An Honest Look At My “Aspirational” Life Of Travel

I spent the last 14 months working for a company completely remotely. I had the freedom to work in a different state or a foreign country. I had the freedom to work in the cutest chic coffee shops that made for the perfect Instagram photos, or naked in my own home. No one really cared where or when I worked, as long as I did what I was supposed to do.

It was freeing and fun and everything you’d imagine a remote job being like, until it wasn’t, and I knew it was time to move on to something new.

Every person I told I was leaving was shocked.

“You have the PERFECT job, why would you leave?”

“You can work from home, why would you want to go back to work at a *real* job?”

“Wait, so you don’t like working at home? That’s my dream!”

People couldn’t even begin to wrap their heads around why I wanted to quit a job that I didn’t have to put pants on for, but that’s because no one talks about the struggles that come with it. Everyone just assumes being a digital nomad is the new ~American dream~, and once you achieve it, everything else is incredible.

Working remotely isn’t easy — at least it’s not for me.

I started my previous job while living in Australia, and I was tremendously excited about it. I landed a writing job with a company I actually was passionate about. Except I didn’t know anyone in Australia. And I wasn’t meeting anyone, because I was cooped up in the house all day, alone. Everyone else was at their physical work address, and I wasn’t.

It was a time in my life when I felt like I was truly falling apart and no one could understand the mental struggles I was facing every day. When you work remotely, you are somewhat isolated from others — your home is your office, and you have to keep your social calendar as full as possible to keep yourself from feeling like an alien. But that was nearly impossible when I had a very limited social circle.

I started falling into a mild depression because of the lack of social interaction I had. I’d cry over nothing, I’d literally count down the minutes until my roommates got home, I’d go to the handful of coffee shops that actually had free Wi-Fi, and just be appreciative to be around other humans. I even considered spending the little money I did have on an office sharing space, but realized I couldn’t afford it on the income I was making in USD while in Australia.

I would spend all day just sitting on my laptop working, because I didn’t know what else to do. It began to completely consume me.

It was time for a change.

I booked a ticket over to Southeast Asia to backpack. I was still working remotely full-time, so you can imagine the challenges that came with this. They were a lot different than the ones I faced in Australia, though.

The challenges in SEA were more self-inflicted. It was taking a Tuesday off because I made friends who wanted to go to an elephant sanctuary, or skipping a trip to a temple with the new friends I just made because I knew I needed to sit down and accomplish my to-do list before I could have fun. The social interaction that I was lacking was definitely there, along with a wide-open world of opportunity to bail every day on work if I wanted, because hardly anyone around me worked, so everyone always wanted to play.

I had to hold myself accountable day in and day out to get my work done, even if that meant doing it on the weekends. It meant going to the beach for a couple hours in the early morning, then heading back in before lunch to work the rest of the day. The face-to-face interaction I was lacking in Australia wasn’t an issue, but the other distractions were huge, giving me new obstacles to overcome.

I eventually flew back home and moved in with my parents, because I spent all my money while traveling, as you do. I left Australia with –$2.25 in my bank account, which they graciously waved for me when I closed it.

The work-from-home life back in my hometown was by far the easiest it’s even been for me. I had friends, I had familiar places to go work, and I had minimal stresses and struggles. It was easy — too easy. So I left, again.

This time when I saved up just enough money I moved across the country to Denver, Colorado. I forced myself out of my comfort zone, because at home I wasn’t growing, and I wasn’t challenging myself at all. I knew I needed a change, and I’ve always been a mountain person.

And, when I got here, the same sense of isolation I felt in Australia came flooding back. There were weeks I felt like I didn’t talk to an actual human in person for days; I was just left alone with my own thoughts and words. It was starting all over again. My mental health was on the decline and I couldn’t stop it, no matter how many strangers I said “hi” to. I was lacking that social life and it started to have a crippling effect on my work.

I felt the same sense of isolation, being alone, falling apart, and desperately needing that social interaction I wasn’t getting. It became battles with myself in my head, and I knew I couldn’t continue this life anymore, no matter how much I wanted to. I knew something had to give. I knew as much as I loved my job, I had to let it go and do something better for myself mentally — and it’s working.

The dream isn’t always what it seems to be. At least not for me.

Becca is a freelance writer based in Denver. You can find her work here and follow her on Twitter, Instagram, and Facebook.

