Dec 14
sitting here Friday evening overlooking the ocean in Fortaleza in my last night in Brazil before heading back to AZ for the holidays. Justin you had subscribed to receive my biannual recap of notable events over the past six months. This is that recap.

Nearly a year ago I moved to Lisbon, Portugal and have been living there since. After having done nearly two years of constant nomadic travel it’s been nice to finally plant in one place for awhile. I had done a travel program called Remote Year which allowed me to work remotely and took me to a total of 18 countries over the course of a year. I’ve been
continuing my role for Pagely as Director of Sales working out of the RY workspace in Lisbon for the past nine months. This has allowed me to meet nine other Remote Year groups that have come through Lisbon and I’ve gotten to be a steward of Lisbon to those people.

The best analogy I can give is that previously I was in a stream of people flowing through a bunch of interesting places. Now I am the rock in the city of Lisbon with a stream of interesting people constantly flowing past me in the workspace. People who sell everything and commit to a year on the road are inherently interesting people to me and it’s
been a unique privilege to meet over 400 of these folks since February.

Over the holiday break last year I created the Nomad Prep eCourse with the goal of demystifying the transition to a nomadic lifestyle and thereby making it more accessible to others who want to make this leap. The course has to date served 90+ students and helped many people prepare to take their job on the road. I realized early this year though that I had committed a typical entrepreneurial mistake in building a product before I had built an audience. To solve that issue in April I launched
Nomad Podcast as a platform to interview nomads, founders and domain experts to both disseminate useful info while simultaneously creating a fountain of prospective students into the course.

The podcast has had a total of fourteen guests so far and I’m proud of the high-caliber content there. I paused the effort however last month because it requires a significant time investment and is not yet delivering the results in terms of paying students to justify that investment. I intend to “reboot” it eventually but with limited spare cycles I believe my time for the nomad stuff is better spent figuring out a different
way to drive enrollments. My last interview inadvertently sold me on a program for solo-preneurs as a methodology for “building the audience before building the product” and I’m currently taking that course and implementing ideas there towards building and serving the prospective nomad audience.

You might ask, “why spend so much of your spare time encouraging the nomadic lifestyle?” I have two motives:

  1. The Remote Year experience was probably the single most-transformative thing I’ve ever done. I have a theory/hallucination that helping to usher more people into that lifestyle transition could unlock & awaken others and recover a few of the Lost Einsteins as it did for me. You can read more here about that theory but that’s motive #1.
  2. I have a goal to have all my living expenses covered entirely by passive-recurring income
    by end of 2019. This podcast episode struck a nerve with me and my takeaway was that the most high-leverage thing we can do is not to marginally optimize our retirement investments but rather to set up a side hustle that produces income on auto-pilot and requires low-maintenance. There are undoubtedly other side businesses which could be easier and more lucrative to start but this is the effort I’m most passionate about so I’m taking the hard road here to try and figure out a profitable model that also accomplishes motive #1.

Speaking of podcasts… I’ve rediscovered this medium in the course of building
my own and I’ve become a big fan of ingesting new ideas in this way. This is my OPML file of the shows I currently listen to. Podcasts are great as a medium (especially for runners) as they allows you to consume all kinds of current, interesting, themed content in audio form.  

In October I did a 30-day plant-based challenge based on this interview on my podcast. Since then I’ve become what I would call a “fair-weathered pescatarian” having added fish and seafood back into the mix but keeping beef, poultry and pork out of the diet. That said, if you put a Christmas ham or Kobe beef serving in front of me, I have zero issues with taking that down ;-) Overall the decision to go pescatarian was largely a function of seeing this talk by the Dr. behind His talk, titled “How Not to Die,” presents compelling evidence-based arguments for switching to a completely
plant-based diet. I’ll report back after more track record. If you’re considering testing out this switch yourself I highly recommend the 30-day challenge from my podcast guest (linked in her interview above).

As far as my work for Pagely, I just finished writing up my annual “State of the Union” summary for our sales department recapping everything we’ve accomplished over the past year. In all it was a lukewarm year revenue growth-wise compared to last year but our team executed a number of important strategic projects which should set us up for success in 2019. I appeared as a guest on a few podcasts, did this talk in Lisbon and received some good press for the novel approach I developed and deployed applying the concept of “scaling personal attention” via interactive video. I’ve been with Pagely now for 3.5 years and intend to see us through an acquisition before transitioning to whatever is next.

On the topic of what’s next: I feel drawn to a project I had started and dabbled with called Charity Makeover. Our Remote Year group executed this event and it was one of the most satisfying things we did. After Pagely I foresee working at least part-time to turn that into a movement similar to Startup Weekend. I’m now reaching out to some people I believe could be linchpins in making that happen and putting a revenue model around it that would enable it to be a self-sustainable effort.  More to follow but a small group of us are intending to finish what we started for and treat that as a pilot of this initiative.

Learning-wise I’m taking a few different eCourses as time permits. I’ve been doing this Udemy course to learn the music DAW Ableton that I see as enabling incredible possibilities for live improv. My hope there is to become proficient enough and to secure a resident monthly gig in Lisbon at one of the live music places for fun and to scratch the musical performance itch. I’ve done the Headspace Meditation program for nearly three years now and feel like I capped out in terms of
advancing my practice via that app. I trialed the app for meditation but found the narrator to be too annoying and ultimately went in search of another program for guided meditation. I ultimately settled on this program after having listened to a bunch of his free guided
meditation podcasts. Jury is still out on whether this helps take that practice to the next level but so far so good.  I’ve been devoting more time to developing my chess game. has some pretty fantastic tutorials and gives you personalized analysis of your past games (pretty slick you load in the chess notation of your past games and it steps through your game and offers advice). I picked up this snazzy robotic chess board which allows me to play with physical pieces against the AI and then analyze my chess game after the fact to learn from mistakes (yea I’m a huge nerd). I also got one for my friend Benny for his 40th b-day which in theory allows us to play each other remotely over the internet although I’m now mobile for the next few months so that will have to wait until March.

