Final Experiment Report: Knowing When To Quit & My Remote Year Review

In May, I started a new life experiment: living as a digital nomad. I wanted a quick and easy way to explore the possibility of making travel a lifestyle instead of a scheduled activity. So I joined a 4-month Remote Year program in order to explore 3 hypotheses:

  1. Traveling more than I currently do will increase my happiness.
  2. A different pace of traveling (a new country every month) will be more satisfying than our current pace (several months in the same place every year and a few short multi-country sprints).
  3. Traveling with other digital nomads will enhance my travel experience.

In all honesty, I knew after 60 days that none of my hypotheses were supported by the data. I wasn’t happier, more satisfied, or interested in becoming a digital nomad. In fact, I felt homesick, missed my husband, and was freshly aware that I take many things at home for granted. Most importantly, I realized that I already have the three things most of the digital nomads I met were seeking: 1) a partner who loves me unconditionally, 2) a clear sense of purpose, and 3) a place to call home where I have deep roots and true friends.

But despite being clear in my analysis after 2 months, I continued traveling with Remote Year.

On To Valencia!

The group transitioned from Lisbon to Valencia and even though I wanted to go home, a part of me felt like I had to “stick it out” for the full 4 month program. I saw leaving early as a failure and believed that doing so would make me a quitter. As someone who sees herself as resilient, tenacious, and persistent, quitting was not an option. So I resolved to grin and bear it to the bitter end.

But it’s funny what happens when you press forward for all the wrong reasons. For me, the universe responds in particular ways when I insist on ignoring my reason (the experiment is over), my intuition (it’s time to go), and my emotions (I’m homesick): everything feels like a struggle. And from the moment I set foot in Valencia, everything around me felt a bit off:

  • The AirBnB I rented lacked promised amenities and after a bathroom flood, I had to retreat back to my shared Remote Year flat.
  • There was a record-setting heat wave that resulted in triple-digit temperatures.
  • It was August, so many businesses were closed for the month.
  • My cohort regressed to high school dynamics (cliques solidified, gossip was rampant, and the ‘cool kids’ relational aggression escalated).

Despite these challenges, I kept myself busy in order to pass the time. It wasn’t hard because Valencia is a beautiful city with plenty to see, learn, do and eat! I took an intensive Spanish class, attended a Battle of the Flowers parade, learned how to eat 5 times a day, connected with amazing roommates, completed 10 of the “Best Things To Do in Valencia“, and ate everything that didn’t move (and a few things that did).

Time For A Reframe

But as much as I enjoyed learning, eating and exploring Valencia, I kept asking myself daily: why am I here? And why am I holding on to something that is no longer serving me?

The only answer I could come up with was my internal story of not wanting to be a quitter. That story drove me to imagine feeling embarrassed if I went home early, dreading having to explain repeatedly why I did so, believing people would negatively judge me, and feeling shame over losing money (I paid for the full program up-front). A little voice in my head just kept saying “winners never quit and quitters never win!”.

But conversations with friends and family helped me realize that “quitting” is just one of many possible interpretations of exiting Remote Year (and it wasn’t an empowering one). Those conversations helped me release the “quitting” narrative and reframe my decision in terms of “completing”. And as soon as I shifted the question from “should I quit?” to “am I complete with this experiment?” the answer was clear.

So clear, that I flew home the next day.

As soon as I returned to Detroit, I knew I made the right decision. Not only was I delighted to reconnect with my family and friends, but my early return meant I was available to:

  • Celebrate the surprise engagement of dear friends
  • Attend my favorite philanthropy conference in New York City
  • Connect with a mentee that I’ve never met in person
  • Celebrate 100 days without alcohol surrounded by people who support my new lifestyle choice
  • Play golf with my boo before it gets too cold
  • Start a 16-week writing workshop
  • Keep our annual tradition of attending the opening football game at our alma mater (my husband and I met on our college cheerleading team).

I know my Instagram feed is significantly less exciting, but what can I say: there’s no place like home!

And it’s okay to quit when you’re complete with an experience, relationship, or group before you imagined. Some people might even call that “highly efficient”.

My Remote Year Review

I receive tons of questions and requests for conversation about my experience on Remote Year. Given that I answer the same three questions repeatedly, I’m going to answer all three of them here.

FAQ #1: Did You Enjoy Remote Year?

Overall I enjoyed my Remote Year experience. I traveled to places I may not have gone otherwise, started writing my next book, funded a new passion project, and made a few friends. But I enjoyed the experience because I had the resources to make adjustments when Remote Year fell short of expectations or didn’t meet my needs.

