Permission to Chase Work You Love
A Q&A with famed investor Bill Gurley
I recently had the pleasure of interviewing Bill Gurley at Johns Hopkins University, about his new book, Runnin’ Down a Dream: How to Thrive in a Career You Actually Love. Bill is a great guy and prominent venture capitalist (Uber, Zillow, etc.). He has also had the kind of zig-zagging career that warms my range-loving heart.
The book isn’t just about pursuing a passion, although that’s certainly a theme, but about how to keep your ear to the ground to listen for what that passion might even be.
Below is a shortened version of the conversation we had at Hopkins.
The Genesis of Runnin’ Down a Dream
David Epstein: The core of this book is about the search for something you’re passionate about. What was the genesis of this project?
Bill Gurley: The book came about because there was a period in my life where I was devouring biographies. There were three particular biographies of people in very different fields where I noticed a pattern of things that they had all done that could be systematized. As a venture capitalist, I think people say we are in the business of pattern recognition. You see a hundred pitches, you only fund one; you start looking for the things that stand out.
One of the people I studied was a basketball player, one was a restaurateur, and one was a folk singer. Those are not industries your parents would tell you to go get jobs in, yet they were all wildly successful. It developed as a passion project; I originally just did it as a university presentation. After that, people started talking about it. James Clear saw it and posted it on his website, and people started nudging me to make it a book. We spent six years turning it from a presentation for an MBA class to a full-fledged book with much more research.
The Resume Arms Race
DE: So how do you see this book meeting the moment right now as people try to navigate this very fast-changing world?
BG: The unfortunate reality is that our kids are caught up in what Jonathan Haidt calls a “resume arms race.” Starting around 12, parents freak out and worry about what the resume is going to look like on a college application. Hence, the kid’s life gets full of cello lessons and sports teams where you fly across the country at 13 years old. There’s not a lot of time left for exploration.
We had a chance to talk to Angela Duckworth while we were writing, and she said if she could write the book Grit over again, she’d focus more on the passion side. Grit has two components: passion and perseverance. We’ve trained kids to persevere; we’ve trained them to grind. But one day, after all the grinding and the work, they wake up stressed out and realize they don’t love what they do. The purpose of this book is for people who need that little push to maybe go chase that occupation that well-meaning parents would tell them not to do. I want to give them the tools and the permission to do that.
The Paramecium Principle
DE: I would argue that a lot of the book is specifically about how to pay attention to things that help you figure out what that passion is. You tell the story of restaurateur Danny Meyer. He went into other jobs—worked in sales, worked on a political campaign—and then he was going to take the LSAT. He wasn’t in love with any of it, but then he looks back at his journals and realizes on family vacations he was always writing about the food. It doesn’t even occur to him until his uncle says, “Obviously, you should start a restaurant.” He wasn’t paying attention to the antecedents in his life where the passion was already there.
BG: Guidance counselors and parents worry about the economic stability of the life of the developing young adult, so they encourage jobs that are supposed to be “sure things.” Now in an AI world, I mean, comp sci went from being the most sure thing to the least sure thing overnight. But there is a better question than whether it’s a sure thing: Do you really love it? I don’t think we should be sending people into careers they don’t love just because they’re safe.
DE: You mentioned Angela Duckworth. I was in her class recently, and she was sharing this idea that you write about in the book, which she called the “Paramecium Principle.” A paramecium decides which direction to go because it senses food or warmth, and it then just pivots in that direction. It follows that path. And if it senses more food or warmth, it follows it a little more. If not, it pivots. In the case of what Angela was talking about in class, food or warmth is interest or engagement in a type of work. It’s an interesting adjustment of the grit concept. Don’t be beholden to long-term goals if you start learning other stuff you’re interested in along the way. Be open to pivoting.
BG: Absolutely. Dave Evans, who teaches “Designing Your Life” at Stanford, ran a study and 10 years after graduation something like 20% of people are still in an occupation related to their major. Just because you have a major or started a career in one direction doesn’t mean you can’t pivot 180 degrees from that if you feel you should be doing something else.
