Life as a Digital Gypsy

Over the past couple of years my wife and I have been experimenting with a form of lifestyle design that I've nicknamed 'Digital Gypsy'.  For us, being Digital Gypsies means we now divide our time between Italy, the UK and North America and have a number of businesses, some of which run on auto-pilot, that generate enough income to allow us to make it all possible.  Digital Gypsies are part of a wider trend that also includes digital nomads and those individuals and families who are by choice location independent.  We are a motley crew that consists of writers, web designers, entrepreneurs, designers, musicians and many other knowledge workers.  What we all have in common is that we use technology, new ways of working, entrepreneurial spirit and minimalism to create a lifestyle that maximizes personal freedom.  In this blog post I wanted to let you into the lifestyle of a Digital Gypsy.

Well first we should start with some definitions. A Digital Gypsy is someone who meets three criteria:

  1. They have a nomadic and unconventional lifestyle.
  2. They move from place to place as a family or tribe.
  3. They utilize new technology to design a lifestyle that allows them to live and work wherever they want.

Digital Gypsy's are different from Digital Nomad's in that Digital Gypsy's travel as a couple, family or tribe whereas a Digital Nomad will normally be an individual who travels alone if indeed they travel much at all. Both groups use new technologies like smartphones, wifi and web-based apps to live and work from anywhere in the world and collaborate remotely with teams anywhere in the world.

My great grandmothers family

My ancestors were Romany Gypsies but being a Digital Gypsy is more a frame of mind than genealogy.  Gypsy's are a nomadic people, originally from Northern India who gradually moved West in search of greater opportunities for themselves and their tribes. Well known Gypsies include Charlie Chaplin, Michael Caine, John Bunyan and Elvis Presley (yes that last one surprised me too).  Gypsies put a high value on honor, work, culture, family, freedom of lifestyle and are natural entrepreneurs.  As a nomadic people they move to where the work and opportunities are and shun traditional home ownership, debt and possessions which reduce their mobility.

There are a couple of trends which are part of the rise of the Digital Gypsy:

Mobile Technology
Devices like laptops, iPad's and iPhones and technology like Skype and Cloud Computing allow anyone to stay in communication and work from anywhere in the world.  I'm writing this from a cafe in Italy with my morning espresso and later on I'll be emailing work colleagues in San Francisco and speaking to customers in the UK via Skype.  For the price of a laptop, a local data roaming plan, a Skype headset and a couple of free services like Dropbox and Google Apps I've unchained myself from having to go into an office if I don't want to.  I also know a young father and engineer who uses mobile technology to allow him to travel with his partner and young children, a project manager who manages an international team while indulging in her love for learning yoga around the world and a musician who runs his entire career on his laptop and cell phone.

Retirement is a worst case scenario
For myself and many of the Digital Gypsies and Nomads the idea of working until you're 65, retiring and spending your remaining years playing golf or whatever is a worst case scenario.  Instead Digital Gypsies talk about the idea of mini-retirements, where you work for 5-10 years, take a year or so off to re-skill and recharge before moving onto the next chapter in your career.  Most people realize the idea of working for one company or even in one industry all your life is something of the past.  Certainly for my generation (mid 30's and European) we know that we'll be lucky to see much of a state pension on reaching retirement age and therefore have to have a Plan B.  Last week I spent the day with an Australian couple in their 50's who are actually in the middle of a mini-retirement. Both have spent the past couple of years working and saving and felt it was time for a change.  They are half way through a 12month world tour and I think at last count they have visited ten countries with another six to go.  They have a daily budget of $50 (around £30) each for their world tour and are only paying for three nights accommodation over twelve months because they are using HomeExchange to get free accommodation in everywhere from swanky London apartments to Italian villa's.  So by the end of the year they would have spent around $18,000 each from their savings, lived like royalty around the world, met lots of interesting people and have the energy and ideas to start a new chapter in their work and personal lives.  I'm not saying that we should work at our current tempo for the rest of our lives and especially if you are currently involved in physical work this is unlikely to be an option.  However as general health and life expectancy improves we should consider working longer even if that is part time.

New Work Patterns
More companies than ever before are happy to allow their staff to telework from outside the office as long as they deliver the results.  The reason is that it allows the company to reduce office overheads and they actually find they get better productivity and commitment from those employees that are given greater control. Yes, for many companies having their staff telework is not viable due to the requirements of a particular job.  However many employees could work from a location that isn't the office even for part of the week.  Consider all those carbon miles saved with employees driving back and forth to the office not to mention the wasted minutes and hours stuck in traffic jams!

I'm a big fan of using outsourced labour if it saves money and/or time. I've used online outsource markets like Elance and ODesk to do everything from market research and online marketing to getting me cheap deals on flights. Most recently I had some competitor research work carried out by someone in Canada who liked outsourcing because it allowed her to combine making a living with the flexibility needed in looking after her elderly mother.  It has only been since the last 100 years that in the West we moved away from work being done by independent workers and craftspeople to an employee culture.  Today if I'm looking to hire someone to do a piece of work sites like Elance means that a one man or one woman business in Toronto is competing on relatively equal terms with a larger business in Paris or London.

To be a Digital Gypsy is to be entrepreneurial and to create a number of businesses and work (Booty in the Romani language) that generate residual income for you and your family.  These don't need to be the kinds of businesses that make you a millionaire but ones that create an income required for your desired quality of life.  The ideal booty is one that puts money in your bank account when you are asleep.  The kind of booty that once up and running no longer requires your day-to-day input therefore allowing you to get on with your other interests.


Gypsies are able to stay mobile because they reduce their possessions to the absolute minimum.  Digital Gypsies follow writers like Leo Babauta of Zen Habits, Colin Wright of Exile Lifestyle, and Everett Bogue of Far Beyond the Stars who look to reduce ones possessions to under 100 items.

Digital Gypsy Recommended Reading

Four Hour Work Week by Tim Ferriss
Vagabonding by Rolf Potts

Digital Gypsy Tools

Google Docs

In Conclusion

Being a Digital Gypsy is not for everyone and I am well aware I'm writing this from the perspective of a middle class professional living in a first world country.  Perhaps at some point I will grow tired of the travelling and follow the path of many Gypsies who have given up their nomadic lifestyle for an apartment and a more conventional home life.  Until that time my wife and I are enjoying the freedom this way of living gives us, experiencing new things and meeting interesting people.

It would be great to get your thoughts on what being a Digital Gypsy could mean so feel free to comment here.

Digital Gypsy office
Digital Gypsy office

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