Ask an Anchor: How do you take time off?

Somewhere aspirational

Somewhere aspirational

Hiya Sarah,

I’m thinking about having a big out of office moment the week of Christmas and the week after—going dark (no posts on social or on my site).

Am I nuts? Have you ever done anything like that?

Out of Office

Dear OOO,

First, a little tough love: You will never feel entirely prepared to step away from your business. The good news is that this gives you permission to stop waiting to be ready and get your vacation on the calendar and flights booked ASAP. While you’re at it, also add to your calendar the day when you need to start preparing for your time away and block off at least two days upon your return. More on the vacation-prep/recovery logistics a little later.

In general, I have absolutely gone entirely dark on social media. In fact, I focus very little on real-time marketing via social media, so I go dark ... a lot. It’s stepping away from my email that is most challenging. A client can need something last minute or (eek!) I forget that I promised a deliverable, so I depend on my email to give me that healthy boost of anxiety. 

Because email is my primary source of communication, I’m tethered to it if I don’t manage myself and my clients/business well. I’ll give you a few examples of how I prepare for a vacation that can help you formulate a plan for your much needed holiday. I have finally figured out that to go on vacation, I may have to work double shifts, handling the work that’s on my plate now AND trying to prepare for the work that might come the week I’m away. 

Here’s the general and somewhat unhelpful advice: “Manage your time better, then taking vacations will be easy!” Slow clap and an eye roll, right? 

There are (and will continue to be) moments in your business when you simply have to suck it up and be “heads down and focused.” This may look like working after dinner or on weekends. If you're somewhat opposed to the hustle, hustle, hustle entrepreneur mantra, this way of working isn't what you're aiming for or enjoy. So when it hits, remind yourself it’s just for a short time and for a reason (i.e. taking a vacation!) Make sure the hustle period actually is temporary, and learn how you can recover. Running a business is a marathon, not a 100m dash, and recovery is part of being a good runner (I love metaphors.)

When my work starts to dig into my overall wellness, that’s when I know that stepping away isn’t just important, it’s a requirement.

I have to take care of my most valuable asset — ME (my brain & my body.) Especially if you’re the primary (or only) point person in your company, tending to yourself is a necessity. There’s a lot of self-care that can happen day-to-day, but there’s something unique about shutting everything down (or as close to it as possible) for a week or two.

Side note: Those of you who aren’t prepping for a vacation can also use the checklist below for a weekly or monthly business health check-in.

I’ve tried to “bring my work” on vacation throughout my life. During school, I always promised myself I would study “at the beach/hotel/between meals.” This never resulted in studying and always ruined my time away. I was either riddled with guilt when I wasn’t studying, or when I wasn’t with my family, partner, or friends. I’m sure you can relate to “just 30 minutes of checking email” turning into three hours. Wouldn’t you rather avoid family vacation time by getting a facial or taking yourself on a solo hike? I know I would.

As a business owner who can “work anywhere,” I deeply prefer NOT to work anywhere. I like my desk, my routine, and my time away. I’ve learned that having a shorter, but actual, vacation is better than slipping in work here or there on a longer one. That said, I do love working on a plane - there’s something delightful about a built-in deadline, white noise and the rare, but satisfying Diet Coke. I know I’m not alone in this. Build me an office on a plane, and I’ll take over the world. ANYWAY… 

To take my vacation, I first create a list of things that have to get done before leaving.

Logical? Yes. Easy? No. Here’s a cheat sheet.

For clients: 

  • List each client 

  • Create a sub-list of tasks you owe them 

  • Communicate your vacation days 1 month ahead

  • Ask them if they’d like anything else from you before you go offline 


  • Send a reminder 2 weeks before you’re offline 

  • Send one more “goodbye” email the night before you are offline - invite them to send you emails w/ subject line rules: 

    • [URGENT] or [ASAP] - only for true emergencies, which you should define for them 

    • [AFTER VACATION RESPONSE] - self-explanatory 

    • [NO RESPONSE NEEDED] - self-explanatory 

For social media: 

  • Invite someone to “take over” your ‘gram 

  • Set up automated posts for each day you want to engage

  • Let people know that you’re offline, but will respond to their comments and DMs when you’re back 

For your business: 

  • You should have a list of weekly or monthly tasks that you like to complete

  • Look at the list and decide how many tasks you can do early during the vacation prep time

  • If you can’t prep (i.e., bookkeeping is time-sensitive... You can’t categorize your expenses or income until they happen) MAKE SURE THAT WHEN YOU RETURN, YOU HAVE A FEW DAYS DESIGNATED FOR JUST ADMINISTRATIVE CATCH-UP

Ok, that last sentence deserves its own subsection: Do you want to ruin your much-needed vacation? Then jump right back into work as soon as you get home. Want to relish in your vacation epiphanies and relaxed shoulders? Schedule a few days between your arrival back into the real world and telling people that you’re home. 

Another option: Hire temporary help

I had a client who desperately needed and booked a month-long vacation with her partner. This was a life or death type of thing: her marriage needed some tending to. 

Being online was not. an. option. We decided it was worth paying someone weekly to monitor my client’s inbox and send my client a single weekly overview email with any responses that needed more information. 

That assistant was able to respond in real-time and, if it truly was an emergency, would send a text to my client asking for her input. 

Nothing burned down that week, but there were some emergencies that their system handled beautifully.  

Amid all of this, hold onto the most persuasive business reasons why you should take a vacation:

The time away helps you see the big picture and identify ways you can manage your time on a daily and weekly basis, so you feel more at ease. This may also mean that you have to adjust your rate and create more value for yourself (and that's a perfectly wonderful thing.)