Because of the work I do for Rockstar Finance, I skim hundreds of blog posts and news articles each week, and there are a handful of themes I see over and over again. Paying off debt, embracing minimalism, building wealth and retiring early are among the top five. But the topic of “quitting your job to travel the world and do what you love” is, without a doubt, at the top of that list.
The success stories sound dreamy. People write about how they live on as little as $1,000/month in various countries, with accompanying pictures of laptops on beaches and books in hammocks. Instagram feeds are filled with ocean views, mountain tops and cold drinks dripping with condensation during afternoon siestas. And the captions that go along with them express nothing but joy and gratitude. It seems like a fantasy come true. However, like so much of the curated content we are exposed to, it’s not the reality for the many of those who are trying to live and work on the road.
The reality looks a little more like this: driving for 8+ hours then barely being able to keep your eyes open long enough to check your email (let alone respond to any). Waking up in a motel the next morning and realizing the wi-fi doesn’t work. Having to shower in the dingy motel bathroom then rushing to Starbucks at 7am, so you can try to get some work done before you hit the road again. And not seeing anything in the city you just slept in, except for the inside of that motel, Starbucks and maybe a grocery store (if you’re low on snacks and want to pick up a prepackaged salad or sandwich).
Driving days are definitely the worst. While you’re on the road, your only concerns are making sure you have enough gas, food, water and podcasts/music to get you through the day. And when you finally arrive at your next destination, all you can think about is relaxing and sleeping. Work doesn’t even cross your mind, unless you’re behind or have missed any deadlines, in which case it fills you with anxiety – but not enough anxiety that you’re willing to stay up all night to get it done. You need to be rested for long driving days, and you know that your sleep (and sanity) is more important.
After a few long driving days in a row, the overwhelming sense of how much work you have to do takes over, and you know it’s time to finally sit down and get things done. Of course, by then, you’ve arrived in a new place where you want to explore and spend time with friends. And wasn’t that the point of this whole thing? To drive around and see people? So then the next struggle begins: trying to balance spending time outside exploring with spending time inside working. (I would also like to point out that pictures of laptops on patios are ridiculous. Working outside in the sun is crazy. You and your laptop will battle over who is going to overheat first, and either way you will eventually both lose.)
Finally, you reach your breaking point and have to accept that you might only see half of what you wanted to in your new city. Whether you like it or not, you need to spend a full day (or even two) in front of your computer. But how can you write about anything other than this amazing adventure you’re on? You want to keep track of all the places you’ve seen, experiences you’ve had and lessons you’ve learned. You do not want to write about the best credit cards or anything else that is so far removed from what you’re living in this exact moment in time.
Your first two articles for a new client are due soon, so you decide to tackle them both in one sitting. When you’re done, you log into the content management system they use (also new to you) to upload them, and discover a requirement for both articles that you never knew about: quotes from interviews. Now you’re frantically emailing your contacts, trying to get two interviews done in the next 24 hours. It’s never going to happen, so now you have to tell your brand new client that you’re going to miss the deadlines on your very first assignments. Who told you working on the road was dreamy? They lied.
The requirement of these interviews mean you’ve crossed nothing off your to-do list, and instead have only added to it. The anxiety deepens, as you worry clients will drop you, or this grand adventure will ruin your reputation as a freelancer. You begin to realize you’re never going to see that park or climb that mountain or eat at that restaurant. And oh my gosh, it’s cute that you thought you were actually going to be able to read any books on this trip. Don’t tell anyone you packed eight, because they will laugh at you for only finishing half of one in the first three weeks.
Now, it’s not all bad. The landscape of each state is burned in your memory, as are the miraculous thunder and lightning storms you’ve driven into. Being alone with your thoughts helps you stockpile ideas for your book. The days and evenings you spend with friends you haven’t seen in months or even years (or ever, aside from online!) are worth all the trouble. And getting to see cities through their eyes is priceless. But every time you get back to their house/your motel, the nagging feeling that you need to open your laptop and work sinks in. This is not a vacation. You have chosen to work.
And therein lies the distinction. I’m not complaining about the struggles I’ve faced while trying to work on this road trip. I’m not particularly sad or stressed about these experiences, either. I chose to work. I could’ve chosen not to, but I thought I could handle it so I said yes. I made that choice and I take all the responsibility for what it has come with. But if I’m being honest, I wish I had said no. I wish I had chosen not to work on the road – because it’s not easy or particularly fun to have to pull yourself away from the adventure aspect of it, in order to get things done.
Am I grateful I even have the opportunity to do both? Sure. I couldn’t have gone on this road trip at all, if I still had a full-time job. But working for yourself is still a job – and trying to work on the road is even harder than working at home. It’s not all rainbows, sunshine, beaches and hammocks. It’s coffee shops with uncomfortable chairs and spotty wi-fi. It’s higher risks of miscommunication with clients and the potential to miss deadlines as a result. It’s a complete lack of routine, which isn’t always great for productivity. And it’s less time that can be spent exploring the place you travelled to.
So the next time you read a story written by someone who claims to love every minute of living and working on the road, try to take it with a grain of salt. Understand there are still long hours, tiring days, sacrifices and mistakes to be made. Through heavily-edited content, we’re made to believe otherwise, but I can promise you it doesn’t always feel like you’re “living the dream”.
Like any story on the internet, this is mine and it’s personal – so it’s not the reality for everyone who attempts to do what I am doing. But I refuse to add to the long list of stories that make it sound like living and working on the road is oh so amazing. I won’t paint you a pretty picture and say it’s easy or even particularly fun. And I won’t say that I always walk around radiating my pure joy and gratitude for having this opportunity. Instead, I will say that this experience has been both challenging and rewarding, and I know I will learn and grow from it all.
And the next time I do something like this, I won’t be bringing any work with me.