By “adjustments” I mean:

  • renting my own AirBnB (when I wanted my own private space or felt uncomfortable with my roommate assignment)
  • paying for co-working space (when Remote Year’s co-working space was sub-optimal for my specific workplace needs)
  • booking AirBnB Experiences (when Remote Year cancelled activities for failure to meet minimum registration numbers)
  • paying for my own professional development (when Remote Year’s offerings consisted of people informally sharing random skills, experiences and personal hobbies)
  • arranging for a plane ticket from Valencia to Detroit when I chose to go home.

I would encourage anyone considering Remote Year to first ask yourself a few questions:

  • why do you want to travel with Remote Year (convenience, community, itinerary)?
  • how do you really feel about roommates?
  • do you have non-negotiable needs when it comes to your living space or work space?
  • how important is professional development to you?
  • are you willing to commit additional resources to get your needs met or would you be better off creating your own travel agenda and finding optimal work space wherever you are?

It’s important to get clear about such questions before you make this significant commitment of time, money and energy. I thought I would be fine with basic accommodations. But I’m at a point in my life where I expect a bedroom to have a closet, a kitchen to have a coffee maker, and an apartment to have a washing machine. I assumed I could work anywhere. But I actually require three things to work effectively: 1) sound-proof conference rooms for confidential calls, 2) a comfortable reading chair, and 3) quiet space for writing. And I imagined I would be okay with Remote Year’s professional development offerings. But I am a voracious learner, former professor, and built an online training company for college faculty. As a result, I have a high bar for what constitutes “professional development” that Remote Year did not meet.

Those are my preferences and needs. You may be similar or you may be totally different. The point is that the greater the alignment between your expectations and the reality of Remote Year, the more satisfied you will feel with your experience. The bigger the gap, the more you’ll have to adapt and/or spend money making adjustments.

FAQ #2: Do You Recommend Remote Year For Women of Color?

I’ve travelled with many groups, albeit for weeks — not months — at a time. And I know how important it is to walk into any travel experience with my eyes wide open. So I did my due diligence on Remote Year by searching online and interviewing current and former participants. While there are many glowing Instagram posts, I also heard a lot of negative feedback about Remote Year. It was described as a hook-up frat culture by former employees. There were painful reports of racism and sexism by past participants. And in a mixed bag of online reviews, many past participants raised questions about how the company functions.

I raised all these issues in my conversations with a Remote Year consultant. She acknowledged each one of them and assured me that Remote Year was aware of the problems and in the midst of launching a company-wide diversity, equity and inclusion initiative. Their willingness to commit to change and a plan to do so were enough for me to allow Remote Year to be the platform for my nomad life experiment.

My first experience of Remote Year’s DEI training was a webinar several weeks before our program began. It was taught by Remote Year’s Director of Community Development and entitled “New Community: Who Dis?“. Here’s a 2-minute snippet on unconscious bias from that webinar to give you a sample of the tone, content and depth of Remote Year’s approach to DEI training:

You’re likely to have one of three responses to that snippet and it’s useful to notice because my sense of how much you will enjoy Remote Year is based on how you see this video:

  1. If you see a well-intentioned guy, who messed up the story but is at least trying to talk about unconscious bias, then you’ll love Remote Year and appreciate their DEI efforts.
  2. If you see this as ineffective, but you’re generally willing to overlook consistent ineptitude and micro-aggressions, you’ll find Remote Year a useful platform and their DEI efforts hapless, but tolerable.
  3. If you’re wondering why a man who just discovered his unconscious gender bias recently (via a podcast) is in charge of designing and delivering DEI training, then you’ll find Remote Year’s efforts grossly inadequate and continually wonder how they manage to do something so important so poorly.

I’m sharing this 2-minute snippet because it epitomizes Remote Year’s DEI initiative as a whole: superficial, ill-conceived, and poorly delivered by unqualified staff.

Personally, I found myself appalled by this DEI webinar (which went significantly downhill after this snippet). I couldn’t believe this was what and who Remote Year put forward as the solution to the racism and misogyny reported by past participants. I considered aborting the trip but I had already paid in-full for the program and re-arranged my life to travel for 4 months. It felt too late to cancel the trip even though it seemed painfully clear to me that Remote Year had no idea how to conduct DEI training and there would be no competent facilitation of the issues that would inevitably arise in a diverse travel group.

Given that I was committed to going, but now realized the reality of their DEI initiative, I consciously and intentionally chose a strategy of group avoidance from Day 1. I didn’t drink, I didn’t go out to bars and clubs with the group, I didn’t volunteer my free labor to teach others about diversity, and I released any need for connection, community or belonging. In other words, I decided from the beginning to travel with the group, but not to be in the group.

