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Adventures in Travel Hacking

Greetings from LHR Terminal 3, soon to be departing to San Francisco after a weekend in London for the U.K. launch of The $100 Startup. We've had a lot of new readers join our community over the past month (hi, everyone!) and I thought it would be good to provide an overview of travel hacking: the means of seeing the world in style while on a budget. For the past five years, I've been to at least 20 new countries a year on my quest to go everywhere. In addition to overland travel by bus or train, I get to many of them through a variety of paid and almost-free plane tickets ...

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The Latest in Travel Hacking: Earn Free Airfare in 2012

Happy New Year!

On Sunday's long run, I pushed it to 12 miles in honor of 2012. I then tried to eat 12 pieces of nutella pie as a reward, but that plan fell through after piece #2.

As you're thinking about a new year, here's a free tip: forget resolutions; think about living intentionally instead.

What matters to you this year? Do that.

What do you hope to build in 2012? Work on that.

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Business Goals for the Travel Hacking Cartel

I was all set to go on national TV Friday morning to discuss travel hacking, but then I got a frantic message from the producer: “Have you been to Egypt?” Why yes, I said, I have—not checking the news, since I was thinking ahead to the segment for which they were interviewing me. The next message came three minutes later, saying they were dropping travel hacking in favor of Egyptian riots. Since bringing democracy to a country that has lived with a dictator for three decades is probably more important than earning a free plane ticket, I decided that decision was fair. I went back inside and changed into a t-shirt ...

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2010 Annual Review: Looking Forward

After looking back on the year that's nearly finished, I spend most of my Annual Review time thinking ahead to the forthcoming year. While I wrapped up the 2010 review and looked ahead to 2011, here are a few of the summary notes I wrote to myself:

As a big 2010 came to its conclusion I felt purposeful and satisfied, but also on the verge of overwhelm. 2011 and 2012 will be even bigger – how can I maintain momentum without forgetting to live in the moment? This is the challenge and the opportunity of the year: to create sustainable growth in all areas while retaining a core sense of identity.

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The Latest In Travel Hacking, “Volcanic Ash Karma” Edition

I lived in Seattle from 2006-2008 without a car, which worked well about 80% of the time. The other 20% of the time, I spent a lot of time waiting on street corners for the bus to arrive. It was frequently late, but once in a while, I'd get to the bus stop right when the bus was pulling up. My friends and I called this “good bus karma” which we ascribed to previous 40-minute waits when we had just missed it.

Last month during the British Airways strike, I walked around a deserted Heathrow airport terminal with departure signs reading CANCELLED. Meanwhile, my flight went out as planned, albeit on a chartered “EuroAtlantic” flight where the meal consisted of a paper bag filled with bananas (seriously) and half a bottle of one-euro red wine. I was grateful for the bananas, but mostly for the flight.

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Extreme Gratitude, D.C. Edition

Friends and readers, greetings from AA flight 84, en route to the Dallas Ft-Worth airport. I’ve been there several times recently, and am thinking of setting up a tent around A-20. Thanks so much to everyone who came out to our meetup in Washington, D.C. on Thursday night. I had a great time and was humbled as usual by all the fun and interesting people who showed up.

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How to Request an Airline Status Match

In 2008 I earned Executive Platinum status with American Airlines the hard way– through lots of flight hours logged all over the world. In 2009 I also earned the same, highest-level status with Northwest, Delta, and Continental, but I flew less than 10,000 miles with each of them.

On a recent Atlanta-Miami flight operated by Delta, my upgrade cleared three days ahead of the flight. I watched as more loyal Delta passengers waited at the gate thirty minutes before departure in hopes of getting a seat up front. Is it fair? Depends on how you look at it, I suppose– but travel hacking is all about gaining some kind of advantage over the system.

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The Monster Trip of 2009

Last year at about this time, I took what I called the Monster Trip of 2008.

It involved four continents, driving through Italy in the middle of the night, visiting Iraqi Kurdistan, roaming by train and bus across the Baltics and Moldova, and finally coming home through Asia – where I mistakenly double-booked myself on two non-refundable tickets home from Japan.

What fun that was. Now it's time to repeat the process, although with a completely different itinerary, and hopefully without getting stranded on a faraway continent three days before I'm supposed to come home.

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The Heart of the Matter

heart-of-the-matter-freetown-sierra-leone Here I am in Haiti, a country I've been reading about for years but have never been to before. My accommodations are as basic as advertised, and that's just fine for a few days. If you ever find yourself in need of humility, come down here and spend the week with nuns and missionaries. That should do the trick.

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What Is First Class Travel Really Like?

Rerouted-Stream The flight attendant escorts me to my seat in 2B. She waits as I put my things down, and offers to hang my jacket. I spread out my books, journal, and iPod over the seat next to me, because I already know the front cabin is half-full and they’ve blocked the seat next to me at my request.

Not that I need the room – the seat is huge. It reclines fully flat so that I can go to sleep after the five-course meal.

As I’m getting settled, another flight attendant comes by with a tray of orange juice, champagne, and water. If I hesitate, he’ll ask, “Would you prefer a mimosa, or maybe club soda with lime?”

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The 2:00 a.m. “Stuck in Portland” Redesign Launch Story

I mentioned in the comments about the redesign that there was a back story to this week’s launch, and I thought I’d share the whole story here for those who are interested. According to the new publication schedule (Mondays and Thursdays for main content), you can also check back tomorrow for a more typical article.

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