The Risk You Don’t Take

Speech published with permission from Mike Fisher (MGT ’00; GRS ’13, management).

Thank you. Dean Medvedev, faculty, families, friends, and most importantly, graduates. Congratulations. You made it. You survived the case studies, the group projects with people who mysteriously vanished the week the deliverable was due, the exams that made you question every life choice that led you to this campus. You made it. You earned this.

I want to start with an aphorism that the famous author, H. Jackson Brown Jr., attributed to his mother. It goes like this: “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

I love that quote and heaven forbid that I disparage anyone’s mother, but I also think it’s incomplete. That statement makes it sound like risk is a sailing adventure, wind in your hair, open ocean, a certain romance to it. And sometimes it is. But more often, risk feels like standing at the edge of something with no guarantee there’s water below. It’s not romantic. It’s terrifying.

So today, I don’t want to give you a speech about being brave. I want to give you a speech about being afraid, and then doing the thing anyway. Because that’s the real skill. And it’s one that no program teaches, but every meaningful career demands.

Let me tell you about a woman named Sara Blakely.

In 1998, Sara was twenty-seven years old, living in Atlanta, selling fax machines door to door. That was her job. Every morning she woke up, put on a suit, and knocked on doors while people tried to get rid of her as fast as possible. She had been doing this for seven years. She had $5,000 in savings. She had no background in fashion, no connections in retail, no experience in manufacturing. What she did have was an idea, and a pair of control-top pantyhose she’d cut the feet off of.

She spent two years developing what would become Spanx. She didn’t quit her day job on a whim. She kept selling fax machines while she researched patents, called hosiery mills in North Carolina that hung up on her, and taught herself the basics of patent law so she could file her own application and save money. She drove to the mills in person because no one would take her calls. When she finally found one willing to make her prototype, a mill run by a man in Asheboro, she later found out he only agreed because he went home that night and told his daughters about the idea, and they told him he’d be crazy not to try.

Here’s what I want you to notice about Sara’s story: the timing wasn’t perfect. It was never going to be perfect. She didn’t have the resume, the funding, or the industry knowledge. But she also didn’t leap blindly. She prepared, she tested, she built something real before she bet on it.

There is a myth that will follow you out of this auditorium and into the rest of your life. The myth sounds reasonable. It sounds responsible. It says: I’ll take that risk later. After I pay off the loans. After I get the promotion. After I feel ready.

I need you to hear me on this: readiness is largely an illusion. The conditions are never ideal. There is a difference between strategic timing and comfortable timing. Strategic timing means you’ve done the work, you understand the terrain, you’ve minimized what you can. Comfortable timing means you’re waiting to not feel scared. And that day doesn’t come.

Sara Blakely is now a billionaire. She built one of the most recognizable brands in the world from an apartment in Atlanta with a fax-machine salary. Not because the timing was right. Because she stopped waiting for the timing to feel right.

Now I want to talk about fear itself. Because I think we have a broken relationship with it.

We treat fear like a verdict. Like if you’re scared, that’s evidence you shouldn’t do the thing. That fear is a stop sign. But here’s what I’ve come to believe: a great life is not the absence of fear. It’s a relationship with fear. Fear never disappears. It changes shape. When you’re twenty-five, you’re afraid of failing. When you’re forty, you’re afraid of being irrelevant. When you’re sixty, you’re afraid you played it too safe. The question was never “how do I stop being afraid?” The question is: Is fear in the passenger seat, or is it driving?

Let me tell you about Reshma Saujani. In 2010, Reshma was a Yale-educated lawyer with a career in finance. She had the kind of resume that makes parents proud at dinner parties. And she decided to run for U.S. Congress in New York’s 14th Congressional District.

She lost. And not by a little, she was crushed. She received 19 percent of the vote. Nineteen percent. It was public, it was humiliating, and it was the kind of failure that, in her world, you don’t recover from gracefully. Her colleagues in finance didn’t understand why she’d left a lucrative career to lose a race. Some pitied her. Others distanced themselves.

And here is where the story gets interesting. Because that failure, that very public, very painful failure, taught Reshma something she couldn’t have learned any other way: the shame of losing was survivable. She didn’t dissolve. Her life didn’t end. And once she knew that, once she had metabolized the worst-case scenario and come out the other side, she was free. Not free from fear, free from the tyranny of fear.

That freedom led her to found Girls Who Code in 2012, an organization that has now reached hundreds of thousands of young women and fundamentally shifted the conversation about gender in technology. Reshma has said that running for Congress and losing was the most important thing that ever happened to her. Not because it toughened her up or taught her resilience in some abstract way, but because it showed her that her identity could survive failure.

And that is the thing I want to name for you today, because you are walking out of here with a degree from Weatherhead, and that degree carries an expectation. People will expect you to succeed. You will expect you to succeed. And the deepest fear isn’t really about money or career setbacks. It’s about identity. It’s the fear that says: What if I’m not who I thought I was?

That question will stop you cold if you let it. It will keep you in jobs you’ve outgrown, in strategies that no longer work, in relationships that have run their course. Not because you can’t see the exit, but because walking through it means admitting you don’t know what you will be on the other side.

So let me say this clearly: you are not your title. You are not your salary. You are not your last performance review. You are the person who shows up after the failure. And the person who shows up after the failure is almost always stronger, clearer, and more honest than the person who was too afraid to risk it in the first place.

Now, I’m not standing up here telling you to be reckless. There’s a difference, and it matters.

Reckless risk is about the spike. It’s the adrenaline, the thrill, the dramatic gesture. It’s quitting your job in a blaze of glory with no plan. It’s putting everything on one bet because the story sounds good. Reckless risk is ego dressed up as courage.

