How To Actually Take a Vacation as a Small Business Owner or Entrepreneur

If you’ve read our article on Why Business Owners Should Be Comfortable Taking a Vacation, you understand just how beneficial a vacation can be for your productivity, creativity, and overall well being. The thought of going on vacation is an exciting one for most people, but when you’re a small business owner or entrepreneur the idea of time off can be somewhat daunting.

Instead of booking flights and planning the details of your excursion, you’re busy thinking about the projects that may get missed or the emergencies that might arise. But vacations are an important part of any working person’s life, regardless if they own a business, and they’re possible if you have a good strategy with a bit of planning.

It can be scary to think about leaving your business behind for a few days or weeks at a time, but we’ve got some advice on how to actually take a vacation and ensure that your business is still thriving when you return.   

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Delegate and Keep Your Staff Prepared

One of the best ways to get your business to a place that it’s well-prepared for your absence is to delegate your tasks – especially the ones you don’t need to be doing anymore anyway. Having a trusted person or group of employees who can handle the bulk of your work while you’re out can ease your mind, and will show you that you can also rely on those people to cover tasks on a normal daily basis too, allowing you to focus on the business and expand your opportunities.      

Having someone that you trust in place to watch the business is only half the battle though. You still have to make sure they’re well prepared to handle the regular tasks in addition to any surprises that may come their way.

Have meetings with your staff well in advance to discuss the types of things they’ll be covering while you’re gone, and run through what-if scenarios to prepare for the unexpected. Train the most important key player as if you were hiring a replacement for yourself, because, in essence, you are (for the short-term anyway). You can leave detailed instructions or checklists for them to access in case they’re still unsure of something while you’re away, and if you’re still not comfortable, set aside a window of time when they can call you each day, just to check in if nothing else.

You may find it useful to do a test run before you actually leave, to make sure everything runs smoothly, or you can take a shorter vacation the first time around and gauge future trip lengths based on how it goes.

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Set Boundaries Ahead of Time and Make Them Clear      

If it makes you more comfortable to check-in here and there on vacation that’s fine, but set your expectations ahead of time and stick to them. Let your staff and fellow vacationers know so they can make plans around them.

Realistically speaking, if you planned ahead and prepare your staff for your absence there won’t be a need for daily check-ins anyway – and it will be better for everyone if you don’t plug-in quite so often. But a block of time here or there probably won’t hurt anything, especially if people know to expect it ahead of time. If your staff has questions, they can wait until you’re available to answer them, and likewise, your family or friends will understand that you’re taking the time so it won’t disrupt any plans.   

If you decide to have scheduled check-ins though, make sure it’s clear that this is the only time you’ll be doing work stuff while away. If you’ve set up boundaries that people know you won’t be working outside of, your work won’t disrupt your vacation nearly as much. If that means you have to turn off your phone or mute notifications outside of these times that’s fine, but you’ll get more out of your vacation if you can unplug often, and your fellow vacationers will thank you.

Let Customers and Clients Know You’ll Be Away

This is especially important if you’re the one that does most of the legwork when it comes to interacting with customers or clients, but it’s a nice courtesy even if you’re somewhat removed. Let them know exactly when you’ll be gone and who best to reach out to if a question or issue arises so that there aren’t any surprises.    

If you have multiple people taking over for you while you’re away, let these employees know ahead of time who will be able to answer which particular types of questions, and then make a list of those people to send to your client so they aren’t getting bounced around if they call.

Preparing your employees and your clients ahead of time increases trust for both parties and sets you up for success, so it’s a win-win situation.  

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Be Okay with Almost Perfect

The reality of the matter is, regardless of how much you prepare, things still might not exactly go as you planned. If you go into your vacation knowing this, not only will you be able to relax better while you’re away, but when you get back you’ll be able to use the issue as a learning experience, rather than a reason to panic.

If you trained your staff well before leaving and set them up for success, the mistakes they do make – if any – are likely going to be minor. With all of the resources you empowered them with before leaving (and with a periodical check-in if it’s needed), they’ll realistically be able to handle anything that comes their way.

If you handle the mistake with a cool head upon returning, your staff will feel more confident when you decide to leave again in the future and will know how to avoid the same mistakes again.

Schedule That Vacation

It can be easy to fall into the trap of thinking that your business will fall apart without you there 24/7, but in reality if you and your staff are prepared, you’ve set up the right expectations, and you have fail-safes like check-ins in place, things are probably going to run just as smoothly as they would if you were there.

It may take a few times of you taking a vacation before the process is perfect, but each time you can fine-tune it until you feel comfortable stepping out whenever it’s needed. Empower your staff, set the necessary boundaries, make preparations, and trust the process if you’re ready to get out there and go on your next adventure.