Practical Tips for Working While on Vacation


When you are an online business owner, taking a break can seem completely impossible. I get it! You are everything inside your business, so taking time off literally means your business comes to a halt while you are resting - especially when you are starting out or if you don't have a team. When your business is your main or only source of income it really isn't an option to stop and sip the mojitos.

I feel like this constantly, but I also know that traveling and taking semi regular breaks is important. At the moment, I take a big (like four weeks off) trip every one and half to two years and then two or three smaller weekend away trips each year and this seems to be keeping me sane! It's important that you listen to your body and know in yourself when you need a little break. For me, taking a break is vital and actually serves to inspire new ideas and renewed energy for my business.

But, as I said, going off the grid is not really possible when you are running your own show. So how do you make working work while on vacation? 


Before you head away on vacation, it will certainly pay to be prepared. This is probably my biggest hurdle when it comes to vacations - I don't do enough preparation and it generally leaves me feeling a little under prepared! Kind of like it a marathon trying to get to the finish line where I board the plane, and in the process I miss a few things! So I have broken down what you should do leading up to your holiday and put it into the following four week guide:


  • Establish your vacation rules (see tip 4) so you know what you will be working on (and not working on) while you are on vacation.
  • Plan out content - will you be scheduling blog posts or emails to go out to your list while you are away?
  • Let your current clients know that in a month you'll be heading on vacation and give them a date by which you'll need any work requests to be lodged in order to process before you head away on your trip.


  • Draft the content you are planning on scheduling. So that means any blog posts, emails, social media posts - anything that you can pre-write and prepare.
  • Create any accompanying graphics - so this might be the images you are planning on posting on Instagram or perhaps the blog post images.


  • Work on those last minute client projects and wrap up active projects that you have going on. I like to send a reminder email to my clients 2 weeks out from departure to remind them I am leaving soon and that their last minute work deadline is approaching.
  • Finalise all your content and schedule it to be delivered while you are on vacation.


  • Finalise all projects and client work and send one last email to let clients know you are away.
  • Turn on vacation status where ever possible (see tip 3 as to why you should do this, even if you are planning on working while away).
  • Check that all content is scheduled correctly.
  • Get your tech and all files you might need ready (see tip 2).
  • Get excited and focus on packing for your trip!


I encourage you to take your laptop rather than a tablet - purely because I believe it's the easiest thing to complete work on quickly. And that's the aim of the game - get your work done quickly so you can get back to the fun. However, if your tablet has everything you might need and you feel like this is the quickest method of working on the move, then by all means, take that instead.

Before you head away on vacation, make a list of all the files you might need. For me, this included brand elements and assets, blog post image templates and client contracts and quote templates, just incase I had a potential client that needed a quick response. I uploaded all of my files into Dropbox (I have a Business account, so I have a 1 TB of space!) that I was able to pull from if needed.

Also remember to keep a copy of all your logins and passwords. I know that on my desktop computer my logins are all saved and I stay logged into most of my services at all times. So when switching to your more mobile, vacation friendly device you'll need to make sure you have access to all your online services like email inbox, mailing list manager, sales cart, website, social media and more.


KINDLE | I recently purchased a Kindle for my trip to Japan and I am completely smitten with it! It's a great business tool in that you can finally read some of those resources that you know will only serve to help your business! The battery lasts forever and I recommend the Kindle Paperwhite version so you have the option of a soft backlight when reading on planes or in the dark. 

CHARGE | You'll also need to make sure you take your charger for all your devices and I also recommend a backup battery pack.


I am a big fan of the vacation status on your inbox, your website, your Etsy shop, your social media - everything! Even if you are planning on being active and working while you are on vacation, putting up the vacation status is a great way of managing expectations. 

While, yes, you are technically available, it's a good idea to cover yourself and the fact that you will be less available for the duration of your trip. It will inevitably take you longer to respond some days and if you find yourself in a situation where you have less than idea access to internet, having the vacation status really does put your mind at ease. 

When clients email you and get a vacation notice in reply, it quickly reminds them that you are human too and need a break. I find people respond really well to the vacation status and when you do reply despite of it, they are pleasantly surprised and essentially, you have exceeded their expectations. I love the notion of under promise and over deliver. This is one of those times! By telling them you are on holiday and then replying anyway, your clients can see how much they really mean to you that you would be willing to reply when on vacation!


My favourite tip when it comes to working on vacation is to set yourself some rules. You really do need to decide on these rules before you go, because once you are in the thick of it, you'll not want to be trying to work all this out! So my first tip for setting vacation rules is to decide what work related tasks you will complete while you are on vacation and what you wont touch.

WHAT TO WORK ON | In my case, I had been approached by a publishing house to submit a book proposal and sample chapter only a week before heading overseas on my trip to Japan. So I knew that this was something that would need my attention while I was away. As a result, I decided I would not write too many blog posts, but rather just write one while I was away (the one you are reading now!). I also decided, that because we were moving around a lot, I would not attempt to do Instagram posts - I was not sure how our access to internet would be, so I left this out of my strategy. I did, however, include this when I went to New York on my last vacation and if you are planning on posting on something like Instagram regularly, be sure to plan your posts before you leave and have them all loaded into something like Plann so you just need to press post and you're done!

WHERE TO WORK | I am guilty of being a workaholic and checking my phone and work emails every moment that I get a chance - like seriously, I have a problem. So this is a hard one for me! It's important that you only work when you are inside your accomodation, in your hotel room or in a designated work area or when you deliberately set out to find a place to do work. So by this, I mean, don't check your work email when you are out and about soaking up the sights. Firstly, that's just plain annoying for the people you are on vacation with and secondly, you didn't fly across the world (or even across the country) to stare at your cell phone! No, you are there to look around, to absorb the culture and to chat with the locals, so make this a non-negotiable rule! A great way to do this is to refrain from being connect to cellular

Remember that your vacation is a time of rest, so don't be afraid to zone out of work for a day or two and if you are having a great time NEVER stop the fun to work. Just do it later. You don't take much time off, so when you do, be present and make it count! Enjoy!