1/3 done already!

It’s been four months since I left for Remote Year, and we’re now 1/3 of the way through the year. Time has really flown by, even faster than I knew it would. I thought I’d give you some reflections on my time so far.


Transitioning my job to being fully remote was much easier than I expected. I do think you can do just about any job remotely with all of the technology and tools we have these days; however, I think I expected it to “feel” different. I expected to feel somewhat disconnected from things back home, simply by virtue of not catching those hallway conversations or water cooler talk. I’ve been surprised that, so far at least, that hasn’t been the case. In fact, it’s been sort of nice not to hear the rumor the mill. My job doesn’t “feel” any different, and several people have commented recently that it doesn’t feel like I’ve been gone as long as I have (which makes me think it doesn’t feel any different to them either).  There’s a real freedom to literally working from wherever I want – be that the co-working space that Remote Year pays for, my apartment, or anywhere else with a strong wifi signal. Month 5 will bring a new challenge, with having to adapt to working night shift, but I suspect even that won’t be as bad as it sounds.

Working from my apartment in Medellin


I love to plan, and I especially love to plan trips. There’s a real joy for me in researching everything there is to do, picking the perfect neighborhood and the best hotel, and having a list of things to do when I arrive. However, the breakneck pace of RY means that I have often gotten on a plane without having much of an idea of what I’ll do in a given location. At any given time I am researching multiple trips and simply don’t have the time to devote to planning the way I used to. That mostly stresses me out, but it’s also proven that things have been just fine without doing that too.

I had a hoped that RY would mellow me out a bit a far as needing to control everything when I travel. To an extent, I have noticed how nice it can be to have someone else worry about all of that for you. Finding flights every single month, picking out the best neighborhood, figuring out how to get from the airport, all of that takes time and when you move every month it can really be a time suck. Letting RY worry about all of those details certainly has its perks.

I expected to get to “side trip” more often than I’ve realistically been able to. I thought checking off 2-3 countries per month would be a fairly easy task, but I really underestimated how full our RY calendar would be and how quickly that month has gone. Maybe that gets easier in Europe, but I suspect 2 countries/month will continue to pretty much be my max. I find when I am gone a lot, I feel like I’m missing out on wherever we’re living, and it’s just stressful to be on the move every week. I’m trying to remember that there are certain destinations I would have gone to eventually regardless, so exploring some of the lesser known destinations in the country we are in also has its merits.

Remote Year as a program

I did A LOT of research in the three and a half years between when I first heard about Remote Year (RY) and when I left for my Remote Year program, so there hasn’t been much that has surprised me about the program itself.

Let’s get this out of the way: Remote Year isn’t perfect, and it isn’t for everyone. With that said, Remote Year is maybe the single best thing I’ve ever done. I’ve been happy with it on the whole, and I think Remote Year is doing a good job of changing and adapting as time goes on. I’m experiencing a very different version of RY than the first couple of cohorts did, or even versus people who just finished their programs, and I think that’s overall a good thing.

One thing that really concerned me prior to leaving was the idea that RY had complete control over booking my flights from one city to the next. While it wouldn’t be as big of a deal for a 2 hour flight, it caused me a lot of anxiety to think about those 10+ hour flights. Beginning with the transition from our 4th to 5th city (our first long haul flight across the Pacific), Remote Year rolled out the option for us to opt out of the group flight, receive a predetermined credit, and allow us to find our own way to the next location. While I likely won’t use this every month, I chose to opt out for our first long-haul flight to Asia and I was really happy to have the option.

The apartments and workspaces have been about as expected, even while I feel like I haven’t had the nicest options available each month. The couple of hiccups we’ve had with workspaces have been in locations that were new to RY, so it’s somewhat expected that they have some kinks to work out. In my first 4 months, with the exception of the Mexico City workspace, they’ve been productive places to work. In Mexico, RY moved to a new co-working space and I’ve found it extremely difficult to get work done there. RY did offer us a month of co-working access once we finish our program to make up for this.

Sam Pessin, co-founder of RY and I

Traveling long term

While I love to travel, I was a bit concerned about being abroad for such a long period of time. I’m used to a lot of creature comforts, and I stressed a bit over where I’d get my hair done, where I’d find an English-speaking chiropractor, or how I’d live without Amazon Prime or pizza delivery. Some things were definitely a struggle (finding people who knew how to do blonde hair), but for the most part, living out of one 50 pound suitcase has not been as difficult as I expected. After four months, I am absolutely sick of all of the clothing I brought (because I wear the same 5 outfits week after week), but it’s amazing how easy it is to say no to buying stupid things when you know you have zero space in your luggage for it. I hope I carry some of that with me when I return to the states again and curb my habit of purchasing things on a whim.

The future

Remote Year has really forced me to live in the present. Part of it is that there is SO much going on, and you’re never really anywhere long enough to truly get comfortable, that you spend a lot of time just figuring out the here and now. Part of it is that we don’t have access to RY calendars for the month ahead until, at best, one week before we arrive. It is extremely tough to plan trips more than a few weeks out unless you’re willing to miss out on any potential activities RY has planned. The other aspect to that is that thinking about the future makes the days the fly by even faster. “Month 13” is something no one in our group discusses – it’s hard to imagine going back to “normal” life after this, and even harder to imagine saying goodbye to our Tramily. We’re all just trying to live in the present and not worry about the inevitable.

I think our toughest months are ahead of us – Asia will be tough for a lot of reasons: many people will be working overnights, it will hot and humid, and no one speaks the languages. Additionally, it’s common for RY groups to hit a “dip” as a group around the 4-6 month marks – the honeymoon period has worn off and the stresses of being away from your family and friends start wearing on you. That’s also an opportunity to band together as a group.

Final thoughts

I can’t believe we’re a third of the way done – our time in Latin America has flown by and it’s been a great four months. I’m pleased with my decision to do Remote Year, and whole-heartedly recommend it to anyone who thinks it may be something they’d like to do. Find out more here if you’re interested in
RY. I feel lucky to have been given the opportunity to make my dream happen, and while I’m nervous about Asia, I’m excited to see what the next 8 months have in store!