different? And six out of 10 said yes.

• 1:29Marina Mogilko?

  Before AI, the wrong career choice cost you years. With AI, the cost becomes colossal. We have this window opportunity that's closing, so we should be working really, really hard right now to grasp this opportunity. How much time do we have?

• 1:44Speaker 02

  Like, I would warn all of your listeners that...

• 1:49Marina Mogilko?

  Bill, welcome to Silicon Valley Girl.

• 1:52Speaker 02

  Thanks for having me on. Greatly appreciate it.

• 1:54Marina Mogilko?

  Thank you. I had a question planned, but there is news that just came out.

• 1:58Speaker 02

  Oh, no.

• 1:59Marina Mogilko?

  Block, the parent company,

• 2:00Speaker 02

  Yeah, I saw that.

• 2:01Marina Mogilko?

  Jack Dorsey is laying off nearly half of its staff in deliberate and bold embrace of AI.

• 2:07Speaker 02

  Yeah.

• 2:07Marina Mogilko?

  Should people be scared?

• 2:09Speaker 02

  Well, I'm gonna say yes, but I'm gonna qualify it a little bit. And the AI tools are out there. They've been out there for two or three years now. They're not gonna be put back in the box. They're not gonna go away. My advice, which is very straightforward for anyone in any field, to protect yourself against AI, be the most AI-enabled version of yourself possible.

• 2:34Marina Mogilko?

  Okay.

• 2:34Speaker 02

  And know what it's possible of in your field. Know the edge of what it's possible of in your field. Use it as much as you possibly can, because one thing I've learned, just in my own endeavors, the types of prompts that you think of giving it increase the more you use it. Like, you start to understand what it's capable of. And so, any lack of leaning into it means you're getting further behind against people that are. It's new in that it's hitting white-collar workers, which I think people had viewed those jobs as safe, which may have been a mistake. And, and look, if you've been replaced, I would really, and this gets into this new book I'm releasing,

• 3:18Speaker 02

  I would ask yourself, is that the role you really loved and wanted to be in? And if not, maybe this is an opportunity for you to go find that.

• 3:27Marina Mogilko?

  Okay, so yeah, we're gonna see a lot of this type of news. You said that playing it safe, and you mentioned safe jobs. We considered them safe. We thought intelligence is something that's gonna get us through our lives. You say safe is now the highest-risk move. Can you explain?

• 3:43Speaker 02

  I think the unfortunate reality is that many advisors and counselors and parents push people towards jobs that they thought of as safe. And the reason I say it's unfortunate isn't because of AI. If you're unfulfilled at work, there's a 2023 Gallup poll study that came out and said over 50% of people aren't actively engaged at work. And the number that qualifies engaged is like 23%. So if you're in these roles you don't really care that much about, and you're not pushing yourself to improve, you're kind of a sitting duck anyway, like, for these things. And I personally believe that all those parents were quite well-intentioned and very...

• 4:23Speaker 02

  Worried about the economic stability and viability of their children's lives. But the truth of the matter is, you only get one shot at this life. If you can find something that you're just insanely curious about, you're going to differentiate yourself so much greater than everyone that's around you. I think in many aspects of life, the economic part comes along if you're really great at what you do.

• 4:49Marina Mogilko?

  Can you, can you give me three traits of a person who doesn't play it safe? What do they do daily?

• 4:54Speaker 02

  Well, first of all, I think having, I think the number one reason I wrote this book was to give permission, give people permission to chase a job they might not have thought was either possible or that they might have thought someone would try and talk them out of. And there's examples in the book of that. Danny Meyer, who's a famous restaurateur in New York and the man that started Shake Shack. His uncle told him, "You should go be a restaurateur." But he was on a path, poly sci major, salesman, taking the LSAT, gonna go be a lawyer. And his father had had some problems with economic trouble and businesses related to restaurants, and it pushed him away from it. His uncle is the one that kind of brought him back.

