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A Day in the Life: Working on Remote Year

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This year, I gave up my apartment in Chicago, invested in a reliable universal charger, and boarded a flight across the Atlantic with no exact plan—except to spend the next 12 months abroad doing a program called Remote Year.

I’ve always been a traveler, but up until this point, “travel” had always actually meant “solo travel.” Traveling alone for long stretches made me independent and adaptable, but it was exhausting, too. Three months had become my limit—I would hit decision fatigue about where to go and what to do, and need a break.

I found myself searching for a sustainable way of making travel a larger part of my life, one that left me inspired instead of exhausted. Cue my decision to sign up for Remote Year.

This is how it works: Remote Year sets an itinerary, and you pay a fee that includes housing, transit between cities, and unique events that can’t be found elsewhere (like exploring caves, touring a shipyard, visiting a brewery, etc.). My group is called Exupery—and I travel with the same people all year, hitting a new city every weeks. We started in Split, Croatia, and are heading to Prague next. Over the year, I’ll be working and living in Europe, Africa, Asia, and South America. Goodbye decision fatigue, hello world!

While traveling, I’m working remotely as Skillcrush’s Director of Operations, calling into meetings from various international coworking spaces and navigating the time differences of each new place. Here’s what a typical (if there is such a thing as typical) day looks like as I work while on Remote Year.
Working Remotely From Anywhere in the World: My Daily Routine

9:00 a.m.
I begrudgingly get out of bed after snoozing my alarm a few times.

In order to have some overlap with my American coworkers, I work different hours here than I do in the States, and that means my whole day is on a delay. I go to work later, go to bed later, and wake up later.

This morning, I take my laptop into the kitchen and perch on the counter to clear out my inboxes. At this apartment, my stove takes forever to cook anything so I’ve gotten in the habit of checking messages while I make breakfast.

A few emails and notifications have come in overnight so I tackle those first—answering the quick questions, and archiving or starring the rest for later. I prioritize messages from my European coworkers because I know they’ll be signing on soon, and I take care of anything that’s a blocker for someone on my team. The rest can wait.

By the time I’ve got a handle on my inboxes, my breakfast is done and I move to my kitchen table to eat and make my to-do list for the day.

This is ritual I always make time for because there’s always a lot going on during Remote Year. It’s easy for me to overextend myself for fear of missing out. Looking at my calendar and my to-dos for the week forces me to make some calls about my priorities—if I want to go to that Spanish lesson and #WineDownWednesday dinner, I probably need to skip the group lunch.

9:30 a.m.
Back in Chicago, evenings used to be my free time to workout and putz around my apartment. Now, mornings are when I relax, run errands, or explore a new corner of the city.

Yesterday, I went to an olive oil tasting and bought groceries. Tomorrow, I’ll go to a yoga class taught by another woman in my group. I don’t have any errands to run today, so I throw a load of clothes in the wash and take my laptop and notebook out to my balcony.

I’ve started using a free app called Marco Polo to stay in touch with family and friends back home. It allows us to send each other video messages that the other person can watch whenever they want. My mom loves it. Just last week, I went to a group dinner and we passed the phone around the table so everyone could say hi to her. (She may or may not have cried.)

I like sending Polos because it’s more personal than a text message and doesn’t require all the back and forth scheduling of a Facetime call when you’re this many time zones away.

I send a few Polos and decide to journal for a while. I keep an art journal all the time but it’s especially important to me when traveling because with so much stuff happening all the time, it’s easy to forget the small stuff that really makes the day-to-day so rewarding.

By the time I’m done, my clothes are, too, and I take a few minutes to pull out my drying rack and hang them up to dry on the patio while I’m gone.

11:00 a.m.
Most months, I’ll have at least one roommate and live in an apartment a short walk from the coworking space. I lucked out this month, though, and am living alone in an apartment right above the coworking space, which also happens to be right across the street from a beach. It makes for a short commute—and means there’s almost always flip flops and a towel in my backpack!

Today, I head downstairs to our workspace, WIP Coworking. The space is broken into a quiet side and a louder kitchen area. I work better with a little background noise so I like to work from the big high-top tables on the kitchen side and am pumped to see that one is free. (They go fast!)

I set up my stuff and head to the coffee machine for my first fix of the day. Their machine makes a mean cappuccino, and I may or may not be averaging 4-5 per day. (They’re super small so it’s fine. Right??)

Fun story: Our social media manager recently posted a stock photo from the WIP space on our Instagram, without realizing it was my coworking space for the month!

