Workcation - Is the grass really greener?
Working When You Want, Where You Want – A Dream Come True Or a Nightmare In Disguise?
Working When You Want, Where You Want – A Dream Come True Or a Nightmare In Disguise?

I always enjoy a healthy debate and looking at issues from all sides. Today’s post is a counterpoint to an earlier post, “Be Prepared as Digital Natives Demand the 4 Hour Work Week Lifestyle“.  Special thanks to Amy Fowler of Boom Online Marketing for this guest post.

‘Remote working’ is a hot topic right now, and if you believed everything you heard, you’d be convinced that within five years, offices will have been resigned to history books,  and we’ll all be gallivanting around in some 21st Century hippie-come-techie lifestyle and working from wherever the hell we happen to be.

Yet I’m not sure this is realistic, or even desirable.

This didn’t come from nowhere; I was spurred on to write this after reading this fantastic post from Nichole Kelly.

When I started reading I thought: a four hour work week, yes please! Sounds perfect – you still do some work, your life still has that all-important purpose to it, and yet pretty much all your time is yours to do with what you want.


How many of us will ever be fortunate enough to live this way? Probably not many. And even if we did, I’m not sure the lifestyle would quite live up to the expectations.

Not that Nichole’s article was really about Timothy Ferriss’ extremely sensationalist book; I took Nichole’s article to be about the freedoms that modern technologies and progressive attitudes could offer us in the near future.

This isn’t about two hour-long working days spent lounged across the sofa in your favourite pyjama bottoms; this is about the freedom to work whenever we want, from wherever we want.

Nichole said,

“There is a wave of employees who want to be “free to move about the country” or better yet the world. We want to be able to travel and live in a perpetual workcation.”

Sounds fabulous doesn’t it? Forget stuffy offices and management peering over your shoulder every five minutes. Fancy working on a crisp white beach? Or In the window of a New York coffee shop? Well you could.

But I’m not convinced a permanent workcation is the utopia it initially appears to be. If we’re always on a workcation, where does our work end and where does the vacation begin? Will we ever manage a real holiday when we’re already, in a sense, on one?

For me, this blurs the lines between a work and life balance too much.  Even if you said to yourself, “right, I’m having a real week’s holiday – starting now”, do you really think you’d be able to stay away from work entirely, when you’d become so accustomed to working in the sun? Or that your clients and colleagues would ever be able to take your break entirely seriously, and not try to get in touch with you?


You’re always going to struggle, at least a little, to get in touch with your colleagues. Of course, modern technologies offer some great solutions:

“We meet virtually if we need to thanks to tools like Skype, GoToMeetingHD Faces, and Google Hang Outs.”

But these are never going to be as quick, easy, and straight-forward as leaning across your desk and talking to your colleague there and then. Not to mention the fact that Nichole is not only advocating flexibility in where you work from, but when you work.

“So if I’m not a morning person and decide I want to start work at 10 am and end at 6 pm, I will. But tomorrow if I decide to go visit the pyramids in Egypt and want to cut out at 2 pm I may start at 6 am.”

But what happens when the colleague you need to speak to has just signed off to go playing in pyramids or diving into the Great Barrier Reef?

Of course, you can always have:

““core hours” that require all employees to be available for certain times during the day while leaving the rest of the schedule up to the employee.”

But there are countless occasions where I need to talk to a colleague there and then, and if they’re not there, it can cause a massive set-back, and result in a task taking far longer than necessary. Core hours are a good idea, but to really be efficient, you need to be in easy reach of your colleagues as much as possible.

Not to mention the question that: is a workcation even financially viable?

Rent and mortgages are expensive. In most regions of the world, endless hotel stays are much more expensive.

Of course, you could always rent an apartment for a few months while you stayed put in one place, but if this is really a workcation, surely you’re not going to go out just on weekends? And save money by cooking most your meals at home? Making the most of your travels isn’t going to be cheap, so, unless you’re fortunate enough to earn an envy-inducing salary, how sustainable is a long-term workcation in reality?

I can’t help but think this is a bit of a case of ‘the grass is greener’

For those of us who work 9 ‘til 5, Monday to Friday, from the same office, the idea of all this freedom is without doubt, very appealing. Yet I can’t help but think that the reality might not quite live up to the dream.

Please don’t take this to think that I believe no flexibility in working hours or locations is the ideal; I think there are loads of benefits to offering leeway in working hours, and equipping staff with the apparatus needed to work from locations other than the office.

In fact, I’d like to think that I’m completely wrong. I’d love to go on a permanent workcation. I just can’t ever see it working in reality.

Please feel free to comment and tell me I’m wrong!


Amy Fowler is an online marketing executive at UK based digital marketing firm, Boom Online Marketing. Amy works within Boom’s SEO team and is also responsible for social media.

As well as regularly contributing to the Boom blog, Amy can be found on Twitter and Google Plus.

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About the Author

Nichole Kelly
Nichole Kelly is the CEO of Social Media Explorer|SME Digital. She is also the author of How to Measure Social Media. Her team helps companies figure out where social media fits and then helps execute the recommended strategy across the “right” mix of social media channels. Do you want to rock the awesome with your digital marketing strategy? Contact Nichole
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  • Good stuff, great post & I definitely agree.. it’s totally a “grass is greener” situation.

