In today’s society, we have a culture centered around productivity. The expectation is that you fill your day to the brim with tasks from the moment you wake up until your head hits the pillow. But even when we have technically called it a night, many of us lay awake on our smartphones checking work emails, posting to the company social media accounts, and obsessing over everything that needs to be done tomorrow. Rest is not a priority, especially for the small business owner or entrepreneur.

The bottom line is that we all need a vacation once in a while, and this absolutely includes the boss. Not only is taking time off necessary to avoid burnout, but it also allows one to recharge and come back ready to tackle the many challenges that come with owning and operating a business. Now, any business owner knows that taking a vacation is not as simple as just booking a flight and a hotel. How do you ensure that everything runs smoothly while you are gone? Who will take care of the day-to-day operations, manage clients and inventory, and handle finances? What if there is a business-related emergency? While these concerns are certainly valid, they often make vacationing stressful, rather than restful. Luckily, there are tips that business owners can use to reduce vacation anxiety and actually enjoy their much-needed getaway.

#1 Appoint your second-in-command.

The first step in making sure you can relax on vacation is assigning someone to be the main point of contact for the team. Assign a trusted employee to be the person that the rest of the team will contact first with routine questions, comments, or check-ins. Make sure to include instructions for your second-in-command so that they are aware of your expectations and know exactly what you expect them to handle while you are gone.

When preparing your instructions, consider whether there are any clients that must be forwarded directly to you, as well as whether your second-in-command has the capacity and skills needed to delegate or reorganize tasks as they see fit. Remember, a team is only as great as its leader. Therefore, you must set up your second-in-command for success, as they will be stepping into the leadership role while you are away.

#2 Set clear expectations for your team.

What are your expectations for your employees while you are gone? If they complete all of their assigned tasks, should they contact you for instructions or use their best judgement to decide what to work on next? Are there any special projects that you’ll need them to take over until you return? Do you want them to take on new responsibilities and grow, or stick to their everyday tasks?

Make a clear list of expectations for your team to follow. This will ensure that nothing slips through the cracks, as well as give you peace of mind that your team is staying productive while you are away. Business owners should consider utilizing a task management system to provide a clear picture of each employee’s workload, easily delegate and reassign tasks, and track the team’s progress. Providing this kind of direction for your team will also give them a sense of confidence from knowing exactly what to do next.

#3 Create clear boundaries for yourself (and stick to them).

Smartphones certainly have their advantages, but being constantly connected to your team can be a double-edged sword. Although being easily accessible in case of an emergency is a definite pro, business owners sometimes make themselves too available without realizing it. Gone are the days where you could go “off-the-grid” for a week. Your team can now reach you anytime, anywhere with just a click of a button.

The key to creating a healthy work-life balance is recognizing what you can accomplish without guilt. Is it feasible to check your emails just once a day in the morning? Rather than being available 24/7, are you comfortable with setting aside one hour in the afternoon to touch base with your second-in-command? Whatever boundary you make, be sure to stick to it. Make sure your team knows if and when you are accessible – and when you are not – and be clear about your preferred form of communication. Not only will this help you to realistically balance your time between working and vacationing, but it will also make logging off that much easier.

#4 Provide contact information.

Although your team does not need to know your complete itinerary and exact whereabouts while you are on vacation, you should still provide them with more than one way to reach you in case of emergency. For example, is your traveling companion comfortable with you providing their phone number to your team if you cannot be contacted directly? What about giving your second-in-command the hotel’s phone number? Keep in mind, however, that you must also set boundaries when providing these additional contact methods. Perhaps your team can call the hotel, but only under a specific set of circumstances or if they have been unable to reach you after a certain amount of time.

#5 Trust yourself.

It is easy to doubt yourself and your capabilities as a business owner when you are not there to oversee and control every aspect of your business. However, you must remember all of the steps you have taken thus far to ensure your business’s success. You have invested significant time and energy into training and developing a capable team, and it is time to have faith in them. Trust that your hard work will not crumble as soon as the plane takes off and remember that you have earned the reward of taking a step back to focus on yourself.


To recap, five tips that business owners can use to actually enjoy their vacation are: (1) appoint a second-in-command, (2) set clear expectations for your team, (3) create clear boundaries for yourself, (4) provide contact information, and (5) trust yourself. Remember, the culture around productivity does not just affect the boss. The overall health of your business can suffer if you spread yourself too thin, and your employees need to know that you have confidence in them. Allow yourself, your business, and your team to grow by giving yourself a break. You’ve earned it.

Information in this article is provided for educational purposes only and not intended to constitute legal advice. Please consult with a licensed attorney in your jurisdiction for help with your specific situation.

For assistance with Maryland business matters,


the Law Offices of Elsa W. Smith, LLC at