In terms of recs for various books/music/gear:

  • This is my Spotify playlist of music that’s resonated ever since I finished Remote Year. It’s a smattering of very different music but there are some gems in there.
  • For books, Principles, Power of Habit & Man’s Search for Meaning would be my top picks. I just finished one called Shadow Divers too which is a fascinating nonfiction account of a dive team’s efforts in discovering and identifying a missing German U-boat from WWII. You can find my Goodreads profile here with all my reading recommendations.
  • Gear-wise the item that’s hands-down had the most ROI for me this past year has been the TRX suspension trainer. I’ve used this in place of a gym membership ever since my gym in Lisboa pulled some shady stuff in June and it’s been a great way to stay in shape. It works great in conjunction with this app for getting an exercise regiment complete with videos showing how to do each exercise and it tracks your progress through the 12-week program. Highly recommend.

In the relationship department I am still single having had a short-lived but intense relationship with one of the participants of the RY Kanyini program. The blessing and curse of this nomadic lifestyle is that while it exposes you to a bunch of amazing people, you’re perpetually saying goodbye to everyone and relationships are destined to be short-lived. I tried my first
“life coaching” session which yielded the assessment that love is the one “broken spoke on my life wheel.” Maybe so but I couldn’t bring myself to continuing the life coaching thing after the initial session because it just seems like the people who become life coaches are the ones who don’t know what to do themselves.  For better or worse I have to feel someone is an authority on a topic before trusting their expertise. I may give it another shot at some point but for now I’m content to execute for Pagely and my own side business initiatives and do a bunch of kite surfing in the process.

Anyways, I head back to Phoenix, AZ tomorrow to hang out with my folks and friends there for the next two weeks around Christmas. I’ll then be continuing on to Mexico City for New Year’s, La Ventana for what I hope to be two full weeks of kite surfing, a wedding in Cabo, 2 weeks in Puerto Escondido, 2 weeks in Bucerias for kiting and then a quick reunion with some
folks from our RY group in Sayulita, MX before returning to Lisbon in March.

If you’re in Phoenix come join us at this happy hour next Friday and let’s catch up in person. And if you listen to podcasts I would be hugely appreciative if you take a sec to subscribe and review mine. Happy Holidays to you and your fam and I wish you a healthy and prosperous 2019.


PS. if you’re on Instagram and want to keep up with my travels on a more frequent basis I post about a photo per day of something interesting and unique from my travels here.
Below is a pic of a magical moment at sunset in Pipa Brazil last week.

Jul 24
Howdy Drew,

You had requested my semi-annual update of what I’ve been up to and it’s that time to fill you in but before I do I have a quick favor to ask: 

I just last week launched this podcast with the goal of helping 100 people get “unstuck” by demystifying location-independent work and making it more accessible. It’s received great reviews thus far but I need your help: I’m trying to crack into the New & Noteworthy Travel section of iTunes because that jumpstarts listenership. I have one shot this week to make it and every download and subscription helps towards that cause. 

If you could take 30 seconds to subscribe & download my podcast via iTunes that would be massively appreciated. If you don’t use iTunes you can visit the link above and get it via any of the other major platforms like Spotify or Google Podcasts using the link in the header. I’ve poured most of my free cycles into this effort over the past few months and have been fortunate to get some really high quality guests for the show. 

Today’s guest is my friend Andrew Hyde, founder of Startup Weekend, cycler of a bicycle across the US, moderator of TEDx Boulder, wearer of a huge beard, traveler of 80 countries now banned permanently from Nepal (find out why) and all around teller of amazing stories. Check out his episode here and keep reading once you’ve subscribed. 

No seriously. Subscribe now. I’ll wait ;-) 

Scroll down for my update once you’ve done that… 

Oh and maybe tell just one friend who has talked about the idea of taking his/her job on the road about the podcast. This is a direct quote from a girl who heard it who just reached out to me: 

Hey Sean, I just listened to your latest video with Eddie. Just wanted to let you know I really enjoyed it! I think it’s valuable for current remotes, premotes, and definitely inspiring to people who haven’t yet taken the leap and deciding to do this crazy adventure (or something like it). I love the realness of it (and I also like that it’s not directly correlated with RY… it feels more believable this way and less sales-y) I’ll be sharing this around. Hope you get some traction man. You’re going to change so many lives out there!!

It would be amazing to eek into the featured Travel section on iTunes and I’m calling upon all my connections today to execute this “thunderclap” of concentrated interest. Apparently the secret to getting featured is the velocity of downloads within a short time-frame and now is that window. Anyways mucho appreciated if you dig the cause and are able to help spread the word. 

Alright. Thanks for that. So now I’ll fill you in on what I’ve been up to since my last update in January: 

 February 6th I moved to Lisbon, Portugal and have been living here since. This city captured me when I was here two years ago as a part of Remote Year and it has my heart. 

 March was cold and rainy. It rained for three weeks straight so not much exploring but I met some amazing people in the Remote Year Excelsior group that month who I’ve continued to remain in contact with. 

 April brought the Sisus of RY and they were my favorite group yet. It was sad to see them leave but likewise I’ve remained in contact and will undoubtedly regroup with these people at some point. 

– In May my folks visited Lisbon and I saw them for the first time since leaving the US. We had a blast while they were here. While they were in town on May 21st after 10mos of hoop-jumping I secured a residency permit which now allows me to live and work indefinitely here and I couldn’t be happier. 

– I lived in Barcelona Spain for the month of June with my friends Trevor and Trish (Trevor was actually my first guest on the podcast). Midway through June I skipped out to Mallorca to surprise one of my best friends for his 40th bday. We then had our 1 year reunion since completing Remote Year in Prague. It was amazing to see 30 of the 50 people who finished the year return to Prague to reunite. Like with any good friend it strangely seemed like no time had elapsed with our friendships. 

– I’ve begun burrowing into the local tech startup scene here in Lisbon and am now the newest mentor for Startup Lisboa and coach a handful of their startups on growth marketing and sales strategy.

– I gave this keynote talk two weeks ago for the Canopy City entrepreneur demo night to share my experience of systematizing the sales process at Pagely. The 7-step framework I show in that talk is a universally-applicable methodology for any growth-stage business and I hope will help other entrepreneurs with a promising product through the challenge of bringing it to market in a more reliable way. 

– Nomad Podcast was a project I started after building and launching my Nomad Prep eCourseover Christmas & New Year’s break earlier this year. I realized after expending a ton of energy to develop the eCourse that I went in with no real strategy for gaining distribution outside of Remote Year. The podcast is a logical extension of that effort to reach a broader audience and embodies the advice of “create value first then harvest some small percentage of it.” I wrote up this blog post over the weekend to explain the motive and why I’m spending all my spare cycles pushing the nomad thing. The short answer is: I believe the “Lost Einstein” phenomenon proposed by a NYT piece is actually at work in adults as well and that an antidote that worked for me is the stimulation that came via this nomadic lifestyle change. 

– In July one of my good friends (who happens to also be the CEO of Pagely where I work) visited and we drove a really fast sports car from Lisbon to Madrid to see one of my favorite bands Pearl Jam. That was a bucket list experience for sure. 

– This past weekend I finally got back into the sport of kite surfing and purchased some gear to be able to do this the rest of the summer season here on the beaches south of Lisbon. This was one of the items on the 10-year plan I made shortly after New Year’s and I’m super stoked to finally be making that a reality. 

– I’m now packing for a 10-day working trip in Hossegor, France with one of my oldest friends and his family. My role at Pagely has evolved nicely and I’ve been able to extricate myself from much of the day-to-day grind and move into a more play-maker role of planning and executing projects that support our sales team in achieving their revenue goals. 

– I have half a dozen interviews I’ve recorded for the podcast now which I’ll be producing and releasing as time permits over the next few weeks. It’s a bit surreal to film an interview from Barcelona with someone in Bolivia and find yourself later on a plane over Lisbon sculpting the content that then gets released from a surf town in France and eventually winds up in ear buds of someone I may never meet in who-knows-where… It’s both completely normal now but mind-blowing at the same time. 

– I believe crypto currency has turned the corner in its 6mo correction and we’ll see it making a rally from here. It may falter for another month but I suspect we’ll see another massive tidal wave of interest as Wall St and institutional money pours into the space. If your investment portfolio currently has no crypto in it I encourage you to first watch this video by the one and only Andreas Antonopoulos so you understand why censorship-resistant money and blockchain is so important and then carve out even just 5% of your savings and investment portfolio and allocate it to a handful of the top cryptos. Gemini and Coinbase are the two exchanges I recommend (Gemini is unfortunately not available in Arizona nor Portugal). 

– As far as plans for the rest of summer, I’ll be in Lisbon likely until November at which point my current plan is to migrate to warmer temperatures maybe at a beach town in Mexico. I’m hoping to spend Thanksgiving and/or Christmas with my folks and potentially my brother’s family in San Francisco. Other than that no plans to return to the US at this time. I should be in La Ventana, Mexico for two weeks in January then back to Lisbon next year. If you are ever out this way please drop me a line and let me show you around this wonderful city that has completely captured my heart. 

If you’ve read this far, thanks as always for taking an interest in my weird life. I hope you and your family are doing well. Send me an update on what you’ve been up to when you have time and live epicly. 


PS. if you’re on Instagram and want to keep up with my travels on a more frequent basis I post about a photo per day of something interesting and unique from my travels here. Below is a pic from this past weekend kite surfing with local friends in Fonte da Telha, Portugal.

Jul 18


Today I’m unveiling a project I’ve been working on for the past few months: a new podcast designed to demystify nomadic, location-independent work and make it more accessible. My goal is to help 100 people get “unstuck” by helping them make this transformative lifestyle change. You only get one chance with a podcast launch and I would love to break into the iTunes “New & Noteworthy” section for Places & Travel. Every single download & review helps towards this cause. If you support what I’m doing please take 30 sec now and download and subscribe to my podcast on iTunes. You can find video episodes and other goodies on

The Bigger Picture and Backstory

This effort began in December 2017 when I read an editorial piece on the New York times that talked about The Lost Einsteins. That article proposed that society today is deprived of an unknowable number of life-changing inventions by would-have-been Einsteins. They theorize that these young future potential contributors grow up without access to the environment and opportunities that would have been the catalyst for them to flourish due to living in poor socioeconomic status households.

