10 Tips to Take a Vacation as a Business Owner

take a vacation

It’s August, and for many of us that means it’s time to put those vacation days to use with a well-deserved holiday. While that may evoke images of sandy beaches or exotic locales, those among you who own your own agency or development shop may have slightly different visions: clients panicking, work piling up, and an unmanageable inbox awaiting your return. How can you take a vacation when you run the show?

Though it seems tough, taking time off is incredibly important, especially as the owner. In addition to helping kickstart your creativity, energy, and enthusiasm for work, taking your vacation time and creating a healthy work-life balance can also lead to lower blood pressure and a reduced risk of heart attack. Plus, what better way to get rejuvenated than spending quality time with loved ones away from work?

So fret not. You too can manage to have fun, enjoyable time off—it just takes some planning. To help you prepare for your next vacation (or to burn time as you sit in the office while everyone else is on a getaway), we've rounded up the best advice we could find around the web, on how to prepare for your own vacation time. From informing your clients to writing a killer out of office message, we've got it all. Let's take a look. 

Are you a freelancer? Check out our Freelancer’s Guide to Taking a Vacation.

1. Put in work ahead of time

Before going on vacation you should make the necessary preparations. Over-prepare if necessary.


The amount of work you need to do before taking off depends on your industry, your particular business, and the kind of team you have. This advice from Opstart means taking stock of all those factors to determine what needs to be done. Is payroll sorted while you're gone? Is your customer service team equipped to handle any questions that arise? Should you leave documentation, processes, and how-to guides for your employees to leverage? Do they need to know what hotel you're staying at? Providing as much information before you leave will help you rest easy and actually enjoy your time off.

2. Be strategic with clients

If you have clients who tend to procrastinate, tell them you're going to leave (or be will be unavailable) starting several days before you actually plan to leave for vacation.

Janet Attard, Founder of Business Know How

There's no such thing as a last minute trip when you own your business. This advice from Janet Attard at Business Know How rings true for anyone with that one client who always gets things to you just under the deadline. By informing them of your vacation in advance, and adding a few days to your start date, you'll save yourself from panicked last-minute emails when they receive your autoresponder. 

This advice isn't just for your procrastinating clients, though. For important clients or partners that you’re working with, giving them a heads up is common courtesy. Let them know that you'll be away a few weeks before you leave to give them time to arrange schedules, bump up work, or reprioritize. Be sure to leave them with a contact person, too, in case things go sideways.

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3. Flex your delegation muscles

Make sure everyone has specific duties and responsibilities that need to be handled in your absence.

Steve Strauss, Author of The Small Business Bible

Steve Strauss in USA Today highlights the importance of spreading out your responsibilities among your staff while you're away. When you've built your business from the ground up, delegating tasks—especially those that you've personally handled since the start—can be especially challenging. But delegation is really important, beyond just providing you the opportunity to take a holiday. Delegation leads to improved efficiency, happier staff, and a more sustainable, long-term business plan.

You should practice delegation before you take off on your holiday so that this isn't the first time your team is left on their own, and so you're more comfortable with the whole situation. Specifying a second in command (see point #6) will help ease the pressure, too.

4. Identify potential disasters

Discuss and write down under what circumstances you want your second-in-commands to contact you while you’re on vacation.

Don Breckenridge, Co-Founder of Hatchbuck

Don Breckenridge, co-founder of Hatchbuck has this advice for business owners. Mitigating for every potential disaster is impossible, but you can at least set standards for situations in which your staff should definitely get in touch with you. Drawing this boundary will help you relax, and help your colleagues know what's a true emergency, and what can be handled when you get back.

This scale varies and depends on your industry, but could include your app breaking, an important client having issues, or a natural disaster—the degree that you want to disconnect is up to you. Just make sure you've been clear about these guidelines, and give your staff a foolproof way to contact you if disaster strikes.

5. Stay home

A simple “staycation” can positively impact your health and your business.