• 5:38Speaker 02

  But his uncle told him, "You know, all you do all weekend long is search for the best restaurants," and even journaled. Apparently, since he was a kid, he journaled about restaurants. But he had never given himself the permission to think of it as a career and go after it. And the reason you're more protected is if you adore something, you're just constantly learning for free.

• 6:00Marina Mogilko?

  Yeah.

• 6:00Speaker 02

  Like, you're not spending, like... The second principle in the book is hone your craft. And I talk about continuous learning. And many people, I think unfortunately, learn in school and they think, "Oh, I'm done now, I'll go work." But the best are just always learning about what they do. And for the best that are hyper curious about that subject area, they gain energy in absorbing that new information. Whereas if you're forced to go to a class on something you don't like, you lose energy, it feels tedious.

• 6:34Marina Mogilko?

  Yeah.

• 6:34Speaker 02

  Which is a great test as to whether you're tilting against the right thing or not.

• 6:38Marina Mogilko?

  So basically, don't listen to everyone around you?

• 6:42Speaker 02

  I mean, there's extreme forms of this. I got to meet Rick Rubin. He said every single career decision he's made in his life, people around him told him not to do it, and they were all the best decision he possibly... I mean, you can take that to an extreme, right? Like, don't just go, you know, on quixotic pursuits. But I think if you become 100% convinced that you want to go try something, and I have testing here for whether you're really passionate at that level, then yeah, I think you should go try. And I think you'll find you're more successful and more fulfilled.

• 7:18Marina Mogilko?

  And I like the continuous free learning. So you're learning not because you're required to, but because it's your passion.

• 7:24Speaker 02

  And you're curious about it.

• 7:25Marina Mogilko?

  Yeah, and you can't stop yourself.

• 7:26Speaker 02

  And you've met people I know that are like that. I think everyone's met people that are like that. Silicon Valley's full of a lot of people like that, especially about new technologies. So, you know, you read an article about Clawbot, and you just can't not, you know, boot one and try and figure out what it does. And if you're that type of person, you're in the right lane. Like, you're so fascinated by the subject that you have to know what's on the edge.

• 7:52Marina Mogilko?

  Yeah.

• 7:52Speaker 02

  And by the way, it's interesting to think about the edge as a place that's safe from AI. So AI and large language models are recording, like, all the best practices that have been written down. But the stuff that's on the edge, that's being discovered today, is not in the models. And so if you're competing by being a person who has that knowledge in any field that hasn't been written down yet, you're out in front of what these models are capable of.

• 8:23Marina Mogilko?

  Yeah, and through try new things.

• 8:25Speaker 02

  Yes.

• 8:25Marina Mogilko?

  I feel like.

• 8:26Speaker 02

  Yeah.

• 8:26Marina Mogilko?

  Since you've been investing for a while, I know you recently stopped, but what benchmark VC will consider not playing it safe when looking at a founder?

• 8:36Speaker 02

  Well, actually, I think that the venture industry writ large has learned that you would never... Have a mindset of safety around choosing a founder. I think the best and the brightest are very independently minded. They think outside of the box naturally. I think if anyone feels, some of them are so dogmatically determined that they they might come across as as a bit, you know, crazy, actually. And I think, I'm not the only one that would say this. I think if you go study what what venture capitalists have written, there's a, there's there's almost a search for that type of persona. And it goes back to like the Steve Jobs ad about the crazy ones, you know?

• 9:22Marina Mogilko?

  It feels like everyone right now should be adopting this crazy mindset to succeed in this world because you're becoming the entrepreneur in your life, right?

• 9:31Speaker 02

  I think, yeah, there's a, I think that's a great way of saying it. There is a, especially in certain fields, there is a so much disruption coming from this new technology that if you don't take control of your your own career path, then you're you're likely at risk. And I I've often said, if you're a high agency, if you're a high agency individual who's who has confidence about driving their own career path, these tools are actually a jet pack. Like, if you if you want to proactively learn, there's been no time in the history of the world where you can learn faster. And, you know, it's it's AI, but it's also podcasts like the stuff you do. There's interviews all over YouTube.

