How to Get a Remote Job so You Can Travel The World (at least, how I got one)

When I tell people that I'm traveling the world (and still working), I'm met with one of two reactions:

  1. Man, I wish I could do that.
  2. I wish I had done something like that before _________ (kids, marriage, medical bills, buying a house, etc).

Until recently, I would've given the first reaction to a friend telling me of her global adventures. No way would my company let me do that, I'd think (and I'd be right). 

But here's the thing: If you work on a computer all day from the same place, you can work remotely. Probably. Maybe not. There are a lot of reasons why not. Here's my giant caveat about privilege and circumstance, both of which enable nomadism.

But okay - you're in a circumstance wherein nomadism makes sense.

You likely won't able to do it at your current company. So, time to start the job hunt.

 
Put on your "get shit done" face. It's business time.

Put on your "get shit done" face. It's business time.

 

1. First things first: do some soul searching.

Honesty moment: I was terrified to look for a new job. I hadn't ever done it. My former boss hired me when I was 19, still in school, and she brought me on full time after college. Tons of unhelpful thoughts raced through my head every time I filled out an application. What if I'm not better than other candidates? What if nobody wants to hire me? What if I'm bad at marketing and never realized it? The imposter syndrome is strong with this one.

When your passion, curiosity, and joy overrule your fear and doubt, cool shit happens. 

For me, the opportunity to travel the world right now / all the time (not when I retire / on week-long vacations) meant that working remotely was a priority in my life. I also don't love the routine of working in an office and am sick of living 30 minutes from my childhood home. I was more than ready for a change - a BIG one.

I went into the job search with two perspectives, one a little more honest than the other:

  1. I will take absolutely any job that lets me afford to do Remote Year (which is not exactly cheap, but the fee is certainly reasonable) and wherein I can work remotely. Except sales. I really hate sales.
  2. I'm changing my life and want to do it right. I want a job that makes me happy to log on in the morning. I want a job that I love and that I feel passionate about.

At first, I didn't dare believe the second perspective. That was my honest thought, but it wasn't quite as important as doing Remote Year in the first place. Living abroad and having a job were the essentials. I saw loving the job as gravy. I'm not sure that helped me out very much.

For the record, the second perspective actually happened.

2. Know what sets you apart and what will get your resume rejected (by some people).

A few companies wanted to hire me. A lot of companies did not. I'm pretty sure of why that was, in both cases.

qualities that helped me get a remote job:

I'm not talking about my GPA (which, TBH, is not impressive) or years of experience. I'm talking about the things that pushed me over the edge from "good candidate" to "hire." 

I'm damn good at what I do.

The difference between confidence and ego is, I think, your track record. I'm confident that I'm a very good marketer and know a lot about a lot of different things. My resume is stacked. That's important when the talent pool isn't "Raleigh / Durham, NC" - it's the entire world. You have to be a better fit than anyone else from everywhere else.

I've worked for startups my entire career.

Startup experience translates well to remote work. Both require a lot of autonomy. Both require exceptional attention to detail. Both require employees to be great communicators internally and externally (no HR department - you've gotta work out spats on your own). And both require a lot of passion. Those traits are generally appreciated at larger companies, but they're vital in startups.

The digital nomad movement and shift to remote work is a very modern concept. A lot of the companies to which you'll be applying will be relatively young, and probably pretty small. Small companies like to hire people who have worked for small companies in the past. Previous startup experience is always a bonus point when you're applying to work at a startup.

I'm methodical and independent.

There's a reason that most Remote Year participants are in one of two fields: marketing and development. A big one, of course, is that both marketing and dev require computer time for 99% of your day-to-day work. 

But there's another side, one that's very important: marketing and dev both attract methodical, highly focused individuals. When I was in college, I thought that "marketing managers" were highly creative people rather than data-driven thinkers. And maybe some of them are, but my version of marketing involves excel a hell of a lot more than it involves brainstorming. 

If your favorite part of the day is a lunchtime meeting wherein you talk shop with coworkers, draw roadmaps on the whiteboard, and bounce ideas off of each other, you might not like remote work. Chloe, my best friend, would hate it. She'd go crazy not being able to talk to her coworkers all day, not being in an office, not feeling that in-person community. 

If, however, brainstorm meetings make you cringe and your favorite part of the day is plugging your headphones in to code or build a revenue model or write a blog post, you might just succeed in remote work.

I have a hunch that it attracts introverts. That hunch is based on a sample size of three people: me and Jeff, who are all about the idea and also definitely introverts, and Chloe, who hates the idea and is the most extroverted person I know. So take that hunch with a giant slab of salt.

I'm passionate.

Everyone is passionate about something. Those passions shift as we age and as our perspective is honed by experience. I've always been passionate about travel. I can tell you the moment that passion was sparked (strolling through Quebec City with my 5th grade French class) and can talk for hours about why it's important to me. My new role is at a company full of people who live and breathe travel. I wouldn't have gotten this job if I were half-hearted about it. 

I'm also passionate about work-life balance and think that being chained to a desk is a damn shame. A lot of potential employers will feel the same way. Don't be scared to talk about why you feel that way - if you do and if it's important to you.

QUALITIES THAT made some companies turn me down:

There are a lot of them, I'm sure, but here are two main ones.

I'm direct, to-the-point, and very transparent.

Hold on. Aren't those supposed to be good things? Is this one of those things where an employer says "tell me your biggest weakness" and you say something that's clearly not a weakness at all?