Ty Kiisel, Editor at OnDeck

You don't need to travel great distances or go on epic adventures to get a break from work. This advice from Ty Kiisel at OnDeck highlights just how impactful staycations can be, too. The whole point of using your vacation days is to relax—if the thought of getting on a plane or camping for a week makes you panic, you're not going to get the benefits of taking time off. 

In addition to being a budget-conscious choice, staycations also save you all the extra stress of packing, traveling, and planning a regular vacation. Whether your staycation includes a spa day, a fancy dinner, playing tourist in your hometown, or something else, you'll be just as refreshed as if you went away. 

Staycations have the added benefit of keeping you close to home, if you're nervous about fully disconnecting from work.

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6. Wait for a slow season

Timing your vacation and having a plan in place for when you’re away are important if you really want to relax and completely unplug.

Zoe Weisner, Marketing Writer at BlueVine

Being strategic is key with this advice from Zoe Weisner at BlueVine. With August already being a hugely popular month for taking a holiday, this may be the best time for you to go, too—clients are also on holiday, and there's a good chance that those still in the office are working at a slower pace too. 

But if that's not the case in your business, waiting to schedule your holiday until your slow season can have a lot of benefits. Not only will travel be cheaper and the chance for disaster at work lower, but with fewer crowds your whole travel experience will be more relaxing, especially since you won't be wondering what your clients and staff are getting into while you're away.

7. Have a second in command

Your second-in-command should take notes for you at important meetings, handle urgent calls or emails if you cannot be reached, and make decisions or answer questions on your behalf.


This advice from Forbes means empowering your colleagues to act on your behalf. Since you've already set boundaries for what constitutes as a real disaster (see point #2), your second in command will be able to manage everything else while you're gone. This requires a good amount of trust, but with the right person you can really disconnect, knowing that they have your business's best interests at heart.

Your second in command can also serve as your contact point. If you're scheduling check-ins (see below) or have set disaster guidelines (see point #2), this person can be the one empowered to reach out to you if needed. That way, you can get a succinct update from one single person, instead of having a dozen voices fighting for your attention.

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8. Have check-ins

If you're not going off the grid completely and plan to make yourself available by phone during your vacation, tell your coworkers or employees the exact times you can be reached.

Robert Half

Sometimes fully disconnecting just isn't possible. In those cases, Robert Half suggests setting up specific times to check in with your work. In addition to keeping you connected with any goings-on, you're also accessible if anything goes wrong. This advice comes with a caveat, though: if you're scheduling check-ins, stick to your schedule. Responding out of time or picking and choosing who to respond to can set a bad example and cause frustration with both clients and staff. Exercise that self control and check in only when you've said you would.

9. Get to the essentials

You’ve got to limit yourself to basic tasks like checking emails, following up with key employees or checking analytics.

Nash Riggins, Staff Writer for Small Business Trends

When totally disconnecting isn't possible, you should also limit the work you're willing to do (in addition to scheduling check-ins; see above). This advice, from Nash Riggins at Small Business Trends, is all about stripping your to-do list to its essentials. Your vacation (even if it's a working vacation) isn't the time to take on new clients or throw yourself into a tricky project. Instead, you should limit your working time to the absolute must-dos—checking email, watching analytics, and checking in with your second in command—and delegate the rest.

10. Schedule your autoresponder

Make sure you get the tone right. If you’re off on an adventure, and you don’t anticipate any catastrophic emails coming your way, feel free to have a little fun with it.

Courtney Symons, Lead Writer at Shopify

Shopify’s Courtney Symons had this advice to share about setting up your out of office notification. While the best autoresponders are succinct, clear, and informative, you can always take yours to the next level with some humor. While crafting your own funny out of office message, just remember that you give readers the information they need, too: when you'll be back, and who they can talk to in the meantime. 

You can find some excellent examples of funny out of office messages across the internet, but we'll leave you with our favorite here:

Book that vacation

Vacations aren't inaccessible to business owners—in fact, it's almost imperative that you schedule time away from work so that you can come back refreshed and ready to tackle new challenges. With this advice, you can make the whole holiday process smoother and less stressful, so that you can really disconnect and relax.

What's your best advice for taking a vacation? Let us know in the comments below!

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