{"feed":"Live-Your-Legend","feedTitle":"Live Your Legend","feedLink":"/feed/Live-Your-Legend","catTitle":"Lifestyle","catLink":"/cat/lifestyle"}

All journeys have secret destinations of which the traveler is unaware.”

– Martin Buber

Memorable Moments in Transylvania: 

  1. Enjoying a free evening walking tour in Brasov, wearing six layers each of our summer clothes, as the temperature dropped to 38 degrees F and the rain and snow started to sprinkle. So much for packing to avoid winter.
  2. The thrilled look on Chelsea’s face when Scott tried to act like Dracula outside his castle. See above.

Days on the Road: 113

Countries Visited: 11

Hours spent on trains in past two weeks: Over 25

WHERE WE ARE… NOW: Nessebar, Bulgaria • LAST: Veliko Tarnovo, Bulgaria • NEXT: Plovdiv, Bulgaria

“Forced” into Transylvania…

After finding out about the rules of the Schengen Agreement, we had a brief moment of panic, but pretty quickly realized how this would force us to venture places we hadn’t yet planned. Enter Romania!

And Dracula’s castle…

There are so many places to discover and explore but for some reason Romania wasn’t on the top of that list (what is, you ask? Slovenia & Montenegro for Chelsea and Bhutan for Scott). Yet we are so grateful for the circumstances that brought us to...

 “Everyone has a plan ’till they get punched in the mouth.” 

– Mike Tyson

Disclaimer: I realize I run the risk of sounding like an ungrateful ass for even bringing up today’s topic, but I assure you this is not me complaining. It’s me sharing a personal challenge that most “location independent” entrepreneurs don’t seem to fully disclose. I’d be doing you a big disservice if I didn’t bring it up. Thanks in advance for going into it with an open mind. I hope it helps.


100 Days Working with No Office (250 to go)…

I’m writing from the Transylvania Sunrise Express – my name for the 6:29 am 12-hour train from Romania to Bulgaria. We could have saved a few hours by bus, but I love trains (well, most of them). Plus, I could use some time to process the past few months.

100 days ago Chelsea and I finally did what we’d been talking about since we started dating a decade ago. We got rid of our (massively overpriced but lovely) 1-bedroom San Francisco apartment, sold our car and most our stuff, packed the remaining essentials into two 45-liter, 28-pound carry-ons (here’s what we packed), and hopped on a one-way flight to Buenos Aires to kick off a year around the world – and test out this digital nomad/location independent life the Internet seems to boast so much about.

We’ve always had a simple personal purpose for the trip… to do something deeply important to us that we knew we’d regret not doing later. To learn, explore...

“What is the point of being alive if you don’t at least try to do something remarkable?”

– John Green

Why are you here?

I took the above picture somewhere between Budapest and Transylvania, a few days ago while on a 13-hour night train to the land of Dracula, our latest stop on day 101 of the world tour. I’ve now officially fallen back in love with foreign trains – between the zooming scenery and lack of activities, distractions and Internet, it creates the perfect space for pondering.

That space gave me time to reflect on something one of the attendees of our Budapest meetup asked me last week, and I realized it’s something I surprisingly hear at pretty much every large LYL event.

She had come at the suggestion of a friend (same way many people find us), and knew nothing about Live Your Legend.  So she walked up, thanked me, and casually asked…

“Ok, so what is Live Your Legend?”

I could have been direct, but instead I decided to respond with why Live Your Legend is here. With what we believe.

Because that’s the magic that makes all this possible. It’s this shared belief about why we’re here, that has allowed all of us to come together around the world, from Kenya to Kuwait, Sydney to San Francisco, Helsinki to Hungary – despite differing languages, cultures, backgrounds and religions, to take a stand for the same thing.

But at times, we forget.

In working to make change and fight the good fight, it’s easy to lose sight of what brings us...

Memorable Moments in Amsterdam: 

  1. Seven days before heading to Europe for five months, we realized that without visas we could only stay for three. Slight change in plans.
  2. An official tour guide teaching us the long-standing Hungarian tradition for good health: a shot of 80-proof ‘medicinal’ liquor first thing in the morning. Plus, how to cure a sunburn by slathering yourself in half a centimeter of sour cream (thankfully we didn’t have any burns needing attention, yet).

Days on the Road: 100

Countries Visited: 11

Cities Visited: Over 30 (including day trips)

WHERE WE ARE… NOW: Brasov in Transylvania, Romania • LAST: Budapest, Hungary • NEXT: Somewhere in Bulgaria…

Our first Euro-Update: We have to admit, we have been horrible about keeping up with our updates! But we are trying to create a better system that will allow us to stay current. That being said, we are skipping ahead to where we are now and will update try to keep these updates real time.

