If You Hate Your Job, This is How to Start Over - Bill Gurley - #1071

**Chris Williamson** (0:00)
What got you into thinking about the idea of career regret? As somebody that's had a very seemingly successful and fun career, why did you think about it?

**Bill Gurley** (0:12)
I spent 25 years as a venture capitalist, and the four years before that as a sell-side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so, I was an early blogger. It was actually a fax, that's how old I am, when I started. And I got in the habit of when I had ideas, jotting them down. And then, you know, either developing them, a lot of them ended up just undeveloped. But if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies. And I finished this third one and saw a through line with these other two from people that were in wildly different fields. And I jotted those notes down. And that thing kind of simmered and breathed and took on a little bit of a life. And I got asked by the dean of the business school here in Austin at the University of Texas to talk to the MBA class one day. And I was like, can I do this? And he said, sure. So I pulled it out and developed it a little bit as a PowerPoint presentation.
Anyway, they posted that on YouTube. A few people noticed, some people that have been on your show, James Clear noticed, and he posted it on his website. And people started prodding me to develop it as a book. And a few years ago, I decided to begin retirement as a venture capitalist. It actually takes a while, unfortunately. And in that window, I thought about doing this. I thought about doing a book. And a lot of people wanted me to do a book. A lot of people wanted me to do a VC book or an investment book or a tell-all book on the Uber experience. And I was more drawn to this idea. And a few other people prodded me who said, you know, like, go, go do. And it felt more authentic. It felt like something that could have a bigger impact. And I was drawn to that at this moment in my life. I was drawn to this particular thing. So I spent like six years working with a co-writer and researcher developing, and developing it further and making it this way. But you use the word regret. We did, along the way, I launched a survey on Survey Monkey that said, if you could go back and start over, would you do a different career? And seven out of ten people said yes. And I eventually took that to Wharton People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of ten, but very similar. And that notion of career regret is interesting. I had the opportunity to talk to Daniel Pink, who you may know who wrote a book.

**Chris Williamson** (2:47)
He's been on the show about regret.

**Bill Gurley** (2:49)
About regret. And in that book, he says the biggest regrets people have, and he showed me a graph, it actually gets worse as you get older towards end of life, are regrets of inaction. He calls them boldness regrets. It's what you didn't do. Like humans are great at forgiving themselves, made a mistake, learned from it, won't do it again, but they ruminate about what they didn't try. And so I, you know, I've thought about this long and hard now since I've been working on it for six years. I fear our current education path has become a bit of a conveyor belt. People, like, we're pushing these children into this meat grinder, and we're pushing them towards jobs that are, you know, typically called safe jobs, at least before AI.
And I think they're learning to grind. That's what Angela Duckworth's been saying now. You know, the perseverance part, we've taught them. But if they don't have the love for it, it turns into burnout. And so the purpose of this book that I wrote is hopefully to give as many people permission to go do what they want in life, you know. And look, I'm sure it won't touch everybody. But if there's a subgroup of people who read this and have the conviction that they can go succeed in this thing they love, I think that would be a huge impact on the world. Like, I think the people that do that are the people, you know these people, like, that just love what they do. And not only are they more successful, but I think they radiate a bit, you know, and spread positive energy.