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Making work holidays “work” for the digital nomad

Making work holidays “work” for the digital nomad

I believe that you are either born with the remote gene or you’re not.  Some people need the structure of a workplace and others (like me) thrive with unstructured time.  Every digital nomad has their way of making it work.  For me, its the work holiday.  When I tell people I am going on a work holiday,  I frequently hear “good luck working there!”  Yet, work, I certainly do!

Let me explain my system.

Perhaps not an industry term, a work holiday is a ritual I developed when I was first completing University.  The premise is you go on vacation utterly alone, exclusively to work.   I recognize that this is absolutely a luxury, however I’m personally willing to invest the money to spend a week of utterly productive time.  Without the distractions of home, I can literally clear my entire plate.  I now take a work holiday every few months, typically when I have the most due. I always come home having completed everything and feeling infinitely more relaxed.  Also, as someone who lives in a winter climate (Canada), going South lifts my spirits significantly, regardless of whether I’m going on holiday to work.

If you like this idea, I highly suggest you give it a try!  Here are some tips to make your work holiday a success:

1.  Go somewhere you will be alone, fully alone.  

Being alone really helps build your creative thought processes.  You’ll probably need Wifi to work (so you wont truly be alone), but try your best to get off the grid a bit.  Lack of conversation leads me to think a lot more and this is  helpful in producing extra creative work and with making big life decisions too.

2.  Be chore free

Create a situation where you don’t have all the annoying chores of home.  I never realize how much my life asks of me until I go away alone.  I don’t have to walk the dog, cook, clean up, commute, look for parking…  I’m free to just lie by the pool and work with my laptop.  This probably gives me at least 4 extra productive hours per day.

3.  Set goals for the work holiday and a schedule 

Either you have deliverables due, or set a schedule for yourself – just as you would at home.  The main difference is that producing these deliverables is much more pleasant.  During my Undergrad, I would wake up at 6am, go on the balcony and type until 10am.  Head down to the pool, highlight in the sun until noon and then relax.  In the evening I would start writing my paper.  The result: four quality 35 page papers, researched and written in 8 days.

4.  Get that busy work done

A work holiday is an ideal time to clear your plate of busy work.  Despite the fact that this week is spent doing a lot of work, the fact that you are somewhere else still has a huge impact on your spirits.  Removing oneself from ones regular routine also makes the busywork seem somehow less annoying.

5.  Find a balance

A lot of people may be reading this post and feeling that work and holiday are mutually exclusive.  I don’t feel that way.  I do take legitimate holidays, but taking work holidays still allows me to have fun and relax.  In fact, I can justify traveling a lot more because I am so productive when I’m away.  Trust me, work is still work, but it somehow feels far less onerous when you are doing it from the beach.


Does anyone else take work holidays?  If so I’d love to hear where you go and what you do!  If not, I’d love to know how you “make it work” as a digital nomad.  Comments are very welcome.