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Finding Happiness in the Pursuit of Big Goals

Some of the greatest stories in history have been large quests. The kind where the hero goes out and returns months or years later after having battled through epic obstacles. They return triumphant a completely different person with more experience, wisdom and possibly a few scars.

Quests are not only the stuff of epic stories but the material for a deeply satisfying life. Some people have made it their lives to teach others about the outdoors or conquer the highest mountains of the world. But they don’t have to be huge, they can also be right in your back yard. Training for 10k runs or half marathons or finding powder to ski 100 days of the year are perfectly good quests as well. What they all have in common is a big goal and a long road of training and preparation ahead of them.

I’ve just finished reading The Happiness of Pursuit by Chris Guillebeau. I usually post these kind of personal development books on my other site,, I felt this one was well suited to all kinds of adventures, especially physical ones like we do outside.

The Happiness of Pursuit is all about quests. The kind that are long and arduous and require a lot of preparation. Climbing a set of 14,000 foot mountains or running every trail in your city or kayaking to every island in a province are all different kinds of quests. Some are small and some are large.

For those who have never read Chris Guillebeau on his website The Art of Non-conformity, he’s spent the last 10 years visiting every single country in the world, all 193 of them. I’d say that’s a pretty big quest. He visited about 10 countries a year and spent considerable time and money doing it. He runs his business online from his laptop so he’s free to pick up and travel whenever he needs to. He also learned an incredible amount about “travel hacking”, a new discipline of getting as many Frequent Flyer Miles as possible through often crazy methods and using those to fly around the world. He would never have been able to afford all that travel otherwise.

The main premise of the book is that everyone can dream up a quest and start it. Lots of people have before. Some of them fail. Many of them are accomplished. It is hard but it’s also incredibly rewarding to set huge goals and complete them.

The goals can be anything. Some stories from the book were walking across the US or cooking a meal from every country in the world. Our human powered adventure offers an infinite number of different goals to be done. The big classics are climbing the 7 summits around the world or swimming the 7 seas but what you do for your quest can be anything you want. You can hike all the mountains in your state or all the trails in your city. Or you run every race in your region or run to every park in your city. The list is endless.

Chris lists easy steps in the book to get started on a quest. There’s not many and it’s pretty straightforward. You might be choosing a very large goal for your quest but the steps to plan it are step by step and not difficult.

What is your goal?

The first step might be the hardest. If you don’t know what you want then you might have trouble figuring something out but there is an easy solution: Think about it more.

Every day think about what you want. Do you want to run or ride or hike or climb? What do you want to do? Where would you like to go? Would you like to do something close to home or something that requires a lot of travel? You will probably want to start with a quest that’s small to see what it’s like. Do you like the format of checking off all those goals or do you like something more freeform?

Remember that you can do anything you want and you can probably do something bigger than you think.

Tally It Up

This part is probably the most important advice in the entire book:

“If I broke down the overwhelming project of visiting 193 countries before the age of thirty-five into a long series of small tasks, most of the problems I had to solve because much more manageable. It all started when I first tallied the estimated cost of scaling up from 50 countries to 100 countries. I guessed that it would cost somewhere in the neighbourhood of $30,000, and that it would take approximately five to seven years to complete. My first thought upon doing the math was: ‘Wow, that’s all?’ “

The whole point of that section was not to impress you with all that money he was spending on travel. In fact he had to live very frugally and travel hack as much as he could to make it work. The point is that he had an exact number to work with. He wasn’t just working with some vague large number and didn’t know any more that. Now he knew exactly how much it was going to cost to do get to every country in the world. Fill in the details. Work out the numbers. Take those little steps.

A quest can be huge to think about at the beginning but when you start breaking things down it because a lot more manageable. Once you know the details you can start to make them happen.

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