    Arguments for office:

    – Value of the face-to-face interaction & collaboration you get within an office (especially as the owner of an agency, I need that quick & high-touch environment). 
    The only way to 1-up the collaboration of an office is if technology found a way to emulate telepathy.

    – An office is a clear separation of work and life.

    – Everyone is on the same schedule.

    – Shared resources (internet, food, printer, etc..)

    Arguments for workcation:

    – It’s “cool” .. “I work when I want” -OR- “I don’t HAVE to work”

    – Talent .. don’t have to rely on the local market for talent, can source and recruit nationally or even internationally.

    At the end of the day, with the right rules and accountability in place, you might be able to have a company that allows for both types of employee.

  • I totally agree with you. As everything in this world has both advantages and disadvantages, similarly Workcation has it’s advantages as well as disadvantages. In my view, reaching targets will come into picture more as compared to when we work in office location.

  • I have been working remotely for the past 6 months. Setting boundaries between work and free time throughout the day has never really been an issue. Just like I would have planned my 2 weeks vacation if I had been working on a 9-to-5/Monday-to-Friday basis, I have been able to set specific times for work and leisure and to stick to that. 
    I do agree that it makes it a bit harder to keep in touch with your team though. In my opinion, such system requires an extra effort in terms of organization (“core hours” can be a good solution), but I do think this is really doable in the end, and above all it shouldn’t discourage us from developing this method. A perpetual “workcation” may not be sustainable, but I am convinced a more flexible workstyle would at least bring a lot in terms of productivity and fulfillment… and I hope more and more companies will open their minds about that in the coming years! 

  • Sylvain Briant

    I am in workcation because i manage people at 6000km from me or from HQ, and for the moment, business trip twice a month to HQ is enought for us.

  • It seems like we’re always pushing to just get one more thing done then we’ll take a break. It is lots more work and a lot less vacation most of the time.

    • Do you work remotely then Sheila? Why do you feel you’re always pushing to get one more thing done? Is this your employer or yourself that makes you work like that?

  • Betsy

    My husband and I are location independent. That doesn’t mean we travel constantly, just that we can when we want. We can also relocate someplace we’d really like to be on a more semi-permanent basis. You need to have the discipline to set boundaries if blurring work with life is a concern. We find that integrating work into the life we want to lead is much more achievable than the elusive “balance” everyone seems to chase.

  • As someone who worked remotely my entire career until just five days ago when I started a gig in corporate America, this really hit home. The flexibility of a virtual environment is wonderful, and, I do believe  very possible and efficient and likely a practice that will gain more acceptance in the future. What really hit me was Amy’s question about where work stops and life begins. This is, indeed, a very slippery slope and one that I know I’ve had very blurred, and one that (even in just four days of being in the office) that is becoming far more separate than it ever has been for me. 

    Technology is wonderful in that it gives us flexibility. We, as humans, however, need to be mindful that it doesn’t turn is into 24-hour workers, tethered to a device and a world that never turns off. 

    Great posts. Thanks for getting me thinking. 

    • Hi Kary, 

      Glad you liked the post and thank you for commenting (and confirming my fears!) :-)

      Even though it’s been only five days, based on your experience so far, which way of working do you think you prefer?

    • Kary – I agree the slippery slope of blurred work and family lines is indeed challenging. As we have to be diligent and have discipline to be successful in a workshifting environment, we also have to be diligent and have discipline to maintain balance. It’s something that does become a struggle, but I personally prefer that struggle to wasting two hours in my car each day commuting to a “corporate office”. ;-)

      Congrats on your new position! I can’t wait to hear about the awesome you create!

  • As the founder and head of a multimillion dollar company Ferris was all set for the 4 hour work week, everybody else keep on wishing and buying his book, he’ll probably cut it to 3 hours.

    • John – Thanks so much for commenting. When I read Tim’s book I was more inspired by the flexible lifestyle and ability to work from anywhere than the literal 4 hour work week that I know he practiced. The literal 4 hour work week is a stretch, I agree. But the ability to work from anywhere is totally achievable in my opinion. What do you think?

      •  Yes, virtual employees are completely viable it’s just a different set of variables. I read a recent study and can’t recall the source that said on average virtual employees are more productive because they tend to have better agreement as to what their goals and objectives are. It takes a lot more discipline than going into an office but there’s a lot more freedom. Management and goals must be better defined, but there’s opportunity for huge savings by reducing real estate expenses. I’ve been virtual for the past 2 years and I am more productive when not in the office. Politically you need to have some face time, but it’s easier to complete tasks and ship without the distractions in the office.

        • Is everyone more productive this way though? I’d bet that a lot of people aren’t. Surely this is another big problem with the idea that whole companies can operate remotely; they’ll have to be incredible careful with regards to who they employ.

          And, if remote working becomes the ‘norm’, where does that leave all the people who aren’t disciplined enough to work wherever and whenever?


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