After an amazing trip home for our good friends’ bachelor/bachelorette parties and wedding, we headed back on the road. It was definitely a mix of feelings. We had been surrounded by friends, family and the comforts of home for a few weeks and we knew that going back on the road this time meant likely not seeing those people or feeling those comforts for another 9 months.

“The interesting thing about entrepreneurship is that it never seems to end.” – Unknown

Time Sensitive: Live Your Legend RAW is open to new members for the next 5 days (until Tuesday 4/21 at 11:59pm PST).

We created LYL RAW as a resource for those of you building your idea, passions, talents or expertise into a business or side-income. It’s my way of giving you a window into my head – uncut, behind-the-scenes access to how I’ve built the LYL business and community, plus weekly guidance and lessons to support you in building your own profitable passion project. It’s a level of business detail I don’t cover publicly on LYL.

I’m in love with the way it’s turned out and how it’s helping the builders and makers in our community like we never have in the past.

Check it out and try it risk-free here.

Now, let’s chat a bit more about building businesses…

From Nothing to Something Tangible

Above is a picture of Live Your Legend Local’s Amsterdam crew, taken last Sunday after a few intense (and awesome) hours together. We had expected 15 and about 50 showed up. I think the ongoing (and unprompted) yelling and screaming about got us kicked out of our family brunch joint venue, which made me pretty proud.

We’ll be doing the same with the LYLL crew in Budapest tonight, after I explore one of these Hungarian bath houses everyone’s telling me about.

Spending time with so many of you, in person, hearing your big ideas, plans, fears and struggles, puts things into...

 “Impossible is just a big word thrown around by small men who find it easier to live in the world they’ve been given than to explore the power they have to change it. Impossible is not a fact. It’s an opinion. Impossible is not a declaration. It’s a dare. Impossible is potential. Impossible is temporary. Impossible is nothing.”

– Muhammad Ali

World Tour Update: After a week of California wedding festivities, we just touched down in Amsterdam to kick off the next nine months out of the country. If you’re in town, come join our LYL Local event this Sunday. We’re expecting well over 30 inspiring Living Legends. RSVP for Amsterdam here.

Next week’s stop is, well, I’m not really sure. Perhaps Budapest or Transylvania. Still sorting that one out.

As for the above photo, I stumbled upon this quote from Muhammad Ali yesterday during our first wander about the city – etched into a widow near a sleepy Amsterdam canal. I have no idea how this is the first time I’ve read it, but it makes for the perfect opening to today’s discussion…

Who would you bet on?

And more importantly, what kind of person would you need to be for others to put their money on?

I recently spent a week in Santa Barbara, California. The place holds a special spot in my heart for all kinds of reasons, but probably most of all, it was the last place I had a real job.

That job was also my first experience doing...

My Birthday Tradition…

Today is my 33rd birthday, so I thought I’d share a little tradition with you.

Every year I like to take at least a few minutes to look back on what’s led me to today. A million things are always at play, but this time around I thought I’d share a talk from the late Steve Jobs. It deserves disproportionate credit in me sitting right here, having the privilege of sharing this with 100,000 of you from all over the world, especially as we get ready to board our one-way flight to Amsterdam to continue our world tour and hang out with a bunch of you in real life!

I can’t believe I get to call this work. I’m so incredibly grateful for what Live Your Legend has become for all of us.

I’ve seen Steve Jobs’ 2005 Stanford Commencement Speech dozens of times. I keep it saved on my iPhone, and for a while, I watched the video monthly. I recommend the same practice to you, and whether you’ve seen it before or not (I assume many of you have), take a few minutes right now to watch it again.

It’s one of the most influential videos I’ve ever seen, and I’d probably call it the best career talk of all time.


One of my favorite quotes…

“You can’t connect the dots looking forward; you can only connect them looking back. So you have to trust that the dots will somehow connect in your future. You have to trust in something;...

“There is no failure except in no longer trying.”

– Chris Bradford

World Tour Image Caption: Say hi to Santiago, whom we met a couple of weeks ago. His family has been farming coffee in rural Colombia for 70 years. This was taken just after he walked us through their farm and whole operation on the outskirts of Qimbaya, a tiny town nestled deep in the Colombian coffee fields.

