My (Very Eerie) RY Story

Jessica Sturdy travel photography hot air balloon at sunrise over Teotihuacan Pyramids outside of Mexico City

As I was reflecting about the last four months and looking through content I’ve written, I realized I haven’t actually told you the real story about how I ended up on Remote Year. Sit down, grab a coffee (or glass of wine), and settle in… It’s a long one. But it will probably give you goose bumps, to be quite honest! And also confirm any suspicions that I am certifiably insane.

I’m not even sure where or how I first learned of Remote Year. The company is three years old, and I swear it’s been on my radar for at least two and a half of those years! I have an email subscription notification on Feburary 25, 2016 for signing up for their “Interested Travelers” list.  Since then, I had followed along and watched the company from afar… I would sporadically look at their upcoming itineraries, but none really ever made sense for me that the time.  But somehow, the company kept coming up as a recurring blip on my radar.

Sometime in early spring of 2017, I was grabbing a drink at Hopsmith in my old neighborhood in Chicago. When the person I was with got into a long-winded conversation with a stranger at the bar, I struck up a conversation with the guy sitting solo at the bar next to me. We were discussing our careers and he mentioned that he had just learned about a program called Remote Year, to which I exclaimed, “OH MY GOSH, YOU HAVE TO DO IT!” We proceeded to discuss how epic the whole idea was and I basically made him promise me that he would apply to get more info, since I wasn’t able to at that time with other commitments I had going on. I could tell that he needed some positive affirmations about taking such a big leap outside of his comfort zone, and I was sort of living vicariously through him. We parted ways that evening and to be honest, I hadn’t thought much of that conversation again until I was in Dubrovnik, Croatia last summer (in August of 2017).

It was the last night of a week-long girls trip throughout Croatia and I was headed to Switzerland early the next morning… It had been a tiring (yet fun!) week, but we decided to make the most of it and take advantage of our last night in Croatia! We were meeting up with a friend-of-a-friend who was also visiting Croatia from Chicago that week… small world, right? We met up with their group at a bar in Old Town Dubrovnik and after chatting, realized he was with a group of Remote Year people, currently stationed in Split, but on a “side trip” in Dubrovnik! Within a few minutes, a guy came over to me and said “I think we’ve met before…” After a confusing few moments, I realized it was the same guy from Hopsmith, currently on Remote Year. Talk about a SMALL. FREAKING. WORLD. It was one of the most mind-blowing synchronicities I’ve experienced to date, that’s for sure!

Over the last year, I’ve met a few new friends that are previous Remotes, talked with friends about how I wanted to do Remote Year in the future, and have also seen some previous co-workers of mine who have gone on Remote Year since we’ve worked together. Somehow, RY popping up on radar up on my radar, again and again and again.

In Australia this past February (2018), there were a few days that I got really introspective. Lots of reading, meditating, and soul-searching, if you will. I can’t really explain it, but there was one night at dinner, when I said something along the lines of “This is going to be the year that I’m going to move abroad, I just need to do it.” I can still picture exactly what I was wearing and where we were sitting, because it felt kind of like an out-of-body experience. I felt like I didn’t say those words, but I heard them come out of my mouth. I fully realize that makes me sound crazy, but right after I said it, I remember feeling a little bit shocked, which is why I think I can remember that point in time so vividly.

Then when I was back in the US in March, I applied to get more information about an upcoming RY itinerary called “Jemison,” but never heard back. But with my crazy travel schedule, I never followed up with the woman I had be emailing with. Looking back now, I don’t think that itinerary ever ended up running!

This past May (2018), I was *exhausted* from traveling so much during the spring. A bunch of my friends were going to Hangout Fest in Gulf Shores Alabama, and even though it was going to be a stretch for me financially (my flight there was more than a flight to Europe because I only booked it a few weeks out!), something in my gut was telling me to go anyway. On that trip, I got the chance to get to know one of my girl friend’s guy friends that I had only briefly met a few times before. He is a fellow U of I grad (same year!), but we never knew each other in college. I learned that he, too, was a previous Remote, having completed a full one-year program. We chatted RY all weekend long and it had me wanting to do a program even more.