• 10:16Speaker 02

  It like you can learn faster than ever before. But if you're if you're, this is part of why I react poorly to the AI anxiety, because that might freeze you. And then you're not like, like, the thing to do right now is to run as fast as you can.

• 10:33Speaker 00

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.

• 11:03Speaker 05

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• 11:33Marina Mogilko?

  Yeah, but also wanted to dig deeper into anxiety because you said something that gives me a lot of anxiety. Sometimes I scroll and I hear people, including you say, "We have this window opportunity that's closing, so we should be working really, really hard right now"

• 11:47Speaker 02

  Yeah.

• 11:47Marina Mogilko?

  "to grasp this opportunity." Can you elaborate on that? How much time we have? How much should we be working?

• 11:53Speaker 02

  Well, I don't think, I don't think the window's necessarily closing. I just think that this tool kind of came at us so fast and it's capable of so many different things that it's, it really behooves any individual to figure out what it's capable of in their industry and their role. And, and once again, to be the person in the organization who knows the most about that and what's possible.

• 12:17Marina Mogilko?

  But do you think we might only have like a couple of years before AGI?

• 12:21Speaker 02

  No, I don't believe in that. No, I'm not a big fan of these dystopian narratives. There's some interesting research you could go look up that the, the anxiety, this dystopian anxiety is like five times higher in the US than in China.

• 12:35Marina Mogilko?

  Oh, really?

• 12:36Speaker 02

  Yeah, I think part of the problem, and I don't fully understand the motivation, but some of, like, Dario's the biggest doomer of all. And he's got the microphone all the time.

• 12:47Marina Mogilko?

  Yeah.

• 12:48Speaker 02

  And it's kind of weird.

• 12:49Marina Mogilko?

  Always trending.

• 12:49Speaker 02

  And I don't think it's healthy for all the reasons we already discussed.

• 12:53Marina Mogilko?

  Yeah.

• 12:53Speaker 02

  So I wish, I wish, I wish that weren't happening.

• 12:55Marina Mogilko?

  But maybe also sometimes when I see those headlines, I'm like, maybe I should double down and work more.

• 13:00Speaker 02

  Yeah.

• 13:00Marina Mogilko?

  It's also, it has a positive angle to it, right?

• 13:03Speaker 02

  Yes, it could. It could spur people into action. It could. But, but, but it also could freeze them, which we already discussed.

• 13:09Marina Mogilko?

  Totally. And something also that you said, that "I'm learning what made you successful before" is really important. How do you, so for me, for example, I'm a very hardworking person. I would say yes to every brand deal because I'm used to it.

• 13:25Speaker 02

  Yeah.

• 13:25Marina Mogilko?

  And I realized that... Probably, but I'm not sure. Probably the next stage of my growth will happen when I learn how to say no.

• 13:33Speaker 02

  Yeah.

• 13:33Marina Mogilko?

  How do you decide and how do you actually do it? How do you unlearn?

• 13:37Speaker 02

  There's a great quote, "Strong opinions loosely held." And I really love that idea.

• 13:44Marina Mogilko?

  Mm-hmm.

• 13:44Speaker 02

  So if you don't have strong opinions, it's very difficult to actually get out there and run every day and accomplish things. But don't view any of them as sacred. Like, don't think of anything as hard and fast and might never change. And I think if you develop the habit of being a continuous learner and know that there's a risk of this thing, then you probably are best prepared to know when to let go of something. I know that may not be definitive, but like, I think awareness that it could be a problem is probably the most helpful thing possible.

• 14:19Marina Mogilko?

  Yeah, so when you start noticing, it's actually in your way.

• 14:22Speaker 02

  Yeah.

• 14:23Marina Mogilko?

  So in your book, you talked about six principles. Chase your curiosity. And this is where I've paused because I'm like, okay, I'm curious about so many things. There's this hype and that hype. I want to study this and do this. How do you pick out curiosity that you can push for for years? And it becomes your career?

