Join us for a 30-min Timely Tour

When work travels with you: the essential working vacation checklist

Last updated on 
January 3, 2020

Check out:

No one ever wants to work on vacation, but for some it’s unavoidable. Key decision makers and the self-employed rarely have the luxury of unplugging entirely, and many others find keeping connection less stressful than removing it completely.

But vacations exist for a reason, and continuing to work can seriously harm your own mental hygiene. To ensure you keep the balance just right, we’ve put together a working vacation checklist for staying healthy, productive and happy:


Before you travel

Schedule your work

Setting a schedule helps you decide what your maximum connectivity looks like and how that work will fit into your vacation plans. Scope out the work you need to do and schedule specific time blocks for them. Be realistic with what you can achieve and keep it basic – you shouldn’t have to wade in too deep or be tasked with something absolutely critical. Should something unexpected pop up while you’re away, do the same: schedule a time to deal with it that doesn’t interfere with your vacation plans. These boundaries are essential for protecting everyone’s fun.

Manage expectations

Let colleagues know you can’t be directly contacted – no one should expect a response while you’re away. Even if you do plan to check emails every other day, give the impression you cannot be contacted as a default; it ensures you only receive important messages and will make for a cleaner inbox. It’s also a good idea to share your schedule with people you’re travelling with to make sure they are aware of your movements and agree with the plan.

Plan your return

The stress of returning to work after a vacation can be effectively contained by making a clear, achievable plan for your return. Note down all the key developments you need to know about – like the status of specific projects or tasks – and the main things you need to accomplish. Take into account scheduled events and reports, and work in time to prepare for them. Then prioritize everything according to urgency. Plan for an easy pace of work with few expectations or interruptions.

Make people update you

Before you go, ask people to send a short breakdown of the key things you need to know about upon your return. Getting a few key colleagues to provide a short, structured debrief of what you’ve missed will make coming back so much smoother. It saves you the stress of trying to piece scraps of information together or keeping up with endless conversation chains while away.

Agree emergency contact

Some communication is harder to mute. You’ll probably want to know about something absolutely critical, where the absence of your input could seriously harm your business. Make sure you set up a procedure with one lead contact for emergencies. They should act as your gatekeeper, vetting the gravity of requests before making the decision to contact you. As a rule, the fewer details you give away about your vacation, the better.

Ensure stable Wi-Fi access

Internet access is your lifeline. Don’t put yourself under extra stress while you’re out there by not having a solution for when things fail. Look into data plans, make sure you have essential apps available on your phone, get phone battery reserves ready for hotspot tethering, and check out cafes and working spaces in the area with stable Wi-Fi.

Make a contingency plan

Should any of the above fail, have a plan ready for any critical work that can be done offline. Consider all the online resources you would need to complete that task and make them available for “Plan B” offline working. Probably not a long-term solution for your entire vacation, but an essential stop-gap fix and stress reliever.

The healthy way to work on vacation

Mute notifications

Unless you turn them off, email and Slack push notifications will 100% suck you back into work mode. They also completely undermine your plan to limit checking messages. Even if you don’t read them there and then, they take your attention away from whatever you’re doing and introduce unnecessary stress. Not cool.

Track the work you do

By tracking the work you do on vacation, you can see exactly what you did, how long it took you and where you got side tracked. It simply shows the cumulative time work took away from your holiday. This is crucial for scheduling unforeseen requests, monitoring your behaviour and making sure you capture any billable time. Try an automatic time tracking app like Timely – it logs everything you do on web and desktop as you work, and can also track time spent on client calls.

Be strict with your devices

Laptops are designed to make mobile work easy, while compact smartphones make it much harder. Choose the latter over the former as much as possible, so you don’t accidentally slip into working more than you’ve allowed yourself. If you do need to work on your laptop, be strict about how long you use it – and put it away as soon as you’re done. Some people find hiding it in a secure place like a safe to be helpful. Whatever works – recognise when you need to stop.

Feel secure switching off

Remember: your work is now secondary. You have an entitlement to relax; it’s precisely why your holiday exists. Feeling guilty, or like you’re letting people down and projecting the wrong image are irrational insecurities that keep us from seizing our right to rest. The thought of returning to work is a lot less stressful when you accept that it will take a few days to get fully back into the swing of things – and that other people don’t expect you to be fully on-point either.

Prioritize your play

It’s what you’re here for. Outside of your schedule, don’t talk about work. Enjoy your downtime, make time for the people that matter most, do stuff you love and enjoy the rare opportunity to focus fully on just looking after yourself.

Keep your team ticking

Timely automatically tracks team hours,
activity and capacity to keep remote work visible.
Lead happier, healthier teams.

Book a demo

Keep your team ticking

Timely automatically tracks team hours, activity
and capacity to keep everyone connected.
Lead happier, healthier teams.

Book a demo

Related articles

Read also

No items found.

Related articles

No items found.
Designed by vikings in Oslo, Norway