How to Become a Digital Nomad: 8 Outsite Members Share Their Stories

Curious about how to become a digital nomad? We spoke to 8 Outsite members who told us what they do for remote work and how they became digital nomads.

“How did you become a digital nomad?” is a question digital nomads get all the time. To many people with traditional office jobs, being a digital nomad seems like such an elusive thing.  As remote work and digital nomadism are on the rise, more and more people are wondering how they can become digital nomads themselves.


We asked some of our members about their life as a digital nomad: what they do, how they got started with life on the road, and what their favorite part of it all is. From passive income to creating their own business to working for remote companies, here are 8 Outsite members who are living the digital nomad dream. Get ready to be inspired! 


Wes Pearce, Resume Writer & Career Coach

How did you start working remotely?
About six years ago, my position was eliminated from a retail store I managed. I was already writing resumes for friends and family on the side. I decided to get a website built for my resume writing business (John Hancock Resumes) and turn it into a full-time gig. Having my own business as a resume writer and coach allows me to work remotely from anywhere in the world (as long as I have good WiFi and cell service).

How did you become a digital nomad?
Becoming a digital nomad just sort of happened based on the flexibility of running my own business. I’ve always loved to travel and set out on my first international trip in Peru when I was 14. My hub is in Kentucky, but I try to set out on a new adventure about every six to eight weeks where I work remotely. I’ve been able to work from Puerto Rico, Costa Rica, Mexico, The Keys, and Colombia so far.

What's your favorite part of being a digital nomad?
I love the flexibility of being a digital nomad. If I want to go take a hike in the afternoon or spend time at the beach, I can schedule my client calls in the morning and work on emails at night. It’s also been great to meet lots of different types of people as a digital nomad who have the same mindset of traveling and working remotely.


Tahira Jamani, Founder of The Chain Reaction

How did you start working remotely?

I knew I needed to start my own business, I felt it in my bones! I built some pieces as a side hustle while I was working full time then took the plunge into running Chain Reaction full time. When I content build, I work remote as it eliminates normal daily distractions, and the change of scenery, people and activities physically puts me in an inspiring space and gets my creative juices rolling.

How did you become a digital nomad?

I’d say I'm a partial digital nomad. My love of travel, adventure, and meeting like-minded connections inspired me to give it go! I enjoy solo traveling and this allows me to integrate my personal life and interests with my work as I choose.

What's your favorite part of being a digital nomad?

Meeting new and like-minded driven people, and being able to surf on lunch!


Mia Kovacevic, Marketing & PR Consultant

How did you start working remotely?

I graduated law school and got a job/internship for the government right after college. It didn’t take me too long to understand that sitting in an office from 9-5 and seeing my future self there in an older colleague is not really the goal I was trying to achieve. Not knowing how to change my job or my career I turned to internet and Googled every remote job available under the sun. Then, the universe spoke in the from of a Facebook ad (that I now understand how it actually worked) and the job found me.

How did you become a digital nomad?

I prefer to call myself  a location independent worker/ consultant rather than digital nomad. As soon as I got my first job (explained above) I decided to move – first to meet with my team members, then to travel and work at the same time. I took a slower approach than most: I stayed in every place for 3 month before moving on. That helped me get a feel of the place, like I’m actually living somewhere, make friends and have routines…while still never getting bored of one place. I tried briefly working and traveling while changing places every 2-3 weeks or so and understood that really is not for me. I get too stressed and chaotic. I think finding your own pace of moving around is an absolute priority. Do what feels the most comfortable for you and your schedule.

What's your favorite part of being a digital nomad?

Freedom. It’s that simple. I can be wherever I want. I can stay as long as I want. I – alongside all other remote workers I know – work probably more hours than a traditional office worker, but we make our own schedule, and that’s what it’s all about. With every new place I learn something new, I meet someone new and I try some new food. The constant newness and learning is what makes me the most excited.

Nicholas Mohnacky, CEO & co-founder at bnotes.co

How did you start working remotely?

I became a full-time entrepreneur in 2010 when I left my position in advertising sales at CoxMedia. During that time, I decided to build out my van and started a blog called usasurftrip.com, where I had an informal sponsorship from GoPro and Billabong to go about creating vlog content. I ended up staying in my van for about four months and drove 16,000 miles all around the US surfing, wake surfing, wakeboarding, kite surfing, and interviewing Watersports athletes.

How did you become a digital nomad?

After a brief stint on the road, I returned to West Palm Beach for an opportunity to consult traditional advertising agencies on their digital media buying programs. Eventually, I started my agency. Our team decided to invest in apps early on which led to the development of a turntable DJ app, called Mixr, for the iPad and a teleprompter app called Promtr (which broke into the Top 20 paid iPad apps for a period of time). Time spent working in the app development space as a marketer and co-founder was the origin of my identity as a non-technical (tech) entrepreneur, and in some ways, my life as a digital nomad.