• 14:45Speaker 02

  Yeah, there's a whole bunch. That chapter that you mentioned, chase your curiosity. I went out and studied all the best practices in the field. And there's like 10 different exercises you can run to try that I've borrowed from these other great people that have done the research. You know, hobbies are a big one. There's a lot of stories in the book of people that turned hobbies into careers and became very successful. Like, if there's this thing that you're doing in your spare time at home. When I was an engineer for two and a half years, I read this book, One Up on Wall Street by Peter Lynch. And I started studying stocks and trading stocks when I got home at night. And I didn't say to myself, oh, maybe that's a sign. But it was, right? And I ended up going to work on Wall Street.

• 15:30Speaker 02

  And so look out for whatever it is that fascinates you. Don't feel stuck. Or don't feel like you have to have an answer to the question. Some of these people um didn't find their perfect fit until they're thirty or forty. And so get as many shots on goal, like it's fine to take a job where you don't know if that's it. And but ask, wake up and ask yourself every year or so. Is this it? Is this what I want to do the rest of my life? I had a mental exercise that I did in my first two stops in my career. Where I at at a couple of years in, I said, do I see myself doing this thirty years from now? And how do I feel about that?

• 16:10Marina Mogilko?

  Hmm.

• 16:11Speaker 02

  Just a kind of a reflection. And in the first two cases, I got to a place where I immediately knew the answer was no.

• 16:17Marina Mogilko?

  Hmm, I love that question.

• 16:19Speaker 02

  And then you start looking for something else. Bezos had a similar thing. He called the regret minimization framework. Where he said, imagine your eighty year old self giving you advice on helping with a career choice.

• 16:31Marina Mogilko?

  Yeah.

• 16:32Speaker 02

  And they're similar in some ways. You're just reflecting over time.

• 16:35Marina Mogilko?

  Yeah, and when you studied those people who are not happy with their jobs, apparently it's six out of ten, right?

• 16:41Speaker 02

  Yeah.

• 16:41Marina Mogilko?

  What do you think was the number one mistake that they made? Were they chasing money? If you want to stay ahead in the AI era, follow Silicon Valley Girl podcast on your favorite platform. New episode every week on AI, careers, and how to not get left behind.

• 16:58Speaker 02

  I think so. I mean, chasing money or or just doing like like we we actually, we did a survey where we asked people if you could go back in time and start your career over again, would you do something different? And six out of ten said yes. And then we would ask them, what did you use in the decision making? And you know, it might be you're at college and a professor tells you, oh, you should go into this because you made an A on a accounting exam or something, or or your parents, there's certain cultures where parents like, you gotta be a doctor, you gotta be a lawyer, and you end up in that path. Like, there's a bunch of different ways you could end up in a pathway where it wasn't an exercise of you saying, what is it that I would love to spend my life doing?

• 17:39Marina Mogilko?

  Yeah.

• 17:40Speaker 02

  And so it is a whole, I think many of these parents and counselors are very well intentioned. I don't think they're out to to make a mistake. A lot of them are worried about the economic stability of the child.

• 17:52Marina Mogilko?

  One hundred percent.

• 17:53Speaker 02

  As you become a parent, like it's this thing that you can't really get out of your head.

• 17:58Marina Mogilko?

  So are there any jobs that you would name, like top three jobs that are AI resistant and top three jobs that won't make it?

• 18:04Speaker 02

  Well, the jobs that that seem to me the earliest threats are ones where so the large language model is really good at language. And so translation, paralegals, like these

• 18:16Marina Mogilko?

  You know, I started with language. That was my whole career.

• 18:20Speaker 02

  Yeah, I mean, those things are are really, you know, where you're just organizing text in a different way. Um, that those are, those are already, it's already happening.

• 18:31Marina Mogilko?

  Yeah.

