What is Remote Year?

Bows & Sequins wearing a white outfit for the airport with a pink Away x Gray Malin suitcase.

“And suddenly you know… It’s time to start something new and trust the magic of beginnings.”
– Meister Eckhart

If you’ve missed my big news in my newsletter or on Instagram, I flew out earlier this week for the longest trip I’ve ever gone on! I landed in Lima, Peru late on Tuesday night and will be living and working throughout Latin America for the next four months with a company called Remote Year. (!!) I’ll be staying in Lima for the rest of September, spending October in Medellin, Colombia, November in Bogota, Colombia, and December in Mexico City, Mexico. I’ve gotten countless questions from friends, family, and readers/followers alike, so I wanted to put together a big Q&A post to have everything in one spot. I opened it up on Instagram with a question box, so here’s mostly everything I’ve been asked so far. If I missed anything, let me know in the comments below! xoxo JRS

(Oh, and if you have any recommendations for this part of the world, please send them my way! Thank you, thank you!)

What advantages does working with the program provide?”

In short, Remote Year handles all of the logistics for someone who can work remotely! They plan the 12-month or 4-month itinerary, set you up with a furnished apartment in each city, provide you with a co-working space (with reliable wifi!) within walking distance of your apartment, and coordinate all travel between cities. (You just have to book your flight to the first city of your program and out of the last city.) Even before landing in Peru, I can already tell it’s so much more than that, though. From a close friend of mine who’s gone on a Remote Year before, his biggest piece of advice was to invest in the community around you that you’re traveling with. Much like anything else, you get out what you put in, and he’s made lifelong friends from his year-long adventure with those people. The Slack community is great, too! There are so many different channels and threads with packing advice, travel tips, and so much more. There are also Remote Year staff in each city… We have a program leader who will be traveling along with us to each city, as well as two local staff members in Lima who are there to help every step of the way. In addition, RY also organizes cultural, educational, and social activities for you to take part in in each city! Those are called “Tracks” and I’m so excited to get to dive into some fun times with the rest of my travel group.

“During the program, do you work your regular job just remotely? Or work locally?”

You work your regular job! As mentioned above, RY handles all of the logistics, but they don’t provide you with a job. (They do have lots of resources available for finding a remote job and will even offer support to help you talk it over with your employer!) In terms of local involvement, Remote Year does offer information about volunteer opportunities for you to opt in to, so you can get even more immersed in your city.

“Can anyone do it? I would LOVE to do this, but I work in retail. Looking for a new job though!”

Anyone can do it! You just need a job that you’re able to do remotely. (Or I guess have enough money saved to pay for the program and support yourself throughout your time abroad! But I will say, I think everyone in the group does have some sort of professional focus, so it probably makes sense to at least be working on something!)

“Please explain how we too can do this program. I thought it was just for young and recent grads.”

You can apply for more information online! I have a friend in Chicago who’s done a 12-month itinerary (and is doing another 4 months in 2019!) and I loved looking through his “yearbook” from the trip. There really are people of all ages, places, and walks of life! (I believe the oldest remote so far was the early 60’s…)

“Did your company agree right away or did you need to use their business case resources?”

LOL, I am my company. But yes, RY does have a designated team to help you do the convincing!

“Do they supply the “work”? If so, what kinds of jobs do they offer?”

Nope, you have to supply the job!

“How do folks who don’t already work remotely do this program?”

Check out this blog post! They have some good info about finding remote work.

“Cost to participate in this program? Does it include food, accommodations, etc?”

The price varies based on the length of your itinerary, and it gets cheaper the longer you’re remote. You can check out the pricing details on their website, but after your initial down payment, it is $2,000 per month. (Which is actually a heck of a lot cheaper than renting a one-bedroom apartment in a major city like NYC or Chicago!) That fee covers your housing, workspace, travel between cities, and various other activities that RY plans for you along the way. It does not include food, you’re responsible for that on your own, just as you would be at home!

“Will you still be blogging?”

Yes, absolutely! I fully support myself from this blog and don’t foresee myself stepping away from blogging anytime soon, even if I am taking on other work or outside projects.

“Are you blogging as work or will you be doing something specific?” “Are you still doing your same job or blogging? Or is this providing you with a different job?”

