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Updated Apr 03, 2023

How to Take a Vacation as a Small Business Owner

These seven steps outline how small business owners can take a worry-free vacation.

Written By: Laura SpawnCommunity Member
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Table of Contents

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One of the upsides of running your own business is that you can set your own schedule and adjust it as needed. However, one of the downsides of being your own boss is that it’s not always easy to take time off. Taking a vacation as a small business owner requires diligent planning and thought, but it is possible and important to take a break, for both you and your company. Here’s how you can take a worry-free vacation as a small business owner.

How to take a vacation as a small business owner

1. When possible, plan vacations around slow periods.

As a successful small business owner, you should be aware of the times of the year when your business slows. However, those slow periods might not always align with the best times to vacation at your destination of choice. For example, your slow period at work could fall during hurricane season in the Caribbean or bomb cyclone season in the Northeast.

Slow periods for your small business also might not coincide with your children’s school vacation schedules. The busiest times for many vacation spots are during popular school vacation periods in the winter, spring and summer seasons. Then you are faced with a decision between pulling your kids out of school to take a break while work is slow or vacationing during their breaks when work might be busy. Building a capable, trustworthy team will simplify this decision come vacation time. 

TipBottom line
Schedule vacations during slow times for your business. For example, if you specialize in ornaments, the summer may be a better time to go than in the thick of the holiday season.

2. Set vacation boundaries for yourself.

Once you decide the best time to take your trip, you’ll want to set boundaries and rules for yourself to adhere to while you are on vacation.

First, decide how connected you want to be. Do you want to completely disconnect from all work for the week or two you will be gone? Some small business owners might have more of a choice in this decision based on the number of managers and support staff they employ.

If it is not possible to completely unplug, decide how much contact you want while you are away. Is a daily check-in on Slack enough? Will you respond only to emails or texts designated as emergencies? Or is it more feasible to be available for an hour every other day, similar to a professor keeping office hours? Regardless of your choice, clearly communicate your work expectations and boundaries before you leave so everyone on your team understands the terms of your time away.

Beyond your accessibility to your staff, what rules do you need to set for yourself? Will you allow yourself one hour a day to check messages and handle any urgent matters? Or would you rather check in at the beginning and end of each day to reassure yourself that everything is holding steady in your absence? Make these decisions ahead of time so you have the best possible chance to truly relax and rejuvenate. [Implement these proven tips for young entrepreneurs to get started in business.]

3. Delegate your work.

As far in advance of your vacation as you can, put a plan in place for how and to whom you will delegate tasks. Is there one person who should handle all your usual daily tasks and to-dos? Can tasks be divided between several people so as to not overload one person?

Beyond delegating, are there any responsibilities you have that can be put on hold until your return? No one likes to come back to piles of work, but if items are not time-sensitive, it’s worth thinking about whether they can wait until your vacation ends. [Read about how to prioritize your tasks as an entrepreneur.]

4. Prepare employees for any foreseeable issues.

When planning your vacation as a business owner, it helps to hypothesize any potential issues that could arise so you can prepare your staff as much as possible. Even if there is a slim chance something could become an urgent matter, it is better to put it on their radar than allow your team to be surprised by the issue while you are gone and not know how to handle it.

Whether you loop in all department heads on potential issues or notify one trusted manager, it is important for both you and your team to have the peace of mind of knowing how issues will be handled during your vacation. Even if you trust your team to problem-solve situations as they develop, it’s reassuring for all parties to formally address matters and outline escalation procedures before you take time away from work.

FYIDid you know
Before you leave for your vacation, update your team on any potential issues that could arise so you can formally address solutions while you're still available.

5. Let important clients know you will be on vacation.

If your business keeps you in regular contact with clients and networking with fellow entrepreneurs, give them advance notice that you have planned an upcoming vacation. This proactive approach not only gives you time to work out any potential issues together before you go, but it also makes your clients and contacts feel valued and important to your business – which, of course, they are.