This article resonated with me but for a different reason. While I agree with the author’s premise and suspect that indeed this is true and happening I hypothesize that the same phenomenon is at work within adults of all walks regardless of socioeconomic status. I believe there are a non-trivial number of privileged adults with all the trappings that came with a graduate education who went through a plinko board of choices in the education system and wound up winnowed into a career that doesn’t allow for the optimal expression of their talents. It’s debatable to what degree this is happening but unarguably this is true for some percentage of adults and it gets only more difficult over time to extract yourself from this rut. We find ourselves in veritable doldrums at points in our lives and while revamping the current education system to address the root cause and get more of the right people in the right roles out of the gate is a longer-arc massive undertaking, I believe there is a simple, immediate antidote for this issue and I want to try and make this more accessible to people in this situation.

Nomadic working travel has been instrumental in awakening me from this adult slumber. I won’t go into my personal story (if you want to read details Remote Year covered it well in this piece) but basically RY was a defibrillator that shocked me back to life, served as a gateway drug to nomadic working travel and ejected me from a personal and professional rut.

Why these three resources?

I spent three months living and working in Mexico, City last winter and had the opportunity to get to know a bunch of the admissions team for Remote Year. I was sitting within earshot and overheard numerous calls with aspiring digital nomads and while I only heard one side of the conversation, I got a high-concentration dose of Customer Discovery insights into the concerns and objections of aspirational nomads who wanted to do this type of working travel program.

I decided over Christmas break to develop a simple eCourse that would package up everything I had learned from my 1.5yrs of location-independent work at that point and give people a resource to help them more confidently make the leap. That project mushroomed into a significant undertaking. The deeper I got into developing the curriculum for that effort the more I wanted to apply what I knew of automation and software to turn it into a personalized coaching system that would not just be a static brochure but a living, interactive preparation tool. I spent most of my Christmas break developing content, gamification, an interactive checklist and automations to create the resource I wished I had going into Remote Year. I launched Nomad Prep a few weeks later with little fanfare and promptly realized I had committed the age-old entrepreneurial mistake of building a product before building an audience. That course continues to receive a trickle of students each week but I realized there needs to be a better way of reaching more aspiring nomads.

Nomad Bloggers (at the time but now changed due to trademark) was a project I had started in our first month of Remote Year originally intended to be a way of aggregating the blog posts from the bloggers in our group. I had modified it to support syndicating posts from other groups and it was growing in traffic. I rebranded it with the Nomad label, sold to Remote Year and used that cash to hire a developer from Upwork to add “Reddit-like” voting functionality and make the blog aggregator more sticky. While this seemed like a promising potential source of aspiring nomads it didn’t move the needle traffic-wise for Nomad Prep.

Shortly after I did a few interviews with prospective clients for Remote Year (they call them “Premotes”) and while the sessions were super-helpful, that approach unfortunately doesn’t scale. It led me to realize though that face-to-face video interaction captured and shared provide a rich way to ask and answer questions. I got the idea in my head that there’s room to do a podcast wherein I interview successful nomads, founders of travel programs and domain experts on subjects that could help educate folks on how to be better at working and living abroad. As with everything, it ended up taking 3x as long as expected working nights to cobble this together but I’m proud today to launch what I believe is the missing piece of the distribution puzzle here. I present to you, the first platform of its kind for sharing stories that can help current and aspiring Nomads.

I’ll spare you the gory details of everything it does but it showcases interviews in HD video via YouTube, is mobile-friendly, has audio-only versions syndicated across all major podcast platforms and each episode includes a bunch of supporting elements like transcript, photos, links, show notes and the ability to ask the guest questions via text comments as well as recording a video via your webcam. I’m hopeful that this will become a resource that helps current nomads be more excellent and helps prospective nomads confidently take the leap to trying this lifestyle and in so doing will have the same transformative, awakening effect that nomadic travel has had on me. If it helps even one or two people have an adventure abroad they otherwise wouldn’t have had that revitalizes them or even awakens the next slumbering adult Einstein then I would find that hugely rewarding.

I have interviews at varying stages of the production cycle now with a number of stellar guests. If you’re onboard with this cause there’s nothing to buy here nor donations to make, just subscribe to the podcast via your favorite platform using the links below and tell a friend who could benefit from it. Thanks for your support.
Apple Podcasts
Google Podcasts

Feb 01

I’m 30,000 feet above the Rockies en route to Sioux City, South Dakota on a brief stopover in the US and figured now is as good a time as any to write you a quick update email. I had originally intended to send these updates quarterly but semi-annual seems to be the frequency they want ;-)

The Remote Year program I joined back in May of 2016 concluded in May of 2017 in Buenos Aires. I never returned to AZ after it ended but instead chose to continue traveling working my way up South
and Central America via Chile, Costa Rica, Nicaragua, Dominican Republic and then making another stint through various countries in Europe. I spent the last three months living in Mexico City and the last two weeks kite surfing and working in La Ventana, Mexico.  I’m now up to a total of 61 cities, 18 countries and 4 continents in the last year and a half while still performing my role for my company Pagely as Director of Sales. It’s been one heck of an adventure.

Remote Year just last week did this piece on me and it’s a great summary of all I’ve been up to since that program concluded if you want more details.

One of the Remote Year groups that followed ours was named “Ikigai” which is a Japanese word that roughly translates to “the intersection of one’s purpose/mission/talents with what the world needs.” Late last year I took a hard look at all the experience I’ve acquired over the past two years in sales, travel, marketing automation, teaching, WordPress, writing and through this lens of Ikigai decided I was uniquely positioned to deliver an online course that would help others to make the leap and do what I had been fortunate to be able to do in taking my job on the road.

