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#009: Turning Points

Hello from Manhattan. Our newborn, Flo, is now smiling, tracking movements, and looking at her hands. I love seeing her consciousness come online and her personality begin to emerge. She’s changing a little bit every day, and I’m grateful that I’m able to witness this transformation and

#009: Turning Points
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#008: Starting a Solo Lifestyle Business

Hello from Tribeca. I spent the first half of the week upstate with my family, enjoying peak foliage and the crisp autumn air. Seeing red, orange and yellow dot the mountains never gets old, and reminds me of playing in piles of leaves as a kid in New England. Transition

#008: Starting a Solo Lifestyle Business
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Sailing in the Present Towards the Future

Imagine you’re in the middle of the Pacific Ocean on a perfect day with sunbeams and a gentle breeze engulfing you, the captain of a majestic 100-foot sailboat with a towering mast and massive sails that can propel you to any destination on the planet. It’s just you,

Sailing in the Present Towards the Future
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Navigating Our Lostness

A few weeks ago I was on a meditation retreat in upstate New York. On the first night, preparing to observe silence the next day, I stood in a dark hallway talking with Jonathan, a prominent psychoanalyst. Behind us, a soft red glow from the EXIT sign above the door,

Navigating Our Lostness
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When Our Fire Stops Burning

I could hear the hum of traffic outside our Flatiron office—sirens, horns, and idle engines—and I might as well have been outside instead of the four hour “partner meeting” I was in. Packed like the Holland Tunnel at rush hour with twelve of my colleagues in a white

When Our Fire Stops Burning
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That Mountain You’ve Been Climbing Doesn’t Exist

On July 4, 2005, as the sun was rising above the horizon and peaking through the clouds, I was climbing the south face of Mt. Adams in Washington. At 12,281 feet, it’s one of the most popular training destinations for climbers gunning for larger peaks like Rainer. After

That Mountain You’ve Been Climbing Doesn’t Exist
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I Just Walked Away From My New Venture Fund. Here’s Why.

A week ago I sat down at my computer. Still staring at the blank screen, my heart rate began to spike. The butterflies in my stomach were going wild, and my inner voice started agitating: Are you really going to do this? Are you really going to walk away from

I Just Walked Away From My New Venture Fund. Here’s Why.
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The Ultimate Annual Review

2020 has stretched us unlike any year in history. All of our lives have been upended. We've had to cope with COVID-19, social distancing, work from home, the election, economic hardships, and much more. This year has been truly unprecedented. Thankfully, it's time to turn the page on 2020 and

The Ultimate Annual Review
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Goodbye NYC...See You In 2021

Today my wife and I finished packing our apartment, moved all of our belongings into storage, and said farewell to New York. It’s surreal to even type these words. I’m filled with a range of emotions: sadness, nostalgia, guilt, regret, and even excitement. As I walked down Broadway

Goodbye NYC...See You In 2021
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40 Lessons From 40 Years

I turn forty today. I can’t even believe I just typed that sentence. Over the past month, I've been reflecting on the lessons I’ve learned directly through experience or indirectly from family, friends, mentors and teachers. I wanted capture and share these learnings for one important reason: I’