What's your favorite part of being a digital nomad?

This is probably a pretty standard answer, but my favorite part is getting to experience people in their elements all over the world. Thoreau has a beautiful quote that captures my sentiment, "Could a greater miracle take place than for us to look through each other's eyes for an instant?”


James Briscoe, Investor

How did you start working remotely?

Fortunately, I was always able to manage my work online so a physical office space was overall an unnecessary cost and in reality, redundant.

How did you become a digital nomad?

On a holiday to Argentina I realized I was getting all my work done so I actually didn't need a home base anymore either. It was just a case of overcoming fears of breaking conventional norms and believing that a simple nomad life was a possibility.

What's your favorite part of being a digital nomad?

The freedom and the connections I make put me into a great state of productivity and flow. Being able to choose your climate is a great bonus too!


Jason Campbell, Hospitality Consultant



How did you start working remotely?

I started working remotely back in 2015, when I was leading a team of managers who traveled full time supporting hotels in a task force capacity. As I began traveling frequently to meet them on location for performance reviews, feedback sessions and relationship building, I found myself not getting the value out of my permanent housing in Miami, my car, or all of the ‘things’ I had purchased, realizing they didn’t add much value to my life. The trappings of materialism some call it. When my car and apartment leases were up in 2016, I decided not to renew either, put what few things remained in storage, and committed to an alternative lifestyle of traveling full time.

How did you become a digital nomad?

I consider myself becoming a digital nomad in early 2017, when I was living in London and launched my own travel planning business. This was after I spent 9 months traveling through Europe, Canada, Hawaii, Australia, New Zealand, the South Pacific and Asia and I wanted to help other travelers plan unique, off-the-beaten path itineraries and share with them the local, authentic experiences I had on my trip. Once I returned to the US in late 2017, I began to consult for hotel and hospitality companies who were creating or adapting their products and services to the ‘next generation’ of travelers.

What's your favorite part of being a digital nomad?

I have three. I think being able to travel by yourself is a very humbling experience. It teaches you how humility and being vulnerable can make you a more open-minded, well rounded individual when you open yourself up to embrace new experiences, cultures, foods and languages. It teaches you to live deliberately and that the world is not a threatening place. Someone along the way told me to consider your mind being like a parachute – it’s best to keep it open. There are countless people I have met and places I have been in recent years that will be a part of me for the rest of my life. The second is the ability to continuously learn, and this lifestyle benefits me both personally and professionally, since I am constantly in the travel community with new people in new markets. This enables me to see innovative and emerging concepts and participate in new conversations all over the world, ultimately allowing me to bring new ideas to my clients. Lastly, I love the feeling of freedom it gives me, not being tied to one single place. It’s exciting and inspiring to have this type of independence for self-reflection and to feel like a Global Citizen. Needless to say, I feel blessed every day I am alive. A word of advice from me to others is to make your passion your profession. If your passion is there, the rest will follow.

Brenda Ma, Real Estate and Stock Market Investor

How did you start working remotely?

I started working remotely when I first wrote my first ebook when I was 16 years old. I had sold around 40,000 copies teaching people how to make money on the internet. I then invested all the money into real estate which are now rentals units. I also invested into the stock market. Both business ventures produces a stable residual income allowing me to travel whenever I want.

How did you become a digital nomad?

Being a digital nomad made sense for me because I love traveling, exploring new cultures and meeting new people. Staying in the same city where I grew up and watching all my friends live in their bubble made me realize that it’s not the life I wanted to live. I wanted to grow spiritually and mentally by living in different countries.  By doing that, I am constantly in a state of wonder while at the same time challenging myself to adapt to my new surroundings.

What's your favorite part of being a digital nomad?

My favorite part of being a digital nomad is freedom, independence, traveling to unique cities, new adventures and meeting interesting people from all walks of life.

Anais Tadlaoui, Head of Marketing

How did you start working remotely?

I joined a startup based in SF that already had a remote team spread out across Europe. I only ever met the CEO in person!

How did you become a digital nomad?

I started traveling for conferences and events for work, which happened to be a flight search app to Sao Paulo, Barcelona, Bali, etc. I stuck around after the conferences for a couple of weeks or months and continued to travel.


What's your favorite part of being a digital nomad?

It’s a lot of things that are all interconnected. It sounds cheesy but discovering new places, new cultures, new people and myself! Constantly being out of my comfort zone and learning to be comfortable with the unknown and uncertain, there's constant stimulus and growth - no stagnation. Learning to be hyper adaptable and flexible, making any place my home. Home is where I am, not where my things are –and with that, learning to be minimalistic and value experiences and people not things.

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