The day I became a digital nomad

It started as a typical workday – my phone was ringing off the hook and my inbox was piling up as I juggled the workload of three different projects. “Konrad, I just emailed you the file. Can you take a look and let me know what you think?” they requested one after the other. Each client had their urgent fires to put out, and like a chef with three burners going, I had to balance them as equally important. Two were large companies and the other a private equity firm, each in the middle of their own respective deals. As always, there was a lot of money at stake for each company and time was of the essence. It was one of those days where my blood pressure was constantly elevated.

The back and forth communication lasted until late in the evening. I finally hit “send” on the last of the three analyses, I said “great work, team” from the conference line. We all signed off. The day’s stress was done. I poured a glass of wine and looked out the window. I don’t think I’ll be getting any fresh air for a while, I thought to myself. I was in my home office in Chicago, and the city was experiencing one of its worst blizzards in history. A nice beach in Australia, Thailand, or Spain sounded pretty good to me right now.

And then an idea hit me. After the myriad questions asked during this day full of phone calls — “take a look at this,” “what did you think about that,” “are you finished yet,” and “hey, I have a new idea” — some of them started out with the “how are you” pleasantries, but not one of them started with a key question: “Where are you right now?”

As long as I answered the phone and responded to the clients’ emails and instant messages, I could have been anywhere and no one would have had any idea or cared! If that was true, the bigger question was, “why the hell am I here, barricaded in my apartment, in the middle of one of the worst blizzards in Chicago’s history?”

It was probably the wine, but I made myself actually answer that question. It’s a big world out there and damn it, I wanted to explore it. I did not want to keep the same scenery for the next five years. It was markets and mountains that I dreamed of, not spreadsheets and boardrooms. The decision was made. I spun the proverbial globe and decided to make my way up the eastern coast of Africa. Armed with my laptop and a Wi-Fi hotspot, adventure was calling. This was my chance!

Okay, the decision was not actually made. I quickly snapped back to reality. I had a job. I had employees. I had responsibilities. I wasn’t a writer, a freelance designer, customer service rep, or any other profession that is typically thought of as suitable for “remote work.” I was helping companies with acquisitions that were often worth hundreds of millions of dollars. There is no way they would go for this.

I vacillated between by reality and fantasy before asking myself the obvious questions: What am I really afraid of? What is the worst that could happen? I knew the potential upside was limitless, but I needed to assess the potential downside scenario. My clients would maybe think I was crazy and pull the plug on our contracts, therefore losing all sources of income. I would burn through my savings and eventually need to return to the States, head hung low from miscalculated hubris, admitting that my traveling venture was a bust. I would need to crash on a friend’s couch until I managed to pick up the pieces to generate business income again or find a new job.

This seemed like the probable outcome, but was it that bad? On my deathbed, would I worry more about a few months of turmoil in my career and bank account, or would I regret never pursuing the adventures I always dreamed of? If I did not do it now, what were the chances I would do it later after getting married, having kids, and attaining even more professional responsibility?

I decided to just go for it. I concluded that it would be better to regret doing it than living with the regret of not doing it.

It’s been nearly a decade since I made that initial decision and I’ve visited approximately 100 countries. I’ve held various jobs, started multiple companies, and returned to the States for short stints. I’ve continued to both travel and advance my career. I generated seven figures in consulting revenue. I raised $6m as the COO of a startup, got the company acquired, and launched TripScout, a company that further fuels (and is fueled by) my passion for travel. I’ve worked from beautiful beaches, countries in the midst of civil war, sophisticated urban centers, and rural mountain villages. I’ve done it as an entrepreneur, an employee, and a consultant.

Since becoming a digital nomad, I have learned a lot about myself and the world. The coffee has been better, I rarely have had a commute, and most importantly, I am happy. I got married, had my first child, and made many friends. I only list these accomplishments to demonstrate how this lifestyle was not about sacrificing my career or finding the one perfect job. It has been a fluid process of pursuing meaningful work with real income, while simultaneously living the life I want – where I want.

I have seen the personal and productivity benefits in my life, so I built this digital nomad culture into the DNA of TripScout. TripScout team members live across the globe — from Washington, DC and New York City to Cairo, Sydney, and Saigon — and while everyone’s situation is different, we make our situation work. Together as a team, we collaborated on a book – How to Become a Digital Nomad – to show you everything you need to know to make the digital nomad lifestyle work for you… and to live a life that you don’t need a vacation from.

Get How to Become a Digital Nomad on Amazon here:

How to Become a Digital Nomad is a practical, step-by-step guide to living a location independent, digital nomad lifestyle – regardless of your career – while making money and doing the work you love.


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The day I became a digital nomad