Self Improvement

The Right Way To Take Some Time Off….& Not Get Burnt On Re-Entry

Mark O'Neill 12-08-2014

My wife always tells me that we need to go away on a relaxing trip — without the smartphones, the iPad, and the laptop — and I always laugh at her.


It’s not just a case of switching the phone off, packing a bag, and off you go to the seaside with your bucket and spade. If you work online, and you have emails, tweets, Facebook messages, and Skype voicemails coming out of your ears, then you need to prepare months in advance, if you want to return to a sane working environment. Otherwise the refreshed holiday feeling won’t even last until lunchtime on your first day back.

The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry shutterstock 171028250

So how can we make things easier on ourselves when we return? Simple. You follow “the process”.

The Process

Before You Leave….

I find it best to schedule my holidays 3-6 months in advance (although my next holiday in February 2015 was scheduled a year in advance, so it can vary in some cases. But 3-6 months is normally enough for the purposes of informing everyone that you will be away.


The key to online sanity when you return is making sure that your colleagues, family, close acquaintances, etc, all know that you are away during a specific time period. This will hopefully make them not send emails while you are off cavorting in the sun with the natives and drinking rum punch with a little umbrella.

But humans being humans, they WILL forget. So you shouldn’t tell them 6 months before you go and expect them to remember. An industrious few might mark it down in their calendars, but you should still assume that it will pass through the Swiss cheese minds of everyone you email, and who emails you back.

So when you book your dirty holiday in the sun, immediately email important work-related people and give them the dates you are away.

The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry workschedule


At around this point, you need to start planning your work schedule from then until the day before you go. Do you turn new work offers down? Can you get all outstanding assignments finished in time? Get the calendar out, and work out your schedule up to the day of departure. Make sure all of your outstanding commitments are taken care of before the plane takes off, so you can depart with a clean slate.

Then once a month, every month, remind people again. Just one reminder. Try and get it drilled into their skulls that you are going.

4 Weeks Before You Leave

It’s time to switch that vacation autoresponder on.  It will reply to all incoming mail and it should look something like this.


Family, friends, colleagues, acquaintances,

I will soon depart for a much needed holiday from DATE to DATE. During this time, I will be offline and completely unavailable. So during the time periods specified above, please do NOT send me any email on any subject. If you do, your email will not be answered because I will be away from the computer and not checking email.

Keep that message running up to, and during, your holiday. If you have a colleague who can take care of some of the emails, add their name, email and possibly phone number to the message. Otherwise, end it with “I will answer all emails on my return“.

24 Hours Before You Are Due To Leave….

Set up a filter to divert ALL mail from the inbox to a label (some people recommend trashing all mail, but to me, that is a bit extreme).  Just have it re-routed unread to a label.

How do you divert everything to a label? Simple, think of a word that would never appear in any of your emails, then go to “Filters” in your settings, drop to the bottom of the screen, and choose “create a new filter” (assuming you use Gmail. Other email providers will have something similar).


The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry gmailfilter

So in my example, I have decided that “pizzaface” will NEVER turn up in my email (cue, lots of pizzaface emails from my colleagues). So put your magic word into the field “doesn’t have“. Choose a folder for all the incoming email (which hopefully shouldn’t be much), and create the filter. Very good my young Jedi. You’re feeling the Force.

Now use your last 24 hours, in between packing and finishing assignments, to try to achieve Inbox Zero Maintain Inbox Zero Daily With This Flow Chart Personally, I try to maintain Inbox Zero despite receiving over 500 emails on a daily basis. That's zero unread emails -- that's right, I address every single email sent to me every morning. And trust... Read More . Yes, that mythical state of being. Except it’s not really a myth because it really is possible if you focus on each email in the inbox and make a decision about it. Boomerang (which I use every day — read our review on Boomerang Schedule Emails to Send Later with Boomerang for Gmail in Chrome Gmail is in ingenious tool for managing emails. Much of what it is lacking per default, is covered by Gmail Labs apps or browser add-ons. Boomerang is a browser add-on available for Chrome that let's... Read More ) is a fantastic tool for making emails disappear and return on future dates. If you use it, schedule everything to come back two days after you return. Confused? I’ll explain later.

You are now leaving for your holiday. Got the suntan lotion? Check. Really loud and embarrassing Hawaii shirt? Check. Left the smartphone, tablet, laptop, & Internet stick at home? Nice try. Put it back. And the PC too. That doesn’t need to come with you.

See you in 2 weeks dude.

The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry sunbathing

2 Weeks Later….

You’re back! How was it? What, it rained all day, every day? Well, that’s what happens when you buy a package deal holiday to Scotland.

I highly recommend spending one more day on holiday away from the computer until you have resettled back home. Get your unpacking done, do your washing, etc. The Internet can wait another day.

24 hours later – D-Day

So, just like the astronauts who come crashing down to Earth, let’s get you re-entered into the crazy tumultuous world of emails, tweets, and Facebook messages. You have to do it carefully though otherwise you will enter into a severe state of “aggressium computerum“.


Re-entering Twitter is easy. Start at the most recent message and don’t even attempt to read the backlog. Otherwise, you’ll be there till your next holiday.

The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry twitternotifications

And see that number next to the notifications? If you are someone who gets mentioned a lot on Twitter (I do, because of Cool Websites & Tools), then that “notifications” number will be quite high if you haven’t checked it in a while. Just clear the number away and move on. If someone really wants to talk to you, they can send the message again.


The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry facebook

Again, with Facebook, don’t bother reading the status messages of everyone in the past 2 weeks. It will take ages. Just focus on answering your Facebook Messenger messages.

All good here, move along.


The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry gmailfolders

Now we come to the biggie. Remember how I told you to divert all of the email to a label, and to schedule your emails to come back 2 days later? OK, let’s go over that.

Scheduling the email to come back 2 days after you return, ensures that you get an extra day off to wash your undies, and another day in front of the computer with a wonderful magical Inbox Zero, to ease back in gradually. All of the email will be in another folder for you to go through at your leisure. So go ahead and delete that filter so all future new mail comes back to the inbox. And turn off the vacation auto-responder.

After deleting the contents of the spam folder with one click, let’s now go to the folder (where the email was dumped).  Hopefully your family and colleagues will have heeded your request and not emailed. This should leave newsletters, bills and invoices, and any spam which escaped the clutches of the spam filter. And any foolish person who ignored the messages and emailed you anyway.

You’re obviously free to do what you want, but if it was me, I would delete the spam and the newsletters, and focus on the “legitimate mail”

One Week Later…..


The Right Way To Take Some Time Off....& Not Get Burnt On Re-Entry stresssmoke

And so it goes on….

How do you prepare your digital life for going on holiday? Or are you hopelessly plugged into the Net 24/7?

Image Credits: Man Writing On Board – Shutterstock, Dog On Beach – Shutterstock, Nervous Businesswoman With a Laptop – Shutterstock, JaysonPhotography /, Stressed Businessman – Shutterstock

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  1. Fik of borg
    August 13, 2014 at 12:40 pm

    I am not familiar with that concept "holiday". Off to wikipedia I go.