• 18:31Speaker 02

  You know, I think some of the jobs that I have this interesting theory where almost any job you could think of it as being an artisan. We all think of Michelangelo as an artisan and we probably think of a great athlete as an artisan, but do you think of a lawyer that way? Or do you think of, and I would say the best in those fields probably, probably are. And so what is it they do? Um, they understand nuance in their field quite a bit. And I think AI is not particularly good at nuance. Um, a lot of people have a theory that that I think is reasonable that that human relationships will matter way more. So do you have a strong peer network? Do you have a strong mentor network?

• 19:13Speaker 02

  Do you have a strong network in general of people who come to you or know you or what you're capable of? Um, that that I think that's super helpful.

• 19:22Marina Mogilko?

  Any other markets that you think are dying?

• 19:24Speaker 02

  Um, dying, um, well, I mean, coding is one where there's a lot of questions that are out there. And I think, once again, you know, the thing about code is it's actually a stricter, more constrained version of language than language itself.

• 19:38Marina Mogilko?

  Hmm, so do you think we'll need less coders?

• 19:42Speaker 02

  Certainly, if you were the person who was just grinding, writing out code. If you were the person that understood, you know, structurally, how one algorithm is better than the other or how to reduce code to make something more efficient. Like those things, I think, will still be valuable. But I would go back to saying the best way to be a software engineer in AI world is to be the one that knows how all the new AI tools work.

• 20:08Marina Mogilko?

  Yeah.

• 20:08Speaker 02

  To be the person in your org that's leaning into them, not out. Like you're, if you're a farmer with a tractor and a drone thing and all this stuff, you're gonna run over a farmer with a hoe and a, and a donkey, right?

• 20:21Marina Mogilko?

  Totally.

• 20:21Speaker 02

  You're just gonna blow them away. And so you have to think that way about these tools. This one came at us fast, I admit. Um, but you have to, you have to roll around in it.

• 20:32Marina Mogilko?

  Let's talk about the tools. You said at the beginning of our podcast, become the best AI-enabled version of yourself. Can you talk about the setup? Because we're all using ChatGPT for search. We use Banana Banana to generate images. We do basic stuff, right? We maybe plan our trips. What is the next step? What should people be doing to advance their setup?

• 20:54Speaker 02

  Even like when I come on a podcast, I can say, I'm gonna go see this person, do this podcast, and we're gonna talk about the book with questions should I anticipate? And it's like, this is my, like, the more you play with it, the more you think about what's possible to do. And, and I was, I was at NYU yesterday, and the students were asking questions at the end. And like, half the questions they ask, I'd be like, well, you could ask me that, but I'd probably put that into ChatGPT. Like, I just, they don't think, like, people don't realize how much you can lean on it. And that's where I think the more you roll around on it, the more you start to use it. And I've been invited to, to go give a TED Talk, so I have a new one on that.

• 21:36Marina Mogilko?

  Oh, are you going to, going in April? I'll be there too. I'll watch your talk.

• 21:40Speaker 02

  All right. And, and I'm, like, you can research and prototype and ideate like simultaneously. I came up with a new theme last night, kicked off something this morning, because I wanted it to find like 20 examples of this idea I had and wanted to talk about to, to make it better. And I haven't looked at the results yet, but I will later.

• 22:00Marina Mogilko?

  So you're basically living in Claude project?

• 22:03Speaker 02

  Yeah, I mean, those were ChatGPT. But yeah, you could, yeah, I mean, you're probably better to try them all.

• 22:09Marina Mogilko?

  What is something that you do with AI now that you've done manually before and now you can never do it manually?

• 22:15Speaker 02

  Almost any information query whatsoever. Like, it just seems easier than, than looking it up. And even like compared to a Wikipedia search or something, like, you can just get straight to the information versus like scrolling through this thing.

• 22:30Marina Mogilko?

  Yeah.

• 22:30Speaker 02

  I haven't set up a Clawbot yet or started getting it to do agentic work on my behalf. I probably should. Part of raising my hand and, and stepping away from VC is, is because I grew tired of like that constant FOMO that's required to be successful.

• 22:47Marina Mogilko?