After the Who Dis webinar, Remote Year “required” us to watch third party corporate training videos on informed consent, harassment, and micro-aggressions in the workplace. The videos were far better quality than the initial webinar, but devoid of context for a travel program. And this “mandatory” training was not mandatory at all because there were no consequences for failing to complete it. Nor were there any incentives or consequences to skipping group meetings designed to discuss the material.

By the end of the first month of our program, micro-aggressions were an everyday occurrence. And the people committing them were the same folks complaining about the existence of DEI training (that they refused to do). By the second month, the DEI training disappeared without any explanation why. I heard through the grapevine that Remote Year was “stepping back to regroup and rethink the DEI training.” Needless to say, when you combine generic training, unskilled facilitation, ambivalence over whether participation is mandatory (or not) and silent retreat, it sends a powerful message: we’re committed to looking diverse on Instagram, but when it gets hard, we’re out.

In hindsight, my strategy of group avoidance worked well for me and my personal well-being. It spared me from the energetic drain of drunken micro-aggressions, but also constrained my possibilities. It was my choice, I don’t regret it, and I take 100% responsibility for making it. But nobody should feel like they have to make such a choice, especially after paying $11,500 for the promise of traveling the world with a supportive and inclusive community. After I returned home, I learned that existing conflicts escalated significantly. So much so, that Remote Year had to remove a male participant from the program. The ineffective corporate handling of the issue left one participant to conclude that Remote Year is Not Safe for Women of Color. I agree with her assessment and any woman of color considering Remote Year should read her entire post (as well as Remote Year is The Most Expensive Mistake I’ve Ever Made) as part of your due diligence.

Ultimately, I really wanted to love Remote Year. As both a start-up founder who has built a successful company and an active investor, I appreciate how hard it is to build a truly diverse, inclusive, and profitable company. But Remote Year seems to be struggling to evolve beyond the very white, very masculine, and very immature culture of its early years. Given that the majority of their clients are women, it’s time to grow up. But in this participant’s opinion, their approach to diversity, equity and inclusion — as well as the implementation of policies and procedures to keep me safe — felt superficial and shaky at best.

Until Remote Year gets serious about change (and serious requires investing significant resources, diversifying the board and executive leadership team, hiring competent program leaders who are experienced in facilitating conflict in diverse communities, and consistently implementing new policies), I encourage women of color to explore alternatives.

FAQ #3: Is Remote Year a Good Option for Academics on Sabbatical?

I have a lot of academic friends, former clients, mentees, and readers of this blog. And many of you have asked me if you should consider Remote Year as a platform for your upcoming sabbatical. The short answer is no.

The primary challenge of the Remote Year platform for an academic sabbatical is the structure of the program. Specifically, you move to a new country every month. The first week you settle into a new flat, workspace, and neighborhood. The second and third week, you explore the city and country where you’re based. And the last week, you get ready to leave (saying goodbye’s, donating unused items, packing, etc…). That structure makes it difficult to get into a consistent writing groove and do deep work. For that reason alone, slow travel or getting settled in one place is a better bet for an academic sabbatical.

It’s also worth noting that the co-working spaces feel far more like a start-up than a college campus. People consume alcohol openly while working, you won’t have a dedicated space to call your own, and there is no privacy. I mention this for academics because if you’re accustomed to working in your office with a door, that won’t happen. If you expect a certain level of decorum and professionalism, you’ll be disappointed. And if you’re used to intellectually curious students and colleagues talking about ideas, that was not common. There are amazing libraries, bookstores, and coffee shops you can find to work in, but that will be on you.

Finally, the primary reason people join travel groups — when they could plan their own travel more cheaply — is the community. So I also encourage academics to imagine how you will feel in a group where “what do you think would be the best celebrity threesome?” or “who in this group would you most like to fuck?” are considered acceptable conversation starters and “let me tell you why I voted for Trump” passes for political commentary. Will that contribute to (or diminish) your intellectual development? Will you find that invigorating or draining? Would such conversations validate your decision to put your sabbatical in the hands of Remote Year or leave you wondering: why am I here?

It’s A Wrap!

That’s it. This is the final installment of my “life experiment reports” and my honest review of Remote Year. I hope openly sharing my life experiment encourages you to design your own. And I hope my FAQ’s are helpful to readers who are considering Remote Year.


Kerry Ann

One Reply to “Final Experiment Report: Knowing When To Quit & My Remote Year Review”

  1. Wow, thank you for your candid review. I had heard of Remote Year, and it sounds like a great idea but the execution sounds problematic. My husband and I are also experimenting with stepping up the travel now that we’re empty-nesters but we’re doing it ourselves and keeping a pretty loose itinerary. We just did our longest trip ever at 30 days — in Costa Rica, so a place we knew somewhat. It was a great start and really confirmed how much we love slow travel.

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