Reflections on my TEDxPrincetonU Talk: How to fail successfully

November of 2013, I gave a TEDx talk on how to fail successfully based on my own experiences. At the time, I was a budding entrepreneur who was working on a multitude of ideas including one that I laugh about most: The Conversation Coach.

The main point of the talk was: “For my entire life I was taught how to be successful, but I was not taught to fail.” But “the only thing that’s certain about the future is that it’s uncertain. So failure is inevitable. And if failure is inevitable, we need to work that into our process of learning and growing.”

I decided to share this message because the first time I failed in a big way, I spent an entire month in a haze of depression. I slept no more than 4 hour a night, lost ten pounds, and spent my days curled up on the floor crying. It wasn’t until I found my next job that I was able to come out of that haze.

Luckily for me, at the same time I was battling my depression, I held on to rock climbing, and rock climbing became the vehicle by which I slowly came to the understanding that failing wasn’t a knock on my personal worth, failing was just part of life.

The lessons I learned from rock climbing on how to fail successfully were:


I still follow these lessons today.

I’m sharing this video now both because I finally got around to creating the transcript and because in taking on my newest challenge as an entrepreneur – starting a non-profit that’s all about building community – I’ve made the space to think deeply about my personal strengths, areas of growth, and leadership development.

And guess what? I still find it difficult to accept that failure is part of life.

Like I said in my most Quarter in Review, “I am afraid of failing. Before, if I failed at something, the person most affected long-term was me. I was the one who bore the brunt of lost revenue, or reputation. But if I fail with #NYCEDU, large or small, I feel that I will have failed a community of people, of people who had placed trust into me and into the vision, hopes, and dreams that #NYCEDU promises to cultivate.”

And so if I were to do this talk again today, I would say that the learning of how to fail successfully is a process in and of itself that never ends, because the problems we tackle will grow in difficulty, that sometimes we’ll even fail at failing successfully. And that, too, is okay.

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