What To Do When the Unconventional Opinion Is Wrong

When I'm not roaming the world, I live in Portland, Oregon, land of strong coffee and tall bikes.

Portland is a fun little place, and it also happens to be one of the most progressive cities in America. You can buy marijuana at a food cart beginning at approximately age twelve.

When George Bush (the first one) visited Portland, so many people turned out to protest that he dubbed the city “Little Beirut.”

Walking down the street on any given day, you'll be accosted by people who want you to save the rain forest or support homeless anarchists.

For the most part, it feels like home.

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Lessons Learned from 11 Years of Travel

Last weekend I had the honor of speaking to 600 people at Frequent Traveler University, a conference devoted to the world of points and miles.

A longtime friend, Gary Leff, asked me to share a few lessons from the 11-year journey to every country that just wrapped up a few weeks ago in Norway. What have I learned?

Good question. I thought about it for a while and here are some of the highlights I came up with.

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The “Help Someone for Free” Experiment: Results & Observations

Greetings from the road to Anchorage, Alaska—or actually the sky, since it's a long drive to Anchorage for most of us.

Last week we had a real-time experiment where I invited readers to offer something for free. We received hundreds of submissions, many of them in the comments thread of the original post and many others through independent blog posts.

Today I'll share a few highlights from the original post, as well as a couple of observations on the process.

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How Can You Help Someone for Free? A Social Experiment

Dear Readers and Amazing People,

Greetings from Austin, Texas. I had a fun time yesterday with many SXSW attendees and residents of this great city. Special thanks to BookPeople for hosting, to Betty Jean for coordinating a large amount of beer and cupcakes, and to everyone who showed up.

Life is good and I'll be going for some of Austin's famous breakfast tacos right after publishing this post.

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Will It Always Be Like This?

The problem is that you want a new life, or at least some kind of substantive change.

You look at what you have, what you do, or who you are, and you long for something else.

It may be a problem of the fortunate, in the sense that you don't have to worry about what you'll eat tomorrow, but nevertheless, it's a problem.

So that's where you're at. What do you do?

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Changing the System

I'm back on the road, talking with interesting people every night. Many of them ask questions about "changing the system.” Everyone agrees it's broken and frustration is expressed all around. But what is this system, why isn't it working, and how can we change it?

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A Tale of 9 Startups

Jon was inspired by a blog post that told him to quit his job and start a business. He dutifully did so, firing off a farewell message to his boss and former colleagues. Having heard about becoming “location independent,” he bought a backpack and went off to the world. What was it about that business thing? How would he actually make a living? He would figure it out along the way, he assured himself ...

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Getting to Guinea Bissau

The biggest challenge was the uncertainty. Stepping onto the transfer bus for Heathrow Airport's Terminal 1, I considered the journey thus far and the upcoming adventure that the next few days would hold. I was coming off two weeks in India with events and media every day. Then I flew to London after two other quick stops in Singapore and Hong Kong. After making it to London I camped out in Heathrow airport for a few hours—due to flight schedules there wasn't room for a day off where I could go to the city—and then I flew down to Lisbon and eventually Dakar, Senegal.

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The $100 Startup Goes to India

Greetings from Hong Kong. I made it in from Vancouver last night and will be flying on to Mumbai shortly to begin the first leg of an extended tour in India. I'm very excited about this trip. I haven't been to India in many years—in fact, the last time I was there was right after I started writing this blog way back in 2008. This is also my first experience in presenting the ideas and stories from The $100 Startup to a crowd that is primarily cross-cultural. I don't expect that everything from the U.S. or “the western world” applies elsewhere, and I try to position myself as a learner. At the same time, however, I also believe that the ability to start a successful microbusiness and earn a good living on your own is increasingly becoming universal.

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Powerful Words

The words we use matter. Here are some examples of words or phrases that are especially powerful.

Once upon a time. The most powerful words in storytelling. No matter how long the story goes, or how complex it becomes, every story has a beginning.

You. Because in business or in life, the more you can focus your efforts on other people, the more they will care about what you say.

“Yes and ...” The two words that keep improvisation going. Hint: they can also keep any conversation going.

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What Is Freedom?

For me, everything began with the notion of freedom—the ability to determine the course of my daily schedule and overall life direction. I was very motivated by the opportunity to decide for myself. A normal job didn't fit into those parameters, so I did everything I could to create my own employment and well-being. But that was early on. Freedom is still extremely important to me. I'll walk away from any business deal or career option that restricts my choices or limits future decisions in a way that doesn't feel right ...

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Lessons from Illustrating The $100 Startup

I'm back on the road to meet readers of The $100 Startup! After a summer break where I hosted WDS 2012 with a great team, traveled to Yemen and Congo, and began work on an upcoming business project, I'm glad to be hanging out with readers again and talking about freedom almost every night. If you've read the book already, you might recognize the great illustrations that accompany the text. These were created by Mike Rohde, a Milwaukee-based artist.

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