My lease renewal was due on May 31st, and I remember looking at different Remote Year itineraries that started in July, when my lease was up on July 1st. But being in three different weddings from July 2018 – July 2019, it just seemed like I’d be flying back and forth internationally a lot. Nothing really seemed right… And I was running out of time. I had been looking around at other apartments and wasn’t really finding anything, so I just ended up re-signing my lease at my current apartment because I didn’t know what to do. And again, this makes me sound crazy, but even as I re-signed my lease at the EOD on May 31st, I had this weird feeling that I woudn’t actually be living in my apartment, but I couldn’t articulate why.

June was a really weird month. It had been a really rough first half of the year, and shit really started to hit the fan in June and July. It was a weird time with work, it was a weird time with personal shit going on, it was all just a lot. I’m sure I’ll get into this more at some point, but I’m not trying to de-rail the current story right now.

Here’s where shit gets really wild…

A conversation with my brother on July 5th sparked something… I needed to get out of my apartment. It was the strangest idea I had probably ever had… I fucking love my apartment and my apartment building, but I just needed a change of scenery for a little while. I emailed to inquire about breaking my lease and it was so expensive to do so, but the building manager told me that I had the option to sublease. And by the end of the day, my apartment was listed on Craigslist.

The next week or two was filled with viewings on viewings on viewings. I was searching for a new apartment (mostly unsuccessfully) while also trying to get my place subletted. I had found an apartment that I really liked, but the girl who was interested in my apartment ghosted. I didn’t want to get stuck with two leases, so I couldn’t sign anything until my apartment was accounted for.

July 20th: Talk to couple that is very interested in subletting, but they are in Boston for the weekend.

July 21st: I leave for Italy for a top-secret project that I can’t post anything about.

July 23rd: I have a friend show my apartment to the couple while I’m in Italy. They’re interested, and they want it fully furnished until the end of the year, December 31st.

July 24th: Sublet applications submitted

July 25th: Sublet applications approved! I fly back from Italy (am dealing with all of these emails with my building and the tenants from the air) and have to go straight from the plane to an event for a blog partnership. Tenants want to move in JULY 28TH, I start to stress the fuck out. Three days?? How the hell will I find a new place to live while packing up my entire life in three days?

July 26th: I end up agreeing to a July 29thmove-in. Hi, my name is Jessica, and I have no boundaries.

July 27-29: New apartment hunt: unsuccessful. I literally do not have anywhere to live in Chicago. No clue what to do, so I end up packing my car to the fucking brim and taking four trips to my brother’s house… It’s a four-hour drive each way so I spend over 30 hours in the car over the course of three days moving all of my shit (minus furniture) from Chicago to their spare bedroom… by myself. What the hell is happening.

July 30th: Leave Chicago and drive to my brother’s house… Looks like I’m moving in with them for the time being? Definitely not where I saw myself a month from my 29thbirthday… Cue panic attack.

July 31st: The plan was to drive up to Chicago on Thursday morning and stay at my friend’s apartment over the weekend since we were both going to Lollapalooza together. I had a little freak out on Tuesday and decided to drive up on Wednesday (8/1) instead. I decided a few workouts and spray tan before the weekend would do wonders for my state of mind.

Now, let me interject this timeline a little bit. I was a fragile, hot mess at this point. What the hell had I done??  What was I doing with my life? How did I get here? Why was I living in my hometown that I hate? There were a lot of questions and not a lot of answers. (And a lot of fucking tears.) But honestly, I was just relying on blind faith that I knew that subletting my apartment was the right thing to do, but I could not articulate why. I just had a feeling. But I just couldn’t figure out why subletting my apartment felt right, but I couldn’t find a new place to live that felt right. WHY. WHY. WHY.

I actually have video evidence* of me saying “I wish an opportunity would come up that would take me out of the country until the end of the year. I need to get away for a little while.”

*I recorded videos of this whole crazy time, in real-time. I felt so disconnected from my life during this period… It truly felt like an out of body experience.  And even looking back now, it doesn’t really feel like real life. I didn’t know what to say to anyone. Everything happened so fast. I never meant to end up without an apartment. Most of my friends didn’t even know what was going on. I felt like I was living a lie, so I just stopped posting on social media and the blog all together. I couldn’t even explain why I had sublet my apartment in the first place. So what did I do? I ended up recording the whole damn thing. Sometimes I deal with shit by holding it all in, and since I wasn’t really letting anyone (besides like 3 people) in on what was truly going on in my life, my emotional release was venting on video. Sobbing as I’m driving away from Chicago? It’s on camera. Packing up my apartment? Recorded. Venting about how I’ve never felt more lost or confused? I’ve got those videos, too. It’s essentially a very emotional video journal. I don’t quite know what I’m going to do with them, if anything. In some ways, I want to share parts of them, because it’s kind of crazy how it all unfolded, but it’s not like I can just put them on YouTube for the world to see… I would sooner post nudes on Instagram. 🤪 Ha, kidding. But honestly kind of serious… Posting these videos feels way more vulnerable. Anyway – back to the events at hand.

