Social entrepreneur on a mission to even the odds for future generations.

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Strain to Gain

“I want to be thoroughly used up when I die, for the harder I work the more I love. I rejoice in life for its own sake. Life is no brief candle to me. It’s a sort of splendid torch which I’ve got a hold of for the moment and I want to make it burn as brightly as possible before gratitude handing it in to future generations.” - George Bernard Shaw

Heat and pressure privilege any lump of coal humble enough to admit its origins, patient enough to endure the struggle, and bold enough to blossom. Diamonds are borne of heat and pressure.

In the last few years, I’ve noticed that my most meaningful personal discoveries often emerge from the periods of greatest strain. Since determining that meaning produces my happiness, and strain (especially when coupled with reflection) produces meaning, I’ve concluded that strain leads to personal happiness.

-Strain doesn’t just come from “valleys” (the...

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Speeches, Essays, and Short Stories that Have Changed My Life, Part I

Personal Growth and Leadership

Personal Renewal, by John Gardner

Solitude and Leadership, by William Deresiewicz

The Disadvantages of an Elite Education, by William Deresiewicz

This is Water, by David Foster Wallace (VIDEO)

Conan O'Brien’s 2011 Dartmouth Commencement Address (VIDEO)

Conan O'Brien’s 2000 Harvard Commencement Address (VIDEO)

J.K. Rowling’s 2008 Harvard Commencement Address (VIDEO)

Eric Thomas’s “How Bad Do You Want It” Speech (VIDEO)

Leaning into Reality

The LeanGains Guide, by Martin Berkhan

Discourse, by Mark Twight (this is a collection of short essays, all of them worth reading)

Nonmoral Nature, by Steven Jay Gould

Surfing: the Royal Sport, by Jack London

To Build a Fire, by Jack London

Effecting Change in the World

Letter from a Birmingham Jail, by Martin Luther King Jr.

Creating Shared Value, Harvard Business Review

Collective Impact, Stanford...

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Books that Have Changed My Life, Part II

This post is a continuation of Books that Have Changed My Life, Part I.

As time passes, I spend less time reading newspapers, magazines, and social media posts, and more time reading books. The information is denser, and the intellectual return-on-investment is higher. Plus, the news cycle is all garbage anyway; I usually find out about important events by asking others what’s happening in the world, then researching the things that sound interesting. But there are so many problems with the news cycle that I usually don’t even think it’s worth participating. More on this another time; the point is that books have become my strong preference, over all other types of media. Here in Part II are mostly books that have shaped my worldview in 2013; most have something to do with the philosophies and practices of peace, conflict, resilience, randomness, achievement, generosity, evolution, and...

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3 Things I Learned Serving as a 22-Year-Old Entrepreneur-in-Residence for the U.S. Government

My post serving as one of five entrepreneurs in residence for the U.S. Government ended in May. It was a huge (and surreal) honor, and a learning experience that still hasn’t fully digested. I’ve been writing and will continue writing about the experience, but here are three quick takeaways:

  1. D.C. may be full of hot air, but many of its leaders know what they’re doing and don’t get enough credit. I was blown away by the open-minded, outcomes-oriented, bipartisan approaches of leaders at the White House and Homeland Security. The Administration is serious about infusing bureaucracy with entrepreneurialism, and its actions speak louder than any words you’ll hear or read in the media.

  2. Government needs more entrepreneurs. Many of government’s problems stem from an overpopulation of lawyers (naturally risk-averse) and lifetime politicians (naturally short-termist). Where are all the...

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31 Things I’d Have Told Myself Before College

It’s been almost a year since I graduated from college. I had an incredible four years at the University of Chicago, and learned more than I could have ever anticipated. Now that it’s in the past, I sometimes wonder: what do I wish I knew before entering college that I know now? Here’s the advice I’d have shared with my 18-year-old self:

  1. Master the art of asking great questions.
    Questions are the driving force of learning. The faster you can optimize your ability to learn, the faster you’ll get where you want to go.

  2. Outside of exams, forget about knowing the right answer—you’re wrong most of the time, anyway. What’s more important is knowing where and how to find the variety of answers that are most likely to be right.

