Ask the Reader: What Quest or Adventure Are You Dying to Pursue?

Regret is what you should fear the most

Ask the Reader: What Quest or Adventure Are You Dying to Pursue?

“Regret is what you should fear the most. If something is going to keep you awake at night, let it be the fear of not following your dream.”

– Chris Guillebeau

The Endless Pursuit of What Matters…

As I write this, I’m wearing a Live Your Legend t-shirt. The back of it says “Do Something That Matters.”

First, do things that matter to you. When you do, they also end up mattering to those around you, and in a way, to the world.

But this was never meant to just apply to doing work you love – it goes for everything we do. Because when we live a life full of meaningful actions, it feels damn good – and it’s a lot more fun. It also inspires others to do the same.

This has gotten me into a number of physical adventures over the years in an attempt to prove what’s possible, including Brazilian Jiu-Jitsu tournaments, stomaching the 12-hour GORUCK Challenge, swimming from Alcatraz with 9-year-olds, running a 50k in those funny FiveFinger shoes (without having run more than 15 miles prior) and eventually attempting a 50-mile trail race and hobbling over the finish line nearly dead last (hours after dozens of men and women twice my age).

It’s also led to a year spent building my first business in Sevilla, learning to surf in Costa Rica, eating my way through Greece (and just about every other place I’ve traveled), and to the creation of Live Your Legend.

But lately the pursuit of a quest has taken on a whole new life.

I’ve spent the past week in the mountains of Lake Tahoe thinking about the 1-2 year plan both for me and Live Your Legend.

I also just finished reading my friend Chris Guillebeau’s new book, The Happiness of Pursuit: Finding the Quest That Will Bring Purpose To Your Life, which hits shelves today.

Chris recently finished a rather big 10-year quest of his own – visiting every country in the world (193 of them). But the book isn’t just about him. He covers dozens of stories of other everyday people’s quests in an effort to provide a framework for developing and pursuing your own life of meaning and adventure. The idea is simple: the pursuit of purposeful pursuits, goals and adventures makes us happy.

A few case studies include:

  • Moving to Japan to become a ninja (one of our own LYL and CWA members)
  • Spending seven months walking across the United States
  • Knitting 10,000 handmade hats
  • Practicing “Rejection Therapy” by attempting to get rejected for 100 days in a row
  • Running a marathon in all 50 states (and 250 in a year)
  • Cooking a meal from every country in the world
  • A man pursuing his wife’s bucket list after she died of cancer
  • Finding and donating $10 to a new charity every day for a year
  • Completing the 4-year MIT computer science curriculum in a year

People’s creativity, drive and potential astound me, and the timing for LYL couldn’t be better…

You see, this January my wife Chelsea and I are setting off on our own quest – a yearlong trip around the world – something we’ve dreamed about for nearly a decade.

Our goals next year are simple: to have fun (and embrace some freedom before it’s baby-making time), and to visit the LYL Local communities around the world. We’ll also live in Italy for a few months, learn some Italian and do our fair share of food and wine experimentation. 🙂

But for a while, I’ve been wanting to tie our adventure to something more specific, with deeper meaning.

Our final plan is still totally up in the air, but here are a few ideas I’ve been toying with for our big trip:

  • Throw a “global dinner party” by hosting dinner parties in each apartment we rent, as a way to bring the local LYL communities together, and for Chelsea to build upon her passion to inspire others to cook simple, healthy, local, plant-based meals (the focus of her newly launched site, The Simple Kitchen). This is currently my favorite idea.
  • Interview LYLers in each country who have made the transition to work that matters and the specific steps they took to make it possible (to share with all of you, of course).
  • Try to crack the code on living a balanced and low-stress life by surrounding myself with “super-chill” people and attending meditation and mindfulness retreats around the world.
  • Focus on a new skill for every month, based on the local customs (think surfing in Costa Rica or meditation in India).
  • Discover and volunteer at a different charity in each city to shed light on some important causes.

These are just a few, and they obviously need plenty more hashing out. But we have four more months to decide. Plus, I’m depending on you to help us out…

I’d love your thoughts on the above and any others you think would make for a worthy adventure, and ideally get as many of you involved next year as possible.

But more importantly, I want you to think about a quest of your own.

Life is a lot more interesting when we put our energy towards endeavors we actually care about.

So… what’s one quest or adventure you want to pursue before your time’s up?

It can be anything.

Mental, physical, supporting a cause or just something selfish that’s always been on your mind. It could take you around the world or all happen in your own kitchen. It could tie into your career or be something totally separate. The fun thing is that one can often lead to the other, if you let it.

Chris defines a quest as something that has a clear goal and specific end point, presents a clear challenge, requires sacrifice and is often driven by a calling or sense of mission. But in today’s case, you can define it any way you want to.

Here are a few questions to think about to help with the brainstorming:

  • What do you get lost in?
  • What about the world makes you really angry?
  • What idea consistently keeps you up at night?
  • What’s always been on your bucket list?
  • What adventure are you dying to tackle?
  • What cause would you love to support?
  • What’s a hobby or passion you’re constantly dedicating time to? How could you tackle it on a much bigger scale?
  • If you could only pursue one thing, what would you craft a life around and do every day?
  • What have you always wanted to do if you had the time, money, courage, etc.?

Once you give some thought to what’s exciting, you start to show up in the world in a different way.

Your conversations change, people see you differently and you begin to inspire others to think about what they too could be doing that matters. And most importantly, your actions begin to change. And so the ripples get set in motion…

The Shift that Ripples Across Your World

A subtle shift happens when you decide to start pursuing things you actually care about.

Even on the smallest scale, as you start to act in a way that’s congruent to what matters to you, you begin to notice more and more actions following suit. People start to pay attention. You and those around you begin to expect it from you. So you continue to show up in a bigger way. Before long, the only actions you take are ones deeply rooted in the difference you want to make.

But that all starts with deciding to pursue that first quest. And that starts with getting an idea out of your head and onto the page.

Living your legend isn’t just about doing work you love. It’s about pursing a life based on what you actually care about, in all walks.

Chris put it nicely near the end of the book…

“If you’re going to worry about something, worry about the cost of not pursuing your dream… Regret is what you should fear the most.”

So, what’s on your list?

– Scott

Two things to do now:

1. Share your own quest idea in the comments (anything goes). And for bonus points, give me some advice on a quest you think Chelsea and I should incorporate next year. I want the LYL community to be a big part of our worldwide adventure (and join us along the way).

2. Check out Chris’s book and grab your own copy on Amazon, read it and then give it to someone else who needs it. The message is so essential to what it means to Live Your Legend and do work that matters. And I’d love to see The Happiness of Pursuit get the traction it deserves.