Ali has been traveling the world while working remotely as a digital nomad for DuckDuckGo as their Director of People Operations. We asked her more about how she started traveling and her advice for aspiring digital nomads.

Tell us more about yourself.

I am originally from a suburb outside of Detroit, MI, and have always had nomadic tendencies, unintentionally. I lived in eight cities in three different countries before I even knew what being a digital nomad was all about.

Some of my early wanderlust occurred while growing up, but as an adult, the amount of time and money I spent buying IKEA furniture only to sell it a year later and repeating the process in a new place, was probably an early warning sign to leave the conventional idea of a home behind.

What do you do for work?

To make this lifestyle work for me I was lucky enough to find my current job: Director of People Operations at DuckDuckGo. DuckDuckGo is a search engine that doesn’t track you. Not only did the mission speak to me, but after learning that the company was “remote first,” and that my co-workers lived all around the world, I knew this was a special opportunity.

I always believed work should be about what you can do, not how many hours you sit behind a desk. Since joining the team a year ago, I’ve been able to roll out US health benefits from Japan, make changes to our team structure from Spain, and kick off new leadership meetings from Colombia.

Outside of work, I love to travel (obviously) and I am a big foodie. I love to cook and go to all sorts of local restaurants. Street food, the hidden hole in the wall or the multi-course fine dining experiences all speak to my love of culinary greatness. I also enjoy hiking, yoga, rafting, and taking pictures (especially of street art) all of which I try to do while traveling.

How did you get started as a digital nomad, and why?

I have always been somewhat restless; I crave new experiences. I love the evolution of getting to a new place, feeling foreign, and figuring out a life for myself. Once things get too routine, I get bored.

It is hard to pinpoint when I became a digital nomad exactly and sometimes I still feel like an imposter. I feel like I am waiting for my “digital nomad” badge to prove myself and I think, “Does it come when I have visited enough places? Or when I have a certain amount of pictures of myself working in exotic locations? Or after I completely ditch my current lease and sell all that furniture again…” And then I think no, it is all part of the same journey and in my journey, a few experiences stick out.

 

What are some of those experiences that stood out?

Studying abroad: You could say I studied abroad twice. I went to McGill in Montreal and had my first taste of a “newness” I constantly craved. It was my first time living in an urban environment and my first time getting by when a second language was at hand. I officially studied abroad my last year at McGill at a school in Dublin, UCD, and experienced leaving North America for the first time. New countries, new foods, new friends, and weekend getaways to Budapest, Paris, Rome, Stockholm, and more. I was hooked!

Moving: After college, I wasn’t sure where to settle down. I choose NYC, but a year later moved to DC for a job opportunity, only to return to Brooklyn a few years after that.  The whole time I felt I was trying to fit a square peg into a round hole. Constantly, I thought a new neighbor or throw pillow would be the key to settling in and sticking around.

Backpacking: In 2014, I officially quit my 9-5 job. I took off to Peru with a friend and then went back to South America a few months later for a mostly solo trip, spending time in Uruguay, Argentina, and Chile. Traveling alone was a unique, rewarding experience. During that time, I also got a few freelance contracts started and had my first taste combining work and travel.

DuckDuckGo Co-workation: In 2016, I organized a “co-workation” for DuckDuckGo. Five cross-functional employees spent a week living and working together in Tokyo. After the official meetup I took some time to explore, and somewhere between watching sumo wrestling championships, eating ramen and rolling out a health care plan for US employees, I had a revelation. Instead of moving every 18 months in a quest to find my place in the world, why shouldn’t I embrace my passion for traveling and continue to work from home with my home being the world (or anywhere in the world with reliable Wi-Fi)?

Digital Nomad Success: This past January, I set off on my first official digital nomad trip spending a few weeks in Madrid and various parts of Italy. From there, I flew to Colombia for February and March.

 

What are some of your best experiences as a digital nomad?

My favorite experience in each city is finding that perfect coffee shop to set up for a few hours of work and sample locally baked goods.

More generally, the thing that is most motivating to me as a digital nomad is the ability to experience the world without giving up my career goals. I create my own schedule based on weather, my productivity, and cool local events. I am currently doing some of the most challenging work of my career while still taking the time to appreciate life more, like the newness of a sunset from a different location after a hard day’s work.

