Backpacking south america at age 23

The Most Important Thing I Learned in My 20's

This morning I woke and for the first time in ten years, I was no longer a 20-something. Today is my 30th birthday.

For those who know me, you’re aware of my love for introspection. And there’s no better moment to consider the lessons of the “defining decade” than today. I can still crisply recall turning 20. I was a sophomore at Brown, and my entire identity was as a Division 1 basketball player.Over the next decade that identity would change from a student-athlete to become a backpacker, a consultant, and now an entrepreneur. I lived in multiple cities on multiple continents, backpacked through more than 50 countries, spent time in the for-profit and non-profit spaces, working at various times as the bottom guy in a huge company and the top guy in a company of one.

When I look back throughout my twenties, I constantly felt this tension, as though my body was somehow holding back the true size of my physical existence. And although I was often scared and intimidated by the scale of my ambitions, when I met those who I revered most, I was consistently amazed that they were normal people just like me. The more time I spent around my heroes, the more the future in which I saw myself seemed attainable. And as that occurred, the grandeur of my dreams seemed less idealistic. They suddenly seemed like the logical place in which I could end up if I pursued my inner truths with optimism, honesty and integrity.

But no matter how hard I worked, or how far I traveled, I always wanted more.

And that I believe, is the defining characteristic of the defining decade — The desire to see more, do more, and become more.

At one point a few years ago when we had built just a few schools, I wrote in my journal that if Pencils of Promise built 30 schools by the time I turned 30, I could die a happy man. Today we’ve opened more than 150… But here’s the important part — I was wrong about being able to die a happy man. I still want to do so much more. As soon as something becomes possible, you start thinking of what you can do next. Each stage on which I gave a speech gave me the confidence to go bigger, each country I traveled to made me hungry to visit another, and no matter how late I stayed out at night, I always had an urge to watch the sunrise.

You will screw up, you will be celebrated, and you will feel like a loser and a winner all in the same day. And that will happen over and over. But the people who succeed are those who dust themselves off and keep going because they’re not motivated by hitting their goals. They’re motivated by getting to a place where they can set new goals that seem just as unreasonable as the ones before them once did.

Take a moment to fully grasp that — The most successful people are NOT motivated by reaching their goals. They’re motivated by getting to a place where they can confidently and audaciously move the finish line further into the distance.

Preorder my new book to read 30 more lessons just like this one.


Co-Founder & CEO of Founder of Dad of twins. Author of

Co-Founder & CEO of Founder of Dad of twins. Author of