Era Two: The Corporate American Refugee (2010–2012)
For two years, Ottsworld wasn’t the biggest thing I was running. This was.
In 2007, midway through that first trip, I spent a month volunteering as an ESL teacher in India through an organization called Cross-Cultural Solutions. A program manager there named Michaela Potter started following my blog for work. She and her boyfriend Michael had just quit their jobs together to travel. By early 2008, all three of us had landed back in New York City at the same time, each of us changed, each of us asking the same question: why is it so hard for Americans to take extended time off to travel?
Other countries encourage gap years and sabbaticals. Americans wear our productivity like a badge and act like that’s what makes us valuable — and then we wait until 65 to see the world. Time away from a routine is how people grow. Other countries do this. Why couldn’t we? We were taking on the American work ethic itself, and our Big Fat Hairy Goal was a career break on every resume in the country.
We called the first version Briefcase to Backpack. In January 2010, over coffee in San Francisco, Michaela and I decided a blog wasn’t enough — people needed to be in a room together — and Meet, Plan, Go! was born. The idea was simple and a little crazy: one night, one shared program, hosted at the same time in cities all over North America by volunteer hosts, most of them career breakers or travel bloggers themselves. The first national event was September 14, 2010.
Eat, Pray, Love had hit theaters six weeks earlier (a friend gave me that book before my own trip in 2006, back when nobody had heard of it — I’ve always said if I wrote mine it would be called Eat, Pray, Reality), and suddenly a whole country was asking why they’d never taken time off. We had an answer ready. A month later, the New York Times wrote about us. The next year we were in 17 cities! I did a CNN interview about career break myths from a family’s apartment in Beirut. I got called a “corporate IT refugee” in print so many times I started using it myself.
That same year, 2010, I turned 40 and wrote the third post in this series: “This is Now.” The subtitle was “40 and Happy.” I meant it. I was leading something. I was helping people make the same leap I’d made, and I could see it working. Looking out at a sea of people who wanted to change their lives, knowing you have an answer for them — that’s a drug I still haven’t found a replacement for.
It was also the era where I figured out this blogging thing could be a career and not just a hobby. I was one of the first travel bloggers working directly with brands and destinations — in spring 2012, a European apartment-rental company sent me to ‘live like a local’ in Rome, Venice, Vienna, and Berlin for a campaign called “Living La Vida Local,” back when “sponsored travel” barely had a name. I drove a tiny car from London to Mongolia for the Mongol Rally in 2011. I was busier than I’d ever been in corporate America, and a whole lot happier.
Then in 2012 Michaela stepped back from Meet Plan Go, and I ran the third national event mostly by myself. It went fine. It just wasn’t nearly as fulfilling. I already had Ottsworld, which I was running completely on my own. I was traveling on my own. I was tired of doing everything by myself — and when Michaela left, I was alone in this too. Meanwhile, Ottsworld was taking off in other directions, and I simply wasn’t capable of running both while living out of a suitcase. So I let Meet Plan Go get smaller, and eventually I let it go.
I don’t count it as a failure. A lot of people took career breaks because of those events. And the person I built it with didn’t go anywhere — Michaela shows up again in Era Six, driving a support car behind my bike across the Dakotas and producing the documentary series about it. Fifteen years, two completely different projects. That partnership is the real thing I built in this era.