How I got 3 remote jobs for van life
Updated: Jul 26
Financial stability seems to be a top concern for road travelers and van lifers–and for good reason. What if your camper van breaks down and costs thousands to fix? What if you get in an accident and have insane medical bills–never mind skyrocketing auto insurance rates now? Or what if you're just the worst at saving money?
I was prepared to skip the "digital nomad" life and be on the road completely jobless because I didn't believe I could make a remote job happen in time. But with a little pep talk to myself and up-front effort, I now have two (but sort of three) remote jobs that fit very well with my lifestyle on the road. Here's how I secured them.
Job #1: I quit my full-time job–then asked to work remotely
Before I started this adventure, I was working a 9-5 corporate job at a marketing company. My role was in digital marketing so all my work was done online. It was just over my two-year marker at this job and I had a good relationship with my team, manager, and the overall company.
This made putting in my two weeks notice hard because I knew I'd miss a lot about it. It didn't occur to me that working remotely could be an option, so I didn't ask when I quit. It wasn't until a few days later when I was on the phone with my parents, they mentioned something like "wouldn't it have been cool if you could have worked remotely"–and I realized I hadn't even thought to ask my manager.
After I got off the phone, I sent an email to my manager and her manager basically saying, "hey, so... I know I just quit, but would you be open to some sort of remote, part-time setup for me? Because I absolutely would be." I listed bullet points about how I could still provide value remotely, and added ways that being on the road could pose new opportunities (my job was very related to PR (Public Relations), which is why I could connect with people that my desk-bound coworkers couldn't).
Come that Monday during my technical "two weeks notice" period, my manager stopped by my desk to say she'd received my email and was open to it. But she needed approval from her manager too. Waiting for that approval took another week or so.
Soon, my manager emailed me a part-time, remote contract to sign! They didn't open up the terms to negotiation, but the nature of the job didn't really allow for that anyway–not sure how to explain it without going into painful detail. More or less, I was going to act as a journalist, where I'd get paid for every article I had published on different websites. So, if I didn't write articles, then I didn't get paid. But if I wrote a lot of articles, I'd get paid a lot!
I believe quitting and THEN asking to work remotely is why I had success
Think about it–there's no better way to show someone that you're willing to walk away if you...literally walk away first.
My company didn't have a lot of remote employees and I believe they had a slight concern that once they approved one person for it, all employees would start asking for it. This notion was why I didn't first ask to work remotely, but I'm glad I didn't.
I doubt I would've had the same success if I had first tried to negotiate a remote job. My managers might have assumed that I wasn't THAT serious about leaving the job. The approval process would've dragged out for months as it would've remained a low priority on my (extremely busy) manager's manager's to-do list. But now that they had a new position they had to fill with my leaving, it escalated things. And it showed them that I was already willing to lose the job completely.
Moral of the story: if you want to try van life and already work in a job role that can be done remotely, consider the same strategy I used. At the very least, ask them about their work remote policies. Especially during COVID-19, companies are more open to WFH than ever.
Job #2: I used Linkedin to network with old contacts
First off–if you aren't on Linkedin, GET ON THERE! It doesn't matter what industry you're in–a cashier at a grocery store, an artist, a sales professional...whatever it is, that exposure can only help you. It helps build the impression that you're serious about your career and "with the times". It's a free way to advertise yourself even if you build it out and forget about it.
During the last two weeks at my full-time job, I started hopping on Linkedin to update my profile as a "freelance marketer". I posted an update telling all connections that I was open to taking on freelance marketing work. It got some "likes" and "congrats on the job switch" comments but didn't result in any opportunities. I knew I had try harder, so I started reaching out directly.
I messaged an old coworker from a startup company we used to work at together. He had since started his own small video production company. I knew he had a strong work ethic and we got along well, so I figured why not. I spelled out my exact situation– "Hey Sean, I'm leaving the corporate world to go live in a van and am looking for some part-time freelance work. Any chance you have some marketing needs?"
Turns out, he'd gone on to Linkedin THAT DAY to start recruiting marketing help. His company had next to zero online presence at that time–they weren't getting press coverage, they didn't have a blog, and they weren't posting on social media. So, I built out a one-page marketing strategy on how I'd recommend building those things out. I sent that to him as a sort of work proposal, and he liked it. A few weeks later, we had negotiated my rate, the type of work, and where I should get started.
Won't lie, this one kind of felt like fate had stepped in. I now got to work with a team I already knew and loved, doing what I knew and loved, at a pace that would work with my new schedule.
Moral of the story: If it's possible and fits with what you're trying to do for work, start by reaching out to old connections for new job opportunities. It gives you an incredible advantage when you already have some kind of relationship in place, as opposed to reaching out cold to random new opportunities where you become "just another fish in the pond".
Job #3: An opportunity came to me but I didn't accept until the time felt right
When I started building out my van, I had these two remote jobs set up (mentioned above). Between these two jobs and building out the van, I was busy! What's more, a big reason I wanted to do van life was to give myself free time so I could understand what a happy life meant to me.
But then an old coworker who had since moved on to a new tech company reached out. His company had marketing needs and he wanted to know if I was interested in helping. At the beginning of my van build, I said no to his inquiry. I was determined to not overwhelm myself.
Then, COVID-19 quarantine hit and after a few months of not working full-time, I was getting a feel for what my new (and much lower) income looked like. I knew I'd be at home for longer than I expected and I started thinking it'd be a good time to get adjusted with a new gig before being on the road.
My old coworker ended up reaching out again and saying they were still looking for marketing help. This time, I took him up on it! I had a virtual meeting with him and his boss, and we arranged a 5-10hr/week position for me.
Moral of the story: Know your limits and don't let the potential of one opportunity in the moment overshadow your overall goal.
Now, I'm 1.5 months into living on the road and I LOVE my setup. Admittedly, the first job has not resulted in income because writing articles took too much time from my other jobs, building out this website, and also exploring in my van. But the other two jobs have given me the financial freedom to not have to put an end date on my van adventures, while also giving me enough time to explore and write blog posts like this! Got questions related to finding work on the road? Don't hesitate to email me at email@example.com!