No Emails Please, I’m On Vacation: Travel Planning Checklist For Entrepreneurs

These tips will allow you to leave the office with peace of mind, ready for a break and able to make the most of your time away.

All work and no play makes Jack a dull boy (and Jane, a dull girl).

So, if you are going away on holiday, there are a few key things you need to remember to do before leaving the office.With more and more entrepreneurs working remotely these days (with remote teams, too) this checklist will help keep you (and your team) on track.


1. Prioritize your to-do list

Whether you are going to be away for two days or two weeks, be realistic with the high priority items you want to achieve before you book your trip. Get the most important tasks with urgent deadlines done first. You can also develop a project scope document to hand-off and delegate to team members (outsourced, in-house, or otherwise).

Your to-do list should detail the highest priority tasks, who is the lead on each action item and what should be accomplished by a specific date.


2. Plan your hand-off with team members

Make a project management checklist to hand-off to your team so they know what’s expected of their workload while you’re away. Ask each team member to share a daily status update using online collaboration and project management tools like Slack, Asana, Glip, so you can always have an “eye in the sky” and keep tabs on what is being accomplished while you’re away.


Photo: © WavebreakMediaMicro, YFS Magazine
Photo: © WavebreakMediaMicro, YFS Magazine

Online task management tools offer the easiest way to track the work of your team in real-time and avoid any communication delays or errors. Best of all, these tools offer mobile apps to keep you informed on the go.


3. Clean out your inbox

Do you hoard emails? If so, now’s the time to get clarity on what to do, delegate or delete. Clear out and action your emails before you leave the office. Sort your emails by sender (to clean up email chains) and create a category filing system to make cleaning out your inbox hassle-free.

If an assistant is checking your emails whilst you are away, ensure that they have the right password and follow proper protocol when sending responses on your behalf.


4. Turn on your ‘Out of Office’ autoresponder

Don’t forget to turn on the out-of-office feature in your email preferences. Consider crafting a response message with the date of your return and contact details for key contacts and urgent matters.


5. Clear your workspace

Leave your desk and work area clean and tidy. De-clutter, empty, shred, get rid of everything that you don’t need or want. Clear your piles and sort through mail. This goes for home offices, leased offices and serviced office space where generally you should leave the premises as you found them.


Photo: © YakobchukOlena, YFS Magazine
Photo: © YakobchukOlena, YFS Magazine


6. Make relevant information accessible

If you plan to work remotely or using a virtual office, make sure you have the required files or information that you will need, preferably uploaded to the cloud. Check that you know the passwords to access the servers on a remote basis, if applicable, as well.


7. Think green and conserve energy

Switch off any unused lights, log out of your computer and unplug it – don’t leave it on standby! Power down printers and photocopiers to save on energy consumption and costs.


8. Practice forward thinking

Review important projects you have been working on and jot down a few “In the event of this happening” notes. Leave a file with your team that can provide background information so if there are unforeseen circumstances, a colleague has a clear picture of the situation and can deal with clients until you return.


Photo: © mooshny, YFS Magazine
Photo: © mooshny, YFS Magazine


9. Remember the practicalities

If you are the person who usually collects the mail or locks up in the evening, ensure that you have found someone to cover for you in these areas that can easily be overlooked.


10. Plan for your return

If you have the time, laying the groundwork on projects that you know you’ll have to do when you get back will make your transition back much smoother. 
This, along with everything else on this checklist, will allow you to leave the office with peace of mind, ready for a break and able to make the most of your time away.


This article has been edited and condensed.

Dean Bassal is the Managing Director of Bunnett & Bassal Pty Ltd in Dandenong, a Melbourne suburb in Australia. As a small business owner, he understands the importance of being able to offer competitively priced services and fast, efficient and friendly service to his clients, but also the need to strike a healthy work-life balance. When he’s not busy handling a diverse client base that ranges from individuals to small businesses from different industries and cultural backgrounds, Dean loves to travel and visit new countries that he’s never been to – his most recent trips were to Germany, Austria and the Czech Republic!


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