12:00 p.m.
Since it’s still super early on the east coast, no new messages have come in since I cleared out my inbox, so I move on to all the reviews I need to do. As a director, I spent a lot of time coordinating with other teams on cross-team work, and reviewing project plans, student announcements, and the like from my own team members. I like to get these out of the way next so I’m not a blocker to anyone else.

Around noon, I throw my laptop back in my bag and head outside to meet two friends for lunch.

Slack is our main mode of communication on Remote Year, and there’s a bot that randomly pairs a few of us for coffee dates once a week. This week, I’m paired with Veronica (a lawyer from Chicago) and Ri (a growth hacker from Pittsburg).

We’ve decided to grab lunch in Old Town. There’s a bus right out front, but we all need to get back to work sooner rather than later. After a bit of discussion, we decide to call an Uber, which will get us there in 15 minutes.

Diocletian’s Palace takes up about half of Split’s Old Town area, and it’s full of restaurants and shops. We decide to just walk around until we find a menu that looks good and end up at an outdoor cafe where I fall in love with a ginger lemonade and make a mental note to come back for the blueberry pie.

1:30 p.m.
Lunch is the most important meal of the day in Croatia so, even in the touristy part of town, it can’t be rushed. We’ve been here a few weeks already so we’ve learned to start looking for the waiter 15 minutes before we actually want to pay.

With our stomachs full and our to-do lists calling, we sort out our bill (thank god for Venmo!) and wander to a nearby coffee shop that Ri has been wanting to try. Veronica decides to work from a nearby cafe, so Ri and I say our goodbyes and head back to the Uber pickup point.

Ri and I spend most of the drive discussing a day trip to Bosnia and Herzegovina. My weekend is already pretty full, but I’m tempted to do more exploring. I tell her I’ll think about it and let her know by tomorrow.

We’re almost to WIP when I get a Slack DM from a coworker. It’s 7:30 a.m. her time and she’s not feeling well, so I tell her to take the morning off to rest and that I’ll give the other team members a heads up. By the time we’ve got her work covered, I’m back at WIP and it’s time for my work day to actually start.

But first, I think it’s time for another cappuccino.

2:00 p.m.
My favorite part about working from European time zones is the “head down” work time. With the majority of my team still sleeping, I can usually squeeze in an hour or two of interrupted work time to focus on more strategic projects.

4:00 p.m.
Now that it’s 10:00 a.m. on the East Coast, it’s time for my meetings to start. Since I only have a few hours of overlap with my team, the end of my day is almost always back-to-back meetings. Twice a week, I’m still chatting with coworkers as late as 10:00 p.m., but on Tuesdays I get to log off earlier, so I’m planning to wrap up by 8:00 p.m.

One of my favorite parts about traveling with Remote Year is that almost everyone in my group is working the “night shift” or adjusting their hours to overlap with American time zones. I’m used to missing group dinners and social stuff when traveling but, with Remote Year, none of us eat dinner until 9 p.m. anyway, and there’s always someone working late with you.

6:00 p.m.
Just as my American coworkers are starting to make lunch, I’m getting hungry, too. I pull out my packed lunch but decide that my sandwich isn’t gonna cut it. I need a sugar fix, STAT.

Luckily, there’s a corner store on the same block as WIP. I leave my stuff where it is and head to Tommy’s, where I stand in the snack aisle for a good ten minutes, partially because I’m always on the lookout for new foods that can compete in my coworker’s Cute Foreign Snack Competition. No new contenders present themselves, so I opt for my old standby—a Bugle-like chip that is fried chicken flavored. (It’s better than it sounds and I am hooked.)

8:30 p.m.
I’m too lazy to move into a meeting booth for my final call,so I take it from the kitchen, where a few others from my group are already unwinding from their days. Two people are playing chess, and others have cracked open a bottle of red.

When they see I’ve wrapped up, I’m immediately handed a coffee mug full of wine. They’ve got plans to head down to the beach bar across the street. I’m tempted, but Netflix is calling. I could use a chill night in my apartment.

9:00 p.m.
Laying in bed with Netflix. I answer a quick Slack, not because I have to, but because I want to.
Then it’s lights out around here!

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Caro Griffin

Caro is the founder of Opsy, a community for operations professionals working in the tech industry, as well as the VP of Operations at Tech Ladies. When Caro isn't in front of her laptop, she can usually be found exploring Mexico City with a dirty chai latte in hand.

Category: Blog