I started formulating an idea for an eCourse in October
and thought “yea I can probably knock this out in a few weekends, no problem.”  Four months later I’m *nearly* done with it (and by nearly, I mean, four months from now I’ll probably still be tweaking the content and learning management system ;-). But I’m proud to finally unveil what I’ve been toiling nights and weekends building: is the first course of it’s kind as an online academy to help the aspiring digital nomad to make a successful transition to this lifestyle.

Jul 23


Hola from Playa Grande Costa Rica!

Here is a quick update from me since my last email at Christmas. I’ve been traveling and working remotely now for the past thirteen months as a part of a group called Remote Year. My travels so far have spanned 53 cities, 17 countries and 4 continents and during this time I’ve been lucky to be able to realize a 70% increase in my sales volume for Pagely vs. the year prior to traveling. I did a lengthy write-up here summarizing the entire year in review. All in all it’s been an incredible experience. I had opportunity to speak at the PressNomics conference in April on how we’ve made this work and gave this talk which was well-received:

^ that’s a solid 30min overview of what’s been involved in making this travel/working arrangement effective over this past year. 

In each city I’ve been diligent about doing a blog post, photo album, narrated walking video and music playlist to capture the local flavor. Here is the recap of all the places I’ve been since Christmas:

Bogota in January: we flew from Mexico City on New Year’s eve and celebrated that night in Bogota, Colombia. I then did two weeks of travel all around the coast and jungle of Colombia with a friend (great pics at that link above). The latter half of the month I spent heads-down on work stuff. Elevation of Bogota is 8,500′ – was great for high-altitude training on the runs there. 

Medellin in February: was one of my favorite cities. We stayed in an area called
“Poblado” with a bunch of great little parks and restaurants. Contrary to the long-running Pablo Escobar stigma from the various films portraying Medellin as an unsafe drug capital, it was extremely safe and welcoming. Medellin is a place I could comfortably live at this point.

Lima in March: Lima had amazing seafood and our workspace there was probably the best of anywhere we’ve been. Unfortunately they had terrible floods while we were there that displaced some 20,000 people in the outlying areas. The highlight of the month for sure was hiking the Inca Trail and getting to walk around Machu
Picchu and Huayna Picchu. I left Lima early to come back for a handful of things that were happening in AZ. 

Cordoba in April: I did a 48hr travel “day” to Cordoba Argentina the 2nd week of April. Cordoba was a nice “rest stop” before Buenos Aires and after Lima in the same way that Valencia, Spain had served that same role between Rabat and CDMX.  The highlight in Cordoba was the work we did via the Charity Makeover effort I started to help a local monkey sanctuary. I remain actively involved in that effort today helping transition the project amongst Remote Year groups that are still flowing
through that city each month. 

Buenos Aires in May: up there with Lisbon, CDMX and Medellin as one of my favorite cities Buenos Aires was our final month in the program. The last month was a whirlwind with a side trip to Iguazu Falls (incredible) and all the goodbyes and farewell parties. Argentina just yesterday announced a promising plan to put it on par with Chile in terms of making it friendlier for Entrepreneurs to start businesses. I have my eye on BA as a potential place to return if/when I start the next thing following the successful exit of Pagely.   

After Buenos Aires I did a trip with a friend to the wine country of Mendoza, Argentina en route to Santiago, Chile where I spent the last three weeks. I arrived in Costa Rica three days ago and enrolled in a week-long surf camp here. Unfortunately yesterday I broke my toe which will likely put a damper on my surfing lessons. Fortunately I was able to get up on the board twice before the toe incident. I’m intending to move north to Nicaragua in a week and then meet one of my oldest friends in Dominican Republic for kite surfing all of July. Our old drummer for Cold Turkey is getting married in Seattle in early August so I’ll be back
briefly in the States for that then (provided I’m not exhausted) bounce to Europe for summer and ultimately plant in Mexico City around October. 

If you want to read the massive recap I did this is the single best summary of everything. I always enjoy hearing from people especially when on the road and isolated from friends. Drop me a line when you have time and let me know what’s new with you. I’ll part with this photo I took last night on the beach of Playa Grande at sunset. It’s beautiful here
right now. I hope you are keeping cool this summer and look forward to hearing from you. 


PS. if you’re on Instagram and want to keep up with my travels on a more frequent basis I post about a photo per day of something interesting and unique from my travels here.

Jun 14

Buckle up: this will be a long post but a juicy one as it’s the distillation of a year’s worth of experience traveling around the world while working remotely.

I spent the past year as a participant on a program called Remote Year which is essentially a “nomadic working as a service” adventure tour company. Our program ended two weeks ago and I’ve had enough time now to process the experience. I’ll share my thoughts here on the experience for anyone curious or potentially interested in doing it themselves.

Quantitative stats

First off let’s look at the year quantitatively examining some stats:

  • I walked/ran an average of 4mi/day over the past year for a total of 1460mi on foot and averaged 9,231 steps/day for a total of 3,369,315 steps.
  • I visited a total of 52 cities, 16 countries, 4 continents and met countless locals from each place.
  • Total travel distance = incalculable with all the side trips but you could connect the dots on the above to get a feel for it.
  • I flew a total of 48 flights, rode 22 busses, 91 ubers, 2 boats, 1 horse, 2 camels and 1 hot air balloon.
  • Spending-wise here in full transparency are my expenses for the past year ($2k of each month went directly to Remote Year):

  • and here are those expenses for the year broken out by category:

    Uncategorized = Cash/ATM and Travel includes the $27k to RY + travel expenses from side trips.

