How I Got My Start Working Remotely and Turned Into Full Time Digital Nomad

By Hailley Griffis

I remember the first time I met an exchange student. I was 14 and living in a town of 300 people, she had just come to Canada from France and my best friend was her host family, but they didn’t speak French and she didn’t speak English.

She quickly ended up spending time at my house so I could help translate. That’s the first time I realized you can leave your country and I’ve been heavily committed to doing just that since then.

I proceeded to convince my parents to let me go on exchange to Hamburg, Germany when I was 16 and I’ve had the travel bug ever since.

Fast forward to today, I’m working full-time 100% of the time remotely in my dream job and sometimes I have to stop and really think through how any of this happened.

So how did I go from enjoying exploring the world to finding a job that let me live my nomadic lifestyle? I’ve narrowed it down to three key things I did to get here and would love to share them with you.

1. I Chose Remote Over Stability

To start, this might sound a little insane, but I chose remote over everything else, including a stable salary with amazing benefits. When I graduated University, I had two job offers right out of the door, both wonderful. I asked both of them if I could work remotely. You see, I’d booked this one way ticket to Colombia and was determined to not have to come back to an office.

Both companies politely declined my request to be their only remote worker so I was left with a few options.

1. Choose stability and a normal job with benefits
2. Run off to Colombia and freelance to keep my dream of remote work alive

I’m sure I could have come up with more options, but I was quite sold on the second one, so I sold most of my belongings, packed up a bag and headed to Colombia. Building a freelance business isn’t easy but I managed to secure some really awesome clients. Mostly through sites like Elance (now Upwork) and word of mouth. Check out Nomad Pass’ 22 of the Best Remote Job Resources to get you out of the office and on the road.

To read a bit more on this: Why I Turned Down Two Job Offers Out of University To Freelance And Travel

2. I Pushed Employers To Think About Remote Options

When I did go back to having a more normal job, I was in Silicon Valley working for a startup. Trying to get as much high tech, relevant experience in my field as I could. Most startups are still figuring out workplace culture, remote practices and about a million other things.

I was super lucky to have a flexible workplace in the sense that once a week we could all work from home, and if something came up with my family, the team understood and let me work remote for a week or so while I went back to help out.

At places where remote work wasn’t yet being talked about as an option long-term (a few months) or short term (a few days / weeks per year) I would step up to start those conversations and see if it’s something that is a good fit for the team because it’s a priority for me. I requested to work remotely for a few weeks from Iceland, and while I was comfortable communicating primarily through video tools and chat tools my work was still new to all of this.

They ended up implementing a remote work policy of one week per quarter, which is super awesome! It was inspiring to see a company go from not having guidelines here to really thinking through why they did things and how remote culture might fit in.

When most of the team is in person, it’s also hard to coordinate with one remote person. I took advantage of the one week per quarter and enjoyed it endlessly. I’m most productive when working from home in my own environment and I’ve always known this about myself.

3. I Focused My Job Hunt on Remote Work

Knowing that remote was always going to be a huge priority for me, I focused on finding a place that was closer to 100% remote in my next role.

There are some great websites like remotive.io that feature only remote positions that I kept a keen eye on. I ended up coming across a posting that Buffer was looking for someone with just my skill set, it felt like the perfect fit!

I’d been following Buffer for years now and I’ve always admired their workplace practices and company values. The whole team is remote and have been fully-distributed since nearly the beginning of Buffer. The amazing thing here is that because the whole team is remote, there isn’t a divide between employees that are in an office versus employees that are remote, which can be a tough challenge for remote workers. At Buffer gets the same perks and this creates such a positive work culture.

Some Fun Being a Digital Nomad

Shortly after starting at Buffer, I graduated from the probation period or Buffer Bootcamp. The same week, I dropped my things off in Canada and started traveling.

With no real agenda in mind, I started showing up in places where I had friends, or a vague interest in exploring. I spent three weeks split between the Czech Republic (Prague and a few other cities) and Vienna, Austria. Then I went back to Colombia. I had the chance to work for two weeks from Whitehorse, Yukon. The most northern point I’d ever been in Canada and as I write this post, I’m working from London, UK.

I recently decided to make Toronto my home base so I’m really looking forward to having my own space again and creating a great community in the city, while balancing it with a healthy dose of continued travel. 😉


Hailley is a Press Crafter at Buffer, where she focuses on sharing Buffer’s story. In her free time, she switches between choosing a new time zone and practicing Brazilian Jiu Jitsu. Currently, home is Toronto. Follow her @hailleymari everywhere on social media.


Our project, Nomad Pass, currently in BETA, enables professionals to work remotely from anywhere around the world. We have listings of unique places around the world where professionals can live & work from and a community of professionals to connect to wherever you are. Read what we are all about here.

If you are interested in guest blogging for us or contributing to the project, email us info@nomadpass.com we would love to hear from you!