How to Plan for Vacation: Your OOO Plan
Written by Ashton Mathai
Published April 25, 2024
So you’re going out of office… good for you.
No, really. I think it’s great that you’re taking time for some self-care and, better yet, planning ahead to make the smoothest transition possible.
Did You Know? The first time we saw “self-care” start to mean “caring for your own health and well-being” – and not being selfish – was in the mid-1800s. I hope that’s also not the last time you took time off…
Too few people take time off. If we’re putting numbers on it, 4 out of 10 people in the U.S. don’t take advantage of their paid time off. Which is a shame. Giving our brains a break makes all of us better at our jobs.
So take your time off…but first, let’s get real. Making an out-of-office (OOO) plan – and taking time away from work in general – can be so fraught. You sometimes even question if it’s even worth going, especially on the day before your departure.
Let me help you: It’s totally worth it. Every time.
Consider this your “how to plan for vacation guide to keep things moving so you don’t want to say ‘#$%@!’ the day you come back.”
(Note: This guide is for longer OOO plans. Don’t extensively plan like this when you’re out for 3 days.)
Catch All the “Flying Pieces” in a Pre-OOO Plan
If someone asked me what I did yesterday, I couldn’t tell them.
I would, however, be able to hand over my detailed to-do list from that day. But here’s the thing about every day: I might start with three tasks, and end the day with 10 completed.
There are a lot of flying pieces (AKA multiple things to do, all the time) for most of us in our daily jobs.
Team members, clients, partners – even the BDR cold-emailing you – bring new questions and requests, which can build up and get lost if you’re not careful.
This is why my first step in an OOO plan is to start a list of things that must be done before I leave. This includes delivering or moving projects that fall in the middle of my time off.
And I do it earlier than you’d think. I recently went out of town for two weeks and I started my list about a month before.
On this list, write down:
Any deadlines and meetings you have planned before and during your OOO.
If they’re happening while you’re gone – try to move them.
If they are unable to be moved, write down the next person to handle that item. (Make sure to transfer ownership of the meeting invite and links.)
Don’t forget any prep for meetings (i.e. presentations, reports) happening during your OOO.
Also, include any cyclical work. For example, I put together client analytics reports on the first and second weeks of every month. At the end of every month, we send out our Carved Out newsletter.
When you think of things to add and get tagged in more projects (and you will), write it down.
Pro Tip: When you start to think about things that need to get done after your time off period, write them here, too. It will come in handy later…
The list can be daunting, but you’ve got time. You’ve likely already completed some tasks.
Doing this ensures things don’t slip through the cracks so you’re not panicking on a beach somewhere in Mykonos when a deadline is missed.
Plus, it feels great when you start checking those boxes off.
Empower Your Team in Ghost Mode
The whole world doesn’t stop when you leave the office; think about what your team usually relies on you for. Then, see if there’s a way to prepare those things before you go, or offer an alternative solution.
Here are a few examples of what I prepped for before my trip:
New pitch angles. To make sure we were covered, I wrote up a few ideas and shared them in our internal Slack channels before I left.
Redirects. If you are someone’s Subject Matter Expert, offer them another resource. I collaborate with our team that runs Instagram every week, so I offered up another content SME to help them while I was gone. (I would recommend the other person is okay with it beforehand.)
Reporting. I made sure the team had my contribution to client reports in advance.
But don’t just think about your internal teams. If you manage or are a critical part of customer or external agency relationships, think about them, too.
As one of those external agencies, our best client team leads make sure to do a few things.
Let us know their out-of-office dates ahead of time.
Put us in touch with an alternative point of contact at their organization.
Get us what we need before they go. For example, one client recently sent us an AI-related pitch deck to help spark content and pitch angles, and deeper conversation before they went to Japan for three weeks.
One of the biggest parts of how to plan a vacation is considering how you empower the people around you when you’re not there. What do they need to do their jobs when a puzzle piece (AKA you) is missing?
Don’t Panic, Don’t Forget: Your Last Minute Checklist
We all know that feeling when you walk out the front door for a big trip. With plane tickets in your app, you hand the suitcase to your Uber driver, confidently get in the car, and shut the door.
As the car pulls away, you suddenly think, “Did I forget to pack underwear?” (Or worse, your passport.) And then watch as your house becomes smaller as you internally swear that you did pack underwear.
If that’s you, welcome. It’s stressful here.
But I’m about to give you one less thing to worry about. Here are some “last minute” things you may not want to forget in your OOO plan:
Any reminders you need to set for yourself
Unless you’re leaving the office for only a few days, there are likely some reminders you need to set for yourself. You can do this in the default reminders app downloaded on most of our phones.
For example, a few of my clients had press releases going live while I was gone. I set reminders for the night before media announcements to make sure their LinkedIn posts were scheduled and good to go.
Crafting the world’s best out-of-office message
Arguably the best part about taking time off: crafting the best out of office message.
OK, you may not need to strive for the best – you have a lot on your plate right now – but I think it’s an underutilized opportunity to get creative and make friends.
Don’t believe me? Here’s one of the best bounce-back emails I’ve ever received:
You know that slightly annoyed feeling when you email someone and get an out-of-office message back? That feeling doesn’t exist when you’re laughing too hard.
Either way, turn on that automated message so people aren’t counting on you for information to meet deadlines.
Your out of office coverage plan template
A full OOO plan for the team is usually one of the last things I do and the most fun. Why? Because you’ve basically already made this list (remember step one?). Now, you’re just making it pretty.
There’s some great advice I always remember: “It’s equally important to communicate with your people in a way that can be understood, but also cannot be misunderstood by them.”
Thus, the birth of my “famous” out-of-office handoff document (famous only with my team). Yes, it’s color-coded.
My ultimate goal is clarity — leaving no way to misunderstand what is happening, what has already happened, and what needs to happen.
When I’m putting together this document, I make sure to explicitly state:
WHO tasks are assigned to (hence, the color-coding).
WHEN tasks are due and WHO they’re due to (an internal or external team member).
WHERE the needed documents are (Pro Tip: always leave links to referenced resources. No wild goose chases or people trying to contact you while you’re out).
Any “flying pieces” of information someone might need to know (and why).
Then, I meet with the team members in my handoff document to explain what needs to be done and why, plus answer any questions they might have. I also encourage them to cross off items when they’re completed and note anything I might need to know about or do (and when) upon my return.
It’s a great way to minimize emergencies, especially if you don’t want to (or can’t) be reached.
I’ve even already started it for you: out of office coverage plan template.
Last Thing… Don’t Make Future You Mad.
I’ll keep this short. You don’t want to leave the office without thinking about what’s happening when you’re coming back. Trust me — you’ll hate your past self.
So track the tasks you need to do and what you need to pay attention to when you’re back, especially if you’re in charge of certain projects.
Pro Tip: Build any “big” tasks you might need to get done that first two days into your before OOO document. For example, I’m not a fan of writing LinkedIn posts on my first day back, so I pre-wrote a few before I left. When I came back, all I had to do was review and send them off! Game-changer.
Congratulations — your OOO plan is ready. I hope you get some meaningful things done in your personal life. We all need some time and, because you’ve prepped diligently, your team can keep things moving while you’re gone.
See you at the beach!