If you know me, you know I am an IT professional (Salesforce Developer, Business Systems Analyst, Support, Web Developer, etc.) and have been working from home/remote for more than a decade. Freedom and flexibility are great benefits of such a working arrangement. One example is working vacations.

By “working vacations”, I’m not meaning taking vacation days yet working instead. No, I mean going somewhere on vacation and working while there. While this may seem glamorous, it is not necessarily as easy and fun as it may seem.

In order to complete my duties and communicate with coworkers and clients, I need reliable and decent internet speeds. Also power and quiet are necessary. I prefer dual screens, and at least an external mouse. One must take your personal and professional requirements/preferences into account to maintain productivity. Especially with regards to internet, one should identify backup solutions (such as a library) and security.

While a working vacation enables a vacation without taking time off, a big downside is being unable to participate in some activities. Even with flexibility, there may be times where everyone else is having fun while you are working. Enjoying your job and being engaged by it help to decrease the feeling of missing out, but it is something to keep in mind.

As with all home/remote working, one must be self-motivated and a self-starter. Working vacations do require a flexible manager/employer. They need to be aware and allow for times where things may not go as planned. Make sure you have some vacation time available for any hiccups. Be sure to take into account any time zone changes and how those may affect start/end times, meetings, etc.

I’ve had one working vacation which was particularly challenging (though I made it work and my supervisor was amazing). I’ve had others where the setup was good and I was not the only one working. I would be doing it again if it seemed like the best option and it were allowed. It can be a good way to visit relatives who are far away.

Remote working vacations aren’t for everyone and every situation. Take into account your circumstances and always discuss with and get sign-off from your supervisor/company before getting too far in the planning process; avoid putting your supervisor in a situation where they feel like they have no choice. Remember such flexibility is a privilege, not a right.