  Yeah. Wow. Yeah, that's, that's, that's a strong one. Let's talk about, uh, just in general, for, for people who are building, since you were investing in them, do you think software is dead?

• 23:00Speaker 02

  I don't.

• 23:01Marina Mogilko?

  Why?

• 23:02Speaker 02

  Um, there are cer- and, and look, I think there are certain types of software that may be if, once again, if, if all the software did was reorient text or, or, you know, create an image or whatever, like, it could be under threat. The other thing is, like, quite frankly, it's not really good at being a database and it's not great at math yet. And there's new techniques where they're getting it to write code, but how many times have you done a query where there's an error? And, once again, depending on the type of software, you wouldn't want it writing errors into your CRM.

• 23:36Marina Mogilko?

  Absolutely. Sometimes I think about the future where now I mostly talk to my Claude or ChatGPT. What if I just ask it to create an app for me to solve some particular problem and I don't need to install any apps?

• 23:49Speaker 02

  Yeah.

• 23:49Marina Mogilko?

  Think about consumer apps, right? I don't know, like a fitness tracker.

• 23:52Speaker 02

  Yeah, yeah, yeah.

• 23:53Marina Mogilko?

  Language learning, right?

• 23:55Speaker 02

  Yeah.

• 23:55Marina Mogilko?

  Exam app, SAT was just released on Gemini. So I'm thinking like there's this whole market that's probably gonna disappear.

• 24:01Speaker 02

  That could be true. That could be right. But that, but that's happened in the past. There used to be software companies that had massive market share that don't exist anymore. So, yeah.

• 24:10Marina Mogilko?

  How should entrepreneurs be thinking about what they're building?

• 24:13Speaker 02

  Every great entrepreneur recognizes that new technology waves create a ton of opportunity. And one of the reasons Silicon Valley gets so excited when these waves happen, I mean, every single venture capitalist, I'm sure that you talk to, all they want to talk about is AI, right? They don't, I think they've forgotten about the companies they invested in that aren't AI. That's all they want to talk about. And the reason they have so much attention to it is because the time when new companies, you know, step around and take market share for incumbents or on these transitions and everyone knows it. And so, I'm gonna sound so redundant, you gotta get out there and play with it. Like, I would, I would warn.

• 24:55Speaker 02

  Um, all of your listeners that it's very hard right now to raise venture capital for non-AI plays. I like to separate whether you're judging that from the reality, go back to this circle of influence thing. The reality is most venture capitalists won't take a meeting with a non-AI company right now. Now, you could decide I'm gonna do it anyway. I think complaining about that's useless because it is the reality. Um, you could decide, well, it'd be a great time to bootstrap one of those companies because VCs aren't paying attention. I think that's a reasonable, you know, response to that. But you need to be aware of that.

• 25:31Marina Mogilko?

  Yeah.

• 25:32Speaker 02

  Like, otherwise, you're gonna get very disappointed when you go out and try and raise money.

• 25:36Marina Mogilko?

  Yeah, and you you left the VC world, you know, right at the, you know, it's it's all hyped up right now, everything's happening. I feel like a lot of people are like you, especially when we're talking about people who chose safer careers, right? And now they they don't know what to do and like erratic behaviors and everything. And I I really like that you said in your book, you need to, and something you keep bringing up in this interview. You should be surrounding yourself with the right people, with the right news that you're consuming to stay calm and focused and motivated. Any tips on surrounding yourself with mentors?

• 26:10Speaker 02

  Yes, well, mentors, and I have another chapter on peers, but but let's take mentors first. I think most people, if you if you're in if you're in the mentor game, most people shoot too high. And they go try and get someone who's not gonna say yes to spend five minutes with them. And and I I would really caution against that type of activity, and I would instead do two different things. Take advantage of all this incredible free information that's out there and build a list of what I would call aspirational mentors. So these are people you admire in your field and just study them.

