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If you search the Web for “how to become a digital nomad”, most guides start with one very big step: become self-employed. They’ll walk you through how to start your own business, attract clients, and generate sustainable income. Easy, right?

I once thought that would be my path, though not with the goal of becoming a digital nomad: I just wanted to be happy in my career. It had been so long since I’d enjoyed a day job, I thought being my own boss was the only alternative. I joined a Mastermind group with the intention of developing my YouTube channel, teaching, writing, and podcasting into a career.

But before I could launch my media empire, I hit the jackpot: I landed at Automattic in a job that is fully remote and which I sincerely enjoy.

The CEO of Automattic is Matt Mullenweg, the co-founder of WordPress, the world’s most popular content management system and one I’ve been using since 2006. If you want to build a website, you’ll probably use a CMS. You may have heard of some of other CMSes, such as Squarespace, Wix, or Weebly — though I’d hesitate to call them “competitors“.

WordPress itself is open-source and free: it’s developed by a community of contributors, anyone can use it without payment or registration, and they can install it anywhere they like. WordPress.com is one of those places. I know, it’s a bit confusing: Automattic makes WordPress.com, not WordPress. But if you create a free website on WordPress.com and sign up for one of the optional, paid upgrades (starting at $5 per month), then that’s my employer you’re paying.

You don’t need to be a developer or a designer to work with WordPress; you can be a Technical Account Manager (TAM), like me! I work specifically at WordPress VIP, which specializes in large-scale business clients such as USA Today, TechCrunch, TED, VentureBeat, and FiveThirtyEight. When one of these clients signs a contract with our sales team, they get handed over to one of several TAMs. We serve as digital project managers and liaisons among the clients, third-party developers, and VIP, ensuring that resources are aligned and timelines are met to ensure a smooth website launch. The TAM role is a great combination of technical aptitude and “soft” people skills.

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Here’s the great thing about Automattic: it’s entirely distributed. The company has 1,000+ employees and no offices. My co-workers are scattered across 79 countries around the world, allowing us to focus on doing our work without wasting time commuting to an office or wasting money on office apparel. This isn’t “working from home one day a week” or “hiring a remote employee while everyone else is in the office”: all of us Automatticians share the same environment, culture, and tools. (Mullenweg hosts a podcast about the benefits and challenges of distributed work and recruiting talented people around the globe.)

On a small scale, this distributed nature means I can work from my home, a co-working space, a coffee shop, or the library. On a large scale, I can be in Boston, Seattle, London, or Sydney. Automattic has no investment in recruiting from one location or keeping its employees in one space. In fact, once I decided to become a digital nomad, I spent weeks putting my plans in place before it even occurred to me to let HR know!

It’s not just the location that’s flexible; the schedule is, too. Employees are encouraged to take time off in the middle of the day to go for a walk, chaperon a child’s field trip, run errands, or catch a matinée, as long as we get our work done within 40 hours a week. We have unlimited vacation time (and we actually use it) — and every five years, we get a paid, three-month sabbatical. This flexibility makes it all that much easier to nomad, since I may sometimes need to use a traditional workday to acclimate to a new environment or relocate from one city to another.

It was a long road to get this job, but it was worth it. Remember all those side hustles I wanted to develop? Those are what led me at Automattic. I was on the adjunct faculty at Emerson College, teaching graduate students about online publishing, when I attended Boston’s monthly WordPress meetup. The guest speaker was Steph Yiu, an Automattician. Her presentation on editorial plugins was a great fit for my class, so I asked if she would reprise her talk for my students. She returned to my classroom many times over the years — but in 2017, she ended her talk with an unprecedented remark: “If any of your students want to work with me, we’re hiring!”

And here I am: remote, nomadic, and happy.

Would your job let you work remotely? Would you want it to? Let me know in the comments!

(Photo by Marek Hrabe)

Ken Gagne

Digital nomad, Apple II geek, vegetarian, teacher, cyclist, feminist, Automattician.

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