Noooonono. Let me elaborate. People THINK they want total honesty, but overall humans are more comfortable with the facade. I am very bad at the facade. I am honest to a point of being strange. I don't really have secrets and I value being genuine very highly. Even when being genuine means being a little distant and matter-of-fact. Not everyone is your best friend and I don't think you should pretend otherwise. 

Newsflash: the facade is valued in the business world.

Putting all your cards on the table in a matter-of-fact way can be disconcerting, even come across as demanding. I'm kind and warm, but I'm also honest and impatient with cagey people.

If I tell you that I need to make $X just to afford the Remote Year fee (+ food etc), that means I will turn down your offer if it's less than $X. Not because I don't like your company or am not passionate about the work I'd be doing, but because I know what marketing managers make and what I need to make to live. For the record, X is a fair number. 

Anyway. I'm bad at being palatable. I'm polarizing. Like Brendan, one of my best friends, said to me a week after we met:

"I find you off-putting."

I'm also kind, warm, friendly, funny, and smart. But definitely off-putting. Not everyone wants to work with off-putting. 

I don't have a business degree.

I studied PoliSci at UNC. I have a good reason, at least a reason that seemed good to me. I was learning marketing at work and was more than a little frustrated that neither the B-school nor J-school (business / journalism) taught new media marketing or really anything related to tech. That has since changed (in the journalism school at least, now called the MJ-school - media and journalism). But in 2011, I got a D on a media plan because I devoted a large portion of my fake client's time and budget to Twitter marketing. That really pissed me off. I didn't want to study how to create a TV ad at Ogilvy or how to succeed as a consultant for PWC. None of that interested me. So I used my on-the-job experience as my proxy to a business degree, and switched to studying Poli Sci. My constitutional law class was my favorite class in college. Overall, good decision.

But a decision that gets my resume tossed unceremoniously into many a "no" pile. Fine with me. I'd like to work at a place that doesn't value higher education above experience. I think it's myopic. But then again, I'm quite stubborn.

3. Start the hunt.

Knowing what you have to offer off-the-bat will make you a much better applicant. When you're flailing mentally, it shows in an application. Direction and confidence are hard to fake. 

Resources I used to find remote jobs:

  • We Work Remotely. This was my favorite site to use (it's quite intuitive) and the site where I found my current job. I checked it twice a day.
  • RemoteOK. This has a lot of the same posts as We Work Remotely, but many uniques as well. I like the interface a little less. Still - very useful.
  • Careerbuilder, Glassdoor, and Indeed.com. I recommend using those tools as a discovery platform and not as a way to apply. Find a post you like on those sites, then apply for that job from the company's website. Indeed in particular makes it way too easy to apply for jobs through their site. That means a company will be inundated with unqualified applicants submitting resumes through Indeed. Your resume will get lost in the pile. When I hired people, I'd completely ignore all applicants who submitted a resume through Indeed.

Protip: Apply for jobs for which you aren't exactly qualified.

Seriously. I applied for product management roles, VP of Marketing positions, and roles devoted to analytics. 

I'd be good at product management and it's something I think I'd love, but my resume has 0 product experience. I do have analytics experience, but not like a data scientist does. 

VP of Marketing? I'm good at my job, but I'm also 25. The only type of company that'd hire me to be VP of anything would be an early stage startup with no funding and no cash flow. But still, I sent in my resume and cover letter.

So why apply? Because, as stated above, a lot of companies that hire remote workers are also startups / small teams. I think the company matters more than the job description.

If they need a product manager, they might need a marketer to sell that product. If they're hiring a VP of Marketing, they might also need a midlevel marketing person. In fact, I got an email from a company in that very situation. They advertised for a VP. I applied and (shocker) didn't get an interview. A month later (three days after signing my offer letter at my new role), the CEO emailed me to see if I would take a midlevel marketing position. I likely would have gone to work for them if Tortuga Backpacks had offered the role to someone else.

Startups are always hungry for great talent. If you come across a company that makes you happy, apply. The worst they can say is no. At best, you get a job that was written for you. Or, like me, you get on a short list of people to email next time that company is hiring.

A miscellaneous thought about applying for remote work:

I found two distinct types of companies when I was searching for remote jobs.

  1. Lifestyle companies. These are the companies who offer unlimited vacation, team retreats around the world, and believe in setting your own hours. Taking a yoga class at 3pm is encouraged. Work-life balance isn't just talked about - it's lived. You'll be trusted and very independent. Company cultures are driven by passion.
  2. The cost-savers. A huge benefit of hiring remote workers: it's cheaper to the company. You don't have to pay for a spot in your office. A company in Boston can hire people in North Dakota and pay them less because it costs less to live there (I'm not saying you should - I'm saying that it's a tactic some companies use). This kind of company sees hiring remotely as a win/win, purely from a financial standpoint. They're very reasonable, logical company cultures and are a step away from a traditional workplace.

I think I might fit with either, but #1 was my first choice by far (and where I ended up). That's not for everyone. If you aren't sure about the whole working-remotely thing, go for the second type of company. Often those roles have the option to be remote, but you can go and work in their HQ if you'd prefer. That gives you freedom to try the lifestyle and see if it's right for you.

If you're thinking about making a change to remote, hit me up on Twitter. I'd love to chat about it.

Header image (and the below image): the incomparable Amanda Adams


Taylor Coil is traveling the world with Remote Year, living in 12 countries in 12 months, while working as a marketing manager.