  • I won’t cite income but job performance-wise I had a banner year for sales at Pagely and was nearly able to hit our aggressive goal of doubling our revenue during this period.

It’s been a good year by the numbers but a better one by more difficult to quantify “quality of life” standards.

Qualitative analysis

The most common question I get (aside from “Which was your favorite place?”) is “How do you think you’ve changed?” Honestly at the age of forty-two my character traits are fairly well-baked at this point and I can’t say that I’ve fundamentally changed personality-wise from this experience. That said, I am different from when I started. In a lot of ways this past year has been like weight lifting for developing virtues. Traits like tolerance, patience, humility, empathy, gratitude, presence, resilience and adaptiveness are the ones that come to mind. I believe this type of roving remote working arrangement also gives a knowledge worker much of the benefit in terms of revitalization you’d get from a sabbatical while simultaneously (and counter-intuitively) enabling one’s best work. I’ve experienced a very real revival of my creativity – more on that in a bit…

Goal-wise, on our first full orientation day they had us jot down our goals for the year abroad. Mine were simple: 1) double Pagely’s revenue 2) perfect my Spanish 3) bank $X in savings 4) make friends while seeing the world. The only one I fell slightly short of was #1 but at 90% of goal I’m totally okay with that outcome. I was fluent in Spanish prior but this year has definitely solidified that. Savings-wise I exceeded that goal thanks to a stellar sales year and some lucky investments. One of the other intangible things I hoped to do was to contribute to the betterment of the group by sharing experience, ideas, contacts, etc. Towards that end I organized Startup Weekend in Lisbon, Charity Makeover Weekend in Cordoba, led a Krav Maga self-defense primer in Lisbon, a Start With Why workshop at the Junction in Cordoba, spoke at a Junction in London, organized what I think was one of the most fun side trips with the day of jet skiing on lake Guatape outside of Medellin and launched the aggregator site that tracks ours (and every other RY group’s) blog posts. I also gave free consultations to a handful of the solopreneurs in the group on the topics of funnel optimization, marketing automation, sales process and customer development. For Pagely, aside from the revenue generation, I was able to contribute two highly-valuable systems which I spoke about in this talk at Pressnomics: our pre-sales knowledge base and our AI sales followup system, Leviathan.

Deconstructing the benefits

I tallied my average monthly sales numbers over the past year and compared them to my year prior with Pagely. Here is that graph:

We’re a privately-held company and therefore I can’t share financials but you can see from the graph above I was able to realize a 70% increase in my average monthly revenue over the course of the year. People have asked, “To what do you attribute that improvement?” I spoke about this some in my PressNomics talk but I believe it’s the confluence of a couple things. We’re in process of publishing a thought leadership piece for Pagely (which I will link when it’s live) (UPDATE 4/13/17 here it is) so I won’t steal that thunder here but I believe it was a combination of having the “whitespace” and creative stimulation of being in these unique places constantly surrounded by novel challenges that gave me the room and inspiration to be more strategic on a project like Leviathan. The timezone offset I believe actually worked to our advantage while I was in Europe and Africa. And I think a decent chunk of the overall improvement can be attributed to things that have nothing to do with Remote Year (our average deal sizes have improved as we raised prices, our sales process is becoming more systematized, we have a marketing department and I have a SDR qualifying and appointment setting now, etc).

Other theories I have on what is happening

Kathy Sierra did a post back in the day to the effect of “If you feel your cubicle is rotting your brain, it probably is.” She then referenced research that indicates that environments devoid of stimulation and high in stress inhibit neurogenesis and that conversely, high-stimulation low-stress environments boost it. I had a brush with a job like that briefly back in 2003 and it scared the shit out of me. There’s evidence to suggest that at a neural level working in this way is beneficial to the brain. There’s no way for me to prove this is true but anecdotally I’ve been far happier working this way than when I was working out of my apartment in Phoenix.

The other thing that’s hard to prove but that’s a theory of mine is that I believe humans carry “primal imprints” or hardwired traits that are the result of having evolved for years living in tribes. On an evolutionary scale it’s only very recently that we’ve adopted the social structure of our current society. In my Junction talk in London I made the argument that our Remote Year group operates as a modern day tribe in every sense. I believe returning to a tribe-like structure, as weird as it sounds, has accounted for some portion of the improved happiness for me this past year. In the same way that I believe gardening where you’re kneading your hands through soil can unlock a primal connectedness to our past, traveling and working this way as a tribe returns us to a familiar social structure in which we’re more evolutionarily adapted to function optimally.

The Dynamics of our Group

We started the year with 75 participants and ended with 50. Here are the 50 who finished on our last night together:

Those 25 that left did so for various reasons: some preferred solo travel to this group travel, some had issues arise at work that demanded they return, some lost the jobs or started new ones in the States and others just weren’t feeling it and wanted to go home. My primary impetus for joining Remote Year was because I had wanted to try this type of working travel originally via a US roadtrip but the more I investigated what was involved, the more I realized this type of solo travel would preclude me from being effective, there was simply too much overhead involved in coordinating the next destination while en route and trying to be effective on the road. I pulled the trigger on RY because it solved all those logistical overhead issues but what I’ve learned over the past year is that while the perceived value prop was solving these logistical issues, the true value prop that kept me involved was the communal bond we developed amongst our group. I’m sure everyone thinks their group is special but we had upwards of 20 Remote Year staff fly in to attend our farewell event. If that staff presence is any indication our Darien group was truly something special amongst other Remote Year cohorts.

