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10 Entrepreneurs’ Advice on Keeping Business Running Smoothly While You’re on Vacation

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As a small business owner, you work tirelessly for your company.

In order to preserve mental health, creativity, and drive, you need to take vacation from time to time.

However, as the owner of your business, taking vacation can add even more stress to the equation. If you’re off the map and disconnected, how can you make sure that your business is operating at full capacity while you’re away?

Well, we asked entrepreneurs like yourself just that. Here’s how 10 of them make sure their business keeps running smoothly while they’re on vacation.

1. Think 10 Steps Ahead and Prioritize

“I’ve found that there are a few keys to keeping your company running smoothly while on vacation. First, it’s crucial to hire trustworthy people and the right people who can keep your business running while you’re gone. I also like to think 10 steps ahead—including contingencies that might come up when I’m gone. And finally, it’s important to hold off on anything that’s not critical to the business right before you’re leaving town. This comes down to knowing what’s urgent and knowing what can wait.”

—Erin Breslin, CEO of All Set

2. Delegate Responsibility

“First and foremost, make vacation a priority. Small business owners are notorious for never taking vacations. You need it—burnout isn’t good for your company. Time off can reduce stress and help you have a fresh look on your business when you return. So it sounds obvious, but you have to make it happen. Put it on the schedule and buy the tickets in advance.

After that, delegate in advance. Delegating responsibility is the hardest thing for me and most other business owners. Think about the things that have to happen while you’re gone. Find someone trustworthy well in advance who you can teach to handle the mandatory tasks. The key here is ‘in advance.’ This won’t happen overnight, so you have to prepare.

And finally, let everyone know what to expect while you’re gone. Make sure clients, employees, and everyone else connected to your business know that you’re going to be taking time off in the near future. By setting expectations early, there will be fewer surprises for people while you’re gone.”

—Chris Brantner, Founder of

3. Set Expectations for You, Your Clients, and Your Employees

“I make sure that my employees and clients are prepared before I even go on vacation. For example, for each client I have, I make it a habit to always have multiple employees on conference calls with my clients. Even if they do not speak every time, clients are used to their names, and the transition for when I am out of office is significantly smoother.

Second, I have trained all my employees to share a beginning-of-week list of proposed tasks they’re working on, in the form of an email. That way I can track progress and see if their work is aligned with my expectations. All employees also send an email on Friday with an end-of-week update, first listing the tasks they were planning on working at the beginning of the week and then the progress they made throughout the week against those tasks. When I am out of office, these regular emails are even more important to make sure that the ship is going in the right direction.

Lastly, whereas I make a habit not to work during my vacation, I’m always available to my employees via text messages and, on rare occasions, for quick clarification calls. As a small business owner, it is, realistically, almost impossible to disconnect 100%.”

—Codrin Arsene, Managing Partner and Chief Content Strategist at Digital Authority Partners

4. Get Your Email and Social Accounts Ready

“In order to keep things running smoothly, I need to anticipate the needs of my audience and the way at which they can reach me.

Posting an automatic vacation reply to emails tends to work well and lets people know when I’ll be responding to their questions. My live chat feature can be turned off so messages are directed to my email. Social media posts can be prescheduled and the occasional remote check-in allows me to address anything urgent.

When I come back, I’ll get caught up on emails and check for any social media messages.  I can then resume my live chat, and it’s business as usual.”

—Leah Leitch, Owner of

5. Put in the Work Now So You Can Unplug Later

“If possible, double up on work a week or two before leaving. It’s not fun, but it will really help you feel like you earned that vacation! If you can’t fully turn offline while you’re on vacation, use downtime to chip away at things that will be due when you get back—at the airport, on a plane, on a bus, and so on. If you weren’t going to be doing something anyway, this can help you relieve some of the stress that comes from being away from work.

Also, work with contractors and employees to handle any urgent needs—or even take on projects in your absence. Empower them to take action when necessary, without seeking your input unless it’s absolutely necessary.”

—Maddy Osman, SEO Content Strategist and Digital Marketer, The Blogsmith

6. Have a Solid Backup Plan

“Taking vacations is often extremely difficult for founders, CEOs, and small business owners because there’s a lingering fear that without you the entire organization will collapse. But the reality is that if you’ve built a successful business, it won’t. When I go on vacation I remind myself of that, but also put into place certain safety measures in case of disaster. I send a document to all of my team leads with an outline of who to contact for decisions or input on different areas, I ensure that all of my expectations from the team leads for while I’m away are outlined (so that nothing falls through), and I also delineate under what circumstances I should be contacted. This last point is actually the most important; everyone needs vacations, especially people in high-stress leadership positions, and it’s important to set limits when you’re taking one.”

—Samar Birwadker, CEO of Good&Co

7. Outline Instructions Explicitly

“The best way to keep a business running smoothly is to have instruction manuals for all sorts of problems. In my business, we have manuals for every single operation, and my employees hardly have any problems. If they do, I usually have a trusted employee who can lead others.”

—AJ Saleem, Director of Suprex Tutors Houston

8. Designate Times to Be Online

“When on holiday, we always ensure a period of time is set aside each day to cater to any urgent problems, or required catch-up. In some instances, nothing needs to be done. But planning for this ensures that there’s contingency time if anything does require attention. While relaxing and not thinking about work is what most look for in a holiday, as a founder, it’s not always practical. Alongside this—we love what we do and often have to be talked into taking a holiday in the first place!

Plus, with remote working on the rise, technology is making it even easier to work away from the office while staying in contact with your teams. We actively encourage working remotely, so we’re already to grips with how to make things work when staff is remote. When we’re away, all of the technology is already in place to support that.”

—Alex Franklin, Co-Founder and Director at

9. Keep Thinking Big

“When we take vacations, our minds are usually more creative. So I recommend that small business owners keep a notebook and a pencil handy to write down any ideas or goals you might come up with while you are enjoying the time off and thinking big-picture. Once you come back, sit down and discuss these ideas with your staff to set new goals.”

—Sean Patrick Hopwood, President and Founder of Day Translations

10. Use Vacation as an Opportunity to Give Ownership

“Knowing myself and other small business owners, the difficulty in going on vacation is more with us than with our teams. We find it hard to let go, but it’s important that we do. Not just because it lets us recharge our batteries, but also because it’s an exercise in making the organization less reliant on us. When you achieve that, then you can work on your business rather than in your business.

When preparing the staff, it’s important to make the responsibility appealing, rather than a burden. Tell the person you are leaving in charge: ‘I think you have real leadership potential. I see this as a way of exercising those muscles.’ Second, draw some clear lines as to what crosses the threshold of being worthy of interrupting your vacation: It has to be both urgent and important. And define those terms. Third, encourage your person responsible to consult the rest of the team, rather than make all the decisions solo.”

—William Gadea, Creative Director and Founder of IdeaRocket LLC


There you have it—10 pieces of advice from entrepreneurs who’ve successfully taken vacation and kept their business running smoothly.

While it might seem daunting to take days off when you’re the one running the show, there are steps you can take to make sure that nothing goes wrong while you’re away.

Remember—as a small business owner, you need to prioritize vacation!

How do you keep your small business running smoothly while you’re on vacation? Leave your best tip in the comments!

Georgia McIntyre

Georgia McIntyre

Georgia McIntyre is the director of content marketing at Fundera. She has written extensively about small business finance, specializing in business lending, credit cards, and accounting solutions. Georgia has a bachelor's degree in economics from Colgate University. Email: