Advanced Travel Planning, July-November 2011

I've been stuck in one place (mostly) for the past three months, working on two projects that required focus: writing a book manuscript on unconventional entrepreneurs, and preparing to host the World Domination Summit this coming weekend. During last year's Annual Review, I knew these two projects would keep my feet to the ground for a while, so I had planned on doing the majority of my faraway travels during the second half of the year.

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The Need for Change

I talked with my seatmate Rachel on the flight to Singapore. She was 6G, I was 6H—Cathay Pacific Business Class. I was sitting up front thanks to my Platinum status and a big stash of Frequent Flyer Miles. Rachel was up front thanks to the global bank she worked for, which after a brief display of frugality was now back to flying even its junior employees in Business. Rachel was the same age as me. She had traveled to much of the world, but hadn't really seen anything. It was always running back and forth, flying to meetings, going to business dinners, arriving late at night back in the big Asian city where she was based before getting up early for more meetings.

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Hello, My Name Is…

I'm not a minimalist. I think it's good to be intentional about what you own and how you take up space in the world, but I have no desire to move to a 300 square foot apartment and religiously track the number of socks that I own. I'm not a lifestyle designer. As far as I can tell, I've been designing my lifestyle since 1978—that's part of never having a real job, pursuing the goals I've been working on for ten years, and non-conformity in general. Technically I'm location independent, but I have a home in Portland, Oregon. I could live entirely out of my carry-on bag if I wanted to, but I don't want to ... so I don't.

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Rain Running

Every Sunday morning that I'm in town, I head out for a long run. Two weekends ago at the waterfront, the weather was glorious. The whole city of Portland took up jogging or cycling. Last weekend at the waterfront, the weather was more to our usual end-of-Spring form ... rainy and gloomy. The whole city of Portland stayed indoors. On the sunny day, joggers and cyclists smiled at each other with a mutual appreciation of our good fortune. The implied message was, “It's good to be alive!”

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Most People Are Good

My friend Danielle has a five-year-old-son. One day he came home from kindergarten, and Danielle asked what he learned. “We learned not to talk to strangers,” he said. “Because strangers are bad.”

“Really?” Danielle said. “Do you think strangers are bad?”

Her son thought about it and wasn't sure.

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The Good Job

I visited a large company to give a talk about non-conformity and adventure. From all appearances, it was a well-run company doing good things. Many of the employees came up to me afterwards to chat, and I asked each of them, “How are things at _____?” Most of them said that things were good, and I had no reason to doubt them.

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Race to the Airport

You thought you had plenty of time, but something went wrong. Having spent too much time thinking about what to pack, you spent even more time reevaluating at the last minute. You overslept, or you forgot about the time zone change. The bus came late, or the traffic jammed up. Whatever it was, as you head out the door, you run up against an uncomfortable fact—you're late. Not fashionably late, not pressed for time, just ... LATE. Thus begins the sense of apprehension. “Will I make it? What will happen if I don't?”

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9 Years, 7 Months, and 20 Days Ago

Over the course of several weeks, I remember following the news of the attacks on the United States and slowly processing how the world had changed. Out of that experience I took a serious look at my life, determined I was unsatisfied, and resolved to make some changes. Jolie and I had been in New York the week prior, and the experience was naturally reflective. Was I ready to die? Was I satisfied with what I had done in life thus far? The answer was clear on both points: absolutely not. I had to find a way to do something much more meaningful than I had done up to that point ...

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