He’s the third generation to carry the torch, and his recently-opened Café de Altura completes the full bean-to-cup circle. He poured our third cup a few minutes after this pic, served alongside homemade guava, cheese and banana cake. So much respect for those who make things from scratch!

Now for my slight rant on failure…

Reframing Failure

Last week we talked about Your Biggest Risk In Doing Work You Love, and pursuing anything meaningful, for that matter. The risk that’s far worse than failure.

If you watched the short video I recorded, hopefully you’re starting to agree.

And since failure still seems to haunt most of us, today I want to take it a step further.

So, here’s how to avoid failure altogether…

This was first taught to me by a mentor of mine years ago, right as this site was starting to get a little traction, but still hadn’t become anything close to resembling a community, movement or business.

I had no idea what I was doing (still don’t really), and was totally overwhelmed by the things I could or should be...

Massively Misunderstanding Risk…

We just got to the tiny beach town of Barra de Navidad, Mexico, and today I wanted to share a few quick but important thoughts about risk. Most the world seems to get risk totally wrong, which makes it nearly impossible to pursue just about any meaningful goal or dream, especially doing work you love.

So below is a short video I filmed on the one risk that I believe is much worse than failure.

In fact, it’s something I’ve learned from years of studying (and attempting to model) some people who have built their lives upon properly understanding and taking the right risks. I’ve noticed that among many others, Steve Jobs, Warren Buffett and Richard Branson constantly refer to this same belief, often without ever mentioning it directly.

I hope you enjoy this new short video format. 

Take 3 minutes and give it a watch below…

Don’t see a video? Click here.

So, how do you see risk?

And would you like to see more video posts from me in the future?

Tell us in the comments below.

Ciao from down south,

– Scott

Memorable Moment(s): Breakfast and lunch deep in the vines, and our chef wandering us through his garden as we gathered the night’s meal, before cooking enough empanadas for a week (see video below).

Days on Road: 72

Wines Tasted: 157

More odd-ball trip stats here.

WHERE WE ARE… NOW: Santa Barbara, California • LAST: Barra de Navidad, Mexico • NEXT: Carmel, California (for weddings)

Becoming one with the vines…

After 70 days on the road, we just got back to California for a few days of recharging while we attend a birthday and a wedding, then we’re off to dive into Europe, starting with Amsterdam.

But for now let’s get caught up on Part 1 Mendoza wine adventures…

We got a glimpse of gorgeous wine country in Cafayate, but Maipu, just outside of the Mendoza city center was pure heaven. At the end of every trip, we do a favorites list (favorite breakfast, favorite lunch, favorite dinner, favorite hotel, etc.) – but since this is a long trip, we decided to do an Argentina favorites list and our stay here topped the charts in multiple categories! Based off of a few recommendations, we stayed at Club Tapiz for 3 nights – it was literally in the vines, like no joke!

We love taking cooking...

Memorable Moment(s): The look on Chelsea’s face when she got into the driver’s seat of our tiny rental car in downtown Salta and realized it was a stick shift – and she’d be navigating 10+ hours of dirt roads over the next week. Scott would have been driving if his ID weren’t floating around in a boat between Uruguay and Buenos Aires – indefinitely. Hope’s been given up on that one.

Oh, and Scott getting nearly eaten by a pack of 7 dogs on a rural dirt road in Cachí – he sprinted until they lost interest. He now runs with a stick in one hand and stone in the other – like that would help.

Oh yeah, and Scott getting pulled over at a regular police check point, a few minutes after deciding to do a little bit of the driving. The cop wanted to see his driver’s license. Perhaps a passport would do…

Days on Road: 59

Washing Machines Used: 2

More odd-ball trip stats here.

WHERE WE ARE… NOW: Panama City • LAST: Quimbaya, Colombia • NEXT: Los Angeles

(if you have local things we MUST do or happen to be in town, send us an email!)

The Art of Getting Lost (A Lot)…

It’s 10:00am the morning after our impromptu dinner party. Scott’s 30 min interview is going on 1+ hours and our Airbnb host knocks on our...

Memorable Moment(s): Unexpected mountain-top spin classes and Argentinian dinner parties that last from 4pm to 3am. Oh, and when Chelsea walked into a nice hotel in the center of downtown Salta and, in Spanish, politely asked “is there a lake around here where we can have breakfast?” Who hasn’t gotten “lago” (lake) and “lugar” (place) mixed up in Spanish every now and again though? Other than that, her Spanish has gotten incredibly good in a few weeks.

Days on Road: 54

Empanadas Eaten: 121

Wines Tasted: 155

Check out all our stats on our newly-created Odd-Ball Trip Stats page here.