If I had to pick three nouns to describe the salient qualities of our group they would be “generosity, inclusiveness and initiative.” Our crew exhibited these qualities and really came together over the course of the past year to “level up” each other. I don’t have any hard figures here but on any given weekend someone was organizing a side trip and leaving an open invitation or putting together a trivia night or a movie showing or a wine tasting or jam session. I completely underestimated the value of this fabric going into it. It’s the single best thing that came out of everything that happened this past year. I formed a number of friendships which I imagine will be life-long and people in our crew have already organized long-term and near-term reunions. Words won’t do justice to the fabric of our group but a couple talented visual story tellers from our group have put together videos that do:

Chris Peloquin’s tribute video:

Eddie Contento’s tribute vid:

Rob Price photo poetry montage:

Kelly Tappel’s one second per day video:

What’s next for Sean?

I’m currently in Santiago Chile staying for another week. We had a handful of holdouts from our group stay after everyone else left to continue traveling. I just said goodbye to the last two other holdouts from our group tonight and I’m the lone Darien now in South America as far as I know. I’m planning to do some solo travel up through Costa Rica and Dominican Republic before heading back to the wedding of our former drummer in Seattle in August. My current plan (provided I’m not exhausted at that point) is to bounce directly back out to Europe for summer and ultimately plant in Mexico City around late October for winter. There are substantial tax benefits to staying outside of the US indefinitely once you build up a year of contiguous travel abroad (research the Foreign Earned Income Exclusion) and I’m not yet ready to return home to the US. One of the ulterior motives of my travel at this point is to scout alternate places I might potentially want to live and gain citizenship. Of the places we’ve been I felt most connected to Lisbon, CDMX, Medellin and Buenos Aires.

Work-wise I’m committed to staying with Pagely to see them through this chapter whatever that involves. I suspect given our rate of growth and dominance at the high end of the managed WordPress hosting space we’ll at some point be courted for acquisition and I intend to stay as long as my CEO and COO stay onboard. I’ve been spending some spare cycles helping the Proyecto Caraya charity we helped as a part of our last Charity Makeover move their cause forward. At this point that project is a labor of love but also an experiment to see whether the baton on Charity Makeover events can be passed in succession to subsequent Remote Year groups that pass through Cordoba City. Ideally I’d love to some day put a model behind that effort and grow it to be a phenomenon like Startup Weekend. As far as what I would do once Pagely runs its course, I plan to take a break and explore Asia following Pagely. Due to the business hour offset, visiting there while working for Pagely will likely be preclusive. I have some ideas for implementing various passive-recurring revenue-generating projects that play to my core skills and involve streamlining foreign investments in domestic US real estate. My ultimate goal consistent with my Why is to create a venture capital firm under the brand Grid7 that places the entrepreneur at the center. I believe there is opportunity to fundamentally rethink some disciplines as mature as Accounting and Finance to account for other dimensions of happiness, congruence, environmental impact and other variables to better align capitalistic incentives with what the world needs.

In my decompression phase of solo travel I’m intending to build some skill Kite Surfing, complete the Reforge Growth series I started, master the Ableton music DAW, and deepen my Headspace practice. When I finally plant somewhere after Europe I plan to seek out the best local Krav Maga instructor and resume my practice in that self-defensive art. Our first sales person for Pagely starts tomorrow and while I’ve enjoyed being front line sales learning and systematizing our process I’m excited for this move to extricate myself from that role and take on more of a VP of Sales role in building out our sales force, automating pieces which can be and growing & supporting our team to meet Pagely’s 2017 revenue goals.

Feedback for Remote Year

It’s crazy we were Remote Year’s fourth cohort and today they have eleven at varying phases. When we started the RY original group still hadn’t yet finished. Fast forward and they’ve now raised $12MM in venture capital and have been on a growth tear now up over 100 employees.

Today it’s a fantastic v1 platform to enable this type of travel and development and IMO was worth every penny I paid for the service. Having met and befriended both founders (assuming Sam and Greg remain in control of the board) I have high hopes that it will continue on its success trajectory. That said, $12MM is a lot of money to raise and their investors must be expecting a $120MM exit which requires a huge market and story, one that I don’t believe is supported by the present incantation of the program. IMO their way forward is to build the mobile app that knits together everything currently handled via silo’d sources and provides a hub of communication for their groups. Once they have a working version that serves current RY clients, open up a diluted version to the mass market of location-independent workers to make some of this info accessible to them. That gives them a far bigger story making them the “AirBnb of Nomadic Working,” gives them a high-volume, low-dollar service they can sell which also serves as leadgen for their higher-dollar current offering. I was fortunate to hang out with the RY digital team across various cities and they have a small capable and enlightened team so this is doable provided they expand that team.

The other obvious move for Remote Year is the real estate play in each of its cities. They’ve already built and purchased workspaces in Split and Lisbon respectively so they’re clearly thinking down this path as well. Once their pipeline can reliably generate a new group each month and they’re now juggling cohorts across a network of cities where they can keep accommodations and workspaces occupied it’s likely a no-brainer for them to buy vs. rent. IMO they don’t use the capital they raised for that. They would be better served crowdfunding that effort or treating them as independent REITs and finding private investors to finance those purchases. They should have a good idea of attrition and vacancy numbers by that point and with the program I suggested as a “re-oxygenation” of the group whereby current participants can vouch for friends to bring in at intervals to fill vacant program slots, I would imagine this becomes a hugely safe bet for investors.

