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The Myth of the Risk-Taker: You Don’t Have To Be Bold To Succeed

Creativity Entrepreneurship
The Myth of the Risk-Taker: You Don’t Have To Be Bold To Succeed


  • How procrastinating can make your ideas better
  • Where creativity comes from
  • What Sheryl Sandberg does to differentiate herself as a leader

Adam Grant is a renowned Wharton psychology professor and bestselling author of Originals: How Non-Conformists Move the World. He recently joined Ryan Hawk, host of The Learning Leader Show, to talk about what makes an Original, the role of creativity and curiosity in non-conformity, and what it takes to be a successful entrepreneur.

This conversation has been edited and condensed. To listen to Adam and Ryan’s full conversation, click here.

Adam: The most consistent common attribute of people who have been widely successful and done it again and again is that they’re dedicated learners. What’s fascinating about them is, no matter how much excellence they achieve, they’re always raising the bar. You see this with a lot of the tech titans—when I talk to Elon Musk or Mark Zuckerberg or Larry Page or Jeff Bezos, the first thing that you see is the more they accomplish, the more they expect of themselves. They always have something new they’re excited to learn.

Ryan: Elizabeth Gilbert said, “The starting point for creativity is curiosity.” How do creativity and curiosity relate to what you do and what you’ve studied?

Adam: Curiosity to me is the starting point for all originality. When people come up with ideas that are not only different but better, without fail, they’ve started by looking at something in their world and saying, “Why is it that way? Who created it? And does it have to be that way? Is there another way to do it?” If that’s your orientation toward the world around you, then you’re going to be constantly coming up with ways to challenge the status quo and [with] new inventions and discoveries.

“Curiosity to me is the starting point for all originality.”

Ryan: Sheryl Sandberg calls you an original. Some of the things you’ve written about [and] said, though, show that you doubt that a little. Do you consider yourself an original?

Adam: No.

Ryan: Really? Why?

Adam: Because I study originals. I don’t think that I’m particularly good at being creative. When I’ve brought insights into the world, my strengths are more about being a synthesizer than a discoverer. I read a lot and [have] done a lot of research on my own, and what always jumps out at me are connections between all the different things that I’m looking at. What I’ve tried to bring to the table is seeing the forest and the trees and helping people come up with frameworks to organize the insights that are out there. A lot of originality is about being a non-conformist, and I’ve always been somebody who’s been more comfortable with conformity. But since getting tenure, I think I’ve become more of a non-conformist and it’s meant that sometimes I am going against the grain and I’m being contrarian. Is that original? It’s not my place to judge. I’ll leave it up to others.

Ryan: How did you and Sheryl develop such a great relationship over the last few years?

Adam: She’s the most extraordinary leader I’ve ever worked with. We met because Lean In and Give and Take came out within about a month of each other and we spoke at some common events and she asked me a bunch of questions about analyzing my data through gender. I had a long flight back to the East Coast after one of these conversations and reanalyzed a decade of my own data and was deeply disturbed by what I found. Women were stuck with most of the office housework—planning meetings, organizing events, taking notes—[and] also did most of the giving and helping that was the most valuable but the least visible. They tended to do the lion’s share of mentoring, problem-solving, one-on-one behind the scenes.

In the domain of Originals, when a man brought a new idea to the table, people tended to celebrate it. They would say, “Wow, you’re so creative.” When a woman brought the same idea, either it was barely heard or she was judged as too aggressive. That really got me interested in understanding how can we do a better job getting ideas heard. We don’t struggle at creativity, we struggle at originality, because leaders fall apart all the time when it comes to idea selection and knowing which ones are good, which ones are bad. Creating organizations that fight groupthink and welcome dissent was something that was interesting to me and [provided] a backdrop [for] my collaboration with Sheryl.

She’s the most open-minded leader, the best listener of anybody I’ve collaborated with. There are lots of times when I’ve said something offhand that other people would have dismissed or ignored and, she’s said, “That’s really interesting. Tell me more,” and, “Do you have data to back that up?” I think that curiosity has led us to lots of new insights together.

Photo by James Pond on Unsplash

Ryan: Shifting gears, I’d love to hear about risk-averse originals. The guys at Warby Parker came to you with an opportunity to invest prior to them launching their company and I want you to share why you didn’t invest in them and why it was a mistake.

Adam: I had this amazing opportunity. [In] the very first class I’m teaching at Wharton, a student, Neil, comes to me and says, “I want to sell glasses online,” and invites me to [talk] and then [asks], “Do you want to invest in the company?” I expected that if you’re going to be a successful entrepreneur, you should drop out of school. But Neil and his cofounders [were] all still in school, and then instead of working on the business full-time, three of the four of them had taken summer internships. I asked them if they’re going to go [to] full-time when they graduate and they said, “No, we’ve all lined up backup jobs just in case this doesn’t work out.” So I declined the investment and, of course, they’ve gone on to be valued over a billion dollars and they just got named last year’s The World’s Most Innovative Company by Fast Company. Which is why my wife handles all of our investments now.

