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What Scott has created at Live Your Legend is mind-boggling. He creates inspiration, the challenge to dream big and bold, and the tools to make all that a reality. But most unbelievable is the community he's developed of people who are passionate about doing something great, and helping each other achieve that."

- Leo Babauta, Creator of ZenHabits

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

Regret is what you should fear the most

“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.

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A 5-Minute Hack to Finding Your Life’s Work

the step that changes everything

“I would do something different if I only knew what to do.”

This seems to be one of the most common challenges keeping people from pursing work that matters. I hear it waaay too often.

And it’s especially common for the new members of the Live Your Legend community just starting the journey (although all of us face it off and on, forever)…

“I don’t know what I’m passionate about. I don’t know my strengths, talents or the difference I want to make in the world. If I did, I’d be doing something about it.”

I’ve been there… a lot. You know things need to change, but without a compelling and exciting vision to work towards, finding the motivation to take the next step can seem impossible.

That’s why the passion discovery process is such an important part of the first steps and why we developed our First Steps to Doing Work You Love Workshop. Because once you start to latch onto what’s possible and an idea you can’t not pursue, the snowball starts to roll.

But “not knowing” is not a free pass to sit and spin your wheels wasting your life doing something that’s not you. That’s how someday turns to never.

So today I want to offer a 5-minute 80/20 exercise that could make all the difference…

Get the answers from people close to you.

While in theory no one knows you better than you, oftentimes we get so deep in our own head, thoughts and fears that we subconsciously blind ourselves from seeing the obvious.

So instead of putting all the pressure on yourself, ask the people who know you best. Because sometimes the honest perspective of an outsider is all we need to finally see the light that’s been shining the whole time.

The process is simple: You’re going to write emails to five people close to you, asking them three questions. 

Choose people who know you well, who will be honest with you and are from different walks of life. I’d suggest a colleague, past boss, spouse, parent, 1-2 close friends and a mentor. Bonus points for sending it to 2-3 of each of the categories (the more data the better), but don’t just ask your whole family. We want people who know you in different settings.

*Note: If you already know your current or future passion project, then change these questions to what’s relevant in your journey right now. Ask about positioning ideas, pricing, products or service you could offer or whatever. Just get in the habit of getting outside your own head.

Here are your three questions, which you’re welcome to modify:

1. What do you think are my biggest passions and why? If you can think of at least two or three, that would be great. Please explain.

2. What do you think are my biggest natural strengths and talents? Please explain.

3. Given the above and what you know about me, what have you always thought I’d be great at doing as a career? Or maybe as a volunteer or hobby? Please explain.

To make it ridiculously easy on you (and ensure you actually do this!), here’s an email template you can use. Be sure to personalize for each recipient…

Your no-brainer ‘Find Your Life’s Work’ email template:


Subject: Need your thoughts on a new career I’m considering - by end of week if possible

Hi James -

As you know, I really want to start doing work I actually care about, so I’ve been spending a lot of time figuring out what’s next. Since you know me well, I’d love your quick help on this. 

I’ve specifically been spending time understanding my passions and the things I like and am good at. 

So, can you take a few minutes to answer the three questions below in as much detail as you feel comfortable with? You likely see me in a different way than I see myself and this would be a huge help. Please be as open and honest as possible.

Anything goes.

Here are the questions:

1. What do you think are my biggest passions and why? If you can think of at least two or three, that would be great. Please explain. 

2. What do you think are my biggest natural strengths and talents? Please explain.

3. Given the above and what you know about me, what have you always thought I’d be great at doing as a career? Or maybe as a volunteer or hobby? Please explain.

You can just reply to this email and type right below each question.

If you can get back to me by end of this week, that would be awesome. I’m spending all day this Sunday [insert xx/xx date] working on this and meeting with a coach, so having your answers by then would be huge. [Note: Be sure your date is no more than a week out. Giving a specific (and honest) reason to have it done by a certain date will help get quick responses.]

Your thoughts on this will go a long way. Can’t wait to see what you think up, and to let you know what direction I take after I get a little more clarity. I’ve put this off way too long. 

Huge thanks!

- Scott


The Worst Step is No Step

“I don’t know what I want to do,” is not an excuse for inaction.

Most adventures begin without having a clue where they’ll lead. But we excitedly embark anyway.

The pursuit of what matters is no different. If you have a change you want to make, you must be ruthlessly dedicated to progress, no matter how small. There is no certain or exact next step. There never is. So any will do. As long as you’re learning, you’re moving forward.

Build the habit of discovery.

No matter what your stage, that’s the name of the game.

Get out of your own head and ask the people who know you best. They’ll provide insights you never could.

Now, start sending!

Your task today: Take five minutes right now and send at least two of these emails. Send the rest before the end of today. Better yet, send them all now. Bonus points for following up their responses with some live discussion, which is usually best over a workout or glass of wine (or three). :)

Then come back and tell us what you learn.



Image credit: Taken while hiking a little beach trail in Paros, Greece. See more of our adventure on Instagram

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