How Having a Quest Has Made My Life 10x Better

By Sean Ogle •  Updated: 09/09/14 •  7 min read

Today, Chris Guillebeau released his latest book The Happiness of Pursuit. It’s all about quests, and why they can be such a worthwhile endeavor. It’s one of the most inspiring books I’ve read in years, and has by far been my favorite of his three books.

Also, despite the opening story, I promise this post isn’t about golf 🙂

I still remember the day. It was March 28th, 2013.

I was with Tate’s family staying in Eagle Crest, Oregon for their annual Spring Break trip.

Each year we take a long weekend, and on the trip we ski one day and her dad and I play golf on another.

Usually we just play the course at the resort, but this time I found something special online.

There was a tee time for $50 to play the Nicklaus Course at Pronghorn.

You see Pronghorn has been one of the biggest golfing developments in Oregon in the last 15 years (next to say, Bandon Dunes).  They built two courses and the club was ultra-private – until financial trouble forced them to make one of the courses public.

I’d been wanting to play there ever since I first heard about the resort.  It was one of those places that you always knew about,  but never thought you’d be able to experience for yourself.

And now for about 1/4 of what a round in the summer would cost, we had the chance to go play.

It was a beautiful (barely) Spring day, and both Kirk and I played really well.  Even just coming out of winter, the course was in great shape, and it was hard not to be in awe of the scenic high desert landscape and strategic shots the course made you hit.

This course is ranked #28 on Golf Digest’s list of the Top 100 Public Courses in the United States. and it was the beginning of my quest to play all of the best golf courses in the world.

The Evolution of a Quest

Now I know that most of you reading this post, couldn’t care less about golf – don’t worry this post isn’t about golf, it’s about the quest that I’ve set forth on.

In 2009 I created my bucket list of all of the things I wanted to do. That ever-evolving list was the original quest which has led me down the path I’m on now.

I wanted to setup a system for accountability so that I’d actually follow through with all of the things I wanted to do in life.  And stop making excuses like “I’ll do that one day” or “I don’t have the time/energy/money/expertise” etc.”

Because of that day in March of 2009 when I wrote out my bucket list, I’ve now done over 1/3 of the original list.

Just a few note worthy things:

It’s because of the bucket list quest that I’ve followed through and created a lifestyle that allows me to do these things.

More recently, I’ve become pretty obsessed with golf.

It was after that first round that I decided I wanted to play the Top 100 Public Courses in the US.

Within 6 months I realized what I really wanted to do was play the actual Top 100 Courses in the US (most are private, and very hard to get on).

Now today as you read this, I’ll be touching down in Edinburgh, Scotland where I’ll be playing 9 of the Top 100 Courses in the World in 9 days.

Edit: I’m writing this from the Edinburgh airport while waiting for my buddy Dan to arrive.

If you’d said within a year and a half of that first round I’d have played close to 20% of the best golf courses in the world I’d have thought you were crazy.

Yet here I am back in Europe for the first time in 7 years, more excited than ever.

Having a quest and tangible goals is what has given me motivation to work so hard on my business and help others with their goals. Very, very few people in the world are fortunate enough to have the time and resources to do something like this.

I’d be doing myself and all of you a disservice not to pursue something big, and that’s what has been so cool about both the bucket list and the golf quests.

It’s not about the golf, it’s about the journey, which has been one of the most fun and exciting of my life.

The Happiness of Pursuit

So, while we’re taking a trip down memory lane, I have to mention one more component, and without this, I never would have started in the first place.

It was Chris Guillebeau who first inspired me to start this blog and write down the things I wanted to do.

He agreed to meet me at a Starbucks in Portland in 2009. I made an excuse at work, walked to the most hipster neighborhood in town, in my ill-fitting suit and tie, and told Chris I wanted to make a change.

For the next year he became a mentor, as I left my job, moved to Thailand, grew my business, and really started living the life I’d always wanted.

He inspired my bucket list quest, and subsequently my golf quest, with his goal of visiting every country in the world.

And today, he released his latest book, which is all about quests: The Happiness of Pursuit.

Chris’ other two books The Art of Non-Conformity and The $100 Startup were great – but this latest one has struck a chord with me that’s much more profound.

It’s validated all of the thoughts I’ve had about my own pursuits, and helped renew my vigor with which to pursue them.  It doesn’t matter who you are or where you are in life, this book has a very important message for you.

It shares incredible stories of the man who set out to shoot, edit, and publish one million photographs; the teenager who sailed around the world; the woman who wanted to see every bird on earth – the list goes on.

When you read The Happiness of Pursuit, you can’t help but be inspired and motivated to create your own quest – however big or small.

So as I currently set off on the unknown, and begin driving on the wrong side of the road, to every corner of a country I’ve never been before I’ll be thinking of a few things.

First, I’m incredibly lucky to have an opportunity like this, and I won’t take it for granted.

Second, I have this opportunity because I made it for myself, and worked incredibly hard to get there.

Third, I don’t care if anyone else understands it or not – I’m doing this for me, and that’s the most important part in any quest.

Fourth, and this one is important, life is short, make good stories.