The stereotype that, to be a successful entrepreneur, to do anything original, you have to be a huge risk-taker, is a myth. Yeah, a lot of the biggest risk-takers are entrepreneurs and doing creative things, but they’re not the successful ones. There’s a fantastic study that came out last year looking at entrepreneurs of two kinds. The risk-takers are the ones who have a big idea, they quit their jobs, and go all in. The people who are more cautious like me (and like the Warby Parker guys) are like, “I don’t know if this is going to work out so I’m going to hang onto my day job and I’m just going to start this company as a hobby on the side and see what happens.”

If you follow those entrepreneurs over a decade, that second group is 33% less likely to fail. That’s exactly what happened with the Warby Parker founders. All of the risk-aversion that they brought to the table meant that they were constantly testing and iterating ideas instead of putting all their eggs in one basket.

Ryan: When I saw your research [and] heard you speak about it, it made me feel better about having ideas and being a creative, but also being a little bit cautious and conservative in the approach. If you have a backup plan as far as money is concerned and your focus [can be] on producing and providing great content or a great product, you’re in a much more healthy place as a business leader when you don’t have to initially think about just keeping the lights on.

“The stereotype that, to be a successful entrepreneur, to do anything original, you have to be a huge risk-taker, is a myth.”

Adam: I found it very reassuring as well, as somebody who is so risk-averse, that I chose the one career where no one could ever fire me. Most of the highly original people that I’ve interviewed and studied and observed think about risk like a stock portfolio, where if you were going to make an investment in a really risky stock, you would then take a bunch of money and put it in some very boring mutual funds, you know, to make sure that nothing horrible happened to your entire portfolio. And a lot of great entrepreneurs think about risk the exact same way.

Take Markus Persson, who worked on creating all kinds of different video games—most of them didn’t go anywhere so he hung onto his day job and made sure that he had a stable income. Eventually, he put a game up half-finished and people started to like it and it becomes Minecraft. He hung onto his job for almost a year before he walked away to make sure that Minecraft was really something worth betting on. You see this over and over again. Sara Blakely sold fax machines for more than two years by day while coming up with Spanx, and then eventually becomes the world’s youngest self-made billionaire. I think it’s so encouraging to all of us who are afraid to make that leap. You can start these things on the side and then see if they gain any steam.

Ryan: The book that I gift the most is Give and Take, especially when I mentor somebody. One of the questions I often get after they’ve read that book [is] when you see a taker having success, how do you deal with that?

Adam: A lot of people, especially leaders who are more senior in their careers, often say, “You know what? I used to be upset when I saw that happen and now I just feel sorry for them.” Bob Sutton, who’s written a lot about this idea in his The No Asshole Rule, said, “Look, you might’ve achieved some career success, but you’re a loser in life.”

Ryan: Going back to Originals, you gave a world-class TED talk [about it] in February of 2016. When it comes to the preparation of giving a speech that could influence and impact so many people, [how] did you prepare?

Adam: I always do things that [are] important to me ahead of schedule and I knew this weight would be on my shoulders if I didn’t have something that I was eager to deliver onstage ready in advance. I worked on different drafts over the course of several months. I gave my first practice talk in front of a real audience in November, and I hated every word of it and threw out the draft, went back to the drawing board. Then Tim Urban and I did a practice talk. We each gave our talks together in December and I couldn’t stand that talk either. I went back to the drawing board again. Finally, I realized I had to take some of my own advice seriously and start procrastinating and give myself a chance for ideas to incubate.

It really only crystallized about a week before I was onstage. I really think being open to revise was the most important thing that made my speech less awful than it would have been.

“I realized I had to take some of my own advice seriously and start procrastinating and give myself a chance for ideas to incubate.”

Ryan: Did you have a coach?

Adam: I actually had several coaches. The most valuable thing that I learned from them was [their] 2×2, [where] one axis is abstract versus concrete. “How much do you gravitate toward really specific examples that you can taste and touch versus more ethereal ideas and concepts?” And then the second axis is logical to emotional. “How much do you resonate with facts versus feelings?” They basically drew the 2×2 and [said], “Adam, you are off the charts on the logical and the abstract in the way you keep giving this talk. And if you look at the other talks you give that have good reception, you do a great job telling stories that tug at the heartstrings. They’re not just all data points. You bring the data to life by creating these characters, giving us examples of givers and takers.”

Drawing that 2×2 has really changed the way that I think about creating a speech because I know that different audience members are going to be in different quadrants. You [need] to fill out all four of those cells and make sure that [you] have some content to speak to each of them. That ultimately was what got me to the talk that I felt comfortable giving.

Ryan: Love it—thank you so much. I appreciate the work that you put out in the world and the impact that you’re having on so many people and certainly on me, life-changing material and I mean that genuinely. It was a thrill to talk to you.

Adam: Oh, Ryan, no, no, no. You’re not getting away with that as the closing. I get to turn this around on you and ask you a question. You’re somebody who lives the giver values. You also have this tremendous passion for learning. When you think about all the people you’ve interviewed and had a chance to learn from, what is the thing that stuck with you most about how to stay in a mindset of focusing on others and being willing to recognize your own mistakes?

Ryan: I think a lot of what I talk about are things that I’ve learned from other people. Kat Cole told me this, but the way to have a positive impact on the world are to have courage and confidence mixed with curiosity and humility, because ego can be a really dangerous thing. That’s what I try to live by.

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