WHERE WE ARE… NOW: QUIMBAYA (tiny town deep in Colombian coffee country) • LAST: Cartagena • NEXT: Panama City

(if you have local things we MUST do or happen to be in town, send us an email!)

Finding Generosity, Community and MATÉ in Salta, Argentina (posted 5/5/15):

After leaving Iguazu Falls, we headed over to Salta – the home of one of the most dedicated Live Your Legend groups. Matías, the LYL Local host, and his lovely girlfriend Lucia offered to pick us up from the airport. Despite our delay, they were there with huge smiles on their faces. We had yet to learn that this would be just the beginning of their generosity…

They dropped us off at our Airbnb and we arranged...

 “If you don’t know where you’re going, any road’ll take you there”

– The Cheshire Cat, Alice In Wonderland

World Tour Update – Day 52: After a few surreal nights on The Galapagos Islands swimming with turtles, iguanas, penguins, sea lion pups and sharks slightly longer than my body, we arrived in Cartagena, Colombia on Monday.

I took the above picture a few blocks from our apartment, while wandering around old town Cartagena yesterday. I don’t think I’ve ever seen a typewriter used in real life, let alone a dozen in the same place. This confirms that there literally is a street stand for everything. And I think the guy in blue might be on break…

Click here to follow the LYL World Tour & Global Dinner Party Project – and hopefully meet us somewhere along the way!

Now, speaking of typewriters, let’s talk about Forward Progress…

The primary goal of LYL is pretty simple – to provide the tools and community necessary to help you make constant progress toward doing work you love and living a life you’re proud of.

And since living your legend is a never-ending journey (that’s the best part), our focus will always be on Forward Progress

No matter where you are along the journey, all that’s important is that you’re always doing something to get you a little bit closer to what matters. No matter how small or big those steps are, the important thing is...

“If only we’d learned how to harness and ride rather than hunt and kill the butterflies that live in the gut of every person who strives to create something extraordinary from nothing.”

— Jonathan Fields

OK, let’s talk about fear…

As I write this en route to play with giant tortoises on The Galapagos Islands, I am honored to introduce my good friend, mentor and informal stress-killing expert, Doctor Lissa Rankin, as our guest expert today.

Lissa has had a pretty significant impact on my life, happiness and stress levels since I met her at an unsuspecting dinner hosted by our mutual friend, Jonathan Fields, a few years back.

After her profession as a massively overworked practicing doctor left her terribly strung out, stressed and sick, she quit to figure out what really causes us to get sick (and to get better).

After years of medical research, this quest led to her runaway New York Times bestselling book Mind Over Medicine.

She’s since been all over PBS specials, TV, TEDx stages and keynoting conferences with the likes of Deepak Chopra and many other household names.

Her work led her to discover that stress and anxiety is one of the leading causes of most illnesses and early death. And the medical data to back this up is shocking.

For me, her findings were terrifying.

Because when I met Lissa, I too was deeply stressed and strung out, as Live Your Legend was growing like crazy, and I had no idea how to properly handle the huge...

Sometimes life makes you feel really really small.

Memorable Moment(s): Our 1.5 hr flight from Buenos Aires to Iguazú turned into 4 hours when the electricity at the Iguazú airport went out 10 minutes before landing. So we started to fly back to BA, but the lights came back on just in time and we turned around again. Oh, and unfortunately the bugs. Too many bugs!

Empanadas Eaten: 110


(if you have local things we MUST do or happen to be in town, send us an email!)


We’re obviously still playing major catch up on these posts – we’ve covered a ton of ground in the past few weeks, but today we’re just talking about Iguazú…

After Buenos Aires, we took a short flight up to Iguazú Falls. It was like nothing we’d seen.

Btw, when we visit more touristy destinations, where we will only stay for a few nights, we sometimes stay in hotels 1. Because often times there are not Airbnb’s in certain locations and 2. It’s nice to stay in a hotel every once in a while.

“If your actions inspire others to dream more, learn more, do more and become more, you are a leader.”

– Simon Sinek

World Tour Update: Yesterday we had an incredible night out with the LYL local crew in Panama City, and today I had my mind blown as I boarded a small boat and descended the locks of the Panama Canal. So much respect for people who build things!

Next stop is back to California (for a friend’s wedding), then Mexico before we board a one-way flight to Amsterdam to kick off the European leg of the LYL World Tour & Global Dinner Party Project – and hang out with a bunch more of you all!