A couple of really cool moments from my travels include:

• Eating dinner in a yatai in Fukuoka, communicating with hand gestures and sharing noodles with other diners.
• Meeting locals at Carnival in Barranquilla and making it to the front of the crowd to view the parade pass by.
• Hiking around Salento and seeing the world’s tallest palm trees. Even though I was disappointed at the time since it began to rain as we neared the famous trees, it was more rewarding than any other Saturday at home.

Any bad experiences while traveling?

Generally, I feel safe traveling as a solo female in most places. I did receive a fake 20mil peso (approximately 6 US dollars) from a cab driver in Bogota and tried to use it at a restaurant, which was pretty embarrassing.

While I was frustrated by that experience, I feel lucky to not have had worse experiences. I do try to be more patient with myself because I find daily life stressors can be exaggerated by new surroundings.

Tell us more about your job with DuckDuckGo. How can someone become a digital nomad like you?

I work full time as the Director of People Operations at DuckDuckGo. Day to day I think about topics such as hiring, company benefits and policies, planning company retreats, and employee satisfaction.

DuckDuckGo is hiring! Click here for more info.

Remote work is not for everyone; we look for this ability when making hiring decisions. In order to be a successful remote worker, you need to be proactive and self-motivated.

My recommendation for people trying to become a digital nomad is to find your outlet and take baby steps. If you work for a company that already allows you to telework or have flextime consider asking them to support you in a situation where you can work remotely for a week or for a month. There are a lot of organizations and communities popping up that you can join to test out this lifestyle and see what works for you.

Another option is searching for remote-first full-time opportunities, like DuckDuckGo. You can look for these job boards in places such as remotebase.io.

Finally, a lot of people making this leap tend to freelance or do contract work. This is what I did when I was first getting started, and it was personally challenging for me. I wanted to find one place where I could feel I was making an impact at work while still being personally fulfilled by traveling.

How do you avoid becoming distracted when working remotely?

This has not been too hard for me, as I have always been a self-starter. My job keeps me grounded and provides a sense of purpose on longer trips when working remotely. Some tactical things I do include setting weekly and daily “to-do” lists, with clear goals and blocking off work time in my calendar with other personal activities such as yoga classes. Oftentimes, for my projects, I write up and share specific milestones or tasks to be completed with my team. This holds me accountable for what to accomplish every week.

I also treat finding a new place to work as a fun activity for the day – trekking to the other side of town to camp out at a café in that cool neighborhood I haven’t been to yet, or stopping into a local co-working space to meet people that can be a good influence on my motivation turns working into the fun activity of the day. Finally, I use sightseeing activities or events as a reward for getting my job done.

What gear can’t you work remotely without?

I am pretty basic when it comes to gear. I usually carry the following with me:

• Laptop (13 inch Mac)
• iPhone with battery pack
• Chargers (and backup chargers)
• A multi-prong international adaptor with USB outlets
• A portable hot spot that I switch on with local SIM cards
• This awesome infinity scarf/blanket that keeps me warm and comfy wherever I go

How has working remotely impacted your family life?

Ever since I left for college, my family has lived in a different state (and sometimes country) so I am used to not seeing them in person frequently. I love FaceTiming with my nephew (he is 3) and showing him all the places I visit. My sister shows him my Instagram pics, and one time I posted a picture of a cathedral in Spain, so he thought I lived in a castle. That was funny! It is cool to share my travel experiences and inspire him to learn more about different countries and cultures at a young age.

I do think about if I want my own family someday, and the challenges of dating and building deeper relationships when you are traveling full time. It is fun to always be meeting new people but sometimes you do want a more meaningful and long lasting connection.

I’ve learned that just because you share a love for traveling or connect on the surface with another digital nomad it does not mean you have the same values or will make a good long-term match. I didn’t have to comprise between work and traveling and I do wonder if this is an area where it will become a choice someday in the future between a nomadic lifestyle and a committed relationship (though I hope not!).

Any plans yet to return home/get a location-bound job?

I just returned to Philadelphia to help plan our company meetup next month. I know I want to continue to travel in some capacity, but am trying to get back into my routine at home and take things one day at a time, especially since summer in Philadelphia is so much fun! On my list are a few US towns, most of Central America and SE Asia, as well as Portugal and a return trip to Spain.

Follow Ali on Twitter or on Instagram.