Sensing Future Boredom and External Learning
DE: In your own story, you start off with a successful engineering career at Compaq. And this is when Compaq was a disruptive, cutting-edge company. And despite the prestige and stability, you write that you were developing a “sense of future boredom.” How did that develop?
BG: I loved programming and computer science, but the development of a physical product at a company like that meant that by the time the third model was going on, the project cycle was very repetitive. You let a model go out the door and then you start developing the next model. The Intel processor was a little faster, the clock speed was a little higher, but all in all, we were going to do the same dance over and over again. That’s where I thought to myself, “I don’t want to do 12 of these.”
I had also started investing, and I read One Up on Wall Street. A lot of it comes from books. One of our six principles in the book is titled “Hone Your Craft,” and it’s about lifelong learning. A lot of people, the minute they get in the door at a career, stop external learning. External learning is to me what you do in your spare time when you’re not at work. You’re developing your craft even further. And I think there are some industries where it’s known people do that, but I think in most industries people don’t do that. The test of it is: Do you love it so much that this external learning feels like fun? Is this something you would research on your own time instead of watching the next episode of Breaking Bad? That’s the test.
DE: Or, you watch the next episode of Breaking Bad and you realize your real passion is meth, so it could be that.
BG: Haha, well that could be…
DE: But really, I love that phrase “a sense of future boredom,” because you weren’t even there at Compaq that long when you started saying I can see where this is going and I don’t want to do it 12 more times. There’s research showing that if you quit something at the right time, it will always feel like you quit too early. You were pretty attentive to this pretty quickly. But how did you distinguish between natural day-to-day frustration versus the realization that this really is not the calling for you?
BG: It wasn’t that I was unhappy; I enjoyed the journey—
DE: Well that makes it even harder to know you should leave…
BG: We have a phrase in the book: “Life is a use it or lose it proposition.” Thinking forward that much—fast-forwarding and imagining 10 years, 15 years—was really illuminating. That was super clarifying.
Short-Term Planning and Financial Flexibility
DE: You pivoted a number of times. It reminds me of research called the “Darkhorse Project,” where fulfilling work was often found through short-term planning rather than rigid long-term goals. You realized you were interested in business, got an MBA, and went to Wall Street. And you didn’t hate any of this stuff—you were pivoting from stuff you liked, which might make it harder. And then when you wanted to switch again to be a venture capitalist, the advice you got from a VC was: “Great, just do 20 years of this first.” The advice you got was to delay the things you were interested in.
BG: Wall Street was a little different. After three years on Wall Street—hustling, working 12-hour days, waking up at 6:00 a.m., and putting on a suit every day—it was very easy to say to myself, “I can’t do this for 30 years. There’s no way.” Despite it being extremely well paying and awesome in so many ways, it had a level of stress and intensity about it that wasn’t going to be something I could spend the rest of my life with.
DE: Do you think it sometimes makes sense for people to take a pay cut in their career when they’re making their pivots?
BG: I think part of it depends on how you live your life. I met a lot of people that would get to Wall Street and immediately get the house in the Hamptons and immediately put their kids in private school. You’re stuck; you have no financial flexibility whatsoever. If you live well within your means earlier in your career, it gives you so much more financial flexibility to make those moves and pivots. Danny Meyer was making the equivalent today of about a quarter million dollars as a top salesperson and took a job at one-tenth that salary to learn about restaurants. So that’s extreme.
DE: I appreciated that story because I’ve gone backward a few times in title and pay, and figured my best professional asset was that I only buy running shoes and books.
BG: There’s a great quote in music producer Rick Rubin’s book, The Creative Act: He has a sentence where he says every career pivot I’ve made in my entire life, all the people around me have told me that’s the exact wrong thing.
DE: That advice, at least in my personal experience, is generally coming from people who have decided to stay, so they may not be the ones likely to encourage a pivot even if it makes sense.
Finding Mentors and The Power of Peers
DE: One of your six tenets in the book is developing mentors. And you did that in a really impactful way. But how do you suggest people get prospective mentors to be interested in you? Do you just send Bill Gurley a LinkedIn DM?
