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Internet Trailblazer Jean Case Shares How to Make Your Failures Matter The Case Foundation CEO reveals why honesty in the face of mistakes will take you far.

By Nina Zipkin

Courtesy of Jean Case

In this series, Open Every Door, Entrepreneur staff writer Nina Zipkin shares her conversations with leaders about understanding what you have to offer, navigating the obstacles that will block your path, identifying opportunity and creating it for yourself and for others.

It's normal to feel nervous about striking out on your own. But if you start to feel yourself hesitate in pursuit of your goals, take Jean Case's motto to heart and "Be Fearless."

Case is the CEO and co-founder of the Case Foundation. She has been running the organization with her husband, AOL co-founder Steve Case, since 1997. Through their work, the Cases are dedicated to dismantling myths about who can be a business leader by providing not only data but resources and funding to help underrepresented entrepreneurs make an impact.

Much of Jean Case's career has been about seeing what others might not, especially in the world of technology. Before the Case Foundation, she worked in strategic marketing roles at early online service The Source and at GE's Information Services Division. She then made the leap and joined the startup that would evolve into AOL.

In addition to her duties at the Case Foundation, she is the chair of the National Geographic Society Board of Trustees and sits on the boards of Accelerate Brain Cancer Cure (ABC2), the White House Historical Association and BrainScope Company.

Case shared her insights about how make your mistakes truly count and how to find the people that will keep you honest and help you identify your strengths.

This interview has been edited for length and clarity.

Can you tell me about a time that you needed to create an opportunity for yourself or others? How did you approach it?

Early in my career, I ended up at GE working on an online service. I was on a really fast track at GE and everything was going swimmingly. Then this opportunity came along for a new startup. It looked like this opportunity could lead to much greater impact in terms of democratizing access to ideas, information and communication. I had to make the jump.

What I find is that every moment where there was some some big opportunity around the corner it was usually preceded by necessitating risk to make that jump. When I think about sort of pivots or turns or opportunities that were created I think back to that. Of course that company would become AOL, but at the time it was a real risk in proving that [it was a good idea]. My mom and friends said, "Are you crazy? You got the best job in the world. Why would you take a risk and go there?" I never considered that a mistake.

Related: This Young Entrepreneur Shares the 3-Step Strategy She Uses to Banish Self-Doubt

Did this experience or any other in your career change how you think about leadership?

I've been pretty public about a failure that we had at the Case Foundation, which was a global water initiative in sub-Saharan Africa. I launched it at the Clinton Global Initiative with President George H.W. Bush and First Lady Laura Bush by my side. It was very high profile. As we got started, things weren't going well. The initiative wasn't going forward the way we wanted it to, there were just problems cropping up everywhere. So we spent about a year trying to course correct and then it became clear that we weren't going to be able to.

So we faced the tough decision of what to do and it was at that moment where I determined I had to be transparent and clear with our stakeholders and the public and just say this isn't working. We need to pivot, we need to walk away from this initiative and find a new way forward in clean water. That's exactly what we did. That was a watershed moment for me because it really was the most public moment of acknowledging failure up until that point in my life. Today, when I speak, particularly on college campuses, I often open with what I call my failure resume because [my talk] will follow this bio that sounds so perfect. Like everything just went as I planned it. Then I talk about whose failures or mistakes I made along the way and how they almost had to happen in order for these other opportunities to emerge.

What surprised you most about opening up about that failure?

We do ourselves a disservice if we don't talk about how the best things don't come easy. I often quote Albert Einstein, who said failure is success in progress. If we looked at it that way, we would probably feel very different in those low moments, because we could really embrace the idea that something great must be around the corner.

[I wrote a blog post about what had happened] and that was going to be our message to the world that we have failed. When I hit send, I was filled with insecurity. I worried about what people would say. But in fact what happened is a number of colleagues and peers started calling, emailing and finding me and saying thank you. No one ever talks about it. So that actually for us began something that was to emerge as a major initiative called Be Fearless. [We looked at] great movements, companies, products and ask experts what's behind them. It always involves risk-taking. You have to be open to the idea that you may fail and if you do fail, make that failure matter, by making it right.

What personal traits or strategies do you rely on to create opportunity for yourself and others?

I learned about myself early on that my true north is that I really love to empower others. There's this myth out there that to find success you have to step on others. I have found exactly the opposite. A great path to success is to focus on empowering others. Chances are that's going to lift you and where you're trying to go -- and at the same time lift people around you.

Related: You Need to Meet Your Challenges With Pathological Optimism at Every Turn

When you experience a setback, what do you do to keep going? How do you get unstuck?

We all have our blind spots. Particularly if you're in a valley, it's really tough to see over the mountain. But it turns out you might have colleagues, friends and family members who can kind of put things in perspective. So first I surround myself with what I call my personal board and I advise the next generation. I always ask them, Do you have a personal board? Those people can be honest with you about your strengths and weaknesses and maybe see beyond what you can see. I turn to that when I have challenges.

For people who want to advocate for themselves, what are actionable steps they can take to make themselves heard? What steps do you take?

Women particularly struggle with self-advocacy. We're brought into this world really championing others. On the subject of how to advocate for yourself, it's really important to have a solid set of folks in your life who know you well and can help you understand what your strengths and weaknesses are, because often we can't see our own strengths and weaknesses very clearly. So once someone points out your great gifts, now you have a list. Treat advocacy like a muscle. Be confident about your strengths and literally rehearse it in front of a mirror if you have to, before you're in a situation where you are advocating for yourself. Be comfortable with your go-to talking points around what makes you uniquely qualified or in a position to do this.

Is there a blindspot that leaders have about opportunity? What should they be doing instead?

If you have a group of people with different perspectives around the table, you are going to end up in a better place, in decisions you make and in things you decide to invest in. Where there are more diverse teams, you can make better, smarter decisions. Leaders think about the point of having diversity as a check-the-box thing, instead of a powerful business opportunity. What I think has changed only in recent years -- and we still need more -- is data to drive to help this become clear for those who need to see it.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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