Working on Vacation: Here’s How to Stay Productive

. 7 min read

“Vacation” and “work” are not two words that people generally like to see together, and we would most definitely recommend against working on vacation if you can help it. But there are numerous reasons why having to complete a few tasks during holidays may be inevitable. If this is your situation, this article is for you!

Below you will find some practical advice on staying productive if you work on vacation, allowing you to get your tasks finished sooner so that you can enjoy your time off!

Working During the Holidays: You Are Not Alone

30% of full-time employees report working weekends and holidays

Business never sleeps. There are numerous reasons why one might find the need to work during the holidays. Even for those who don’t usually work remotely, other factors may require them to work during the holidays:

  • Many industries find that the end of the year or holiday season is their busiest time, and the employees have to accommodate the increased workflow;
  • During the holidays, when many employees are taking time off at the same time, someone will have to be left to pick up the shortfall;
  • Those working in highly dynamic industries may face the situation where they have been granted leave at what was presumed to be a ‘quiet’ time, only for the business’s needs to change, requiring them to work.
  • Some employees carry out highly responsible roles within the company or have a skill set that can’t easily be reallocated. While this is a great position to be in, it can also come with downsides. Hence why they might have to work during vacation.
  • Small, self-owned businesses are certainly demanding on one’s free time. Often the owner of such a company may be faced with the genuine prospect that if they don’t work, they don’t get paid!

Problems Faced When Working on Vacation

Working on vacation might not be so bad if it was easy. Unfortunately, working remotely can be challenging, both mentally and logistically. Here are some of the issues that people face working remotely, especially while on vacation:

#1 A Lack of Support

Being on vacation can very much be a case of ‘out of sight, out of mind’. If an employee is in the office, there are people to ask if any unexpected problems are encountered. You may be used to working with every single piece of information you need at hand: if you don’t have it, you can quickly locate someone who does. Being ‘off-grid’ can mean that you don’t have this safety net. Issues that might seem small in the normal working environment can become magnified. This can take a toll on your efficiency and productivity.

Possible solution: When you are going on vacation, do you pack your bag with the things you think you might need, or do you leave it to chance? It is vital to apply the same logic to any work or tasks that are waiting for you. Provided you think and plan ahead, there shouldn't be too many problems that can wrong-foot you.

Now would be a great time to develop your skills in self reliance. The first step would be to come up with a contingency plan: "If I can’t do ‘X’ then I will do ‘Y’". By thinking of these situations and anticipating them before they happen you can ensure that you bring the right tools for the job with you ‘in your suitcase’.

#2 Motivational Issues

It can be hard to stay motivated when your body and brain want nothing more than to remain in ‘vacation mode’. There is bound to be the temptation to do anything other than work, especially during holidays. It is also too easy to become disassociated with ‘the job’ when it’s half a country or even half a world away!

Possible solution: Whilst the temptation might exist to ‘get away’ from work, you can create a balance and satisfy both your professional and personal goals. Think about it, which is the better option of the following: To work a little and be able to enjoy your vacation or holidays knowing that everything is ‘squared away’, leaving you to enjoy your free time? Or… To bury your head in the sand, all the while knowing in the back of your mind that those deadlines still exist, and will certainly be waiting for you on your return?

Knowing what is going on in your ‘working world’ and still feeling a degree of accountability may help you to stay motivated and productive, and enjoy your free time with clear conscience once you get the work out of the way.

#3 Technical Difficulties

Even minor technical issues can become a sticking point when you are out of the office. This can take many forms. Maybe the file that you need to complete a report arrives corrupted or in an incorrect format, or you feel that you weren’t able to hear certain vital parts of a meeting? If you are there in person in a meeting, you can simply ask a person to speak up. When facing the prospect of having to send numerous emails, or await the minutes of the meeting to see what you missed, instead of enjoying yourself, it is easy to see why work can fall by the wayside.