Purposeful risk is different. Purposeful risk is about alignment. You accept the downside because the upside moves you closer to the person you want to become. It’s not about the spike, it’s about the trajectory.

Reid Hoffman understood this better than almost anyone. In the early 2000s, Reid was already successful. He’d been part of the founding team at PayPal. He had money, credibility, and plenty of comfortable options. He could have spent the next decade advising startups and collecting board seats. Nobody would have questioned it.

Instead, he started LinkedIn. And what’s important to understand is why he started it. Reid didn’t wake up one morning with a flash of inspiration. He had a thesis, a carefully developed thesis, about how professional relationships would evolve in a networked world. He believed that a person’s professional network was one of their most valuable and underutilized assets, and he believed the internet would make it possible to map and activate those networks at scale.

But here’s the key: even with that thesis, he knew the first version would be imperfect. He’s famous for saying, “If you’re not embarrassed by the first version of your product, you’ve launched too late.” Think about that. He wasn’t waiting for perfection. He was accepting imperfection as the cost of forward motion. Because he understood something that most people don’t: waiting for perfection is its own form of cowardice. It disguises itself as diligence, as high standards, as professionalism. But often, it’s just fear wearing a nicer outfit.

LinkedIn went on to become the world’s largest professional network, over a billion members, and was acquired by Microsoft for $26.2 billion. But Reid will tell you that the success wasn’t the point. The thesis was the point. The risk was purposeful because it was rooted in something he believed about the world and about what he could build. Every decision along the way was filtered through that belief.

So as you leave here today, I want you to ask yourself this question before every major decision: Is this risk moving me closer to who I want to become? Or is it just moving me away from something I’m afraid of? Because those are two very different things. One is purpose. The other is escape. And they feel almost identical in the moment.

Here’s the last thing I want to tell you, and it might be the most important.

We talk about risk like it’s an individual act. Like it’s about grit and willpower and personal courage. And it is, partly. But the truth is, your risk tolerance is shaped enormously by the people around you. The people in your life either expand or contract your sense of what’s possible.

I know this because I’ve lived it.

I didn’t grow up in a family of risk-takers. Quite the opposite. My father was raised by parents who lived through the Great Depression and my mother by coal miners in West Virginia. My father served 27 years in the Air Force and my mother over 30 years with AT&T. A stable risk-free life was what they cherished.

When I was young, I had a summer job pouring concrete. If you’ve never poured concrete in the summer in Virginia, let me paint the picture for you: it’s backbreaking, it’s hot, the hours are long, and the pay is modest. I quit that job. And my parents? They were not thrilled. They fretted. They worried. They couldn’t believe I would walk away from a paying job with nothing else lined up.

But I did it anyway because I knew from friends that there were better jobs. And within days, I had landed a higher-paying job. It turned out great.

Now, that might sound like a small thing. A kid quitting a summer job. But it was the beginning of a pattern I didn’t fully recognize until much later. Because the same thing happened again, and again, at higher and higher stakes. I left the military, and the people around me worried. It turned out great. I landed a software engineering job at GE that jump started my career in tech. I left PayPal for a startup, and people thought I was out of my mind. It turned out great. That startup was acquired by AOL with me as the CTO. Everytime it felt like stepping off a cliff. And always, people fretted.

But here’s what I learned through all of those leaps: I had to choose who I surrounded myself with. Because not everyone in your life is going to believe in the risk you’re taking. Some people love you and will still try to talk you out of it, because their fear for you is louder than their faith in you. That doesn’t make them bad people. It just means they can’t be the ones in the room when you’re making the decision.

Over time, I learned to build that room. My wife, who didn’t flinch. Who looked at the uncertainty and said, “We’ll figure it out.” Friends who didn’t question my sanity but asked the right questions and believed in what I was building. They didn’t remove the fear, the fear was very much there. But they kept fear in the passenger seat. They helped me keep my hands on the wheel.

And this is what I want you to understand as you go out and build your careers, your teams, your organizations: the people around you are not incidental to your success. They are foundational. You will rise or shrink to the level of belief in the room. If you are surrounded by people who see risk as reckless, who respond to every new idea with all the reasons it won’t work, who value safety above all else, you will internalize that. You won’t even notice it happening. You’ll just gradually stop raising your hand.

But if you surround yourself with people who believe in purposeful risk, who challenge you, who hold you accountable, who are honest about the downsides but refuse to let the downsides be the end of the conversation, you will do things you never thought possible. Not because you became a different person. Because the people around you gave you permission to be the person you already were.

As leaders, and make no mistake, that is what you are now, you won’t just be taking risks yourself. You will be creating environments where others feel safe enough to take purposeful risks too. That is the job. That is the real work of management. Not the spreadsheets and the strategy decks. The permission.

Graduates, you are leaving here with extraordinary training. You understand markets, operations, strategy, leadership. You have frameworks for analyzing almost anything. But the moments that will define your careers, the ones you’ll remember, the ones that will shape who you become, won’t be the moments when you had the perfect analysis. They’ll be the moments when the analysis was incomplete, the outcome was uncertain, and you moved forward anyway.

Don’t wait for the fear to pass. It won’t. Don’t wait for the timing to feel right. It can’t. Don’t confuse recklessness with courage. And most importantly, don’t try to do it alone. Find your people. Be that person for someone else. And when the moment comes, and it will come, remember that the risk you didn’t take is the one that will keep you up at night twenty years from now.

I’ll leave you with this, from Søren Kierkegaard: “To dare is to lose one’s footing momentarily. Not to dare is to lose oneself.”

Dare greatly. Congratulations, Class of 2026.