Both! I will definitely keep blogging (all the stuff you’re used to seeing – fashion, beauty, wellness, travel, etc), but I am also working with Remote Year to help their social media team create content during this four-month program.

“How will you continue to work with brands when you’re abroad?”

I plan to work with brands in a similar way that I am now! I worked hard to get a few fall projects shot before I left, I have a few products with me that I’ll be shooting while I’m traveling, and I think it’s totally possible to keep coordinating deals as they come in.

But to be totally honest, a large majority of my sponsored Instagrams have been in-person events this summer, and I’ve already had to turn down several campaigns for the upcoming months that included local events. It’s definitely kind of terrifying that most incoming partnerships have been event-based, but I have faith that it will all work itself out how it’s supposed to. I think there’s also potential to take on potential partnerships within new cities!

“What kind of work will you be doing?” “What will you be working on while on this program?” Congratulations! What will you be doing specifically with the organization? Will we be able to follow along? :)”

For Remote Year, I’ll be experiencing the program first-hand, just as every other Kahlo remote is. It’s my job to story-tell based on my experience(s)! You’ll be able to follow along @RemoteYear, #RYKahlo, #RemoteYear, and of course, on my blog and Instagram, too.

“What will you be doing while you’re there?”

Living and working, just as I would be in Chicago! (Same, same, but different, haha.) I’ll be going to our co-working space M-F, finding great spots to both eat and work out, having meetings with the social media team, shooting content, writing, working on my blog content, launching my podcast, working on getting another side project off the ground, etc. Oh, and exploring Peru, Colombia, and Mexico in all of my free time!!

“Do people in the program actually get any work done (like a true 8 hours)?”

TBD, haha. In all seriousness, considering people still maintain corporate jobs while doing Remote Year, I’d assume so! I think it’s a common misconception that people who work remotely while traveling don’t get much work done, but I think social media is to blame for that. Everyone posts their pretty pictures, but you don’t always see the long hours put in to make it all possible. I’ve heard that you learn to become much better at time management while on Remote Year! (Crossing my fingers, tbh.)

One thing I’ve noticed from working from home (and for myself) for the last three and a half years is how much time I previously wasted while “working” in an office. If you’re freelancing or an entrepreneur, you’re not collecting a regular salary… You get paid for the work that you actually produce, not for clocking hours in an office.

“Do you know anyone else going on the program?”

Oddly enough, yes. Initially, I did not, but I just found out on Friday that someone I know from a previous job in New York is on the program, too! Such a small world, isn’t it?

“Of all the remote year options, what made you choose Latin America?” “How did you decide on LatAm? Is that the only option? Are you afraid to go to LatAm by yourself?”

This particular work opportunity offered this specific itinerary, but it’s definitely not the only option in terms of itineraries to choose from. You can check out all of the upcoming itineraries here! (Personally, I think the January – April program through Cape Town, Marrakech, Lisbon, and Valencia looks TO. DIE. FOR. Check it out here!)

I am definitely a little bit nervous, as I’m going somewhere that I’ve never traveled to before. But the great thing about Remote Year is that you’re not really by yourself! You can mix and mingle with the rest of your cohort, but are totally able to do your own thing if you want to do that, too! Plus, Remote Year provides you with a “program leader” who travels with you, as well as local staff on the ground in each city to help get you acquainted, provide recommendations, help if things go awry, etc.!

To be totally transparent, this probably wouldn’t have been my first choice of an itinerary. On paper, it doesn’t have the glitz and glam of some of the places that are on my bucket list that Remote Year travels through on other itineraries – Portugal, Spain, South Africa, Thailand, Croatia, etc. However, I honestly think that’s going to make the experience even better! I don’t have crazy high expectations about the destinations, and I’m going to a continent that I’ve never explored at all before. But with that being said, Macchu Picchu, Cartegena, and Mexico City have all been on my bucket list for quite some time, and how cool that I’ll get to check all of that off and then some!

“What is Kahlo?”

