How To Work Remotely While Vacationing


It’s the dream. Being able to actually contribute to your job while visiting famous places around the globe and having fun? With the arrival of remote work – the New York Times reports that about 43 percent of employed Americans engage in some form of it – and its popularization, that dream might not be so far off. What can you do to make this reality of simultaneously working and vacationing further within your grasp?

Be Realistic About It

This is a big thing that most people miss when they’re trying to reach any major goal. Just think of the examples of traveling the stars, curing cancer, or the automation of tasks. These are really desirable things we have the technologies for solving, but also things that we have to do one step at a time for them to be feasible and complete. Even when it comes to businesses, close to 30-40% of all startups across industries fail within their first four years.

Overestimating our potential seems like something that’s built into our very veins and there is no success without any risk. So, the first step to anything is to get a good estimate of where you stand. The most obvious feature of a self-evaluation of this kind would be to question the type of job you have. For instance, there’s no way you’re going to be able to do trash collecting or working as a repairman remotely.

The first question to ask yourself is whether or not your job can be handled effectively, efficiently, and productively from a remote position. That’s bad news for a lot of jobs that require physical roles, but on the whole, it’s actually one of the plus sides of aiming to get a remote job. If you think about it, a remote job will almost always be a managerial or information-based job due to the limitations of being “remote” to begin with.

That means that the first step to getting your foot in the door of this dream of working while relaxing involves getting into a managerial position or a position that requires a lot of technical expertise surrounding information dissemination and sharing (i.e. things involving the Internet). You’ll notice that all of the jobs mentioned in this stereotypical listicle published by The Balance deal with some form of information distribution, and that’s not a coincidence.

However, using our example from above, it’s also possible for you to do a great job at your current job and get promoted to a managerial position. A construction worker can become a foreman that oversees projects and a private might become a captain. What next?

Test Out The Flexibility of Your Job In a Remote Setting

Nowadays, many employers now allow their workers some leeway when it comes to working remotely. This applies especially to you if you’re an office worker or someone that occupies a similar position within the managerial structure of a big organization. If you’re part of the growing force of freelancers globally, you determine your own productivity and your own effectiveness since you’re your own boss.

So really, for the people who are working in middle management or jobs that traditionally are tied to a physical setting but have recently begun to open up to remote possibilities, the job market is in the process of pivoting. A poll conducted by Gallup indicates that about 37% of the U.S. population now telecommutes on a part-time or full-time basis. That means about four out of every ten people have some sort of schedule worked out where they go home on some days and do their job.

If you’re part of this category, you want to really test out the difference in feelings you get from working at home in comparison to working at an office. There’s an ongoing debate about whether or not working from home makes you more productive, but the answer usually will involve you actually asking for some days of your job to be remote and seeing how you fare in comparison to when you’re in a more formal setting.

Meanwhile, if your job centers around more influence-based jobs or work involving information dissemination or manipulation, you will have a head start on this goal of working remotely while enjoying yourself. Your schedule already follows a timeframe that you’ve set for yourself so you’re immersed in remote work, clients, and contacts right from the get-go.

Playing While You Work

Don’t forget about the end result. What will it actually look like to you when you’ve created a schedule that allows you to travel and party while remotely finishing your duties and communicating at the same time?

Truthfully, the hardest part of this entire thing might be getting used to working and recreation at the same time. It’s a bizarre notion if you think about it – you’ll be planning trips to foreign countries like Singapore while also on the phone with clients or busy busting out some key part of a project for your organization. Sometimes, the reward is the journey rather than the prize, but what happens when you get the prize and the journey never ends?


About Author


Wife, mother, grandma, blogger, all wrapped into one person. Lover of coffee, crime shows as well as humor. Loyalty, honesty and positivity is what attracts me to a person as that is what I try to project to others. Hard working and driven to a fault helps me help others and in turn helps myself in my daily work and life.

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