Pre-vacation checklist | Charlotte Isaac

Pre-vacation checklist for small business owners⁠

A pre-vacation checklist to help you switch off

Bookmark this to get ready for your next holiday!

Have you ever caught yourself stressing out about your endless to-do list while your brain’s supposed to be in Flight Mode?

Maybe you’ve come back from holidays, sat down at your desk, all energised and excited to get into it… only to cringe at how much mess you’ve left for yourself?

Guess what? It doesn’t have to be that way.

Taking time off should be enjoyable!

Over the past 2.5 years I’ve been fine tuning a checklist that I run through before I take time off from my business (as a one-woman show!). It’s all about creating space to enjoy time apart from the laptop and making sure I don’t come back to an overwhelming mess.
Here’s what I do to keep the wheels on while I’m away, and you can too!⁠

Enjoying time off in South Africa, thanks to my pre-vacation checklist! Overlooking a waterhole with elephant playing, while drinking a mimosa.

Lean on your systems

Get your scheduling tool to protect your time

Last minute meetings aren’t fun—neither is coming back to a fully-booked calendar. If you use a scheduling tool to organise your meetings:

  • Block out your last 2-3 days in the office. Worst case scenario, you have space to deal with mini client emergencies. Best case scenario? Work on some of the biz projects you’ve been pushing to the side.
  • Keep your first day back completely free. Ditto above!⁠
  • Carve out extra time towards the end of your first week back for discovery calls and client meetings.

If you don’t use a scheduling tool, go check out this post where I break down the core business tools every service-based business needs.

Build workflows to make sure your new leads are taken care of

Ever sat in a cafe in Japan, quickly firing off an email to a new enquiry letting them know that you’ll be back soon, and you’d LOVE to talk? Pre-checklist Charlotte has. (Spoiler alert, her husband wasn’t very impressed.)


  • Create a workflow that’ll respond to any new inquiries for you:⁠⠀
    • Keep it simple, send over something that covers common questions you get and invite them to book a call with you, via your scheduler, as soon as you’re back.
    • If you do want to follow up while you’re away, get your workflow to remind you to do that in a couple of days.⁠⠀


Charlotte writing out her pre-vacation checklist, sitting at a table surrounded by plants.

Get organised

These few little things can really make a big difference to how you feel when you come back to your laptop.

Clear the clutter

…Because it’s impossible to maintain the holiday vibes when previous-you’s mess hits you right in the face.⁠⠀

  • Wrangle your inbox. Delete what you can and unsubscribe to things you won’t be *thrilled* about when you get back.⁠⠀
  • Tidy your desktop. If you can’t be bothered, at least put it into a folder called ‘Clean Me’.⁠


Remove temptation

  • Forward any personal or travel related emails to your personal inbox, so you’re not tempted to jump in and start looking at work things.⁠


… and enjoy the freedom you’ve created!

Has getting organised made you realise there’s more scope to streamline your day-to-day business operations? Enroll in my free course: 7 Steps to Automation to get an inside look at how I use automation to create more free time!

who's charlotte?


I like to drink my flat white while it’s hot—it’s the little things, right? You can enjoy your morning coffee too by creating systems that work for you. Client experience is my specialty and through automation with Dubsado, I help you find the freedom to actually enjoy your business.

Hi! I'm Charlotte!