What stories are you creating in your life? Need a little kickstart in the right direction? Please, please go read Chris’ new book. Regardless of where you are in the lifecycle of your personal quest, I promise you’ll enjoy every page.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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15 comments on "How Having a Quest Has Made My Life 10x Better"

  1. What an awesome post Sean, love it! I read The Happiness of Pusuit and couldn’t agree with you more, Chris’s best book yet by far. Do damn awesome and inspiring. Speaking of awesome and inspiring…. The quest you are currently on is incredible! Love seeing all your Instagram pictures, very cool. Thanks for sharing your stories, ideas, and insights… I think they’re awesome and even more so, you’re awesome! Cheers!

    1. Sean says:

      Dude thanks for the kind words and confidence boost 🙂 Always appreciated!

  2. Debashish says:

    Great post, Sean. Your bucket list was one of the things that drew me in to L180, in the first place.
    I’ve finished reading Happiness Of Pursuit, and I completely agree with you – this book is profound. If someone were looking for a kick in the butt, to get started with a quest, this book would be it.

  3. Great post. First, I love Edinburgh. It is a beautiful city and the Fringe Festival there is a fantastic time. I hope you enjoy the time there.

    I’m going to have to check out this book. I heard about it on a different blog too. I applaud you for your quests and for achieving many things on your bucket list. It has encouraged me to write a bucket list for myself and to figure out some quests I want to go on.

    You are absolutely right that life is short so you should make the most out of it and experience and live it up to the fullest. Thanks for the inspiration Sean.

  4. Leroy says:

    Great post Sean, feeling really inspired to set out on my own quest

  5. Chris Krohn says:

    There is nothing more powerful than passion combined with commitment. I ‘d like to read this book. Thanks!

  6. Chris Krohn says:

    I really like your approach. I think we are conditioned to do what is practical, instead of following our hearts and fully expressing the unique talents and passions we have. Passion plus committed action leads to authentic success.

  7. Am going straight from this post to get the book, Happiness of Pursuit… the title alone caught me. Been writing out my own bucket list after making attempts to create the life I should have begun right after college instead of working job after job that never was fulfilling. Working for myself isn’t always lucrative, but it’s rewarding. Can always use tips on living it to the fullest. This book comes highly recommended and I’d be foolish to pass it by. Thank you !

  8. Erik Huss says:

    Inspiring post Sean! I think it’s really motivating to see you working towards fullfiling your goals. And you have to be proud because all your passion for golf have gotten me to add to my bucket list: Learn how to golf!

  9. This is the third time I’ve heard that book mentioned… but there again, I am an avid blog follower, I don’t even watch TV because I get the best stuff from my favorite bloggers. It’s always amazing reading posts from people who are self made, who have started completely over and have a new take on the world around them, and are willing to pass that along to the rest of us. It really is all about perspective, and after that? The willingness to see it done, take the risks, and trust that it will all work out in the end.

  10. Stacey Olson says:

    This is a very timely post. Big shifts happening in our life, and as it’s easy to get overwhelmed by the challenges, I know myself well enough to know that the best way for me to meet and conquer a challenge is to meet it with a bigger and better challenge. That said, I think the best bigger and better option right now is to identify and dig deep into a quest of my own. I like the idea of bringing some new, concrete goals into this crazy drive I have to live life boldly and with creativity. I have no idea what my next quest will end up being, but I do know that you and the L180 community hold valuable inspiration and I appreciate all the bad ass, life changing moves people are making to improve their circumstances and lifestyle. Thanks for this post and the challenge to take on a new endeavor!

  11. Jan Koch says:

    What a great story Sean, thanks for being so open with us!
    It’s been a while since I’ve visited your blog and now I feel that I have to go through all the posts I missed to catch up with what you’ve been doing 🙂

    Similar to your story, Chris Guillebeau was one of the first inspirations of mine too, through his $100 Startup. Back then I was employed and looking for a way to start my business on a budget. It really struck me how business were built with basically no costs attached. I just couldn’t not start my venture.

    Looking forward to read the other posts I missed, I’ll leave a comment here and there 😉


  12. Isaac says:

    Fantastic post. I’ve lived parts of my life where it seemed like I had no vision or a compelling future- and I just felt so dead. Even the Bible says, “without a vision, we perish”. It’s so important to have something to work towards in life- for me it gives me a sense of purpose. When I have a vision, I feel secure knowing that the world will be a better place because I was here.

  13. Mandy says:

    This is great, Sean,

    This really motivates me to just quit my god damn job and create my own bucket list of all of the things that I want to do. Clearly doing that would make me happier, as I am just spending all my free time reading articles like this……..

    The main thing that stuck out to me in this blog was to stop making excuses, and prove it to yourself that it is really easy to stick with your plans and goals in life. Stop procrastinating and making excuses like “I”ll do that one day, and I don’t have the time to do this now”. Everyone is guilty of that, and I feel like the more we push things back the more we resent ourselves for allowing it to happen. We are digging ourselves even deeper, in an unhappy and unpleasant lifestyle. Sometimes a change in perspective, and a change in location can make all the difference!

    Thanks for the insight,


  14. Jon Bowes says:

    Thanks for this Sean.

    It’s easy to sit back and not take chances, not pursue, not have a quest. At least, it’s easy in the short term.

    Long term, there’s nothing more frustrating than wondering what if… What if I had tried? What if I had pursued something epic? Breaking it down into goals and following through on the small steps to get to those goals is irreplaceable.

    Keep it up!

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