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How to travel the world and keep your job: Jenna Winn on working a Remote Year

Remote Year Jenna with Penguins

Jenna living her dream to see penguins in the wild at Simons Beach outside of Cape Town.

Word travel is usually reserved for retirees, lucky Brits on “gap year,” professors on sabbatical, or lottery winners. Remote Year is working to change that, by enabling you to keep your job and see the world at the same time.

Jenna Winn, a member of the Remote Year product team, is a South Coast local who spent last summer with us at Groundwork between trips. In this interview she shares her experiences going remote around the world, and how it helped her learn to appreciate the good in everyone. (Sounds a lot like coworking, right?)

Can you describe Remote Year for us?

Remote Year is a way to see the world, meet amazing people and keep your job. We organize work & travel programs that take groups of remote workers traveling for 4 or 12 months at a time, to a new city every month.

Think of it like this: instead of paying rent or a mortgage to live in a house in one place, you pay Remote Year and we provide you with a place to live, a place to work, travel between destinations, local experiences in each city, 24/7 support in case anything goes wrong, and a community of 30-75 people to share your experience with.

All you need to bring is a job you can do remotely and a sense of adventure!

Remote Year group photo

Jenna’s group– one week into the year they spent together.

How did you get involved with Remote Year? What were you doing before?

A friend sent me an article about Remote Year when they launched three years ago and the concept really resonated with me. At the time, I had been working at an e-commerce company for five years in Project Management and was feeling the itch to travel. I ended up getting laid off from that company, took my severance and went backpacking through Latin America for 4 months. After returning I moved to Seattle for a new job at an e-commerce startup but the idea of taking my job remote and traveling was always in the back of my mind.

I was new to Seattle and didn’t have many friends there, so one Friday night I was drinking a glass of wine by myself and decided I was going to apply for Remote Year and figure out how to convince my boss to let me take my job remote. I saw that Remote Year was hiring, so I applied for a job instead. That was that.

My first job at Remote Year was Program Leader where I managed the logistics and support for a group of 72 people for a year as we traveled to twelve different cities. It was a 24/7 job but one of the best years of my life! Now I’m working on the Product Team designing new experiences for our customers. Last month we launched a 2-week travel experience focused around personal development called Journeys.

What is your community like? Are there common characteristics among people who participate?

Everyone is open. Open to new cultures, open to meeting new people, open to thinking about life differently, open to trying new food or doing something they’ve never done before. This isn’t unique to the community I traveled with– I’ve visited seven different Remote Year communities and I’ve always able to make fast friends. It’s magical!

A lot of people who find Remote Year are also going through a transition in life and looking for a change, whether it is a break up, a new job, wanting to make new friends etc., they are looking for something new and I think that in itself makes people more open to each other and to adventure.

Remote Year - Portugal

Learning to make Piri-Piri hot sauce on a Lisbon rooftop at their welcome to Portugal event.

What are some of your favorite places you’ve visited so far?

I love every place I visited but one of my favorite cities is Valencia, Spain. It is such a pleasant place and every time I go there I feel at home. It has a beautiful green park that runs throughout the city and it is always filled with locals. On top of that, it’s on the Mediterranean, so there are amazing beaches, warm water and delicious food. It is a city I would consider moving to, if i ever pick one place.

Another amazing place I visited was Nuqui, Colombia. It is on the pacific coast and only reachable by a very tiny plane. No cars, no internet, nothing to do but go for a swim, read a book in a hammock, go for a walk in the jungle, and watch the beautiful sunsets.

How about a surprising or unexpected moment that happened during your travels?

We were cleaning a beach in Rabat, Morocco when a local family walking by decided to join in and help us. After a few hours I used my best body language (we didn’t have a common language) to invite them to join us at the nearby coffee shop. At the coffee shop the family invited us to their family couscous lunch in their home later that day. I wasn’t able to join but two participants from Remote Year went to their house in the Medina and had an amazing time. The genuine kindness of this family really stuck with me.

Remote Year Morocco

Jenna cleaning up a beach in Morocco with a local family.

Do you notice any changes or transformations among people who participate in a remote year of work?

So many! I don’t think anyone can travel for a year and not change. The biggest change I saw within my group and even in myself is the ability to look past initial quirks or things that might initially bother you about a person to really get to know them.

You learn to appreciate something about everyone even if they get on your nerves sometimes, just like family.

In everyday life you can pick and choose who you spend your time with,  but in Remote Year life you are living, traveling and working in the same space, so you learn to appreciate everyone.

Any advice for people who want to travel more and are afraid to take the plunge?

Do it!!!! Stop making excuses and take the plunge. Even if your ultimate goal is to return back home, travel will shake you out of your comfort zone and give you inspiration you can take back into your day-to-day life. You won’t regret it, I promise.

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