When connecting with your clients before vacation, discuss any projects you are working on together, any issues that still need to be resolved, whether those issues can be adequately addressed before you go or if they can wait until you return, and who their main point of contact will be while you are unavailable. 

Most importantly, make sure your clients know they will be taken care of while you are away and that they have a go-to team member available to handle anything that needs attention during your absence.

6. Establish a second-in-command for urgent matters.

In order to give yourself the best possible break, consider identifying someone on your staff as your second-in-command, or temporary replacement, while you are gone. You are more likely to get a real break from work if you have someone acting on your behalf and handling anything that you would normally handle.

The person you designate as your backup should be someone you trust implicitly to make decisions on your behalf. But that person should also be someone who is not afraid to say no – and someone who can act as your gatekeeper, helping to protect your precious time off. 

Then communicate to the rest of your team who is acting on your behalf while you are on vacation. Otherwise, you might have team members contacting you about issues that could have been handled without interrupting your vacation.

Bottom LineBottom line
It may be beneficial to have a second-in-command who can make decisions on your behalf whenever you're away or unavailable. This will avoid interruptions to your vacation or your team's progress.

7. Enjoy yourself.

As a successful business owner, you care a great deal about the businesses you created and the teams you have nurtured, but nurturing yourself is just as pivotal to your success. You deserve some time off!

Indeed, business owners can work a seemingly endless number of hours to ensure they are doing everything they can to contribute to the prosperity of their companies. Working that hard can lead to burnout if you aren’t getting the relaxation and playtime you need as well. “Work hard, play hard,” as they say.

All the work it takes for any small business owner to go on vacation can exhaust you even before you arrive at your destination. The planning, packing, putting mail on hold, making sure the pets are taken care of and other preparations can be overwhelming. But just as much care and planning needs to go into your business when you want to take a vacation.

The more you can look ahead and put plans into place for how the work will be taken care of while you are gone – and who will be responsible – the more you can rest assured that everything will run smoothly in your absence and the more you will be able to properly relax and enjoy yourself during your well-deserved vacation.

Why you should take a vacation as a small business owner

While it may seem counterintuitive in our fast-paced working world, taking a vacation has a number of benefits for both you and your business. Here are a few:

  • It helps maintain your health. By taking a vacation, you’re refreshing yourself mentally, physically and emotionally. Burnout often occurs when people feel they’re trapped in the same cycle of work and stress. Vacation time helps break that routine and gives you the opportunity to decompress.
  • It shows confidence in your team. When you’re reluctant to take vacations, this can spread the message to your team that you feel the need to watch them closely to prevent mistakes. By taking vacations, you demonstrate confidence in your team and that you trust them to conduct daily business successfully in your absence.
  • It demonstrates your priorities. When you, as the leader of the business, take a vacation, it shows you place a high value on resting when needed and maintaining physical and mental well-being. In turn, employees will feel comfortable taking breaks themselves, which can avoid burnout.
  • It allows you to practice more delegating. Taking a vacation as a business owner means delegating duties to other employees. Before leaving, entrust important day-to-day jobs to your second-in-command or a trusted advisor.
  • It helps you prepare for unforeseen circumstances. By making preparations for your vacation, you’ll inadvertently be setting plans in place for future unexpected situations that could befall your business. Before you leave for vacation, examine current systems to make sure nothing will fall through the cracks in your absence. If such systems don’t exist, going on vacation will force you to set up and test them.

 Additional reporting by Sean Peek.

Written By: Laura SpawnCommunity Member
Laura Spawn is the CEO and co-founder of Virtual Vocations. Alongside her brother, Laura founded Virtual Vocations in February 2007 with one goal in mind: connecting jobseekers with legitimate telecommute job openings. Laura has nearly two decades of experience working from home and spends her days overseeing Virtual Vocations' team of more than 50 remote employees and contractors, who together have helped more than two million jobseekers over the last 12 years. Laura holds a bachelor's degree in public agency service management from Northern Arizona University. She lives in Oregon with her husband, three children, and two dogs, Ivy and Jilly.
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