A few months ago a good friend of mine moved back to the Bay Area to start working at one of the most powerful companies in the world. One night, after we spent three hours eating burritos at Chipotle and planning what kind of themed progressive we could throw at IKEA, I drove him back to the Caltrain station on the eve of his first full day on the job. As he got out of the car, he looked me in the eye and said, “Molly, I’m scared. I just want to work at Jamba Juice.”

As you can expect, my jaw dropped (and along with it my Diet Coke).  John exuded confidence. He had been extraordinarily successful at Stanford, had just spent the last few months seeing more of the world than Carmen San Diego had and was about to jump into an entry-level position at one of the most successful companies in the world. And now all of a sudden he wanted to work at Jamba Juice?

But his comment, although uttered half-jokingly, was not completely unfounded. John was at a juncture that every one of us has faced and will continue to face for the rest of our lives. He was about to jump from the comfortable rung of wild success up and onto the next unsteady rung of the ladder, that step up that is inextricably linked with the ambiguity of success or failure. His desire to work at Jamba Juice had less to do with his projections of a personal smoothie-success rate and more to do with the fact that his new “dream job” invited the possibility of the unknown–it invited the possibility of failure.

A few months ago, one of my very best friends from home became the North Dakota Truman Scholar. Although I was absolutely thrilled for him, I couldn’t help but also feel a little disheartened. I had made the leap from the small pond of Fargo South High School to the Pacific Ocean of Stanford University and was nowhere near becoming a Truman Scholar. As I was whining to a dear friend of mine about whether or not I should have stayed closer to the small pond where success was a sure thing, he looked at me and said point-blank, “You wouldn’t have been successful. You would have been stagnant.”

As much as it pains me to admit it, he was right. I would not have been happy had I stayed in North Dakota just as John would not have been happy working at Jamba Juice. Although we may be absolutely petrified the moment we take the leap into deeper waters, we also know that the risks of missed opportunity vastly outweigh the risks of potential failure. It is far easier to say “Why not?” than it is to say “What if?”

Five months later, John has found both his cloud and his silver lining. He hates his job, but at least he is SURE he hates his job. As he reflected to me on what his life has meant in the past few months he remarked, “This is the first time I’ve ever seen this in myself; I KNOW I can’t do it. Somewhere deep down there’s a gear that I don’t have that will keep me from truly succeeding in this position…But I knew I had to try it.”

John had to try it because he wouldn’t have been happy if he hadn’t. As much as it may kill us to know that there is a limit to our potential, it kills us even more to think that we may not be truly living up to our potential. One of the greatest things I have come to love and admire about my peers at Stanford is that there is no limit for what they can imagine. We are not going to stop dreaming until we are broken, until we finally reach that rung on the ladder that so vehemently and violently shatters our egos and our self-worth that we are thrown off the very precipice of our success, no longer wondering “What if?” but screaming “Thank God!”

Simone de Beauvoir once said, “There are people filled with such horror at the idea of defeat that they keep themselves from ever doing anything. But no one would dream of considering this gloomy passivity as the triumph of freedom.”

Until we reach that point of defeat we are going to keep climbing, an act I believe is simultaneously one of the most admirable and terrifying characteristics I have ever discovered to exist in people. That refusal to be stagnant, that blind determination that prevents us from settling for anything short of our absolute maximum potential is one of the greatest indicators of success I could ever hope for. And although ultimately you have to just do what you feel, I believe there is far greater fulfillment to be found in being broken but triumphant than stagnant and still dreaming, “What if?”

Molly’s life goal was achieved at age 17 (when she got into Stanford) and she has consequently spent the last three years (unsuccessfully) searching for a new one. E-mail suggestions to [email protected].