August 1: I was driving back up to Chicago and was somehow in a really zen, chill place. I had just confided in a few friends about the current state of affairs and said something along the lines of “Whatever’s meant to be, will be. I really can’t figure out what to do right now, so I just need to do nothing for a little bit. I just need to relax and let it flow.”

… Thirty minutes later, I get a text from a friend, the same guy whom I had become friends with at Hangout Fest who was a Remote Year alum. He sent me a link to a job description that was posted on RY’s internal Slack channel. Remote Year was looking for an “influencer” to come on one of their upcoming 4-month itineraries through Latin America. August 26 – December 29th.


  1. When the hell did Remote Year get 4-month itineraries?? How did I miss this?
  2. This was it. This is what I couldn’t picture, but somehow knew was coming. I had never been more sure of anything in my whole life.
  3. I was fucking terrified.
  4. The timing was EERILY perfect… My apartment was subletted through the end of the year.
  5. And oddly enough… I had nothing on my calendar for September, October, November, or December. No trips planned, not a single flight, not a single concert ticket, not even a meeting.

August 2nd: Day 1 of Lolla. I have two different content partnerships over the weekend so I’m focused on those for the time being. One thing at a time.

August 3rd: Day 2 of Lolla – Phone gets stolen.

August 4th & 5th: “No phone, no home, no problem” becomes the phrase of the weekend, haha. I was truly at the end of my mental sanity rope, but tried to just have a fun weekend with my friends.

August 6th: Get into my storage unit and find my old phone. Get to AT&T to get it activated and order a new phone with insurance. Drive back to my brother and sister-in-law’s house.

August 7th: Took the whole day to apply for the RY position. (Wrote a pretty bomb cover letter, if I do say so myself.) But v nervous I’m too late at this point. The program starts SO SOON!

August 7th– 15th: Learn how to manage the highest levels of anxiety I’ve ever had, while simultaneously adjusting to living with my younger brother, sister-in-law, 5-year-old niece, and 6-month-old nephew, and down the street from my dad. What a time.

August 15th: FINALLY hear back from RY. Schedule interview for August 17th.

August 17th: (Friday) Phone interview day. Tell them that I’m actually in a wedding on September 1st, so I wouldn’t be able to leave until after that. Praying to God that doesn’t affect the outcome. Learn that the compensation for the position is not at all what I would have hoped, but there isn’t any flexibility. I should hear by Monday!

August 20th: (Monday) Send a quick Thank You email that I realized I had started on Friday and forgot to send. Why am I fucking like this?? Cue self-loathing.

August 21st: Radio Silence

August 22nd: Freaking out and can’t concentrate for shit, but just start writing. I decide that I’m going to write my “announcement post” for going on Remote Year. Manifest that shit, you know? I feel like I’m sort of getting my hopes up, but let’s be honest, they’re already up. I’m sitting outside at Starbucks in my hometown, writing said announcement, and look down at my phone and see an email from the guy I had been speaking to at Remote Year… See the words “you’ll be a great asset” and instantly burst into tears. Didn’t even read the whole email. Honest to God, I’ve never sobbed harder. Have to go sit in the car because I’m too much of a mess to be in public. Kelly thought I was calling her to say that I didn’t get it because of how hard I was crying, haha. (And yes, all of this is on video, too.)

… Now I just have to tell my family. I didn’t want to get anyone else emotionally involved until I knew for sure, so I haven’t told anyone in my family that I even applied for this. Now I just have to tell my conservative family OH HEY, THANKS FOR THE HOSPITALITY, BUT I’M MOVING TO SOUTH AMERICA. Hope you don’t mind that I’ll be leaving all of my stuff in your spare bedroom for the remainder of the year. I go to my dad’s office and ask if he has time to chat (it’s times like this that I always wonder what parents think you’re going to tell them… haha) … He couldn’t have been more shocked, I don’t think. Asked me if it was safe, also told me it didn’t really seem like a wise business decision, but that “it seemed like something I would do.” Alrighty then. Brother and sister-in-law were a little shocked, mostly that it was such a quick turnaround, but also excited and interested in the opportunity. Holy shit, this is happening.

