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

PS. if you would like to receive a quarterly email update from me with a distillation of all my learnings from the previous quarter, add your email below:

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3 Responses to “Unpacking It All: Remote Year in Review”

  1. Keith Wiley says:

    Awesome post sean, looks like an incredible experience! Looking forward to seeing you in the DR!

  2. Erica Lucci says:

    Wonderful wrap up. Congratulations on such growth!

  3. […] as Tierney puts it: “Everyone who hears about it is like, ‘Oh, I wish I could do that.’ Well, you […]

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