"Be Fearless" - Talking to Jean Case About Making a Big Bet and Pushing Past Fear

Chris Schluep on January 31, 2019

Fearless.jpgJean Case has had the kind of success story people dream about. She was a scholarship student in high school (a local community leader paid for her private school scholarship), and she went on to eventually establish a career as a technology pioneer, investor, and philanthropist. As CEO of the Case Foundation, she runs a group that invests in individuals, nonprofits, and social enterprises aiming to connect people, increase giving, and catalyze civic actions.

Case has a new book out, Be Fearless. I asked her about the title and she told me:

"The book is called Be Fearless--but fearlessness is not the lack of fear, but rather the ability to stare it down and push past it. I really think anyone who is thinking about taking an idea forward, even if they feel fearful, that should not stop them. You can look fear in the face and keep going. That’s what many of the people in these stories did, and it's a big part of the reason I wrote the book"

Be Fearless is built around five principles and uses stories of people who started with an idea, and saw that idea through, to highlight how we all can accomplish something big. Here is part of my conversation with Jean Case:

Why did you decide to write Be Fearless?

My work, both at the Case Foundation and in my technology career, has taken me to communities around the nation and around the world. And one thing has become eminently clear, and that is that people everywhere have ideas about how to make the world better—but often they look at themselves and assume they need some special quality that they don’t have, whether it’s a rare genius, or the right connections, or going to the right school, or whatever. So about six years ago at the Case Foundation we became animated by this question of why do some people take their ideas forward and succeed and others don’t? And we specifically looked at the core qualities of change makers, innovators, and entrepreneurs. And we looked back and around to contemporary times. And we looked across sectors. And it turns out it really is five simple principles that are present wherever transformational change comes through. And what’s great about this is we were able to debunk this idea that it takes some rare superhuman quality to break through. So it’s really based on that research that we did about six years ago. And we’ve been out talking to people and sharing the principles, and we’ve seen the power to move people to action who previously may have felt I can’t be the one.

The first principle is to make a big bet. right?

We like to say: Make a big bet and make history. And the idea there is that you’re aiming for a big idea, not settling for incremental change. I think every single example we looked at across time and across sectors had someone who started with a big idea. Now what we like to make clear is that it’s actually incremental steps that get you to a big bet. But your aim, your focus is high.

This seems important because people will run into a barrier and just say, well, I guess I missed my chance. But you talk about taking the long view and not getting discouraged. This seemed like a powerful point to me.

We talk about the big bet as the first principle, but then we talk about the importance of risk taking and being bold as the next principle. And just to your point, I think people have to understand that if they are trying to do something extraordinary, they’re going to have to take risks. Trying new things requires doing some things that have never been tested before. And in that particular principle I talk about risk taking as R&D, with the idea that in R&D, as in so many fields—whether it’s science or medicine or technology—we understand that it’s trial and error. So if we can go in, as we’re taking our big bet forward, with smaller steps along the way, and recognize that sometimes we are going to be successful and sometimes we’re not—and that’s ok, that’s part of the improvement process as you move forward, to make your idea even stronger. I think for some that will be a motivation to keep going in the face of failure.

And you also talk about "Failing in the Footsteps of Giants," which was a great chapter. Can you talk about that?

That’s one of my favorite chapters, too. Obviously, the book is a series of stories that try to bring the principles to life. Yes, it’s based on the principles, but it’s a storytelling book. Many of the stories readers will never have heard before. But particularly in "Fail in the Footsteps of Giants," I tried to draw out well-known success stories, where maybe the failure stories behind some of those success stories aren't as well known. Like Oprah being told she wasn’t right for television and fired from a newscasting position. Or Stephen Spielberg, who was rejected from film school. Or Steve Jobs—fired from the very company he founded, and he came back and made it the most valuable company in the world. So, I think it’s really important to tell that part of the story, too. My concern, as I’ve gone around and talked with folks through the years, is that we hear these success stories, but often they get sanitized. And I think it’s very easy to believe that, oh, they never had a failure. And even I, when I’m introduced sometimes, my bio sounds so perfect. And then I’ll follow it up with a failure resume to make it clear that there were so many failures along the way of getting to any successes that I’ve had.

In the book, you talk about how you were your mother’s big bet, is that right?

