The Creative Entrepreneur’s Quick Guide to Taking Time Off

As you’re reading this, I’m probably running around like a mad woman trying to figure out if there are enough diapers, snacks, and toys in my backpack. Hoping against all hope that I didn’t forget to pack our toothbrushes. And praying that the public transit gods will rule in my favor and get me to the airport on time.


That’s right. I’m flying home for Christmas.


This is our first real vacation since moving up to the Pacific Northwest and my first extended time off since starting Wild Olive. And while I (sadly) don’t have any tips for travelling with a toddler without stress, I do have plenty of advice for how to prep your business for your time away.  


Here’s what I learned in the weeks leading up to this adventure:


Start Early

Don’t be like me and wait until the week before your vacation to figure out your to-do list. Ok, I didn’t actually procrastinate quite that much. But still, I wish I’d started preparing much sooner. Trip dates have a way of sneaking up on you all of a sudden. If I could do this whole thing over, I would start planning the moment I bought plane tickets.


Get at least a rough to-do list together right away. That way, you can start at least knocking things off it when you have a spare minute. Staring at your screen while you wait for a client to get back to you? Outline one of those blog posts, schedule your out of office message, or set up some Instagram posts. You don’t want to be writing 4 blog posts in the week before your trip. Trust me.


Decide on your approach

In theory, I’m all for unplugging completely and forgetting all about your business while on vacation. In reality, I know I’ll be dying to get back into some things by the second week. And I’ll want to be checking my Instagram daily. Rather than setting myself up for guilt trips, I’m intentionally setting some time aside for work.


Figure out how you want to approach your time off. Do you want to completely unplug for your whole vacation or reserve some time for work? Neither is wrong and there’s no need to feel guilty about checking your email while you’re away if it’s what works for you. This is your time off and you get to use it however it works best for you!


Prepare your Clients

When I took on my current clients, I made sure I was completely upfront about my time off. Right off the bat, I let them know our work together would be on hold while I was out of town and that things would take a little longer than usual because of that. They were both completely fine with that and probably appreciated that I wouldn’t be emailing them on Christmas eve!


Include your time off in your contracts or let your customers know when that your shop is going to be closed. Remind them several times! And let them know exactly how available you’ll be during your vacation, if at all. Don’t want to hear from them at all? Tell them (nicely and professionally)! Being upfront and honest always works best.  


Queue up Content

I took a break from blogging back in October, dipped my toes back in November, and really wanted to get things back off the ground in December. So I put Sara Frandina’s writing process to work, gave batching a try, and had 4 posts already scheduled by Monday night.


Consistency is key and keeping up with your content schedule while you’re away is totally doable. Decide how many posts you’re going to need to publish over your vacation, batch your writing process, and make use of that handy scheduling feature. That’s one less thing to worry over or feel guilty about during your vacation!


Make time for personal errands

I gave myself a solid no-nonsense deadline to wrap up all my work and told myself that no matter what, the bulk of my work had to be finished at least 3 days before we left. No crazy last-minute late night blog post writing. No wrapping up client work in the airport. Nope, those last 3 days were set aside for personal errands.


Travel always means a hefty list of to-do’s on the personal side of things. Getting travel size conditioner, finding reasonable airport parking, finally cleaning the messy apartment… Make time for those things, too! They’re just as important and you’ll be so glad you dedicated time where there was nothing else to worry about.


Leave plenty of wiggle room

Just like I gave myself a 3-day buffer ahead of my trip, I also scheduled a few days off at the tail end. I know I’m going to get home exhausted, have tons of laundry to do, and miss my family like crazy. The emails and calls and everything can wait just a little bit longer.


For some reason, sitting on a plane is pretty exhausting. Don’t expect yourself to jump back in the moment you get back. Give yourself time to rest, unwind from the airport madness, and get ease back into your patterns. You’ll get back to rocking your business soon, I promise!



All the prep work done ahead of time is worth it! Nothing beats feeling accomplished and relaxed as you start your vacation and knowing you’re headed into a time of real rest and reconnection.


Want to follow along on my trip? Follow me on Instagram and tell me how you prepared for your time off this holiday season!

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