Expert tips to tick off your to-do list and actually switch off on holiday

Ever feel like booking time off work is more trouble than it’s worth?

You end up staying late the day before you head off, stress out over all the stuff you have to do, reply to emails that keep coming in despite a clear OOO message, and return to the office to find yourself immediately overwhelmed by tasks and your holiday zen a distant memory.

This isn’t healthy.

We all need and deserve proper time off, where we can actually switch off from work and rest, recuperate, and remember that our jobs are not the be all and end all.

But doing that can feel tricky.

Alicia Navarro, the founder and CEO of deep work startup FLOWN, reckons the key to actually being able to relax and enjoy your holiday lies in that final day before you head off.

Ahead, she shares her top tips to clear you to-do list and get going.

Manage expectations early

‘Face facts,’ Alicia tells ‘You’ll never genuinely clear your work to-do list before you go away.

‘Tasks are always incoming, and feedback loops mean you’re unlikely to neatly cross the last thing off your list at 5.30pm on your last day in the office.

‘So, shortlist the things you’re going to prioritise before you go, and make sure your boss and your team knows what is and isn’t on your shortlist.

‘It’s fine to say “I won’t get to this until I’m back”, as long as everybody important hears you say it.’

Prioritise progress

Recognise that you can’t tie up all loose ends.

Alicia says: ‘Know you’ll be going away in the middle of a long, arduous project? Frame your efforts around making progress, rather than despairing that you’ll never finish.

‘If you can drop some impressive progress on your boss’s desk before you saunter out of the office, you’ll go on holiday knowing that your absence isn’t blocking anybody and your graft has set your colleagues up to make similar progress while you’re away.’

Don’t try to multitask

Multitasking doesn’t work. Stop trying it in an attempt to get more done.

‘Instead of having a load of things whizzing around your head at once, prioritise tasks based on the things you’re going to deliver before you go, and work through them one by one,’ Alicia recommends.

‘Better to deliver progress on a few important things than have nothing to show for your pre-holiday sprint.’

Try timeboxing

Alicia says: ‘Timebox your to-dos in the run up to your holiday. This means allocating a finite block of time to a task and completing the task in that block, no matter what!

‘Think of a realistic, pressure-free time allocation, then halve it.

‘imeboxing works because it forces your brain to focus. It also silences the inner critic in your mind – there simply isn’t time to listen to it.

‘Do the work, then move on. Tick!’

Don’t forget to take breaks

It’s tempting to get into the mindset of: ‘well, I’ll rest when I’m on annual leave, so I just need to work flat-out now’.

That isn’t a good idea – you still need breaks throughout the day.

‘Make sure you recharge your focus often,’ Alicia suggests. ‘Take sensible breaks during work hours, or you’ll spend the first few days of your holiday unable to relax.

‘Take walks, do some breathwork, be creative. You could even dedicate five minutes between work sprints to do some mindful packing.’

Make sure your out of office message is super clear

Don’t give anyone an excuse to bother you while you’re on holiday.

Make it very clear in your OOO message that you’re off work from this date until this date and that you won’t be looking at your email while you’re gone.

Make sure to say who people need to contact in your absence.

Set boundaries – and stick to them

Listen to this. Take it in.

Do not check your emails. If you do check your emails, do not respond to them.

If you set boundaries and then undermine them, you send a message to other people: your boundaries don’t need to be respected.

Or to put it in more practical terms, if you reply to an email after saying you’re not checking emails, people will expect a response. Then you’re just stuck working on your hard-earned time off.

Don’t do it.

Decide on your return-to-work boundaries

Alicia tells us: ‘Decide before you go on holiday whether you’ll check your email on the Sunday that you return, or whether you won’t.

‘Don’t ruin the last day of your break agonising about it.’

Really, genuinely switch off

Alicia recommends: ‘Use an app such as Freedom to block work apps, or at the very least move your work app icons to another home screen (ideally at least five swipes from your default home screen)!

‘The more hassle you can make it to get to your work apps, the more time you’ll have to question whether you really need to look at them.’

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