How to take a vacation: A checklist for freelancers

how to take a vacation checklist freelancer

You know those people who are self-employed and always go on and on about how much work they have to do and how impossible it is for them to take a vacation? Yeah, I used to be one of them.  Whether it was over a Christmas break, several city trips, weekend getaways and summer vacations – there I was, stuck in my hotel room on the phone while people were waiting for me to get ready, frantically searching for Wi-Fi to check on several social media updates or consulting on impromptu projects that just came up. It took me almost 4 years to realize that I was the only one to blame since I repeatedly told clients that yes, I would be out of the country on vacation but of course, I would be taking care of everything just the same (not even accounting for time difference, which sometimes meant answering urgent emails at 2am in the morning). So last year, with my honeymoon in Vietnam and Cambodia approaching, I decided to make this work and reward myself with a proper, true vacation. As I’m leaving soon again on a road trip from Chicago to New Orleans, I thought it would be helpful for other freelancers and solopreneurs to share my approach and a few pieces of advice on how to manage to take an actual vacation every once in a while.

1. Manage expectations.

First things first: You have to give your clients a heads up as early as you can (to me, that's at least 4 weeks). Talk to them about upcoming projects and whether they should be finished before your vacation or can be tackled afterwards. Readjust deadlines accordingly. If needed, find someone who can replace you during your time off - a fellow freelancer, a virtual assistant or an intern, for example. Also, accept the fact that your income will most definitely be lower that month you're taking a vacation. Don't panic - you'll make up for it in the time before and after, I promise.

2. Do as RiRi says.* (*workworkworkworkworkwork)

There's no getting around it: The weeks leading up to your vacation will probably be more stressful, hectic and a lot busier than usual. Do what you always do: Write your to-do-list, prioritize like a boss and take care of things one after the other. Even if it's 8pm - turn up the music, pour a glass of wine and get to it. Just think about those magical days when you won't be doing anything work-related and you will find motivation for it all.

3. Pre-draft, pre-schedule, pre-pare.

Have a look at your carefully planned content plan (No such thing? Find out how to create one here) and pre-draft blog posts and newsletters. Schedule them along with social media updates (I use Buffer for this) and prepare an automated email response, even when you're planning on looking at your emails from time to time. It's good to let people know you might need a little longer to get back to them than usual. 

4. Get outta here.

Make sure you are actually taking time off - whether that's a digital detox, a time for not checking emails or simply reading 7 books in 7 days, clear your mind, relax and take your time. In order to not set yourself up for failure once you get back, make sure you prepare your workstation and to-do list for your arrival: Note down everything that needs to happen once you're back. I also like to give myself one day between arriving home and being accessible to clients where I can go grocery shopping, do the laundry and cuddle my cat.

In order to make this even easier for you, I have prepared a checklist listing everything you need to think of before going on a well-deserved vacation. Just fill out your details, print it out and get to it. See you later!


Thanks for taking the time to read this! I'm Melinda and I offer creative and strategic coaching for passionate solopreneurs and freelancers. Connect with me onTwitter or sign up for my bi-weekly newsletters for more information and resources on #AFreelancersLife.