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IT’S 11:26 a.m. in California and Tim Ferriss, who has turned his personal tactics for streamlining life’s chores and savoring its pleasures into best-selling books like “The 4-Hour Workweek” and “The 4-Hour Chef,” is timing himself to see how fast he can get from his house to his departure gate at San Francisco International Airport.

Using Uber, a cashless car service, and Clearcard, a fast-pass for airport security, he zipped from home to gate in 20 minutes. A friend making the same flight spent 33 minutes on the security line alone.

“I had lunch and polished off two conference calls before my friend even got his shoes back on,” Mr. Ferriss said.

If there are upsides to obsessive-compulsive behavior, traveling efficiently is one. I consider myself a nimble traveler, able to fold a dress into the size of a croissant and get out of the airport before most passengers can even find the baggage claim. But as I grilled Mr. Ferriss and a handful of his Silicon Valley peers, who have made a sport of stripping time and pain out of routine nuisances, it was clear that even I could learn a thing or two. (Like when to pack a starter pistol, but more on that later).

For a certain type of frequent-flying entrepreneur in and around Silicon Valley, travel is an art form — one that doesn’t require private jets and fat wallets. Rather, they have perfected the art of traveling comfortably, without anxiety or wasted time. I caught up with half a dozen of these travel aces from companies like Google, Klout, Yelp and LinkedIn and pumped them for pointers on how to make planning and taking vacations as effortless as shuffling an iPod.

More at Designing Your Trip


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