Remote Year names each itinerary, since each lineup of cities is different and has different people on it. I’m pulling this from the website, but ours is named after Frida Kahlo. Kahlo was a Mexican artist who became famous for her outspokenness and bravery. She battled injury, illness, and social oppression to follow her passions and defy social standards. She acknowledged her insecurities and her flaws, and created life and beauty out of them. Like Frida, we’ll embrace duality and seek out the contradictions in the places and people we meet. Remote Year Kahlo is for those who understand that a country’s story is as important as its beauty (though every city on this itinerary has both). Your surrealist dreams will turn into reality when you witness Medellin’s stunningly lush panoramas, Lima’s Oceanside cliffs, the majestic mountains surrounding Bogota, and the dynamic Magic of Mexico City.

Do you speak Spanish? Or will it be an immersion program?”

I took Spanish from 7th grade through my first semester of college! So, about 6 years in the classroom, but I’m in no way fluent since it’s been eleven years since I’ve practiced regularly. But I’m no stranger to the language, so I’m hoping it comes back to me a bit. The cool part of this Kahlo itinerary is that each of the four cities is Spanish-speaking, so RY has actually planned Spanish classes for us in each of the cities we’re living in. They’re twice a week and there are a few different levels, so I’m hoping that I’ll be much more conversational come 2019.

“Do you have to be fluent in Spanish to participate in the program?”

Not at all! Most itineraries go all over the world and there’s no requirement for you to speak any of the different languages.

“How many others are you traveling with?”

Including me, there are 25!

“Are you coming home for any breaks or holidays? It seems like a hard time of year to go!” “ Do you think you will miss Fall/the holidays in Chicago? I love this time of year!”

The program ends December 26th, but I plan to fly back to be home for Christmas, probably on the 24th? No breaks since it’s such a short program! I think some people do visit home once or twice when they’re on a 12-month itinerary. (You can come and go as you please!) I am kind of bummed to miss fall in Chicago and the fun part of the holiday season (and Thanksgiving!), BUT on the bright side, January and February are usually so depressing in Chicago, so it will be fun to get to catch up with friends and colleagues then! Both my niece and nephew have birthdays in early December so I’m sad I’ll miss those parties, but such is life. I’m really lucky I’ve gotten to spend so much time with them these last five weeks that I’ve been going back and forth between their spare bedroom in my hometown and friends’ couches in Chicago!

The question is totally valid, though… When I was in college, I always said I would never study abroad in the fall semester because it was always my favorite to be on campus. I just keep telling myself, that there are many more fall seasons to come! Whereas, in the future, I probably won’t be able to pick up and move to Latin America at the drop of a hat.

“What are you doing with life logistics? Lease, furniture, etc.” “What are you doing about your apartment while you’re away?” Did you sublet?”

I sublet my Chicago apartment fully furnished! (Listed it on Craigslist in July and was out by the end of the month.) I moved all of my personal belongings to storage in my hometown and then packed what I needed for this adventure!

“Why so many flights to Peru?”

I didn’t want to pay for four months of parking in Chicago ($$$$) so I put my car in storage in my hometown. My hometown is a four-hour drive from Chicago, so I flew from my local airport to ORD. (Only cost $120 for that leg of the trip and didn’t inconvenience someone having to drive me hours away to an international airport.) There’s not anything direct from ORD to Lima, so I had to connect in Houston. So that’s why there were three legs of the trip!

“Are you coming back to Chicago after you get back or are you officially a nomad?”

The plan is definitely to come back to Chicago! But to be totally honest, if you had told me a month ago that I would be living in South America for the rest of the year, I would have laughed out loud. You really never know what can happen and all it takes is one email or call or text for something magical to happen! Previous remotes have said they definitely weren’t ready to come home after four months, so who knows what headspace I’ll be in come December. (And TBH — that Kuungana itinerary looks amazing!)

“How the eff did you pack for this?”

LOL – ask me again in a few weeks/months. I filmed a video as I was packing and will be doing a few packing posts – what I brought, what I should have left at home, what I wish I would have brought, what I would do the same/differently, etc. I packed one 29” checked suitcase, one carry-on 21” roller, and a big shoulder tote as my personal item. Do let me know if there’s anything specific you have questions about!

“Why are you doing the program?”

