(2/5) How to work remotely while traveling the world

If you haven’t read the intro to this 5-article series about working remotely, read the first one here.

This post will dive a little deeper into how to actually make this happen: What to keep in mind when applying to part- and full-time remote jobs that let you travel the world while working.

First of all, this can be in 1 of 3 ways:

  1. Landing a gig with a company that runs remotely. This is a company that’s used to hiring remote people, used to communicating via IM apps, video calls, and having teams whose working times might not always overlap. (easiest)
  2. Landing a gig with a non-remote company, a traditional company that may or may not have any remote employees augmenting their on-site team. (more difficult)
  3. Building a personal business where you are your own boss, and you provide services over the internet to people that need them. (most difficult, but totally worth it)

Method #1

While it’s no piece of cake, this is the method that is (relatively) the easiest. This company operates as if it’s any other traditional company, but meetings are over Skype instead of in conference rooms, and communication is over an app like Slack instead of walking over to someone’s desk.

The other employees and the management team work remotely as well, and there are tried-and-true project management and communication systems in place to overcome the barriers that come along with remotely-run teams.

The hardest part about this method is that you’re not trying to stand out among other applicants in the city, you’re trying to stand out among all possible applicants all over the world. This is likely a much larger pool you’re throwing your resume into.


Bosses and hiring managers of remotely-run companies are tired of hiring someone that looks great on paper, but who can’t handle a fully remote gig once they get going.


Working remotely is hard. You can choose to work at home in your pajamas or at your favorite coffee shop, but keeping up to date with your team and being nearly constantly available to people at odd working hours is draining. You can set your own hours, but you won’t be successful if you decide you want to take a whole day off and then end up pulling an all-nighter on Sunday to meet a weekly deadline.

Remote work requires you to be fully responsible for getting sh*t done even when no one is looking. And that’s harder than you think.

You won’t be surrounded by people on your team. You won’t be in a productive space with people working towards a common goal (the closest thing might be joining a coworking space). Working remotely can be very lonely, and the concern you need to address when applying to remote roles, is that you can handle this responsibility.

The #1 thing you can do is write a kick-ass cover letter that succinctly showcases why you can address their specific concerns. Why should you, this person that they’ve never met and probably never will meet in person, be trusted with a full-time role on their team?

This involves careful and clear wording in your cover letter and resume. Do you “excel at time management,” or can you link them to a project with a tight deadline that you helped achieve, because you took lead as the project manager and had the foresight to put extra manpower on it halfway through?

Are you a “reliable communicator,” or do you have a recommendation from a past colleague or boss talking about how they could always get in touch with you if they needed help?

Do you “push yourself to the limit,” or do you constantly strive for success, knowing that if you can’t finish something by the deadline you set for yourself, you’ll communicate why and deliver a quality project at a new given date?

Hiring managers care less about what you say you can do and more about how you show them, and how you plan to help them, specifically.

Method #2

Believe it or not, almost the same exact process goes into applying for a remote role with a non-remote company. Except it’s way harder. You’re not addressing a specific, known concern of an experienced remote manager, you’re convincing a manager without remote colleagues that you’ll be just as useful, if not more useful, than an on-site team member.

They don’t know what they don’t know.

Tell them their concerns, and then solve them.

career entrepreneurship

To a manager that’s never managed remote employees, bring up how your experience in startups has honed your communication skills at all hours of the day. If they’re in New York and you’re in California, talk about how you can be given an assignment as they leave work, and they’ll see it in the morning, taken care of.

Bring up their fear that you’ll just disappear and cease communication abruptly. Comfort their anxiety by providing references that talk about your character, or your dedication to teams, or your inherent desire to help people or make an impact with a meaningful company. Take the time before applying to anything to reach out to old bosses and colleagues, mentors, teachers, and team members and request letters of recommendation (LinkedIn even has a built-in tool for this). It’s perfectly okay (and expected by seasoned recommenders) to ask them to focus on A, B, and C traits, or to reference specific moments they were impressed by you.

Know your hiring manager’s pain points, what their boss might be expecting, and address to the best of your ability their concerns in your cover letter and resume. If you need help with this, use the Contact page to talk with me! I have 5 years of experience in managing on-site and remote teams, HR, copywriting, hiring, and strategic content.

Method #3

First off, this method is TOTALLY worth it, but a lot of work. A lot.

But it’s also the most rewarding method to start working where you want, when you want. This method’s success is a matter of finding your value proposition, and learning how to sell it.

Are you passionate about graphic design? You can take courses on all the latest design technology, on how to built your own website, and how to get your first client.

Are you passionate about creative writing? You can take a course on resume and cover letter writing, and get to work on freelancing sites like Upwork and about a million others. From experience, I’m telling you that you CAN land consecutive book editing, ghostwriting, and blog writing gigs, enough to be part or full time.

A ton of awesome courses are all over Skillcrush, LinkedIn Learning, and various Facebook and networking groups (Bucketlist Bombshells for my boss babes out there). Take some time, even if you have a 9-5 right now, to learn something new every day, every week, or every month, that might add to your value as a freelancer or personal business owner.

If you need some help (and I definitely did), use the Contact page to talk with me. Let’s work together.

Which method sounds like your cup of tea? Are you already in the midst of one of them? Let me know in the comments below what you think, and how it’s going!!




Post (3/5) will cover how to use content creation as your full-time marketer.


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