Now, for today’s fun…

The Fastest Solution to a Miserable Job

That’s what we’re getting into today, and I have none other than Simon Sinek to drop some wisdom on us.

I published my first interview with Simon on LYL a few years ago, and it quickly became by far the most popular interview I’ve shared.

Simon’s Start with Why concept (“People don’t buy what you do, they buy why you do it”) has become somewhat of an international sensation over the past few years. His first TED Talk on How Great Leaders Inspire Action, now ranks as one of the top TED Talks of all-time at over 21 million views (I personally account for over 20 of those).

I thankfully stumbled upon his work just as I was creating LYL,...

“The more I write, the more I discover.”

– Unknown

The writer’s unexpected path…

This picture was taken a few days ago at a small farmhouse in El Calafate. The night before, a man was shearing sheep on that lawn.

Two days later we’ve found ourselves in the tiny port town of Ushuaia in Tierra Del Fuego, Argentina – the furthest southern city of South America. Today we’re off to explore a small island inhabited with thousands of penguins.

And tomorrow we might try our luck at one of the tour offices that says “Antarctica LAST MINUTE” on a little white paper taped to the window.

Who knows…

And that’s the point.

It’s impossible to know where one decision will lead, so all that seems to matter is that you keep making them.

And that is why I host the Start-A-Blog Challenge twice a year and give away one or two $500 tickets to World Domination Summit in Portland, Oregon.

And with that, our 2015 Blog Challenge starts right now!

Click here to join the free challenge, get the free 7-day dream job writing habits course and be entered to win a free ticket to WDS 2015.

Or read on for why I believe this matters so damn much to all of us…

You see, none of this would have never existed if I had not decided to start a blog 8 years ago.

Chelsea and I would not be on this yearlong adventure around the world. And if we...

From Buenos Aires, we took a day trip over to Colonia del Sacramento. We were a little unsure about it because tickets were hard to purchase and it was going to be a full day adventure… and considering these Argentineans don’t even think about going to bed before 2:00am, a 7:00am wake-up seemed like a lot to volunteer for. Nonetheless, we decided to go and it ended up being one of the highlights of our time in BA.

There were so many adorable little places to sit and enjoy a mate, a café, or a cup of vino.

Reminder? Don’t let a few hours of sleep keep you from an adventure!

Chelsea and Scott

“I could die right now and be happy.”

– Chelsea, spoken numerous times in the past three weeks, and most recently during this little breakfast oasis in the vines near a tiny town outside Mendoza. And no, this did not come easy. All the set tables are downstairs but we wandered up a tiny spiral staircase to find the ultimate breakfast nook. So we brought everything up in about 3 trips. #SoWorthIt

World Tour Update: This morning I’m writing you from a rather spacious patio in our 2-bedroom Airbnb in the center of Mendoza, Argentina. A few hours ago this same patio was flooded with water – thanks to our second failed attempt at using a foreign washing machine.

And if any of you are in Mendoza or Bariloche (our next stop), please reply to this and let us know. We have a dinner party brewing!

Follow our World Tour & Global Dinner Party Project and join us for the adventure here.


Now, time to get very serious…

Today’s article is an “Ask The Reader” post, which means the value of it, for all of us, comes from YOUR response. Live Your Legend has always been a two-way street. It’s not about what my team or I create. It’s about how you and I interact and integrate the big topics we all discuss.

That means today I’d like you to read this and then take a few minutes and give me your honest response in the comments.

The question I’d like you to answer...

“If in doubt, just walk until your day becomes interesting.”

– Rolf Potts, Author of Vagabonding – The Art of Longterm World Travel

Most Memorable Moment(s): Scott losing his ID in Uruguay & Chelsea helping an old woman from being washed away in a torrential downpour street river (See above – you should have seen the woman’s cry for help 2 seconds earlier!)

Where we are… Now: Mendoza • Last: Tilcara • Next: Bariloche

(if you have local things we MUST do or happen to be in town, send us an email & let us know!)

The latest from Buenos Aires and Uruguay (1/31/15):

Welcome to update #1 from the Dinsmore World Tour & Global Dinner Party Project! We’ve covered a lot of ground in our first three weeks, and due to some surprising reasons (more on that below), we’re a little late on our first update. So for now we’ll just cover our first two spots, Buenos Aires & Uruguay, and catch up from there…

Our Top 10ish…

We spent the first week in Buenos Aires and took a day trip to Uruguay. Here are some of the things we loved:

1. The small green grocers that were everywhere, Malbec, empanadas, dulce...