• 26:48Speaker 02

  Like, create a Google Doc, I don't care what, like, and, you know, find the podcasts they're on, uh, find books, find YouTube interviews. Ask AI about them and just build like a digital profile of each one of them and be a fanboy the way someone might be of LeBron James. Right, and I think that exercise will give you more confidence, it'll give you. It also tests whether this is the thing you're curious about or not, if that sounds tedious, what I just described. This, you're not in that.

• 27:18Marina Mogilko?

  I think it's, it sounds really exciting, that I'm thinking, you can do this for your whole like dream career, right? Or you're like, I'm trying to be this, here, here are the people that are already doing this. Here is, I don't know, what are my dream house?

• 27:33Speaker 02

  Yeah, no, Danny Meyer did this, like when he, when he decided he was gonna go be a restaurateur, he built these ten profiles of these people. And like, I think it, I think that exercise of ruminating in that is super helpful, it makes you, gives you confidence that it, that it's achievable. It helps, it's disinhibiting that this may be a tough way to go. And then on, on real mentors, just come down the ladder a couple rungs. If you're the first person that calls someone and asks them to be a mentor and no one else has asked them that before, they're gonna be flattered that you recognized who they were.

• 28:06Marina Mogilko?

  But how do you ask them, you're like, reach out to them and say like, hey, could you be my mentor, or you ask a specific question?

• 28:11Speaker 02

  Well, there's some nuance to that as well, so I wouldn't walk up to someone and say, will you be my mentor?

• 28:16Marina Mogilko?

  Yeah.

• 28:18Speaker 02

  That's a lot of weight. Yeah, I think you approach people with recognition of who they are and an authenticity, I wouldn't be overly like programmed as you go in. And with a, with a smaller ask to start your relationship. Hey, I'm working on this problem, you know, there's these two paths, I'm sure you've thought about this before, any advice on what I should do?

• 28:39Marina Mogilko?

  Yeah, and when you mentioned that a lot of people ask you things they could ask ChatGPT, I'm thinking now, before asking people to become your mentor and ask, answer this question, create a project with all their knowledge base and ask that project first.

• 28:53Speaker 02

  You can have a virtual mentor, you could tell, tell AI to, you could dump a book, dump an interview, dump a transcript, and create a project around an individual.

• 29:03Marina Mogilko?

  Yeah, I do that a lot, AI is my strategic partner 100%. Really, really helpful.

• 29:08Speaker 02

  But I, let me also mention this, this separate chapter on peers. Cause this is my favorite chapter in the book and it's a human connection that I think most people don't do. I would just heavily encourage anybody, whatever rung of the ladder you're on in your career journey. Try and find four to six like-minded people on the same journey. Hopefully outside your organization. They need to be trustworthy, they need to be comfortable sharing and create a peer group. You know, and, and once again, these tools are so available, like you can do a WhatsApp or you could create a Google space. If you're really, you know, inspired, you could do a Slack, whatever. But you create one of these things where you all share ideas together.

• 29:50Speaker 02

  And it increases the surface area for learning, it increases your mentor opportunities, your network. You'll see more job possibilities through everybody. They'll be there for you when you're having a crappy day. Like, which is really important, like everyone has bad days. You might be in, in a job where you don't know if it's me or the company I'm in. Like, I'm having, I'm not happy here, but is it, is it because I don't love this career path? Or is it because I don't love this company? If you have five other people that you talk to, you, they, they may help you figure that out.

• 30:22Marina Mogilko?

  Yeah, I, I did that as a YouTuber. Like having other YouTubers just brainstorm ideas in your niche.

• 30:28Speaker 02

  And there's a story in here about a one YouTuber named Jimmy Donaldson that did this at the age of-

• 30:34Marina Mogilko?

  He was the one who started all of this and we just copied.

• 30:36Speaker 02

  He was doing the same thing.

• 30:38Marina Mogilko?

  Yeah, yeah, cause yeah, I think he shared it at a conference and I thought, oh my God, I should be doing this too.

• 30:42Speaker 02

  Yes, yes.

• 30:43Marina Mogilko?