Image via Unsplash

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  • Lauren

    This is a wonderful, honest article. I’m experiencing something similar — I’m at home for the summer studying for the bar exam. It’s my first time “working from home” without a regular school schedule, and it is terribly isolating. I thought I would love it, but I’m glad I know that I don’t before I decide to commit to a work at home job for the long term. Best of luck on your new journey <3

    • Rebecca Ann

      Good luck on the bar exam! I’m sure you’ll find a job that will keep you exceedingly busy soon enough 😉

    • Holly Trantham

      Good luck on the exam, Lauren! I love working (mostly) from home, but I have to say the isolation aspect is true — I can’t imagine what I’d do if I lived entirely by myself. Having my boyfriend or roommates around is beyond helpful for that!

    • Becca

      Thank you Lauren! I’m glad you figured that out early on. Good luck with your exam also!

  • Jack

    I love this, thank you for being so honest!! It’s nice to know that “the dream” isn’t the dream for everyone.
    I’m the sort of person that thrives on a regular schedule, and sometimes I don’t know where I’d be mentally if I didn’t have my amazing coworkers to see every morning. They are like my little family away from home.

    • Becca

      Of course, I always try to write as honest as possible. I think that’s important. And I totally get that, I love having a schedule and people to see every day, it gives you something to look forward to.

  • Savanna Swain

    This piece really spoke to me. As someone who is in the middle of transitioning to full time freelancing, my biggest challenge has also been the isolation. And sure, I’m the kind of person who loves to be alone, but after a while, it can become a struggle to even maintain even those few close friendships and not get caught up with work. Heck, I still work my job as a substitute teacher primarily for the social interaction – even if it is with middle schoolers and a few teachers in a staff lounge. It’s something!
    I hope everything works out for you! Sometimes doing a complete 360 is the best thing we can do to find out what we really need to have the life we want. 🙂

    • Becca

      Thanks Savanna! I’m still lucky that I am working part time jobs so I still have that time during the day to write alone, but I also have an actual job to go to where I get that social interaction. I like to think of it as the best of both worlds now!

  • Judith

    Isolation like this is one of the reasons I’m really happy with my office job. During my exam periods I used to become more and more depressed, and without daily or almost daily interactions with other humans I was living in my own micro-world while getting more distanced from the actual world around me.
    This is such a great article, I think it’s really important to talk about these things and how different people react so situations like this. It’s not something that gets talked about a lot.

  • lateshift

    The isolation and time management factors are important, as anyone who’s tried to freelance will agree – but I’m kind of thinking the fact that halfway (?…none of the time frames are all that clear here) through this experience you were basically earning negative dollars is the actual reason, even though that problem only gets a fraction of the words. Sure, personal fulfillment and quality of life is a big reason people hope to work at their dream jobs…but having money so we don’t starve or go homeless is actually the biggest reason. You really can live like a queen in Southeast Asia for well under $20 a day, and one of the best things about a flexible job is the ability to book the absolute cheapest travel – that ticket with two layovers and etc that costs half what the others do, leaving aside the fact that regional travel in SEA from country to country tends to cost less than a monthly MetroCard.

    So I guess what I’m saying is: it sucks that this job was a lonely experience. But even if it weren’t, it WASN’T the “perfect job” – because even though, unless I’m missing something, that bank balance mentioned is the only actual number, dollar figure or percentage included in this story ON A FINANCIAL WEBSITE (!!!), it sounds like the position didn’t even pay you enough for baseline survival in one of the cheapest places on earth. That is not a “dream job.” It sounds like a nightmare. The cold, hard reality appears to be that you actually had to quit this job because it made you broke, which is the opposite of the thing jobs are supposed to do.

    • Maria S

      Yeah, I was surprised by the fact her own company wouldn’t spring to pay for a desk at a coworking office somewhere for her. That’s usually pretty common at companies with remote workers because the bosses are aware of how socially isolating remote work can be — and it’s kinda weird to expect an employee to pay for that out of their own paycheck. And some coworking offices arent that expensive for a membership! The one I work from is $150 a month but I’ve seen some as cheap as $50 a month and some expensive as $400 a month, depending on how fancy the place is and what the membership entails.

  • Sara

    Sooo, since you don’t want it….can I have it? 😉