The Out-of-Office Checklist for Online Business Owners
July 13, 2024
Being able to take time off whenever the hell you want to is one of the main reasons so many people start an online business in the first place. And yet, taking legitimate time off when you’re the one running your business? Far scarier than cashing in on your vacation time at a 9-5.
But hopefully, this out-of-office checklist will help because it covers everything you’ll want to do and consider before you jet off to somewhere sunny and warm for your summer (or winter) holidays.
1. Figure out the kind of out-of-office experience you want to have
Before you work your way through the rest of this going out-of-office checklist, you absolutely must decide one thing: are you trying to actually take a fully OOO vacation? Or are you planning on working while you’re away?
Because if you truly want to be out of office and not have to check your email, Instagram, or work on anything while you’re away, you need to make that promise to yourself now so that you can actually get everything done before you leave.
Okay? Okay.
(And if you’re doing a working holiday, too, that’s fine, but this out-of-office checklist is for those who want to sign out, log off, and not think about running their business while they’re away.)
2. Make a list of EVERYTHING that needs to get done before you go
Type it up in your notes app or pop it into a list on Notion and brain dump absolutely everything you think you need to do before you leave.
Consider:
- Client tasks (forms that need sending, projects that you’ll want to wrap up, deliverables that need finishing, client gifts that need to be ordered and sent, etc.)
- Marketing tasks (weekly newsletters, blog posts, content for Instagram, Pinterest, or another social media platform)
- Team tasks (things you need to train your team to handle while you’re away)
And yes, this list might be a tad overwhelming, but it’s absolutely crucial that you sit down and do it, so that you can figure out when and how you’re going to check every item of your to-do list before you go.
Once you’ve got your list written out, figure out what the absolute MUST dos are, the stuff you couldn’t skive off if you wanted to. I’d recommend moving those to the top of your list and then assigning yourself actual due dates for ALL of the things you want to finish before you go out of out office.
(And if you have a team or a virtual assistant, you can look at that list, figure out the deadlines, and pass off whatever tasks you’d prefer they do.)
3. Tell your team (or virtual assistant) you’re going out of office
As soon as you know when you’re taking a vacay, you’ll want to tell your team so they have plenty of time to prep. And if this is your first time leaving them to run things on their own, it might be helpful to have them keep an ongoing list of things they have questions about before you leave.
And don’t forget to share everything they need to run stuff without you. (Like login information, or what to do if something goes wonky in the backend for your digital products, or whatever you’ve noticed your team reaching out and asking questions about.)
Oh, and another ridiculously important part of prepping your team? Communicate. Do you want them to contact you if something goes wrong? If so, where and how? When will you be available? Would you prefer for them not to contact you at all? Will you be able to get their messages if they send them? Make sure to set clear boundaries so everyone’s on the same page.
4. Start telling your current clients that you’ll be going out of office ahead of time
Nothing makes for a worse client experience than a service provider who heads out on vacay without telling their clients they won’t be able to contact them while they’re gone. Whether you work on a project by project basis or with retainer clients, you’ll want to let your current clients know you’ll be on vacation ahead of time.
And you can do that by letting them know in any of the meetings you have, adding it the P.S. in a few of your emails, or sending out a specific email to all your current clients to let them know when you’ll be gone.
If you fancied, you could even send out an extra email a week or so before you leave, reminding clients that you’ll be out of office the following week, and to make sure there aren’t any last-minute things they need before you jet off.
5. Batch your bloody content and schedule it, if possible
If you plan to be completely logged off during your vacay and still post while you’re away, you absolutely must make the time to sit down and batch your bloody content.
Pinterest. Instagram. Weekly newsletters. Blog posts. Wherever you post.
Make the content, write the content, upload the graphics, get it all done ahead of time.
You won’t regret it. You will, however, regret having to say no to your friends when they ask if you if you’d fancy a bevy on the beach. (All because you didn’t write your weekly newsletter ahead of time.)
(And if you want people to know you’re out-of-office on your social media, you can always post something that says so.)
6. Block off your calendars
While this looks different for everyone based on the systems you use, you’ll want to remember to block off all of your calendars—whether that’s your Dubsado calendar or your Google Calendar (or both). That way, clients won’t have the ability to schedule a call with you while you’re gone.
7. Set up your automatic responders
Another ridiculously important to do on this out-of-office checklist is setting up your automatic email responder so any time someone sends you a message on Gmail, they’ll receive an immediate reply back, letting them know you’re out of office and won’t be responding to them until you get back.
(If you need help setting up your Gmail automatic responder, check out this article.)
If you’re using a CRM like Dubsado and have an automatic inquiry response set up (which you should and if you don’t, all you have to do is follow the 4 steps in this blog post!), you’ll want to make sure to edit your message so it lets people know that you’re OOO until whenever you get back.
You might also want to set up an IG automatic response too, so if a potential (or current) client messages you, they’ll know exactly why it’s taking so long for you to get back to them. (Here’s a whole blog post about how to set up automatic messages on Instagram.)
8. Get ahead on the work you can
Usually, right before I head out on holiday, a million and one things pop up that I have to deal with. But ideally, I’d give myself enough time to not only finish all of the work I absolutely needed to do, but also get a tiny bit ahead on some of the work I’ll need to do when I get back.
And while you certainly don’t have to get ahead, I promise you that using any extra time you have to get a head start on your to-do list will help you keep your wits about you when you come back from vacation.
9. Double-check your backend systems for your current clients
Before dashing off, give your current client list a look-over. Are there any emails that are going to be sent to them while you’re out of office? Are there any invoices due? Are there any clients being offboarded or onboarded while you’re gone?
Thanks to the best CRM ever, Dubsado, my systems are set up to do all of these tasks automatically, but I still like to go into each client portal and give everything a look-over to make sure there’s nothing wonky going on.
10. Schedule in some wiggle room
While this one also isn’t absolutely necessary, it sure as hell helps. Because after coming back from vacay, it takes time to get settled in and get back into the groove of running your business—and giving yourself a little extra time to do so changes everything.
Maybe instead of getting back late on a Sunday, you fly back home on a Friday so you can take the weekend to unpack, buy groceries, do some laundry, and feel human again. Or maybe you schedule your first few days back as half days so can ease yourself back in.
Whatever works best for you.
11. Lastly, and most importantly, enjoy your time off!
It’s easy as business owners to make ourselves available to clients 24/7, but taking time to disconnect from everything business-related is vital to not burning out. (And it’s an essential to-do on this out-of-office checklist!)
So don’t let yourself feel guilty about being OOO or worrying about what’s happening in your inbox. Instead, just indulge in loving every second of your vacation because you deserve it.
And your work and clients will be better off when you come back refreshed.