BG: You want to have a list of “aspirational mentors” that is separate from the people you’re going to get tomorrow. Danny Meyer made a poster board of the 12 people making a dent in the industry and studied them. He didn’t cold-call them at that moment, but they were out there as proof points that you could go and do this thing. We use the word “disinhibiting” in the book; knowing that other people have done something is really helpful.
Then start with networks you already have. If you start with people one or two tiers down from the super famous, they are flattered if you know about them. Research the hell out of them and be very nuanced in how you approach them. If they give you advice, do it. Then tell them you did it. Get them on your side where they feel like if you’re winning, it’s because of something they did. You want them on your team.
DE: Another tenet in the book is to “embrace your peers.”
BG: When I first got to business school, I thought networking was a social activity. But now I think it’s about finding people who are on the same journey as you are, who you can co-learn with. And there are some amazing examples in the book of this. My favorite example is Jimmy Donaldson. So that’s MrBeast. When he first got enamored with YouTube at 17, he met three other people who were equally enamored. They ended up on Skype calls together 16 hours a day for four years in a row, co-learning and co-sharing ideas. They each had their own channel; they weren’t sharing channels. And he said they all became millionaires. He says if you had been on those calls, you could be a millionaire too.
I’ve never read a personal development book that said, “Go get a great group of peers.” And I’ve tried to push it in some of my companies. I’ve tried to encourage CEOs to get their direct reports to go learn externally and report back, and it’s very awkward to a lot of people. It oddly relates to some of the concepts in Range, because If you can get four or five people who do what you do—maybe in a slightly different industry—and meet with them, you’re going to learn so many things that are helpful to your organization, because those are the things the organization doesn’t already know.
DE: To your mention of Range, I had some serious confirmation bias while reading this book so thank you for that! But regarding peers, you advocate not being territorial and just sharing with reckless abandon.
BG: I benefited greatly as a professional investor from the fact that people like Warren Buffett and Howard Marks would continuously write down their best thoughts and share them with the world, and I don’t think it stopped either of them from being highly competitive in their field. I think it’s a myth that you have these thoughts in your head that are so importantly private they need to be protected. If you give those away, you’re going to get far more back.
Permission to Tilt
DE: There is a quote in the book that you mention is used at Benchmark, where you’re a general partner: “Good judgment comes from experience, which comes from bad judgment.” If people go on a journey like the kind you’re describing, they’re going to take some wrong turns. You also write that “My number one objective for writing Runnin’ Down a Dream, was to give everyone as much permission and as much confidence as they need to tilt against a career they love…Life is a use it or lose it proposition. How do you want to use yours?”
BG: In his book Greenlights, Matthew McConaughey tells a story about telling his dad he wanted to switch to film school. He’d told his family his whole life he was going to be a lawyer. He finally tells his dad, and his dad says one thing: “Well, don’t half-ass it.” In that one phrase, his dad gave him a push, permission, support, obligation. If that’s what you want to do, go do it as well as you possibly can. For people who are thinking about it, that speaks to what I hope to convey.
Thank you for reading, and thanks to Bill for inviting me to do the interview. Runnin’ Down a Dream is hot off the presses.
Lastly, I recently started a YouTube channel. I just posted a new video, which talks about the power of hobbies and side projects. In the previous video, I summarized 34 books I love in about a minute each. (A helpful commenter put the full list below the video.) If you take a look, let me know what you think.
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Until next time…
David
you know what lots of pivoting is called..... DANCING! I love this topic - it puts into perspective that life is full of unknowns and one should see that the unknown is a gift, not something to be anxious about.
This idea is one of the many reasons I chose to homeschool my son - so he can have the free time to pursue whatever fancies him, and I can witness it.
I myself quit my career after a few years in because I could not imagine doing it for another 5 years even though I enjoyed the day to day. The same for my husband - we both got out before the golden handcuffs were clasped on. It definitely makes life more challenging, yet more rewarding and worth living imo.
Great conversation. As someone who has done pivots, permission to pivot has been foundational. That, and grace for a few wrong turns along the way.