Working On Vacation | Tips to Keep Productive if You Must

“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

  • 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

#1 A Lack of Support

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

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

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

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

  • 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.

Surprising Benefits of Work on Vacation

  • 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.

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:

Are You Ready for Your Vacation?

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!

Originally published at on March 1, 2021.

Otter is a note-taking and collaboration app that empowers you to remember, search, and share your voice conversations. Visit to sign up free.

Otter is a note-taking and collaboration app that empowers you to remember, search, and share your voice conversations. Visit to sign up free.