Why not?! I don’t have anything tying me down right now (kids, pets, mortgage) so I figured now was as good of a time as any to take advantage of such a neat job opportunity! I’ve looked into doing Remote Year as a true remote (not working with the company) for the last few years and honestly, the 12-month itineraries just never worked for me at the time. I’m in the phase of life where all of my close friends are getting married and it’s a personal priority for me to get to be there for their big days, and an honor to stand up in their weddings. I would have been looking at large airfare bills flying back and forth between the program and weddings, so it just never really felt like the right time. So when I found out about their 4-month itineraries, and this opportunity lined up perfectly with me not having any major obligations I’d have to miss out on, I couldn’t say no!

“How did you decide you wanted to do this?”

It’s honestly a freaky story. An “ask and you shall receive” and a “leap and the net will appear” situation. It gives me goosebumps even thinking about how it all went down! Not to leave you hanging (or am I?), but this Q&A is nearing novel status, so I’ll save this for another blog post.


I hope this helps to explain everything! Thank you so much to the hundreds of people who submitted questions on Instagram. I tried my best to condense and answer them all, but I’d love to chat more if you have any other specific questions. (And I’d especially love to chat if you’re considering the program yourself!) I hope you’ll follow along these next four months, I think it’s going to be quite the adventure.

Make sure you’re following along on Instagram! (You can follow the hashtags, too!)

@bowsandsequins   #SturdyAbroadRY   #JetSetJRS

@remoteyear   #RYKahlo   #RemoteYear

Current Faves

Leave a Comment


  1. 9.7.18
    Julie said:

    This is awesome!!! Congratulations on your new adventure!

    • 9.7.18
      Jessica said:

      Thanks Julie, so happy to have you following along!

  2. 9.7.18
    Jessica Camerata said:

    I can’t wait to follow along with you on this adventure. If I didn’t have a dog I think 100% I’d be on board with this. I’ve been meaning to look into other companies that do smaller trips like 2-4 weeks to get to experience cities with other freelancers. I think you’ve just sparked the search! Good luck and can’t wait to see how it all unfolds!

    Oh and as a blogger, my question is will you have brands ship you stuff? If so, are you handling the shipping fees since it’s international? That’s been on my mind since I started contemplating something like this! Even thought about just doing 2-3 months in Paris for fun and work and bring the dog!

    xo Jessica
    My Style Vita

    • 9.7.18
      Jessica said:

      My plan is to handle it on a case-by-case basis! I was driving myself crazy trying to figure out how to logistically solve problems before they came up. I’ve heard shipping can be a nightmare in Peru, but we are able to use our co-working space as a shipping address, and it’s recommended to use FedEx and make sure it’s insured with tracking. I have a mailbox at a UPS Store in Chicago (they accept all deliveries — USPS, FedEx, carriers & messengers, etc.) and someone I’ve hired to check the box and retrieve packages for me every so often. If there’s a situation where I need to get the product and the brand isn’t willing to send it here, I’ll have her get the package at my box and then ship it to me here, in which case I’d have to cover the extra shipping. We’ll see how it goes!

      And I totally hear you on the dog, that’s honestly why I haven’t gotten a dog yet, even though I’ve wanted one so badly. I think it’s totally doable to bring the dog along for a month in Paris… That’s my dream, haha! 🙂

  3. 9.7.18
    Teresa R. Sturdy said:

    Jessica, I am so proud of you as you embark on this new adventure in your life. It makes me happy that you love to travel! I will be waiting anxiously to hear about all the great experiences you have, food you eat and amazing sights you see during the next four OR eight months!! Enjoy every minute of your trip.
    I love you!! MOM

    P.S. I started that book.

  4. 9.7.18
    Laura said:

    This is amazing, congratulations!!! You’re going to LOVE Mexico City, it blew me away when I visited ~2 years ago!
    Can’t wait to hear all about the adventures in store, and yes I for sure want to know how/what you packed for such an extended trip!!
    I hope you’ll do a post at the end of how your expectations were or were not met: what went well, what didn’t, etc.


  5. 9.8.18
    SG said:

    Amazing opportunity! Keep us posted on your adventures! Living abroad is something everyone should do when/if they can.

  6. 9.11.18
    AG said:

    I see you’re going to Cusco. I cannot recommend Cicciolina enough! The food was great! http://www.cicciolinacuzco.com/cicciolina.html

    • 9.13.18
      Jessica said:

      A few people in our group went there for drinks last night! Maybe we’ll try it for dinner tonight.. Thank you!

  7. 12.23.18

    That sounds beyond amazing!