I think there were two characters in the book who I was amazingly close to. My mom, of course. I think it took me some time and reflection to realize that I was her big bet. She sacrificed it all, as a single mom with four kids, working full-time as a waitress at night, basically to enable me to have a better life. I also talk about my sixth grade teacher. We are very close to this day, and she read some of the early manuscript pages of this book. We’re just ten years apart—she was twenty-one and I was eleven when she had me in her class. And we’ve remained friends. And you know she came back and said to me, “gosh, I really wonder if I’ve made a big enough bet.” She was worried that maybe the book would make some people feel, I’m not sure I can make a big bet. And she said her big bet was teaching students and investing in their future. So I think it’s important to realize that some big bets will be well known, public, change-the-world kind of things, but there are people out there, who, if they change one life, it can make a big difference.

That really is the point of this book—to give people the tools to help others. Would you agree with that?

I would. I really wrote it as a clarion call and as a playbook for anyone who has had ideas about how they can make a difference. My view is—particularly for people who live in the comfort zone of life—they often aspire to do more, often to dig a little deeper and do something more bold and more ambitious, and really the book is out there for anyone who has an idea and asks the question Where do I get started? And as you know, Chris, the first chapter of the book is "Start Right Where You Are," where I really try to draw out stories of people who have had little or no resources, little or no connections—people where nobody looking at their life would say, they could do something great. And they just got started, step-by-step, toward a big idea.

Later in the book, you inject a sense of urgency into how people can approach whatever problem they’re trying to solve. Don’t think too much about it, just do.

That’s right. We say, Don’t overthink or overanalyze. Do. And you can. I obviously bring out some of this research as well, which is not our research but the research of others, which points out that if you sit with something too long and overanalyze it, you’re much less likely to act. And there is this sort of special clock almost, where as you’re putting your idea together it’s important to act urgently on what you do. But the other side of that is knowing the role that urgency and, frankly, discomfort plays in getting people to move beyond and do something bold. So I write about chef Jose Andres, who as Hurricane Maria was threatening Puerto Rico, dropped everything and headed down there to try to bring some food relief to the island. And here he is: one chef, he knows how to do one thing and that’s cook. He did have some friends that he called in to be helpful. But he’s never really specialized in large scale disaster relief. He goes down there and ends up serving 3.7 million meals to Puerto Ricans. And now he’s stayed on the island—I was just with him last weekend—where his team is really building a resiliency on the island and putting a whole new food support network together in hopes that they can be more sustainable in future natural disasters.

When you were writing the book, did you have a specific kind of reader in mind?

I said in the dedication to each person who has heard a voice whisper, "This is your moment." I would say that’s who I had in mind. And even since the book has come out, it’s been quite rewarding, Chris, because I’ve heard from teenagers, college students, CEOs, moms, you name it, and I purposely put together a variety of stories, as you saw, with the hope that any reader can find something of himself or herself in the book through the stories. I just believe—as I said in the start of this conversation—I see people everywhere, really with a burning desire to make a difference. What they really need is a starting point and a framework to take their ideas forward. And that’s who I had in mind.

One of the things that I personally picked up from the book was using your calendar to reflect what really matters. What’s on your calendar these days.

As you might imagine, trying to make sure that this book gets into the hands of people. We are deep in the throes of making sure people know about the book and have the opportunity to read it. And you know sometimes I think when you work on a book, there could be a tendency to think it’s a self-gratification thing. For me, I so believe in these principles and in the inspired nature of these stories that I’ll do all I can right now for the book. I’m glad you brought up the calendar because it’s almost one of those “duh” things, but actually it really is important—the intentionality that you bring to anything you’re trying to get done. And particularly for people who can’t drop everything and go chase their idea. Maybe they’re struggling with one or two jobs, or maybe they’re raising a family, or they have something else that is really requiring most of their time. It’s especially important for those folks to start scheduling time, hopefully each day, but certainly each week, to get one thing done to move them closer and closer to taking forward their big idea.

Finally, you literally returned to Normal (the town in Illinois where you grew up) to write this book. What was that experience like?

It was really a powerful experience for me. As I said in the epilogue, I think it played a really important role in keeping me grounded to my past as I told this story. You know, it’s quite an extraordinary journey I’ve had, which is going from a recipient of philanthropy—having been able to go to a private school due to the generosity of others, I was on full scholarship—to coming around having this great career in technology, and now being in philanthropy and being able to hopefully empower others as well. But I’m a pretty long way from those days in Normal, and going back was really important in terms of keeping the book authentic and giving me almost an extra passion around telling these stories.

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