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How to Schedule a Vacation When You Work From Home

Work from Anywhere, part time jobs, relaxing on the beach: Home Office Careers

Rebecca is a newlywed and an aspiring fiction author that got her start in content creation five years ago with her beauty and lifestyle based blog and YouTube channel.

If you are a remote worker, scheduling a vacation may be harder than you initially thought.

This year has been a trying one for me and my family (you may know this if you read about my journey into freelance) and as such, my husband and I really need a vacation.

Even though I have been working from home for over five years this is actually my first year doing so as a freelance writer. As a freelancer, all of my money comes from assignments with multiple clients rather than from one remote job where I have benefits and vacation times available. Meaning it’s all up to me. I decide when and where I go, without the need to run it by a boss.

That’s not as awesome as it sounds. It means that I either have to get the same amount of work done in half the time, or I have to forgo some work and have less money that month. And let’s be real here, if I’m on vacation I’m already spending a lot of money so it’s likely that my four day trip will leave me with some very low funds.

So, how am I going to plan my vacation so that I don’t end up losing money? Below I’m going to go over how I am planning my vacation as a freelancer, just in case some of you are in a similar situation, and then below that I’m going to share with you some vacation planning tips for other types of work from home jobs.


How to have a vacation when you work freelance


Here is the bare bones plan for remote, freelance workers like myself:

  1. Crunch numbers
  2. Create a plan of attack
  3. Notify clients
  4. Have a heck of a lot of fun

First, I need to make sure I understand the ins and outs of my finances. I know, it’s not fun to crunch numbers but every remote workers needs to know exactly how much they need to make each month to cover their bare essentials before taking a trip. If not, you could accidentally cut down too much while you are deciding what work to tackle before your vacation.

Secondly, you need a plan of attack. This is why knowing your finances is so important. Now that I know the bare minimum articles I need to write for clients in December, based on the clients I have now (this list could change as we get closer to my trip since I’m always sending inquiries), I need to divvy them up throughout the month.

Can I evenly spread these articles out through the weeks that I’m not on vacation? Or will I need to do some of the work in the car on the way to my trip? Will I need to work more on the weekends to make up for my trip? Should I work during my vacation? Here you need to understand what your limitations are.

In my experience from when I was working for the Ben Team, I burn out too quickly if I work on both Saturday and Sundays. I do work a little bit on Saturdays but it’s at a much more relaxed pace. So working three Sundays in December is out of the question. So really, should I do some of the work on my trip? With my previous experiences at theme parks – the hours of sun exposure and walking will not yield an awesome article on my part.

So I’m leaning more towards saying no to work and yes to magic (and butterbeers) while on my vacation.

So then what will my limitations let me do? I still need to meet that bare minimum amount of work I figured out in step one so I’ve decided to work an extra hour, two days a week, for the month of December. Know your limitations. I’ll be okay working until eight two days a week, would you be?

Last but not least, you need to notify the people you freelance for, or are under contract with, that you will be out of town within a week or two of your trip. This is the easy part. Draft up an email saying up until when you can be reached, assure them that any outstanding projects will be done at a certain time, possibly include an emergency only phone number (depending on your type of work), and send.

You should also set up an “out of the office” message to auto respond to any potential clients that follow up with you over email while you are out of town.

Now, you are ready to enjoy your trip. Finally!


How to go on vacation for all kinds of work from home employees


If you are a contracted worker with a set end day to your work, the easiest way to plan your vacation would be to plan your trip in between different work opportunities. If your contract is revolving, able to end at any moment, then you need to have a discussion with your temporary boss to see what he thinks.

Approach it humbly, discuss with the boss when it would be possible for you to take a break without it interfering with the project. If you talk about it enough in advance, the project can find a way to work around that date.

If you have a more traditional job, just done in a home-office setting, than you have a bit of an easier time setting everything up. Many jobs have automated systems where you just submit your hours a month or two in advance so if this is available at your job, you are set!

If not, just schedule a quick meeting with your boss over Skype or email to ask them if there is any period during the year that would be too busy for you to take some time off.

Make sure that you never, EVER assume a date works with your company without checking. For all you know, your boss or another employee has already requested that time off — making your work more necessary during that period.

And if you have no way that you can stop working for a few days, take a working vacation. With some very strategic planning, you can make this work. Many fun vacation activities are available at night anyway so book your trip, bring your laptop, work your usual hours in your vacation location, and then have an awesome time every night until you have to head home.


Do you have any tips for those that are going to try and get work down while on their trip? Have you had trouble setting up a trip in the past? How did you resolve it?

2 Responses to “How to Schedule a Vacation When You Work From Home”

  1.' Margaret Tibbs says:

    Rebeca,after reading your information I found it to be quite helpful, although I do not have any tips to add because I am just getting started and hope that I can plan and get my freelance business going as you have. The information you gave will surely be helpful because you have covered everything that should be considered when working remotely and making vacation plans. Keep writing, and thanks for the good tips you gave in your message.


    • Hi Margaret! So happy to hear you found Rebecca’s tips helpful! Good luck to you as you begin on your own work from home journey, and please feel free to continue stopping back and taking a look at our latest articles and useful tips! Take care!

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