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How to Prepare Your Creative Business for a Sabbatical (& Still Have Work to Return To)

by Carrie Ashley

Hang Around


Ever since I started my business in 2016, I’ve never stopped being grateful for the perks that come with being a business owner.

I can step out for a Target run at 10 AM – no questions asked. (Just a sweet pupper with a sad look on her face that says, “Please don’t go.”)

I can rock leggings and an oversized sweater every day if I choose.

I can take an extended lunch break to get in a HIIT workout.

And I can set my own hours and gift myself a fair amount of days off.

Though, when staring down another PCS (permanent change of station for my non-military friends), I’ve learned the hard way that I need more than just a handful of days off to pack up and get to the next location.

I need to take a sabbatical. (Think a whole month off.)


I know what you’re probably thinking. An entire month off means you’re missing out on a good chunk of change, or you may even lose some clients.

But I’m here to tell you it doesn’t have to be that way, sister.

I know that for a fact because I’ve done it – twice. So if you’re thinking about growing your family, moving, or you just need a long, much-deserved break from being the boss that you are, I’m here to share what I’ve found actually works to prepare your creative business for a sabbatical (& still have work to return to!).

And if you’ve got a, “Yeah, IDK. There’s no way,” mindset right now, just you wait. It’s actually pretty simple.

Here we go…

1. Start with the big picture – your why

It sounds cliché, but it’s going to lay the foundation for your time away. Do you need this sabbatical to:

  • Focus on spending more time with your family and making new memories? You know, because you’ve been working long days and maybe even weekends?

  • Travel? Hey, a change of scenery is always necessary.

  • Or, in my case, pack up to move and get settled into our first house as owners? Oh, and get my bearings around our new neighborhood (like how many minutes it’ll take me to drive to the nearest Chick-fil-A)?

Whatever’s pushing you towards taking some serious time off—your why—jot it down and get it engrained in that brilliant brain of yours. You’re going to be referring back to it often (especially when/if you start second-guessing your decision).

2. Map out your time off

Now, for the fun part. Sit down and map out how many days you can realistically be away from your business.

What I mean by realistically is – you need to get real about the money and relationship side of things. You know how much you’d be comfortable with sacrificing for the sake of investing in yourself. (I’ll share how to make this the least of your worries in a minute.) And whether or not your family’s finances would still thrive without your contributions for some time.

Plus, no one knows your clients better than you. After all, you’ve worked hard to cultivate relationships with them. So, you probably have a decent idea of how they’d respond when it comes time to share your sabbatical news.

For me, I knew that I was going to be logging off around the holiday season. The good news about that is the majority of my business friends were, too. And some for a good chunk of time (mid-December through the New Year). I could rest assured knowing they wouldn’t be working away in the office wishing I was logged in and could throw them a content lifeline – for the most part.

With that info in my back pocket, I was able to figure out my exact sabbatical dates (+ some wiggle room = Dec. 18 through Jan. 20). Dates that I, along with my clients, could be comfortable with. And I did this as soon as I could (about three months prior). That way, I could quickly move on to step #3…

3. Create a plan to work ahead & maintain boundaries

I’m going to let you in on a little secret: time off doesn’t always have to equate to money lost.

And that’s where working ahead comes into the sabbatical picture. The concept of working ahead is what’s going to help sell your time off to your clients.

I knew how long my sabbatical would be, and when exactly I would kick off my time away from Woven Copy Studio. So, to maintain “business as usual” (sans my active presence 9-5, M-F), I had to commit to doubling up* my workload the previous month (aka November), tracking all my tasks in ClickUp for each collaboration.

Was this challenging? It always is. I was working long days, nights, and weekends to weave together content.

Yes, I had to sacrifice watching an episode on Bravo TV during an extended lunch and quiet weekends with my husband and Jules. But I kept a firm grip on my “why” to push me through it. It wasn’t a forever thing. It was for four weeks so I could enjoy a full month off without worries of parting ways with longstanding client relationships and a consistent workload.

That reminds me…while you’re creating your own plan to work ahead, you can’t forget to set clear boundaries so you can truly focus on fulfilling your “why.” For example, I never like to keep my business friends waiting on a reply back, but I agreed to toss up a thoughtful OOO message and check email no more than 2 times a week. I also deleted Trello from my phone. *cringe* It had to be done.

*What’s all this talk about doubling up on your workload / working ahead? I have monthly content creation projects (think a set number of blog posts, social media posts, e-newsletters, etc. For that reason, I had to essentially combine two months of work into one. So, even if you don’t have projects that you can work ahead on, think about other possibilities to diversify so you don’t miss a beat – whether that’s developing a digital product, opening up your calendar for advanced booking opportunities/creating a waitlist for your services, or offering a supplementary in-demand service that you can provide multiple times in one month (in my case, that’s proofreading/editing services + content strategies).