Possible solution: Using a reliable means of working if at all possible, particularly when it comes to software. The simplest solutions are often the best; by reducing complexity, you mitigate the risk of something going wrong! If poor connection is a risk, tools and software that lets you store the information locally are an obvious answer. Make sure to have a solid backup strategy, so that anything is easy to recover and you don’t waste your precious vacation time on recovering files or doing the same work twice.

#4 Poor Connection

It is a fact that remote working usually relies on having access to a stable internet connection. You may be going on vacation to a place where this can’t be guaranteed. Alternatively, your home connection might be temperamental. Either way, a degradation in your ability to connect can heavily influence your productivity and ease completing a task.

Possible solution:  make use of the high-quality transcribing technology. With, even if you are in an area where the connection isn’t reliable, you will still be able to access full records and accurate transcriptions of your audio and video conversations, meaning that even if the line was breaking up, no information will be missed. And the best part? If you have poor connection during some important calls – or even miss those calls altogether – you can always go over the transcriptions when you're back in the office, as they will be stored safely in your Otter account!

This is only one of the ways Otter helps remote workers and businesses stay productive, regardless of the location.

Top 4 Productivity Tips for Work on Vacation

Below are some tips to keep you on track while at work during the holidays!

  • Plan Your Working Time. Time off shouldn’t be all about work, so be rigid in planning the “work” hours and make sure they don’t eat into your personal time. Maximize your remote work productivity to make the most of time spent ‘on the job’, and enjoy the rest of your time guilt-free. Provided you are realistic in your goals, there is no reason why you shouldn’t be able to work and enjoy yourself.
  • Be Disciplined (For Your Own Sake). Motivation can be a valuable commodity even on vacation. Failing to be disciplined and complete your tasks means that they will be mounting up. This isn’t something that can be looked forward to on your return to work, so it can actually degrade the quality of your vacation time.
  • Have Some ‘You’ Time. There is no worse feeling than being always connected to work. It’s your vacation, and you are allowed to switch off. Even if you’re permanently bombarded with emails and calls, most modern software solutions will give you the ability to be ‘away’ during your personal time. lets you record and store the work conversations during holidays and come back to them after the holidays when they are back to the office
  • Triage Your Tasks. If you are using the right tools, you can perform any task, just as if you were in the office. So the question is: if you were at work, would you do whichever task cropped up first? Or would you organize them into the order of importance? By working smarter, you can get the most important things done and out of the way, which will give you some ease of mind and more flexibility to relax later.

Surprising Benefits of Work on Vacation

While it’s definitely best to refrain from working during your time off if possible, there are some good news for those who don’t have that option. Working on vacation could really be your chance to shine. Among other things, being flexible and getting things done even on vacation:

  • Offers recognition. Have you ever needed help and nobody seemed to be keen on helping? You could be the opposite of that by bringing value to your organization and to yourself, all at the same time. Many employers recognize the sacrifice and ‘going the extra mile’. By agreeing to work during the holidays if needed, you might gain the benefit of being given a bonus or extra days elsewhere, at a time of your choosing.
  • Creates a favorable reputation. If you and a colleague are both being considered for promotion, which looks better to your peers? The person who spent an hour each morning making sure their project was running on rails even whilst on vacation, or the person who dropped the project for a two week holiday?
  • Keeps you as part of the team. There’s no worse feeling than returning to work and feeling ‘out of the loop’ or watching your former team be steered in a different direction because you dropped the ball. By staying involved and active, you can ensure that you are still a key player, and that effort won’t go unnoticed.

Are You Ready for Your Vacation?

The aim of a vacation is to relax, but a little work can sometimes be necessary. In this instance, you will want a solution that makes work as effortless and painless as possible. By having the ability to work away, but in a way that ultimately saves you time, you’ll be able to get the most out of your time off without your productivity suffering.

Software such as enables you to do exactly that. If you are in search of a smart tool that can offer numerous benefits for remote work productivity, take advantage of Otter’s 600 monthly minutes of free transcription today!