August 23rd: Realize that I actually forgot to respond to Remote Year, haha. Respond to them. Look into flights for getting to Peru and when that is going to be feasible with my bestie’s wedding happening after the program technically starts.

August 25th: Speaking at Create & Cultivate so have to be back in Chicago for the weekend.

August 27th: Back to my hometown to pack and figure out logistics.

August 29th  – September 2nd: Back to Chicago for the weekend for the wedding I’m in. My friends also throw me a birthday / going away party. Get shots for South America. Figuring out more logistics in every waking hour that I’m not doing bridesmaid duties. Drive back to my hometown on the 2nd.

September 3rd: Pack up my suitcases at my brother’s. Leave my car in a garage stall at my Dad’s.

September 4th: Fly to Lima. You know the rest!

Honestly, re-hashing this timeline still feels like an out of body experience. It’s all just so crazy how it all worked out. I honestly wouldn’t be sitting here in Mexico City writing this had I not followed some ‘weird feeling’ of subletting my apartment without other living arrangements lined up. There were already so. many. logistics. to figure out on such a short notice, I don’t think I would have also been able to completely pack up my apartment, move all of my shit to storage, and also find subletters in the week notice I had to leave the country. And I definitely could have never afforded to keep paying my astronomical rent in Chicago while living in Latin America and simultaneously taking a pretty significant pay cut from having to turn down so many projects while being here.

It’s funny, though… Right now, in some ways, I almost feel like I’m in that same unknown position all over again. (Albeit in a seemingly much more emotionally stable state, haha.) I have exactly one week left on this Remote Year adventure before I fly home for the holidays. I really don’t know what’s next, but if I learned anything over the summer…

Stop forcing. Relax. Let it flow.

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Leave a Comment


  1. 12.17.18
    Rena said:

    OMG! The story is unbelievable! Even that you met this guy again … Thanks for sharing, it was really so interesting to read.
    xx from Bavaria/Germany, Rena

  2. 12.17.18
    Caryn said:

    you are amazing!! going with your instincts when you couldn’t see the ending point to those actions is beyond brave. I’m sure so many people envy your remote year experience- you are encouraging others that while life is messy and EMOTIONAL {af} at times, continue to do what you feel is right for you. love.

  3. 12.17.18
    Dana said:

    Wow…just wow! It was clearly meant to be, and the best things in life happen just like this, don’t they…?

  4. 12.17.18
    Claire said:

    What an incredible life chapter! In the face of such chaos and stress, you are an amazing and unstoppable force! Such wonderful things to celebrate this holiday and New Year. You and yours must be so proud!!! You. Go. Girl.

  5. 12.18.18
    Carla said:

    You have no idea how much I needed this post. One this story is amazing! I have been on this journey of learning to listen to my intuition and having faith and I have had the universe show up in many smaller ways and it’s amazing to see how crazy awesome it is when it shows up in big ways like that. One of the things I really want to do in the next few months is some full time travel but I’ve been very unsure about how it’s going to work out as well as going in the face of others opinions! So I think reading your post was the universe saying to me look what we did for Jess! Slow down and trust that it’s going to work out. Thank you so much for posting! I have loved watching your journey over these past 4 months!!!

  6. 12.23.18

    Wow! this was such a crazy story, but it sounds like an amazing experience. Glad you decided to take the risk and do the Remote Year. 🙂

  7. 12.24.18

    Love how this story played out! Best blog post ever!

  8. 12.25.18
    Amber said:

    You are incredible! I love how honest and real you are. I feel like this sometimes, too, and appreciate you sharing. I followed along during your time on Remote Year, and am so glad you did it!

  9. 12.28.18
    Meghan said:

    Things always work out the way they are supposed to! I can’t wait to hear about this adventure of yours!!

  10. 1.4.19

    What. A. Rollercoaster!! My goodness, thank you for sharing – that was a wild ride and I was HERE FOR IT!!


  11. 1.27.19
    Nathalie said:

    What an incredible story! I love how you honored your intuition and when with the flow.
    I suggested you to for the Lively Show because this is a wonderful example of flow.

    • 1.30.19
      Jessica said:

      Oh my gosh, it’s my FAVORITE podcast. I’ve talked about it quite a bit here on the blog! You’re totally right, an amazing example of flow. xx