Workcation on your Mind? But WTH is Workcation- A Complete Guide!

The Easy Wisdom Media
9 min readJul 11, 2020

What the hell is workcation? I assumed workcation to be a common phenomenon in the corporate world, but it turns out that only a very few are aware of it. As a business professional, I have been workcation and logging in remotely from vacation destinations for so many years and strongly believe that working vacations are the next ‘wave of future’.

Also Read: Are you Ready for Work from Home? 5 Work From Home Tips that will make you productive

As the concept of remote work and work from home is picking up real fast in this new pandemic world, work-life balance is going for a toss. Workation is an answer to this ongoing struggle to create a barrier between work and life, by combining them. Instead of taking actual time off from the work (no e-mails, no-con calls), employees who want to holiday without burning a hole in their vacation days are increasingly opting for working on the road. The idea is to unwind from daily rigmarole, and travel without compromising much on work.

Also Read: When Work from Home is No Longer a Perk — Mental Health Challenges of Working from Home

So, what is workcation all about?

As the name implies work plus vacation is workcation. It is a new concept fast picking up in many new-age companies and startups which are looking for feasible ways to promote the concept of work-life balance by balancing and combining holiday time with remote work in a never-ending ordeal to retain the talent. These are working vacations by design. This trend from Silicon Valley is an evolution of work from home concept.

With connectivity easily available across the globe, remote work is practically possible from anywhere from the world helping you turn into digital nomads. In past days remote work was available only to freelancers, but now full-time employees and business owners are opting for workcation breaks as a chance to swap office workstations & bounty retreats.

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A workcation is always temporary and the workcationers are required to go back to the office or to their home after the workcation is over and this duration and work-vacation ratio depends on the agreement between the employer and the employee.

Is Workcation actually happening?

New-age companies and startups are increasingly offering innovative services like creche services, leave pool policy, adoption leaves to increase productivity, and check retrenchment. The latest offering in the kitty for the employees is the new ‘workcation’ policy- where the employees can vacation any time of the year provided, they clock in for some hours every day and mandatorily report to the respective Manager at least once a day.

Companies are doing?

Startups and other high-pressure role companies are already offering Workcations to its employees with many of its employees logging in from beaches in Goa or hilly trails in Manali:

Workcation Requirements or Rules

1. Choosing a place with seamless connectivity

Companies are offering workcations in locations that are domestic as opposed to foreign locations owing time zones consistency, and good connectivity options like wifi, cellular data network & VPN to log into the system.

2. Connecting with the Reporting Manager

The companies require all the workcationers to report to the reporting manager on a daily basis at a set time and complete the assigned work.

3. Provide Weekly or Daily Updates

This is an obvious requirement which calls for workcationers to provide daily or weekly reports & updates as mandated by their Manager as per the work requirements.

4. Daily Minimum Logging In requirements

Companies require the staff on workcation to login from the system for a minimum prescribed time daily of 4–5 hours or as per the agreed metrics.

Benefits of Workcations:

1. Improves Employee productivity and morale

Every time you have a productivity crisis, you can go for yoga near the beach or choose to take a walk by the palm trees, or just let the ocean fiddle with your feet. And then you are back to your laptop by the poolside sipping Pina-colada and suddenly find yourself full of energy and rediscover the lost productivity.

2. A perfect talent retention initiative for corporates

Experts call workcation as a Talent Insurance Policy — insurance against losing top talents and high cost of new hiring as it eases out employee performance pressure to a great extent and gives more reasons for the talent to stick with the company.

3. Helps bring fresh and new ideas

Many companies are of the opinion that such a practice helps the workcationers to rejuvenate and return with fresh ideas as it can lower stress without going on an actual vacation This is crucial for startups and creative companies as they constantly need out-of-the-box thinking.

4. Best way to reward success

Employees will save on money by saving on precious vacation days and not have those days counted against vacation time. They can travel to their favorite destination, spend time with family and friends in the evening whom they don’t get to see a lot, visit their favorite tourists’ spots over the weekends, and still get paid. This is one of the most innovative compensation and benefits strategies worthy of consideration by corporate HR.

5. Keeps the workcation staff connected to work

It helps employees avoid the stress of being disconnected from work when on normal vacations and helps them readjust easily to normal work life post workcation.

6. A good team-building exercise

It offers an effective platform for team-building exercises if several employees from the same company do a workcation together.

