Going Freelance, Going Digital

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A very insightful and honest piece about being your own boss online from Tom Kuegler (@tomkuegler7) called “4 Harsh Realities Of Working As a Full-Time Digital Nomad.”

While Mr. Kuegler jokes about living it up on beaches as he downs Mai Tais and finishes his next job on a laptop computer, his beach chair sinking comfortably into the white sand of a pristine beach, I’ve actually been that guy – and let me tell you something, it’s not all it’s cracked up to be.

From 2007 to 2009, I spent two years traveling the world. For the 24 months I was crisscrossing continents, I worked full time as a freelance writer, editor and translator. I did in fact work on beaches in Fiji, Australia, Vietnam, Spain and Bulgaria, to name but a few beautiful places. I raced up and down Venetian bridges trying to find a WiFi signal; leaned my computer out windows in Kampala in search of the same thing; hung out in Bohemian cafes in Prague, Lisbon and London; and worked in more airports than I care to remember.

The lessons I learned? 1) “There” is no better than “here.” 2) Working on the road is stressful. 3) Italy is stuck in the Middle Ages when it comes to technology. (P.S. Rome, stop losing everybody’s luggage!)

I’m now grounded and settled in Toronto, and while I have yet to purchase my dream pad (Come on, lottery numbers!), I’m much more productive working in one spot.

Per Mr. Kuegler’s piece, however, the four realities he refers to are:

1. It’s Not Going To Happen All At Once

2. There’s No Real “Road Map” To Success

3. The Timing Is Never Right —You Just Have To Jump

4. You Have To Really Want It — Or Else You’ll Fail

True dat. But where there’s a will, there’s a way,  I’m told. And there is. If going it alone is what you really want and you think you can handle the new pressures and challenges, by all means take the plunge. Although there are countless pitfalls to deal with along the way, the reality of this reality is simply that working remotely – being a digital nomad as it were – represents the future for so many of us. Doubly so if you dislike set hours in the same office, day in and day out, 52 weeks a year.


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