Thinking of a Digital Lifestyle? Is this the time?

Where would you consider ‘pitching your wigwam’ for one month, several months, or perhaps years if you do choose to take the plunge and opt for a digital lifestyle?

In a couple of previous lockdown blogs I considered the reasons why a digital lifestyle might become a part of the new normal rather than the exception. Let\’s now discuss some of the location options in a post-Covid19 world.

Whether it\’s moving your current professional activities away from the hum drum of corporate life, or you have unfortunately been relieved of your corporate livelihood altogether due to circumstance or changing technologies, you may now need to strike out on and seek your fortune, follow your dharma or whatever.


Never fear, there are many options available and just several basic considerations that many fail to address adequately ahead of departure and fall foul of local or home authorities, or worse, their own families.

Photo by Raphael Koh on Unsplash

The beginnings of a digital career

As I write in my garden on a sunny Monday afternoon, Europe is is various levels of lockdown. We can only hope this whose situation is temporary until vaccines or treatments arrive on the market. In the meantime, everywhere, we face a new world of masks, social distancing, government by social media and a level of social control hitherto unheard of.

From my vantage point, sitting in the west of Ireland under the main air corridor from Europe to the Americas, I can gauge the health of the world generally. And, it\’s not good – I am lucky if I see a dozen flights a day whereas under the old ‘normal’ you should see the vapour trails from up to twenty aircraft on a fairly consistent basis throughout the day. For now, at least, we just have to sit and enjoy the clear blue skies, wind-blown clouds and envy the freedom of migrating seabirds seeking easy pickings on empty beaches.

My own accidental retirement started a couple of years ago. After three decades in the oilfield, and three market crashes in my career, I traded ‘voluntary redundancy’ into a depressed consultancy market. This led to a re-invention in renewable energy, not a million miles from what I had before. I now believe that I should have moved further quicker and moved to the digital marketing space – definitely on the right track now!

In the interim I have acquired a mixed bag of new skills as a travel photographer, online copywriter / marketer. More importantly I have taken responsibility from the great corporate gods and taken control of my future, which I hope will see me through and to time, geographical and in time freedom.

Maybe my previous comments sound somewhat familiar to you?

Given the recent upheavals around the world, a dodgy economy, a murky outlook for our health in the near future, and various other calamities that might cause us to re-trim our sails, it would be prudent to consider where we might indeed like to move to … even if everything else in your control goes swimmingly.

I have been fortunate enough to have lived around the world in several locations over my career, since I was nineteen actually, so I have been blessed from that point of view. The one thing I can say is that despite the press, there are no really bad places, everywhere has good points, and the people themselves tend to be pretty decent trustworthy bunch generally. It just seems to be the leadership and their minions, non-inclusive politics and poor education that causes confusion, conflicted ambitions and indeed conflict in the majority of \’problem areas\’, but that is another story …

Let\’s talk a little bit about the \”where\” in the story.

If you think choosing your destination for an annual holiday is interesting, just wait until you are in a discussion with the family or significant others as to where you would like to spend your next three, six or twelve months – even assuming you are still talking when you advise them that you are finally going to abandon your career in favour of a nomadic digital lifestyle!

That is where “the rubber meets the road” as they say. The question of a long term destination in which to base your business and future life is a vast topic that could take more than several blogs to even outline.

There are a few headline items to be considered on a checklist basis. This list is not in a particular sequence but should be ordered and weighted based on your particular circumstances such as your health, wealth and lifestyle aspirations over the coming years and decades.


As you begin to look for your dream location from which you will deliver value in whatever form you chose to your international audience would be as follows whether you are looking at Europe, the Americas, Asia or wherever:

Photo by JESHOOTS.COM on Unsplash

The main variables

  • Climate – goes without saying.
  • Cost of Living and Taxation – critical in your consideration and depends on your current income (exchange rates), social security or government sponsored income situation and whether you can collect your pension savings, imported goods costs, travel all add up. Count your tax days
  • Activities and Recreation – whether you are one for coastal living, sport (golf or skiing) or the arts as you leisure preference, you will need to look at your destination critically in terms of cost and access. There is little point in moving to an area with lovely golf courses (from the air anyway), waiting lists of five years and exorbitant membership and green fees that would break the bank!
  • Banking and Infrastructure – Not as much an issue across Europe or the US, but you need to be sure that you can move your funds from your home country on a regular basis and ensure that your banking facilities can also accommodate your side-hustle, without undue stress. Local IT infrastructure must support your chosen path, so be sure to verify and physically check these points before you commit to a long term residence.
  • Safety and Security – Your location will need to be fairly secure and your residence and lifestyle will need to be sustainable.
  • Medical Care – whether public or private, access and insurance and whether you own extended international medical insurance covers you for all eventualities, or whether you need to return home periodically will affect your planning.
  • Home Visits – whether you are currently away from home, or you leave close family behind, family visits are always a consideration whether others need additional care or not, local facilities, transport all need consideration.

Finally, in closing …

I just want to touch on some of the opportunities that are beginning to appear as the world adapts to pandemic living and what I consider an unstoppable trend towards remote working.

When you have a preliminary list of possible destinations, it would be worth looking at the incentives that several countries are beginning to roll out to encourage people to visit for longer and help rejuvenate their own economies.

These can begin with a wide range in marketing approaches from cheaper extended return flights, accommodation incentives, tax breaks and at the top end of the scale in places like Panama where they have full retirement planning and discounting across the board for those who chose an early retirement in that country.

I have found that over the years, the best way to assess an area is to go there on a package vacation, and if you like it, extend the flight home as far out as you can and just get to setting up your housing once you have had that few weeks to assess the area and its quirks and foibles … and believe me, every country has them!!!

And that’s where I will leave you for now – more to follow … I would love to hear your comments below or if you wish to get more informations, please pass on your email for updates and occasional newsletters.

And meanwhile, for more on building your own digital lifestyle:


Jim Houlihan

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