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

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0:45Bill Gurley:The thing to do right now is to run as fast as you can. 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. 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. Before AI, the wrong career choice cost you years. With AI, the cost becomes colossal.

1:21We 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?

1:29Bill Gurley:Like, I would warn all of your listeners that... Bill, welcome to Silicon Valley Girl. Thanks for having me on. Greatly appreciate it. Thank you. I had a question planned, but there is news that just came out. Oh, no. Block, the parent company, Jack Dorsey, is laying off nearly half of its staff in deliberate and bold embrace of AI. Yeah. Should people be scared? Well, I'm going to say yes, but I'm going to 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 going to be put back in the box. They're not going to 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.

2:19Bill Gurley:Okay. 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 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 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 look, if you've been replaced, I would really, and this gets into this new book I'm releasing, I would ask yourself, is that the role you really loved and wanted to be in?

3:08Bill Gurley:And if not, maybe this is an opportunity for you to go find that. Okay, so yeah, we're going to 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 going to get us through our lives. You say safe is now the highest risk move. Can you explain? 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.

3:49Bill Gurley: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 sit and duck anyway for these things. And I personally believe that all those parents were quite well-intentioned and very 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.

4:27Bill Gurley:I think in many aspects of life, the economic part comes along if you're really great at what you do. Can you give me three traits of a person who doesn't play it safe? What do they do daily? Well, first of all, I think the number one reason I wrote this book was to 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.

5:06Bill Gurley:But he was on a path, poli sci major, salesman, taking the LSAT, going to go be a lawyer. And his father had had some problems with economic trouble in businesses related to restaurants and it pushed him away from it. His uncle is the one that kind of brought him back. But his uncle told him, you know, all you do all weekend long is search for the best restaurants and even journal. 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.

5:45Bill Gurley:Yeah. 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, there's, 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 yeah which is a great test as to whether you're tilting against the wrong the right thing or not so basically don't listen to everyone around you uh 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?

6:41Bill Gurley:Like, don't just go, you know, on quixotic pursuits. But I think if you become 100 percent convinced that you want to go try something. And I have tests in here for whether you're really passionate at that level. Then, yeah, I think you should go try. And I think I think you'll find you're more successful and more fulfilled. And I like the continuous free learning. So you're learning not because you're required to, but because it's your passion. And you're curious about it. Yeah, and you can't stop yourself. And you've met people I know that are like that. I think everyone's met people that are like that.

7:16Bill Gurley: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. Yeah. 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.

7:56Bill Gurley: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. Yeah. And through trying new things. Yes. I feel like. Yeah. 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? Well, actually, I think that the venture industry at 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.

8:42Bill Gurley:I think if anyone feels, some of them are so dogmatically determined that they might come across as a bit crazy, actually. And I think, I'm not the only one that would say this. I think if you go study what venture capitalists have written, there's almost a search for that type of persona. And it goes back to like the Steve Jobs ad about the crazy ones. 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? I think that's a great way of saying it. Especially in certain fields, there is so much disruption coming from this new technology that if you don't take control of your own career path, then you're likely at risk.

9:33Bill Gurley:And I've often said if you're a high agency, if you're a high agency individual who has confidence about driving their own career path, these tools are actually a jetpack. Like 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 AI, but it's also podcasts like the stuff you do. There's interviews all over YouTube. like you can learn faster than ever before. But 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.

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10:56So when your mind won't switch off, you've got something that can help. Erasing thoughts and restless nights won't stand a chance. Find Oli Sleep Solutions for the whole family at Oli.com. That's O-L-L-Y dot com. Yeah, but I 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 to grasp this opportunity. Can you elaborate on that? How much time we have? How much should we be working?

11:32Bill Gurley:Well, I don't think the window is 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 really behooves any individual to figure out what it's capable of in their industry, in their role. And once again, to be the person in the organization who knows the most about that and what's possible. But do you think we might only have like a couple of years before AGI? 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 anxiety, this dystopian anxiety is like five times higher in the U.S.

12:13Bill Gurley:than in China. Oh, really? 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. Yeah, he's always trending. And I don't think it's healthy for all the reasons we already discussed. So I wish that weren't happening. But maybe also sometimes when I see those headlines, I'm like, maybe I should double down and work more. It has a positive angle to it. Yes, it could. It could spur people into action. It could. But it also could freeze them, which we already discussed. Totally. And something else that you said, that unlearning what made you successful before is really important.

12:56How 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. 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. How do you decide and how do you actually do it? How do you unlearn?

