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Jason

The Five Best Moments of Your Life

It’s nearly 2:00am. I’m sitting across the table from an extremely successful investor at a 24/7 dinner. I order a decaf. He orders a house salad and a milkshake. I can’t figure out if this is the smartest thing I’ve ever seen, or the most pointless. I still don’t know. This guy is made of money. Before he was an investor, he was an executive at a Fortune 500 company. If he stopped working today, several generations of his family would still be able to live in luxu...

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How to run away: using a personal retreat for gaining power over your reality

A confession: I’m a bit of a flake, at least concerning my relationship to life and the world. Sometimes, we get along. Life seems… Overwhelmingly beautiful, enchanting, and lucid Like something I can savor and enjoy as it unfurls Like something that I can control, shape, and create, where I’m limited only by the confines of my imagination, focus, and energy Other times, we don’t. Then, life’s more like… Impossibly confusing with no hope of ever being controll...

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Understanding the mind: 9 design flaws

When I was six years old, my Dad asked me two questions that would change my life. He asked, “What do you want to be when you grow up?” I said, “A professional magician!” He followed with, “Why do you have to wait until you’re an adult to do that?” At six, I was blessed with naiveté and optimism and couldn’t come up with a good answer to his question, so I put together a little magic show and performed at my neighbor’s birthday party. By ...

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You’re never really ready. That’s Ok. Lets Begin. Or, how a pair of jeans triggered an epiphany

I’m almost embarrassed to admit this: a pair of jeans once triggered an epiphany for me… Hong Kong, 2006: I was 19 years old and studying abroad in Hong Kong. I always admired the way guys dressed there. They seemed so cool and put together, like the people who pick up on the trends before they’re actually trendy. Me? I was just some kid from the American suburbs trying to fit in with his Abercrombie shirt and ironic Mickey Mouse watch (and no, I don’t love admitting...

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What no one tells you about leaving the beaten path

My college roommate, Will, and I had a tradition. On the last night of each semester we pushed our beds together and fessed up to all the stuff that we hid from one another during the semester (And yes, I’m aware that’s weird.) Generally it was stuff like, “I used your hair product for 3 weeks ” or, “I made out with a girl on your bed.” But this time, I had a real confession. A fear.  He knew that I had plans to drop out of college and travel the world sta...

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