A 39-year-old who’s been self-employed for 20 years reveals his strategy for staying productive while travelling the world

Remote work travel
Manage your day by tasks, not by hours. Thinnapob Proongsak/Shutterstock

Chris Guillebeau travels outside Portland, his home base, at least 10 days out of every month. He’s also a New York Times bestselling author, international speaker, blogger, podcast host, and workshop instructor.

Previously, the now 39-year-old travelled consistently for 11 years, while working as a freelancer, aid worker, and founder of several small businesses. He was on a quest to visit 193 countries, a feat he accomplished just before his 35th birthday.

Guillebeau has become an expert at managing work and travel, and he tells Business Insider there’s one strategy he’s picked up that’s likely the key to his success: Instead of managing his day hour to hour, Guillebeau manages his day by tasks.

“Something I’ve learned to do — which factors in a lot if I’m travelling around the world and in different time zones — is I base my productive output entirely on deliverables and not on a time-based schedule or calendar,” he said.

Guillebeau began writing “The Art of Nonconformity: Set Your Own Rules, Live the Life You Want, and Change the World,” the first of his four books, around 2008. Since then, he’s aimed to write 1,000 words a day, rather than focusing on writing for a certain amount of time each day. While he hasn’t always reached the mark, he says that goal helped him develop the “powerful” task-based approach over the last several years.

“[I]t’s always like, ‘OK what do I need to produce today?’ and I’m going to adjust my work calendar, my life calendar, to accommodate that,” he says.

Other productivity experts have lauded the benefits of task-based work days, including Laura Vanderkam, who says you shouldn’t live by the same, 24-hour daily routine, and Chris Bailey, who sets three specific goals every morning to accomplish by day’s end.

“I don’t like to generalize about generations … but I do think it’s becoming more and more common that maybe younger generations are much more embracing this idea of, ‘OK what do we actually have to produce? What are the deliverables? The outcome? And then how do we make that happen?’ As opposed to, ‘Here’s our 8 to 5 schedule,'” he said.

Ultimately, Guillebeau says, “the greatest productivity tip” is finding work you truly enjoy doing.

“I don’t believe this whole thing, ‘If you love your work, you’re never going to work a day in your life’ — I hate that. But I do believe that if you’re excited about what you do then you’re naturally going to be more productive,” he said.

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