I would love to see Remote Year bake in some personal and professional development content to their program. They’ve got bigger fish to fry for the time being but for v2 of their platform I’d love to see programs like Simon Sinek “Start With Why” added to the program. I’ve talked with a number of Remotes about how they would adapt the offering and the consensus is that it was pretty on-point for what it strives to be currently. The most common complaint was that they occasionally skimped on accommodations (likely to preserve margins). I had mostly decent accommodations with maybe only one or two cities where it’s not somewhere I would have lived by choice, but I took that as part of the experience and understand that RY is a business like any business and needs to make a profit in order to be sustainable. Overall I’m extremely satisfied with the experience and their receptiveness to feedback at every level. If anything the line blurred many times with our relationship to Remote Year staff and group members as we viewed them as colleagues instead of staff.

Final thoughts

Contrary to my writing style I’m not a hugely analytical person. I’m a creative person and a teacher by nature but I tend to try and distill things to tangible takeaways for this blog. The final week of Remote Year was an intensely emotional one. We had a group that had become extremely close with a ticking clock on this social experiment that we knew was winding to a close. Our final meal together was a brunch on the last day and I found myself sleep deprived and at a loss for words overcome by emotion in hugging people goodbye.
I’ll post my farewell Slack message to our group below as it captures some of those feelings:

Warning: long sappy message from Sean coming… TLDR; I <3 you guys.

I hope everyone has gotten (or is process of getting) home safely. I’ve had a day to process yesterday and sleep and just wanted to say a few words while it’s all fresh.

Sorry for ducking out early on the final brunch. I feel like we’ve been successfully staving off sad emotions with a week-long going away party celebration. The tribute videos from Rob, Eddie and Chris got me a bit on Monday night but the levy that was keeping these big emotions at bay fully broke yesterday as I was hugging people at brunch. I walked to my AirBnb and two songs that have been in my spotify rotation this month played in sequence and for the first time I allowed these emotions to sweep through. I typically process things through music and I don’t know if these two songs will have the same effect for you but next time you’re somewhere alone and in a headspace for this, I invite you to listen to these tracks back to back and let that wave hit you squarely in the chest and stay with it. Listen in this order if you do this exercise and let the images of all the incredible things we’ve done this past year play like a movie reel in your head:

The fate to lose
and forge ahead.
through the burden,
through the death.
The howling
and humble hearts.
know the answers,
find the rest.

Apparently a crystal sea
winds into my hands.
But when I breathe,
all I see
melts into the sand
So I’ll be letting go now.

This one ^ captures the mix of emotions from closing the chapter that was this adventure: 1 part grief saying bye to each other, 2 parts reflection and nostalgia, 2 parts peace and 100 parts sheer gratitude for the rare opportunity we’ve all had in this experience… the people, the places and the void of material things. Valencia Project shirts never lie ;-)

Consider this: a direct quote from Tony Robbins (regardless of what you think of him, this is powerful):

Gratitude is the antidote to the things that mess us up. You can’t be angry and grateful simultaneously. You can’t be fearful and grateful simultaneously. So, gratitude is the solution to both anger and fear, and instead of just acting grateful, I think of specific situations that I’m grateful for, little ones and big ones. I do it every single day, and I step into those moments and I feel the gratitude and the aliveness.

If you feel a wave of gratitude sweep through you, sit with it. Remember it. Let it permeate your being and overflow the cup that normally accumulates other negative emotions. And try to do that going forward.

ok chapter closed… what next?

Door’s wide open
You know what were saying ’bout us now
He’s a legend
I’m a legend
And we both go tripping through the door
Set sail!

This one ^ to me captures the emotions of hopefulness and promise as we all sail off in our different directions to open our respective next chapters. We are all legends guys. This year has changed each of us in magical ways. I believe know that we will go on to do amazing things and change the world in positive ways. So grateful for this family, the support system and strength that exists in it. Use the support system as you need it and let’s be there for each other like the tribe we have become. I love you guys and I look forward to the inevitable reunions we will surely have around the world. See you on the road.


My PressNomics talk on Remote Work had some of those same emotions towards the end. I realize I’ve been incredibly lucky to have the opportunity to have this experience and I’ve done my best to capture and share that here with friends and family. I faithfully did a blog post, video and photo album for each city. Those are linked below:

If you’re considering doing Remote Year I encourage you to talk with a handful of the people who have done it. Everyone’s experience will be different and by gaining enough sample size you’ll have a good cross section of views on this program. To me, this type of extended cultural exploration and ambassadorship has awakened me in wonderful ways. The fact that we’ve been able to be good ambassadors for our culture in these places and forge friendships with locals that I can now go back and visit one day is the icing on this cake. This type of one-on-one bridge building I believe is the antidote to hate, fear and all the negative stereotype reactions that accrue amongst cultures fed by calculated media propaganda designed to keep us fighting each other.

If you watch only one 3min video today, take a minute and watch this:

It’s career wisdom from an ex-CIA operative and it’s the crux of how we develop tolerance and unravel the deep cross-cultural vendettas that plague our future.

Lastly, I’m not religious and don’t even consider myself spiritual but I do believe the universe has a symmetry and unknowable karmic forces that hold it together. Call this what you want but this song to me is an ask of the universe to watch over our group of travelers as they disburse across the globe and go on to open their next respective chapters.


Hiking Huyana Picchu, Peru

Hiking Huyana Picchu, Peru

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