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What I’ve Learned From Three Years Being a Full Time Traveling Digital Nomad Entrepreneur

by | Apr 20, 2024

My digital nomad family of six has been traveling outside our passport country full-time for almost three years supported by our digital nomad entrepreneur endeavors as I write this. And we have no desire to stop anytime soon.

Quick Important Note

First, I struggled to create this list. Everything I kept listing had very little to do with the entrepreneurial side of our lifestyle. I kept listing things about my family. But, to honor the title of this post, I’m keeping my list to the business side of things. If you would like to hear about the family side of things, let me know.

My Biggest Lessons Learned as a Digital Nomad Entrepreneur

My Team is the Key

Hands down, my remote team has been the key to our success as a digital nomad family. My team currently lives in Bulgaria, El Salvador, India, the United States of America, Mexico, and wherever I happen to be. I have to hire VERY slowly.

The Biggest Change I Had to Make Was My Leadership Style

I used to be a “manage by walking around” leader. When we lived full-time in the States, I would see my team working, see the results of their effort, and could give feedback right on the spot. I detested meetings at all costs. But that style of leadership didn’t work well when I transitioned to a digital nomad lifestyle.

I tried having “digital” updates on projects, tried a variety of project tracking tools and systems. I even tried to keep our communication entirely asynchronous. But, finally, I had to conclude that, for me, we would have to have a system and rhythm of live meetings.

I now meet once a week on Zoom with each of my direct reports and require them to do the same with any direct reports they have. I also have a weekly leadership team meeting. And, we are currently instituting a weekly project tracking meeting.

Have a Coach or Be in a Mastermind with Other Digital Nomad Entrepreneurs

Being an entrepreneur and business owner is already isolating in itself if you aren’t careful. Add on full-time travel and an always-changing community, and it gets that much harder. I had to find a new community to be part of that stayed consistent when everything else was set up to be changing. I found that in my mastermind group of other digital entrepreneurs.

And, having a coach to bounce ideas off of, test theories, and for accountability has been one of the most valuable investments I continue to make for myself.

My Calendar Became The Most Important Productivity Tool I Have

I used to keep a rough idea of my schedule in my head and had a calendar for meetings. Now, mainly because of changing time zones and working across a multitude of time zones, having a calendar with everything on it is crucial for me. I calendar family time, planning time, personal time, chores, work projects, and meetings. I even schedule a weekly calendar review meeting for myself.

I Need an Office Space Even as a Digital Nomad

Some digital nomads can work in different coffee shops every day, and others like working in coworking spaces. I’ve tried these, but nothing has been as effective as having a small office in the Airbnb we rent to live in wherever we find ourselves in the world. I like being able to pop out and talk with my wife and kids. I like being available to them. I like eating meals with them. I like not having a commute. So, I do have to plan walks and workouts, but even those I like to do with my family. For me, ensuring our Airbnb has a dedicated office and great WiFi has emerged as my best digital nomad working environment.

People Assume We Are On Perpetual Vacation

As I write this, it’s Saturday morning. On Monday, we are flying to Colombia for a week for vacation. We are spending a year in Costa Rica for my wife to attend a Spanish language school.

This last week I mentioned to two clients, “I’ll be on vacation next week.” Both of them said something like, “You are going on a vacation? I thought your life was a vacation.”

It’s important to take breaks from your work. I take one day a week and do ZERO work. It’s typically Sunday for me. And, a few times a year, I take a vacation with my family. On vacation, I do no work. Other times, we take trips; on trips, I do still work.

All in all, this lifestyle is amazing! Getting to watch our kids discover who they are while exploring this vast world of ours has been significantly more rewarding than any time we spent living in our passport country. Don’t get me wrong. It’s not all sunshine and roses. It’s extremely hard to be away from family in our passport countries.