Hate Your Boss? Here’s How to Become Your Own

NPR’s Guy Raz has a game plan to help you realize your start-up dreams.

Smiling woman holding a box of office supplies
Photo illustration by Slate. Photo by Jovanmandic/iStock/Getty Images Plus.

Tired of your job? Desperate to be your own boss? Plotting a start-up that will land you on the cover of Forbes? Guy Raz has a game plan that’ll help you realize your dreams. As the host of NPR’s How I Built This and author of the new book of the same title, Raz has talked with hundreds of entrepreneurs about their motivations, setbacks, and successes. He knows the idea that sparked Warby Parker’s eyeglass revolution and the early failures of Airbnb’s founders. And in the latest episode of How To!, Raz shares what he’s learned about how you can break away from your boring job and build something new, all while relying on the safety of a back-up plan. This transcript has been condensed and edited for clarity.

Charles Duhigg: Why did you become interested in telling the stories of entrepreneurs?

Guy Raz: As a storyteller and and a journalist, I was always really inspired by the hero’s journey. It’s Star Wars. It’s Harry Potter. Pretty much every story has the same narrative arc: There’s a hero, and the hero has this wild idea and is banished because everyone thinks the hero is a little nutty. Then the hero goes on a journey, fights a dragon, finds a mentor, has a near-death experience. It’s a simplification of it, but that’s basically the story of most businesses. Building a business or a brand has all the elements of a great drama. There’s triumph. There’s heartbreak. There’s struggle. There’s unbelievable anxiety. And there are also these moments of just incredible success.

The stakes are so high in so many cases. People are putting everything on the line. Oftentimes, if you fail, there’s a price to pay—a financial price, a reputational price, or just the misery of failing and having to get up off the floor and start again.

But the first thing I’ve learned is that you have an incredible advantage over many other entrepreneurs [if] you have a skill, a transferable skill like being a nurse or being a clinician. Jane Wurwand, who started Dermalogica—a cosmetics brand that was eventually sold to Unilever for a quarter of a billion dollars—was trained as a beautician. She always knew that if her business idea didn’t work, she could always go back. So if for some reason the plan doesn’t work out, you have a safe back-up plan. Now, of course you don’t want to do that, but knowing that already puts you ahead of the game because it gives you the peace of mind to kind of push forward and leap into this thing.

That makes sense. But starting this new thing, even with a back-up plan, is still nerve-wracking. How do you decide if you’re ready to make that leap?

It reminds me of a story that Jim Koch, a founder of the Boston Beer Company, tells. I’m sure you’ve heard of Sam Adams—the beer that really launched the craft beer revolution in the United States. Before he launched the Boston Beer Company, Koch was a consultant for the Boston Consulting Group. He was making a very comfortable salary. But you know what? He was miserable. He wasn’t happy at his job. He had this kind of crisis in his life where he really believed he had to pursue something on his own. He came from a family of brewers—his grandfather, his great-grandfather, all brewers—and he started to really think about building a company around a craft beer.

When he was thinking about this decision, he had remembered this concept from his time doing a wilderness program—a concept of things that are dangerous and things that are scary. So, for example, if you were to walk up a gentle hill covered in snow, that could be very dangerous because you might actually trigger an avalanche. But if you’re climbing up a cliff and you’ve got ropes connected to you, that’s scary but it’s probably not dangerous. As he thought about his options in life, he knew leaving Boston Consulting Group was scary because he was giving up security and stability, but if it all failed, he could always go back to being a consultant. He had that skill. So there are times when things are dangerous that we want to avoid, and there are things that are scary that we have to sometimes push ourselves to go and pursue. And it might be dangerous for you to stay at your job for the rest of your life because you’ll be dissatisfied.

So let’s say you’re ready to make the jump. How do you deal with the people who say it can’t be done?

A classic example is Airbnb, right? In 2008, the founders went to 20 investors. They heard back from five, two agreed to have coffee with them, and zero invested. They were asked “Who in the hell is going to stay at a stranger’s house? How is that ever going to work?” Airbnb is the single biggest disruption to the hotel industry in modern history, but at the beginning, everybody told them they were nuts.

It was the same story with Southwest Airlines’ Herb Kelleher. In the 1970s, he was asking, “Why is air travel so expensive?” He thought air travel should be really inexpensive, airlines should be more efficient, service should be good—and all that should be easy to do. Well, it was very hard for him to start Southwest. It took Southwest four years before they were able to take off, but eventually they completely changed the airline industry.

Everybody told Ben and Jerry’s that they were crazy when they wanted to start a social enterprise. Now, every company is a social enterprise. Everybody told Payal Kadakia that ClassPass was a waste of time because studios weren’t interested in coordinating their class schedules. That company now has a billion-dollar valuation. So every big idea, every disruptive idea is going to have tons of pushback. Joe Gebbia of Airbnb says if your idea doesn’t make people uncomfortable, then it’s possible that your idea actually isn’t yet good enough. So when people do push back, when people do say that that’s impossible, you might be onto something.

It’s easy to look back on those companies now and see why they became successful. But what about the inevitable failure you’re going to face along the way?

That’s right. Most entrepreneurs I’ve interviewed had previous failures before they struck on the idea that worked. I think in most cases, they have an unshakable belief that this is a problem that needs to be solved. That is an incredibly powerful motivating factor. It took James Dyson, for example, eight years to come up with that vacuum cleaner, but he knew that a bagless vacuum cleaner would be a better product. Even though lots of people told him it was crazy and he was bankrupted at the age of 42, he was unshakable in his view that this was a problem that needed to be solved and that he could solve it.

One of the ways that entrepreneurs manage their emotions and failure is by having somebody along with you for the ride. It’s why oftentimes co-founders are more successful than individual founders, because you’re always going to have a period where you’re in a trough. But step onto a balcony—a proverbial balcony—and try to look at the situation from a bird’s-eye view as best you can. The other thing is to share your thoughts, fears, and anxieties with other people. Oftentimes it’s those people who can help you see what you can’t see clearly when you’re in the middle of a crisis.

As you’ve talked with these entrepreneurs, have you noticed anything that’s different about how they think of risk and reward and how that helps explain their success? 

I think there’s a myth about entrepreneurs that they are kamikazes, that they leap out of airplanes without parachutes. I have rarely encountered an entrepreneur like that. By and large, most entrepreneurs are Clark Kents. They’re like us—the only difference is that at some point they went into a phone booth and they put the cape on and then they started to fly. There are all kinds of things that could go wrong. There could be a pandemic, you know? We just don’t know. You know, the greater the risk, the greater the reward, but you always want to figure out how to mitigate that risk as much as you can.

But in almost every case the person knew when they had to do this. Something inside of them said, “Hit the ‘go’ button. Now. Now. Now it’s time to do this.”

To hear Guy Raz give specific tips to an aspiring entrepreneur who wants to disrupt his sector of the health industry, listen to the episode by clicking the player below or subscribing to How To! with Charles Duhigg wherever you get your podcasts.