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Two days after learning of the layoff, Kyle was out jogging when tragedy
struck in the form of a pickup truck that ran into her at a crowded intersection,
sending her flying a hundred feet from the point of impact. Her injuries weren’t
life-threatening or permanent, but as you’d expect, Kyle was badly hurt. After a
week in the hospital, she spent several more weeks at home, unable to walk and
with so many bruises that she couldn’t even type—thus ending the side gig with
AOL, which was done on a contract basis. “Between my husband’s layoff and
getting run over by the car,” Kyle told me with a straight face, “it was kind of a
bad weekend.”
Kyle and Seba had been married for nearly three years at that point and hadn’t
ever had a real honeymoon, so they decided they might as well take vacation
time while they could. Instead of looking for work, they booked flights to Italy
and spent several weeks seeing Europe for the first time. Before the accident,
Kyle had been dabbling in wedding photography. She had never really tried to
make a career of it, but before flying out she updated her website and announced
that she was accepting new bookings. A request came in right away, giving Kyle
confidence that she might be able to make some kind of career out of it.
When they returned to Chile, Kyle and Seba decided to try photography full-
time, “at least until the bookings stopped coming and the money ran out.” To
their surprise, request after request arrived in Kyle’s inbox, and the schedule
quickly filled up. Two years later, they were making $90,000 a year and were
fully booked another year in advance.
They now work all over the world, doing weddings in Argentina, Spain,
England, and the United States. You might wonder what the big deal is with
Kyle’s work—since there is no shortage of other good photographers available
locally, why do clients fly her from country to country? Kyle says that her clients
are usually well traveled themselves, and aren’t afraid of hiring someone from
afar. “They know that the world is a small place,” she says, “and they like our
work because we build relationships over time.”
Case Study 3: The Spreadsheet King†
A description of Bernard Vukas’s work space is typical of roaming
entrepreneurs: “I work from anywhere, anytime. Time zone and location are
irrelevant. All my property fits in a single backpack, including the laptop,” he
told me in an email from a beach in Koh Tao, Thailand, where he was living on