Travel

In September 2009, JetBlue introduced its All-You-Can-Jet pass: $599 for a month of unlimited flights anywhere in its network. I spent most of the month crossing the country, staying in hostels and taking red-eyes when an overnight flight could double as a place to sleep. The adrenaline of constantly landing somewhere new got me hooked, and it showed me that travel could cost a tiny fraction of its sticker price.

After moving to San Diego, I got deep into the miles-and-points community: forums, conferences, spreadsheets, and the whole culture of turning credit-card points, mistake fares, and award-chart sweet spots into flights and hotel nights that would otherwise have been unaffordable. I spent a good chunk of the 2010s on the road this way, including a fully nomadic year from mid-2013 to mid-2014 and another stint from mid-2018 to mid-2019.

Those years are also why I worked the way I did: independent consulting meant I could work from anywhere, long before remote work was ordinary. I'm more settled now and travel less easily, but I have no regrets about shaping that chapter of my life around it.