Worksheet: Build a Career Path that Lets You Work Remotely and Travel

Being able to work from anywhere in the world—whether it’s from your own living room, from a cafe in Spain, or from a vacation rental in Vietnam—gives you a level of freedom that’s missing when you need to commute every day. And if you’re able to choose your own hours, it’s that much better: you can work during the times that you’re most productive and alert.

But what about forging a whole different career path—or something adjacent to what you do? Maybe you’re working in retail and want to open an online store of your own. Or maybe you’re a graphic designer who’d like to make a shift toward web design.

It can be a bumpy road to get there, but it’s not impossible!

Seven years ago was the last time I worked in an office. My commute was 40 minutes each way, I worked 10+ hours’ unpaid overtime every week, and didn’t get to do any of the projects they’d described during the interview process. One day I got a voicemail from one of my bosses about a color they chose for an email header—it looked a little different on their phone versus their laptop. I trusted you to do this, they said. I’m coming in and we’re going to rebuild the email together and send it to everybody again. This is embarrassing.

The voicemail cut off in the middle of a sentence. I deleted it, went home early, and after a good cry, started coming up with a plan to get out. All I could think was: I can’t spend my life working for idiots. At least if I built a business of my own, I wouldn’t know how much of an idiot I am and may not be as miserable.

Six weeks later I quit, struck out on my own as a communications consultant, and in less than a year, was earning over $20,000 per month.

What Are You Good At? What Do You Like?

The two things I knew going into this were that I wanted to work fully online, and wanted to build a business of my own—no applying to salaried positions. I was lucky in that a great deal of my work leading up to that point could easily be done from a computer: lots of marketing campaigns, with even the print campaigns requiring minimal face-to-face interaction.

The project below is the very first thing I did when I began my career change.

I opened up a notebook and wrote down a list of everything I could think of that fell into these categories:

1. What are you good at?
2. What are you ok at, but want to learn more about?
3. What is something you don’t do at all, but would like to learn how to do?
4. What are you not-so-good at and don’t really care to learn more about?

And then organized those same items into a second list:

1. What do you like to do?
2. What are you ok with or neutral about doing?
3. What do you grudgingly do?
4. What do you really hate to do, and want to avoid?

I put these questions into a simple XY axis to compare them, and it was eye-opening.

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I’d assumed I would go into freelancing for website design, or maybe graphic design. It seemed to make sense: I’d done a fair amount of both, had an ok portfolio, and some of my friends had found success as freelance designers. What I found, though, was that I wasn’t actually interested in either of those things—instead, I was much more interested in (and better at) analytics, web development, and other projects that weren’t as visually creative, but that were very satisfying!

Why Did It Work?

Looking at the analytics angle, I asked why that was fulfilling:

1. Numbers could tell me things that other people—including myself—might not see, particularly when it came to understanding trends and response to campaigns. It was fascinating to get to know who our audiences were and what they wanted to see, versus what we thought they wanted to see (or who they even were!). Tracking progress and seeing success from incremental, informed changes was always a huge win.
2. Digging into analytics was more of an independent undertaking than a team one—this gave me the opportunity to think through all aspects of my work uninterrupted and at my own pace.

On a design project with any of my employers, I’d usually zone out and wait until the person with the loudest voice or most impressive title could browbeat others’ opinions and feedback to fit their vision. By removing myself as a designer, and instead being a numbers nerd, I could participate on creative projects without having to do the creative work.

And then looking at the web development angle—not design—I came to these conclusions:

1. The most satisfying part of any website or application work was cleanup: making sure it works properly, isn’t outdated on the backend, and is easy to navigate and use both as an administrator and as a visitor. And I loved finding ways to improve functionality, or building entirely new things that didn’t exist on the site before.
2. A great deal of web development work is tied to SEO, and if there was one rabbit hole that I absolutely loved going down with any marketing project, it was that!

So I settled on building a digital communications company that focused on SEO and website development and management. I could work with designers to help make their jobs easier, but my involvement in the creative process would be minimal.

The worksheet was the first step in my career change journey. It clearly and quickly outlined what I liked and what I was good at, what I wanted to learn more about, and what I just shouldn’t focus on because it didn’t make sense. It told me what to put effort toward, and how to move forward.

It wasn’t easy—it took about five months before I got my first client, and it was terrifying! But very soon after that, I got my second client, and then a third, and before I knew it, I was earning far more than I ever did in a salaried position, and I loved my work.

Over To You!

This worksheet is designed for you if you’re feeling a little lost or overwhelmed with what exactly you want to do with your career. It’s just a first step, but you may be surprised to find some ideas you hadn’t considered in finding a new path!

Even if you’re taking a different journey than I did–say, finding a job in a field that interests you, rather than creating a job from scratch—you can absolutely use this worksheet to get started.

I didn’t consider travel when I started down this road, but it opened me up to it, and about a year after I opened my company, I got rid of almost all of my possessions and became a digital nomad. Bouncing around Canada, Portugal, Panama, Costa Rica, and other destinations while working full-time in a job that I loved was something that seemed so unattainable, but that was made possible by taking that first step.

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About the Author

As the editor-in-chief of Frayed Passport, my goal is to help you build a lifestyle that lets you travel the world whenever you want and however long you want, and not worry about where your next paycheck will come from. I've been to 20+ countries and five continents, lived for years as a full-time digital nomad, and have worked completely remotely since 2015. If you would like to share your story with our community, or partner with Frayed Passport, get in touch with me at sarah@frayedpassport.com!