What I wish I knew before Digital Nomading

Amman Waseem
6 min readNov 14, 2022

All of your digital nomad dreams are about to come true.

You’ve secured a remote job or business, the flight is booked, your accommodations are ready for a WFH lifestyle, and the friends you’ve au revoir-ed are excited to visit your new home.

Before you run off on your beautiful new adventure, I want to share a few lessons I’ve learned chasing wanderlust the last 3 years on my Nomading journey. I stumbled into the lifestyle after being offered a remote role 8 months before COVID & its provided a life that I never would have imagined, filled with surprises & sacrifices.

This article, I hope, will help you take advantage of the surprises and manage the sacrifices to the best of your ability.

How to take advantage of Remote Nomading:

1. Slow Down your Pace

It’s no secret remote work will allow you to experience the joy of being in a foreign place — you’ll undoubtedly go to the top spots in town & the attractions seen on social media. However, with your extended amount of time, there is the unique opportunity to take advantage of the slow pace of travel unique to your situation.

Instead of hitting all the tourist sites, back-to-back, in an exhausting 4 day vacation, you’ve got something extremely valuable — time.

Use the longevity of your stay to engage in a longer-term travel experience unique to your location. Depending on the location — the beach, a lively town square, a small cabin in the mountains — you can join the surfing school, take language-courses at a in-person language center, or spend days hiking a harder trail.

The point here is instead of run & gun dopamine hits, you embrace the compounding experiences of travel that carry weight. These experiences not only contribute to the local economy, but also will provide you with community, a deeper connection to your destination, and a skill to take everywhere you go.

2. Understand the bounds of your freedom

After commuting to the office & being stuck in the 9–5 grind, being given the power to work remotely pulls you out of the matrix. You realize how you are truly spending your time. Days no longer go by so fast that you have no idea whats happened when you reset your Monday morning alarm. You get to reflect, pause, and be intentional about your work/life balance.

Secondly, if you work remotely in different cities you begin to understand the economics of a new daily lifestyle & how it defers from home. Working from NYC vs working from Medellin will give you different lifestyle opportunities as you debate a $7 vs a $2 cortado. Explorations while swinging from one side of the economic pendulum to the other have revealed what truly matters to me & what commercial behaviors I engage in because everyones doing it.

Take the time to understand your financial habits & create space for the purchases that have the highest return. The money dials concept by Ramit Sethi has been an incredible orienter during my time abroad.

3. Strangers are friends in strange lands

If a good friend is like a mirror, then the friends you make while traveling are a carnival house where you distort, stretch, change shapes, and come out on the other side with a new perspective on yourself and your environment.

I was fortunate enough to travel with a group during the middle half of my nomading journey and I can still honestly say it was the best part of my travels. The novelty of any place, no matter how special, wears off like a mirage. However, the people who color its walls never do.

Making an effort to be open to different viewpoints and most importantly, keeping up special relationships will consistently provide you with perspective. Good people will lead you to travels in other parts of the world that you never imagined. Take the opportunity to pick the brains of those you meet randomly in strange hostels. The strangest characters have the best stories to tell.

The Costs of Remote Nomading

1. You miss out on deeper relationships

I began to land in old destinations & miss the people I had been there with. I began to travel to new destinations alone for short periods of time and make great relationships, but they were fleeting.

It’s not just about traveling with others on your nomading journey, but also about up-keeping relationships from back home and those you cherish. Getting lost in the sauce of every new attraction will lead you chasing for more, without realizing that you could have used less but better — A place where you belong, a community you belong to, and friends that have been there since day 1. Never forget the Day 1s.

There is no doubt magic in the random connections that you will make, but also a different type of serenity in the relationships that compound and provide a sense of connection.

2. There’s always a better hand-squeezed, all-natural, orange juice cart

Although remote nomading can be slow travel, it’s still filled with FOMO. You will inevitably feel a sense of guilt in every city for not going to all the “best” spots , trying “the best orange juice”, finding “the best coffee”, and not visiting “the most insane restaurant”.

I’ll let you in on a little secret. Theres always another most insane restaurant that no one can ever get a reservation at. Theres always another amazing ice cream shop thats the best in the world. Always a better orange juice cart that you should have tried. In every city, there will always be more.

My solution has been to use my own values as a mental model instead of falling into the siren calls of FOMO — I don’t really care that much about orange juice so I’ll skip. It helps to cut down on the guilt and the time spent doing things that you probably wont remember a few months from now. Don’t forget about the things you actually care about — the relationships, the spots you truly want to visit, or about passion projects — that get pushed aside for the best orange juice place in the world.

3. Exploration vs Building

Remote work has given me plenty of opportunities & lots of freedom, but with this freedom comes a responsibility to use it wisely. Travel is about different things to different people but one thing for certain is that you are not at a unique advantage in your foreign destination.

Living in a place for 1 year vs 1 month has distinct advantages depending on what your objective is. Exploration is great but also being able to know that one late-night corner shop guy, the room that you can make your own, the secret spot by the lake has it’s own benefits — one that can only be reaped from the amount of time you spend in one place.

Making things yours in your own space vs exploring things belonging to other people have two very separate joys. Both have their own brilliance and I think at different points of your life have different advantages. The important part is not to forget that there is a cost to whichever path you choose.

A time & a place & a person

Regardless of the costs and the advantages, I’ll still be returning to the nomad road at different stages of life. As a nomad, sometimes you can feel that you belong no where & everywhere. This is both dangerous & a blessing. Once you go down this road, know that this could also be the case for you depending on your experiences. However, you’ll definitely grow grow feathers in your wings, neurons in your brain, and feelings in your feels for the places that have changed you as a person. I’ll leave it to you to decide, and I hope this journey will grow you & lead to more freedom.

Cheers,

Amman

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Amman Waseem

First-Generation South-Asian Kid, Storyteller-at-heart, Digital slomad — creating for clarity, building for freedom.