  3. Talk 20% of the time; listen 80% of the time. One of the fastest ways to win someone’s favor is to give them permission to talk excessively about themself—you can do...

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Why Leaders Exist

It’s easy for us to complain, bicker, and point fingers at power.

It’s a lot harder for us to rise to the occasion, to stand up and fight for what we believe.

The fight worth fighting is not easy. But for those of us who somewhere deep down believe in the possibility of a better future, the difficulty of action is no excuse not to act. We know hope is real. We’ve felt it. We’ve seen it. We’ve seen a single flame, ignited out of thin air, light a pitch black room. We know what we need to do and it’s our job to do it. We must lead.

In On Leadership, John Gardner explains why leaders exist: to offer “hope in a world that often gives little ground for hope; the quest for justice in a world only fitfully committed to justice; love in a world that is often unlovely and unloving; the hunger to understand things that elude understanding; the capacity for awe, wonder, reverence…”

The world...

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Books that Have Changed My Life, Part I

Charlie Jones said “The only difference between where you are today, and where you’ll be a year from today, are the books you read and the people you meet.” Since I started reading voluntarily at the age of 14, books have had a huge influence on my life. Most of the books below are ones I’ve read multiple times, dog-eared dozens of pages in, and given as gifts. They and their authors have shaped who I’ve become.


Time Management, Career, Behavior, and Health

Mastery, by Robert Greene

The Startup of You, by Reid Hoffman and Ben Casnocha

The 4-Hour Workweek, by Tim Ferriss

The 4-Hour Body, by Tim Ferriss

The Power of Full Engagement, by Tony Schwartz

Philosophy, Pyschology, and Worldview

Meditations, by Marcus Aurelius

Letters from a Stoic, by Seneca

Tao te Ching, by Lao Tzu

As a Man Thinketh, by James Allen

Man’s Search for Meaning, by Viktor Frankl

How We Fall in Love...

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Quotes that Have Changed My Life

If you follow me on Facebook, Twitter, or Linkedin, you know I’m always posting quotes. I’m a total quote junkie. It’s how I get through the day. Here are the ones I’ve printed out and taped to mirrors, written on my hands for inspiration on sad days, crammed into the front covers of Moleskines, and have memorized for opportune recitation. ;)

“If you’re going through hell, keep going.”

  • Winston Churchill

“It takes conviction and vulnerability to believe in something, and absolutely no balls to tear it down.”

  • Eileen Guo

“It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or...

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Nothing Beautiful Happens in a Vacuum

“Only in the synthesis of the most diverse fields of knowledge does life reveal its full intensity. Today, in a time of globalization and collapse of national identities, this is as true as ever. The age of specialization is over. Mixing together aspects of life that have apparently little to do with each other will be the essential talent of the twenty-first century. It is time for an athletic philosophy: a philosophy forged through muscles and heart; a philosophy born out of the union of body and mind, of pragmatism and utopia, of sweet sensitivity and a warrior’s determination.

Martial arts are no exception. Restricted to "insiders only,” they are nothing but a ghetto. Grey. Small. Limited. No surprises. No horizons. Not a single great vision can live within its borders. Only when martial arts become part of a larger picture can we see their full potential and beauty. Traditionally...

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Nature Loves Courage

‎"Nature loves courage. You make the commitment and nature will respond to that commitment by removing impossible obstacles. Dream the impossible dream and the world will not grind you under, it will lift you up.“ - Terence McKenna

It takes little courage to dream.

Dreams are just fantasies, and fantasies are a dime a dozen. Whether it’s of a different career, different colleagues, a different family, different children, different friends, a different partner, a different body, a different face, a different set of talents, different habits, or a different past, we all fantasize. We all dream.

It’s comfortable to imagine a distant fantasy in which we’re happy and satisfied. Living in a dreamed-up delusion, we begin to feel these emotions prematurely and we become addicted to them. It’s comfortable to sit waiting, wishing, hoping. It’s comfortable to pass the time. It’s comfortable to...

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