  This is a very interesting time, right? And I have two kids, a six-year-old and a four-year-old. I was raised by my Soviet parents telling me you have to study, study and study. That's the only way to grow, that's the only way to build a sustainable life. So I was studying from 8:30 AM to 8:30 PM. Will this still apply in today's world to our kids? Or should I be teaching them something completely different?

• 31:09Speaker 02

  Well, I think the culture you came from is a little different than

• 31:12Marina Mogilko?

  It is.

• 31:13Speaker 02

  Which is true here. But I still think, I think the thing that's happened in North America, which is a version of that, is it's become so hard to get into universities here that, starting in the sixth grade, parents are worried about Jonathan Haidt calls it the resume arms race. You're worried about them getting into college, so you want your

• 31:32Marina Mogilko?

  Not worried now, not sixth grade, now, four-year-old.

• 31:35Speaker 02

  So you start worrying about the college application. And here, I think it might be better if they just studied 12 hours. Instead, here, you add in chess lessons, lacrosse lessons, like volunteering at the SPCA. You're like, and these kids are so scheduled. Like, and what I fear is that they get to the end of the college and they're just burned out, like, because they've been Angela Duckworth says they've been taught to appear severe, like we've trained them.

• 32:05Marina Mogilko?

  Isn't it good?

• 32:06Speaker 02

  The area where it might not be good is that they never take a breath to explore and figure out what they want to do. It used to be in the US college system, they wouldn't allow you to pick a major until the end of your sophomore year. Now, at many schools, you have to apply to the major as part of the application process. And so, we're asking people to specialize early and earlier, and then maybe they never had a chance to really figure out what it is they enjoy. And they might have fallen into one of those pathways for random reasons, like we talked about before.

• 32:35Marina Mogilko?

  So what would be your advice to modern parents?

• 32:38Speaker 02

  Take a deep, deep breath and create as much opportunity for exploration as possible for the kids. Just expose them to a lot of different things. And try and get a sense of genuine interest on their part.

• 32:53Marina Mogilko?

  Yeah.

• 32:53Speaker 02

  You know.

• 32:54Marina Mogilko?

  Love it. Okay, if someone's watching right now, they're in a job they don't love, but they're afraid to make a move.

• 33:01Speaker 02

  Yeah.

• 33:02Marina Mogilko?

  What is one thing they should do this week?

• 33:03Speaker 02

  I think you can role play this new path you might go towards. And part of this, I'm borrowing from a professor at Stanford, Dave Evans. He talks about like battle carding scenarios. So the same exercise we said where you could go study this person, you could say, okay, I'm gonna be out of here within six months and create a digital like role play of, okay, what am I gonna go do? And you could do that for maybe three different directions, right? And roll around in it, like scenario plan, right? What is the first? And once again, you know, an AI tool could help you do this. Okay, I would like to repop myself into this career within six months. What should the first week look like? It'll give you something.

• 33:47Marina Mogilko?

  Love it.

• 33:48Speaker 02

  It'll spit something out. And you may disagree with that, you may reorganize it, but the thought process of going through what it might look like will help you versus just being frozen, right?

• 34:00Marina Mogilko?

  And the power is coming back to it every single week with new data. Like I tried this, here's how it worked.

• 34:06Speaker 02

  And if you did the battle card of like three different ones, you know, I think you'll start, as you fill in the details, you'll start to have a sense of which one you prefer. Whereas it may just be too abstract at the high level.

• 34:22Marina Mogilko?

  Thank you so much.

• 34:23Speaker 02

  Yeah.

• 34:23Marina Mogilko?

  I think it was very useful and very practical. And I encourage everyone to read your book. Can we show it?

• 34:28Speaker 02

  Runnin Down a Dream.

• 34:29Marina Mogilko?

  Love it. I love the name.

• 34:30Speaker 02

  Thank you so much for having me on.

• 34:31Marina Mogilko?

  Thank you so much. If you enjoyed this episode on the future of work, you're going to love my recent conversation with the CEO of LinkedIn. We went deep on the exact same topic. Link is right below. Check it out and I'll see you in the next one.