Are you ready to be an Outlier?

Our Home in Sunriver, OR

We love to work outside whenever possible (laptop just outside the shot!)


There are a load of people in the world who would love to fit work around their travel lifestyle.

Most of them won’t ever achieve that. Some of us do.

So what’s the difference?

In this post I’m going to borrow shamelessly from Malcolm Gladwell’s fascinating book ‘Outliers’ which I stumbled upon amongst the crowded shelves in our latest home exchange pad. It leapt out at me a few days after hearing Chris Brogan reference a quote on stage at a conference which he couldn’t remember the origins of; 300 people chimed in, in unison, with the credit. That’s enough of a recommendation for me.

Those of us who call ourselves digital nomads, location independents, travel bloggers, or whatever other term is currently used, are outliers. We exist outside of the norm. Is it because we are special? Lucky? Just plain annoying? What’s the secret? Let’s dispel some myths.

  • ‘Opportunity is all very well if it comes your way’

    There is an opportunity that exists at the moment for all of us. It’s called the internet. There is no way Chris and I would be able to live as we do if the internet hadn’t exploded into the mainstream at just the right time. When I got my first job I used paper and pen. When I got my second job I was shown to my cubicle which housed a grey, chunky and ominous PC. I wasn’t sure how to turn it on and that was only 10 years ago.

    For me, opportunities have taken the form of a husband who is a techie geek. A job which no one had done before in the public sector which trained me to spot a massive gap in the market. In Oregon where we are currently based there seems to be something in the water that breeds a disproportionate number of inspiring, entrepreneurial freedom seekers. Your opportunities will take all sorts of different forms, from a hobby that is developing freakish popularity or contacts who can pull you along on their coat tails until you have found your feet. Your chances might not look like anyone else’s, but they will be there.


    work life balance

    Do you have the right work/ life/ family balance?


  • ‘Don’t work hard work smart’

    Location independent types are pretty good at making our lifestyle look like a breeze. Stick up a few photos of an office on a beach and no one is going to actually think you do any work. But the truth is it takes a lot of hours. Do you really think that a lifestyle this awesome is going to land in your lap?! Take the guys who hang out in south East Asia. They may specialise in jaw dropping scenery shots and the appearance of living like playboys but you’ll also find some of the hardest workers we’ve met. In Thailand you can spend 50 hours a week scowling at your laptop and still look like you’re on permanent vacation.

    Getting to the position where we can work where we like and wander the globe at will didn’t take too long, but honing it to a fine art, where we can travel efficiently and work part time hours did. Of course ‘work smart’ is great advice- but I’m just saying that you won’t find too many successful lifestyle-changers being afraid of hard work either. As our neighbour here in Oregon says, when you are retired every day is a Saturday. By that logic, when you are location independent most days kind of feel like a half day Friday.


  • ‘Easy for them, they are naturally gifted’

    As appealing as it is to think that our current successes are a result of god given talents, the truth is there are things which come easy and others which are more of a struggle. Of course it helps if you are naturally quite creative and entrepreneurial. But most skills can be learnt (or outsourced) if your natural predispositions lie elsewhere. There is not a ‘digital nomad’ gene. See points one and two. If you have particular skills, don’t expect them to flower naturally. You need to nurture them, practice, be guided by people better than you to let them develop. Then you need to use them in pursuit of your goals


    Living the dream with a snow cone

    Chris living his dream- that’s right it’s a snowcone!


  • ‘Not everyone can be different..’

    One of the most captivating chapters in the book was about the influence of cultural norms in plane crashes (they’ve fixed that problem now, don’t worry). When you have a co-pilot socially programmed not to question authority and a pilot who is tired/ hungry/ stubborn or otherwise a bit below par, you have a problem. We also exist within societal norms. Many of us have grown up believing the same as the generation before; we’ll be offered a job, climb the career ladder, get a mortgage, look forward to a comfortable retirement. So we all conform, accept our responsibilities and live like a grownup – always looking forward to the weekend. It’s up to us to break those cultural constraints ourselves. We don’t have to wait for someone else to give us a job, we can create our own. We still have an important role to play even if it doesn’t involve the slow attrition of back to back meetings and 6am starts. We don’t have to put our real dreams on mute all year round so we can be happy for just two weeks in the sun. If co-pilots can be trained to speak up, surely we can all learn that it’s ok to live a little.

Do you think a more flexible lifestyle will find a place in the mainstream?

Or would you prefer to remain an outlier?


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3 Responses to “Are you ready to be an Outlier?”

  1. Great Post! I love that you highlighted the fact that you can’t be a digital nomad without loving hard work! We always mention to people who think we are vacationing for a year+ how much work we have been getting done. It is frustrating at times, but we know that the work is enabling us to design our own lifestyle and live as outliers :)

    • You are not alone Caroline, am pretty sure that all our family at home think we are on holiday right now! The parting comment whenever we speak to them on the phone is ‘well I am glad you are having a good holiday!’

      • Hannah and Chris
      • Reply
  2. My husband and I are striving for fully-sustainable location independence. We fund our live-aboard sailing lifestyle in the Caribbean mostly through savings, a few contract jobs throughout the year. But, he just finished composing the entire score for a video game right on our boat! We’re looking forward to more stuff like that in the coming years (whether on land or at sea!).


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