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Prepping for a Vacation as an Entrepreneur

Small Business Vacation Advice

Just a few weeks ago I headed out of the office for a 10 day vacation. And to be honest the workload of preparing for my vacation as an entrepreneur was almost twice as much as my normal workload! When you’re the only employee of your small business, or one of very few, it can be stressful to take time off of work. We don’t get paid time off from our businesses! Before any vacation (or even just a few days out of the office) there are a few things I do to plan ahead.


Block Your Calendar

Way before you even get close to your vacation I recommend blocking off your calendar. This makes sure you don’t accidentally book anything like a call or photoshoot during the time you want to take off. I block off time as soon as possible and even block off days like Thanksgiving, loved ones birthdays, my own birthday and a Christmas holiday so I know I’ve got some down time to look forward to.

I also recommend blocking off at least the day before you leave and the day after you get back to give yourself extra time. If you’re anything like me, the day before vacation is focused on packing and last minute errands. If I didn’t block that day I would have to juggle work in between all my other to dos!


Warn Your Clients

Be sure to also warn your clients that you will be out of the office. I outline my upcoming out of office dates in my email signature at least a month ahead of time. This includes days where I’ll be at weddings so no one is expecting a response and I can focus on the couple I’m with! I also set up my autoresponder to start at least a day before I leave. Include a clear expectation of how long you’re gone and when they can expect an answer. I also link my Instagram in the autoresponder so they can keep up with all the behind the scenes while I’m out on vacation!


Wrap Up Projects & Schedule Content

Make sure you are on track for all projects before you head out of the office. My best tip for a small business vacation is to wrap up not just the projects due the week before you leave, but most of the work due the week you get back. This will allow you an easy transition coming back to the office. I also prep and schedule any content, like newsletters or blog posts, so that I’m still staying active on social media without any of the work! When I was gone at the beginning of the month, my followers still had 3 new blogs posts, two newsletters and social media posts to look at. This made sure I was still top of mind!


While You’re on Vacation

From here there’s two way you can handle things – you can either check out entirely or schedule some time to check in throughout your vacation. If you want to check out entirely that autoresponder I mentioned above is a must! Make sure your clients aren’t waiting for days wondering where you’ve gone. I also recommend outlining some kind of rule for emergencies. For example, I say in my autoreply that if it’s an emergency, clients may send me a text or call (they have my cell phone number at this point) so I know to check in. If you don’t want to give out your cell phone number look into a program like Zapier, that will ping you with a notification.

If you’re up for checking in a little (for the most part this is what I do!)  be sure to start by setting a time limit. For example, I try to only glance at my email for 10 minutes in the morning and in the evening when on vacation. This gives me just enough time to see if anything urgent has come in or there’s a new inquiry I should reply to sooner rather than later. You run the business so you get to decide how you want your vacation to look. You can be as flexible with your time as you want!

A third option is to have a virtual assistant manage your inbox for the week. Many are paid on an hourly basis, so even if you don’t have someone working for you on a regular basis you can still hire them to check in on things a few times while you’re gone. Just make sure you include time to prepare them in your pre-vacation planning!


When You Return to the Office

When you head back to your small business after vacation make sure there’s a buffer in place!  Never hit the ground running with a shoot, project deadline or meeting the first day back. Give yourself grace and have a day or two to ease back into work before returning to 100%. Most likely the first day or two you are back will be spent on catching up on emails you’ve missed and wrapping up any to dos for that week. Don’t expect to be working the same amount as normal. You likely won’t be!


As an entrepreneur, you will likely never hit the perfect work-life balance entirely. It’s a myth! It’s more likely there will be certain times where one is just more of a focus than the other. You do however, deserve to relax and rest! Make sure you think through this small business vacation advice thoroughly before your next trip and set some boundaries for yourself. Enjoy that vacation!


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