Grant and I couldn’t quite decide how to “do” Chicago. We had booked cheap flights months ago—one of those fares that pops up and feels irresponsible not to buy—and told ourselves we’d figure out the details later. As the trip got closer, we still didn’t have a real plan. That’s when I did something bold: I let Grant take the lead.
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This is how we choose our travel destinations. Grant randomly searches GoogleFlights and finds a spontaneous sale on a nonstop weekend flight to Chicago in November. He turns to Emily and me at dinner in Cafe Coyote (San Diego) and goes “want to go to Chicago? He waited a few seconds to make sure no one objected and the response was pretty quiet. Which was his queue to proceed with “I am going to book three flights.” Once again no major objections. And just like that…we are on an adventure to Chicago.
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