Taking Time Off is Good for Business: How to Prepare Your Business for an Out of Office Vacation

As a small business owner, do you ever feel like scheduling in a vacation is tricky? Your subconscious tells you that you’ll fall behind, miss leads and new clients won’t hire you, or your current clients will be frustrated about not being able to reach you? 

You’re not alone—entrepreneurs often grapple with how and when to take a vacation and usually struggle with the idea of detaching from work obligations and concerns when out of office. 

It’s believed that entrepreneurs have a greater likelihood of mental health challenges, with the compounded stress and responsibility of owning a business. It could even be argued that entrepreneurs can’t succeed without taking a vacation, otherwise it could be difficult to avoid burnout, stress, and even depression. 

On average, self-employed entrepreneurs work well over 40 hours a week, and 80% of self-employed individuals believe they work too much. A UK study reports that entrepreneurs work 63% more than other workers, some working over 72 hours a week. 

But research supports that time away from your desk not only improves mental health but also physical wellbeing, and a planned vacation can even drive productivity—it’s the carrot at the end of a stick. 

In our fast-paced society, where "the hustle" is equivalent to "making it", working professionals often forget the power of pressing pause. A pause can be a shift in gears; it's like driving up a hill—it takes some work, it takes effort. However, even a short pause and a shift in gear helps build momentum to steadily get up a hill—and the momentum is dependent on that shift in gears. 

Travel and time away from the office can lower stress levels, provide fresh perspectives, and in the event of a vacationing CEO, time off can help company morale. 

When leaders model and value a healthy PTO policy, employees can better understand that taking time off isn’t a sacrifice, but an integral part of company success. This kind of behavior often leads to a more engaged, productive, healthy, and satisfied staff.

Here are some tips to consider when planning your extended time off:

Book Your Ticket

Bite the bullet and snag that ticket you’ve been stalking on Google Flights fare alert. By choosing to commit to your trip, you’re making a conscious effort to invest in yourself, your peace of mind, and even your business. Pro tip: “working” vacations don’t count. Don’t book your vacation as a bookend to a conference or seminar. Reserve at least one vacation a year for absolutely no work. 

Plan Ahead

Once your travel is booked, you can give your team, collaborators, suppliers, and/or need-to-know customers an advanced heads up for your time away. This will also allow you to book your important meetings or initiatives around your vacation. 

Pro tip: Don’t schedule important events, campaigns, or launches the week prior to or following your vacation. This way, you can avoid last-minute issues, mistakes, or problems before you leave. 

Stay on Schedule

Make sure you’ve reviewed all scheduled content for social media, blog posts, and email marketing that will publish while you’re OOO. Get those pieces on the calendar, and make sure you have a reliable system in place to ensure the content is published on time, even when you’re out. 

Don’t promise things you can’t deliver before—or during—your vacation. If a client is expecting something from you, do your best to ensure your team gets the deliverable to the client before your vacation, or that a plan is in place to move it off your company plate before you return. This way, an out of office doesn’t impede a project from moving forward. 


Have a Back-Up

To ensure things run as smoothly as possible while you’re away, enlist the support of a back-up. If you have a team, delegate as much as possible in the lead up of your vacation. Task someone with the duty of being your second-in-command, and set up a pre-vacation and post-vacation check-in with them to ensure you don’t miss anything important. Running solo? Consider hiring a virtual assistant to manage your inbox, social media accounts, and phone calls in your absence. Give your second-in-command or an assistant your reliable phone number so, in the event of an emergency, you can be easily reached. 

Define “Urgent” and “Emergency”

A smart way to avoid unnecessary interruptions while away is to clearly define what constitutes an urgent issue. Get ahead of any issues by anticipating them before they occur. Create a list of possible worst-case scenarios, and then outline clear instructions as to how your team, assistant, etc., should handle a particular problem. Without a plan like this in place, things can escalate quickly! 

Make Another List

In addition to your Emergency List, be proactive and create a list of important dates, phone numbers, log-in credentials, customer FAQ, etc., so that your team can appropriately respond to and/or manage any non-urgent issues that come to them. 


Set-Up Your OOO Auto-Reply

Yes, auto-replies can be a little annoying, but it’s even worse to be left hanging without any idea of when to expect a reply. Before you leave for your trip, make sure to provide a clear and easy-to-understand auto-response for your email. 

Be specific. Don’t just say you’ll get back to the sender at your “earliest convenience.” Give a specific date for when you will likely review and reply to their email. We recommend giving yourself a buffer of 1-3 days after you return to the office. It’s OK to give a date range, too. 

Prep your OOO auto-reply to show that you’re human and that everything is being taken care of, and remember to include a call to action. Why miss out on the opportunity for a new client or a new subscriber?

  • Assure your sender that things are being taken care of in your absence—if you have an assistant or co-worker that could aid with anything while you are gone, include their name, title, and how to reach them. 

  • Include a brief direction of where your email sender can learn more about what’s new at your company by linking to your company blog, newest product or service, or include a link to schedule a consultation, appointment, etc. 

  • Make sure you block out your time away in your calendar so that no one accidentally books consultations, appointments, or other meetings with you while you’re out of the office. This sounds like a simple thing to remember, but it is often the last thing addressed.

Enjoy Your Time Away 

Now that you’re ready to get out of the office, remember these takeaway tips from our team:

  • It’s OK to disconnect. Our Administrative Manager, Maura, shares since it’s hard to fully unplug from work, her favorite places to get away are those without cellular service or easy access to wifi. We challenge you to take extended breaks from your technology while you are OOO! 

  • Take a deep breath. As soon as a work-related thought pops into your mind, take a deep breath, trust your preparations, have faith in yourself, your business, your customers, and your team; believe that everything will be taken care of appropriately. 

  • Explore. Whether you enjoy a staycation or an around the world trip thousands of miles away from home, remember to fully experience your surroundings. As avid travelers, we’ve learned that every place is unique in its own way and can teach us something new and valuable—stay present and engaged with your trip and you might find some inspiration or new insight that could help you be more successful upon returning to the office. 

  • Have Fun!

Enjoy your time away from your desk, and you’ll notice a remarkable change in your stress levels.

Are you looking for support to help you feel better doing the work you do? 

Contact us to set up a free mini-coaching session with our in-house certified professional coach. Coaching can help you find for ease, confidence, and joy in your business.