13:15Bill Gurley:There's a great quote, strong opinions loosely held. And I really love that idea. 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're, you probably are best prepared to know when to let go of something. I know that it may not be definitive, but like, I think, I think awareness that it could be a problem is probably the most helpful thing possible.

13:58Yeah. So when you start noticing, it's actually in your way.

14:01Bill Gurley:Yeah. So in your book, uh, you talked about six principles, uh, chase your curiosity. And this is where I 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? 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.

14:38Bill Gurley:You know, hobbies are a big one. There's a lot of stories in the book of people that turn 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. 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. 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.

15:18Bill Gurley:Some of these people didn't find their perfect fit until they're 30 or 40. And so get as many shots on goal. It's fine to take a job where you don't know if that's it. But 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 a couple years in I said, do I see myself doing this 30 years from now? And how do I feel about that? 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. I love that question. And then you start looking for something else.

15:59Bill Gurley:Bezos had a similar thing. He called the regret minimization framework, where he said, imagine your 80-year-old self giving you advice on helping with a career choice. And they're similar in some ways. You're just reflecting over time. Yeah, and when you studied those people who are not happy with their jobs, apparently it's six out of 10, right? Yeah. 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.

16:36Bill Gurley:I think so. I mean, chasing money or just doing, like 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 10 said yes. And then we would ask them, what did you use in the decision-making? And it might be you're at college and a professor tells you, oh, you should go into this because you made an A on an accounting exam or something, or your parents. There are certain cultures where parents are like, you've got to be a doctor, you've got to be a lawyer, and you end up in that path. 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?

17:19Bill Gurley:I think many of these parents and counselors are very well-intentioned. I don't think they're out to make a mistake. A lot of them are worried about the economic stability of the child. As you become a parent, like it's this thing that you can't really get out of your head. 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? Well, the jobs 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. You know, I started with language.

17:57That was my whole career.

17:59Bill Gurley:I mean, those things are really, you know, we're just organizing text in a different way. Those are already, it's already happening. Yeah. 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 are. And so what is it they do? They understand nuance in their field quite a bit, and I think AI is not particularly good at nuance.

18:41Bill Gurley:A lot of people have a theory that I think is reasonable that human relationships will matter way more. So do you have a strong peer network? Do you have a strong mentor network? Do you have a strong network in general of people who come to you or know you or what you're capable of? I think that's super helpful. Any other markers that you think are dying? Dying. 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. so do you think we'll need less coders 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 Like to be the person in your org that's leaning into them, not out.

19:51Bill Gurley:Like if you're a farmer with a tractor and a drone thing and all this stuff, you're going to run over a farmer with a hoe and a donkey, right? You're just going to blow them away. And so you have to think that way about these tools. This one came at us fast, I admit. But you have to roll around in it. Let's talk about the tools. You said at the beginning of our podcast, become the best AI enabled version. yourself. Can you talk about the setup? Because we're all using chat GPT for search. We use Nana Banana to generate images. We do basic stuff, right? We maybe plan our trips. What is the next step?

20:30What should people be doing to advance their setup?

20:33Bill Gurley:Even like when I come on a podcast, I can say, I'm going to go see this person, do this podcast, and we're going to talk about the book. What questions should I anticipate? And it's like, Like the more you play with it, the more you think about what's possible to do. And 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 chat GPT. Like I just they don't think like people don't realize how much you can lean on. And that's where I think the more you roll around on it, the more you start to use it.

21:11Bill Gurley:And I've been invited to go give a TED Talk, so I have a new one on that. Oh, are you going to go in April? I'll be there, too. I'll watch your talk. All right. And you can research and prototype and ideate 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 make it better. And I haven't looked at the results yet, but I will later. So you're basically living in quad project? Yeah, I mean, those were ChatGPT. But yeah, you could, yeah. I mean, you're probably better to try them all.

21:48What is something that you do with AI now that you've done manually before and now you can never do it manually?

21:54Bill Gurley:Almost any information query whatsoever. Like, it just seems easier 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. I haven't set up a claw bot yet or started getting it to do agendic work on my behalf. I probably should. Part of raising my hand and stepping away from VC is because I grew tired of that constant FOMO that's required to be successful. Yeah. Wow. Yeah, that's a strong one. Let's talk about just in general for people who are building since you are investing in them.

22:36Do you think software is dead?

22:38Bill Gurley:I don't. Why? There are certain, and look, I think there are certain types of software that may be, if once again, 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. Absolutely. Sometimes I think about the future where now I mostly talk to my cloud or chat GPT.