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One Man’s Quest to Leave the Oil Industry and Complete a 100-Item Bucket List

Matthew Bailey left the opportunities of the booming oil town that he grew up in to live a more authentic life. Ten years later, and with over 100 bucket items checked off, a new, bolder Matthew is still dreaming up more audacious quests to accomplish.

I'm a small town guy who grew up in Northern Alberta. Although it seemed normal to me at the time, the town I grew up in is anything but - it’s an oil town where almost anyone can make six figures a year, regardless of education or age. Instead of cashing in, I escaped.

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When You Need to Escape, Build Your Own Countdown Clock

Before my dad packed up his cubicle and moved to a beachside office, he created a spreadsheet that displayed the number of days that remained until his retirement age.

It soon became a topic of dinner table conversation: “Hey, Dad, how much longer at the day job?” I’d ask. He’d respond with something like, “Oh, I don’t know exactly . . . well, I guess I do. Looks like I have 673 days and 4 hours to go.”

When you’re trying to escape a dead-end job or any other undesirable situation, create a calendar and count down the days to freedom.

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Escape to Reality

It's a fairly typical island, as these things go. It took a while to make it here, with connecting flights through Hong Kong and Kuala Lumpur. It operates on island time, where breakfast goes until 11am and happy hour is at least a four-hour period beginning in the late afternoon and continuing indefinitely.

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