4. Fill your clients in ASAP

Okay, you’ve got your dates + your plan to work ahead. Next up? Break the news to your clients ASAfreakingP.

Here’s the note I sent to each one of my business friends in September in prep to take my sabbatical in December:


We’re officially under contract on our home! What does that mean for our collab? Well, we’ve outlined our moving dates, and I’ll be “out of office” from December 18, 2019 – January 20, 2020. 

I say “out of office” as I still plan on responding to any emails, etc. every week (as was the case when we moved last year). But I’m committed to completing the majority of content creation for January AND February 2020 by [INSERT DATE]. That way, we can really focus on getting settled in and tackling some serious house projects!

I’d love to get a virtual coffee date scheduled for early October to identify the content roadmap moving forward for the next few months. Click here [INSERT LINK] to find a time that best fits your schedule.

And, lastly, I truly value our partnership and am so appreciative of your ongoing support. That said, please don’t hesitate to share any initial thoughts or questions you may have and we can discuss in greater detail during our chat.

Thanks so much!

You’ll see I highlighted my exact OOO dates, my “why,” expectations, and boundaries. And because I value face-to-face convos with my business friends via Zoom Room, I also included an opportunity to schedule a virtual call to discuss the sabbatical plan together. Totally optional, but I highly recommend it!

5. Delegate your day-to-day tasks

We all get by with a little help from our friends.

And it’s no secret I can’t do what I do without my associate copywriter and my mom (aka Penne), Woven Copy Studio’s BTS manager. That was especially true during my sabbatical.

As soon as I knew I was going to be taking some time off, I connected with my team on open project needs and additional to-dos that I’d needed a hand with tackling throughout the month, as well as outlined deadlines (on ClickUp, of course!).

My associate copywriter handled writing blog posts while my mom scheduled out a slew of content on social media and blog platforms.

Long story short, don’t hesitate to ask for help. If you don’t have trusted contractors on your team, reach out to a VA in your circle to see if they offer one-time services that will help maintain the flow of your business.

Not sure where to start? Milspouse friends – put your feelers out in the MilSpouse Creative® + Entrepreneurs with Moni Jefferson group. For my other biz owner friends – start with the Creative Lady Directory.

6. Put your business on auto-pilot

Time to get really real with you. I’m not the best at this step. But when YOU do this and do it right, you’ll be winning IMO.

The easiest and often most obvious to-do is to write an engaging out-of-office reply message, and get that thing scheduled.

Here’s mine to help get your creative juices flowing:

Hey there! 

Thanks for your message. I’ve wrapped things up in the office and am enjoying my month-long PCS sabbatical. 

For current biz friends, I’ll be checking email every week for any time-sensitive project needs and will be back in full swing on Tuesday, January 21, 2020.

If you’re inquiring about a future collaboration, first off – thank you for reaching out! Please note that I’m currently booking for early March and beyond. I’ll send you a message back within 72 hours.

And in the meantime, if you want to follow along behind the scenes until I’m all settled into my new office, you can do so at @wovencopystudio.

Happy Holidays & New Year to you and yours!

See you when I get back,


Now, here’s where I failed: the behind-the-scenes content I mentioned in my OOO message.

WHY am I so good at helping my biz friends stay consistent with their social and blog content, but SO awful at it when it comes to WCS?

Because I don’t make the time for my own biz. (Hello New Year’s biz resolution!)

The good news is, Planoly makes it super easy for you to get that content scheduled so you don’t go radio silent on Instagram (and even Facebook – there’s a toggle option to automatically push posts there, too, if you’re comfortable with repetitive content across platforms).

I also highly recommend writing and scheduling out a few blog posts to go live during this time.

And, while I’ve never personally used this feature of Quickbooks, you can even create recurring invoices to automatically send out to your clients at the end of each billing cycle.

7. Breathe deep (& remember those boundaries)

Whew. You’ve tackled all the prep work there is, and now there’s only one thing left to do: start that sabbatical, sister!

And remember: while it’s never easy to step away from your business for any amount of time, it’s going to be nothing but WORTH. IT.

Believe me. You’re going to be happy you acted on your desires to invest in yourself and your family, and make the most of the time you can’t ever get back.

Will unexpected requests or “fires” come through your inbox? They’re sometimes inevitable.

But keep those boundaries top-of-mind and circle back to your why, often. Oh, and give yourself permission to open up that computer of yours to work for a few hours one week when a wave of creativity hits you (which it will because it always does when you least expect it).

I’m over here cheering you on every step of the way!

Need help prepping your sabbatical content?

Send me a note today so we can get to work on creating a strategy to weave together words with purpose.

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