Concerns with Workcations

There are some concerns and fears associated with workcations:

  1. What if workcation becomes a real vacation as you are easily distracted and are busy the whole day with sight-seeing. What if you are not really productive as your brain is not consciously attending to the con call conversations. Think about work first and stay productive. Workcation shall not be taken in lieu of an actual vacation.
  2. What if connectivity and time zone becomes a major deterrent to workcation and an urgent e-mail gets attended only to be answered 10 hours later. Communicate effectively and be aware of connectivity and time zone sensitives. Keep a tap on your business emails and calls.
  3. What if you are not available when you are urgently needed as you are busy getting a Thai massage and your colleagues are reaching you out for urgent skype call. When you work remotely, you tend to have your own schedule and do things at your own pace. Rather have a structured framework of the office hours and communicate real-time with your team of last-minute changes in schedule and updates.

Can Workcation happen to you one day?

The reservations with respect to workcations make it really hard to negotiate with, let alone getting the final approval. Not all the bosses will be on board with the idea of workcation, especially if the organization doesn’t have flexible-work policy or the nature of your job is not in line with the remote work framework. But if you are an ardent advocate of work cum vacation and are determined to have one, you have to convince your boss.

  1. Define your working hours to your manager and make sure to mention about time zone difference if there is one. Be very clear about when you will be working and when you will be off. Let your boss and the team know exactly what to expect.
  2. Communicate your holiday or time off while on workcation and keep your manager updated if you are planning to keep a day off or an afternoon off during your time away.
  3. Define the best way to contact you while you will be on workcation and make sure to inform your manager about ensuring data roaming plan and wifi availability at the chosen location. Also, let your manager know if you will be available on chat? How often will you be checking your e-mails? How would you be contacted in urgent situations? Who will take a call on important business decisions on your behalf if you cannot be reached?
  4. Delegate the tasks which are important and which you won’t be able to do while workcation and complete all the important work before you try to convince your manager.
  5. Be proactive in communication with your team, manager, and the clients and respond to emails promptly, get all the news updates beforehand, and be aware of all the major office events to cover up for your physical absence. It is also a good idea to decide which meetings you’ll be able to attend and plan for how will you join in. This will surely pacify your manager before he cuts off your workcation days and asks you to report back immediately.
  6. Allocate enough time to work and treat it like a real job by ensuring your productivity is not hampered by touristy distractions. Keep your vacation plans for the evening's post-work and on weekends.

How to choose your workcation location?

Choosing a perfect place that is ideal for workcation is a little different from choosing one for an actual vacation. In your best interest, you would want to avoid a location

  • Which will make you upset as you have so much to explore and work is keeping you away from tons of places you want to visit
  • Where main attractions happen during the day

Good options for workcations are:

  • Domestic cities due to time zone and connectivity issues
  • Cities where you have lived before. This means you do not have much to see around as you have already covered the main attractions but you still have plenty of time post-work, in the evenings, and during the weekends to visit your old friends and family.
  • Destinations which are relaxing destinations with resorts and beaches where you can feasibly sit by the pool and work.
  • Destinations with Wifi hot spots across the city — malls, public parks, hotels, tourist spots, etc.
  • Destinations offering staycations where you don’t bother yourself much about site seeing.

How to stay productive while on Workcation?

  1. Understand when are you working and when are you are logging off and be firm about it to avoid the trap of either working too much leading to burnout or working not at all as you are busy drinking since 3 PM.
  2. Take regular breaks while working as you do in regular remote work or work from the office to stay more efficient.
  3. Change your work location to avoid monotony to seep in. There is no harm in working by the pool one day and working from the neighborhood café another day rather than working from a hotel room every day. Just make sure you are connected.
  4. Organize technology like a laptop, a VPN, a smartphone, headset, hotspot, Wifi, etc beforehand.

Limitations of Workcations

Workcation as a concept is very interesting but the downside is that there is an only a limited number of roles which lend themselves to this kind of program:

  1. Work cum vacation is only possible with tasks that can be digitized or can be done remotely. Not every task, role, or profile may hence qualify for a workcation.
  2. It is not possible for roles and profiles which require physical presence and day to day monitoring. For this reason, most of the blue-collar jobs do not qualify for a workcation.

In the end, we all must agree, that workcationers can easily be distracted and not be able to maintain the fine line between work and vacation. But if handled properly, it may mean the best of both the worlds. So why to mix apples and oranges and rather have a normal vacation and relax completely? However, for the adventurous lot, and for those you can plan it really well and perform, mixing work and vacation can mean reaching your Zen. So, give it a chance, it might surprise you.

“Is the workcation detracting you from the vacation you planned or is it enabling the vacation you otherwise wouldn’t have had” — Kenneth Mathos

Originally published at on July 11, 2020.



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