Pack Your Bags: How To Set Up Your Business To Go On Vacation

Pack Your Bags: How To Set Up Your Business To Go On Vacation

Lifestyle | Posted by - June 25, 2019 at 12:30 am

Going on vacation is not just a lofty ideal, research shows that breaks are crucial to keeping your stress in check, your health at optimal levels, and renewing your enthusiasm and productivity. But if you run or head a small business, you might find going on vacation feels daunting. How do you set everything up so you can slip away for a week here and there, or even longer?


Going away on vacation is the perfect opportunity to encourage employees or co-owners to step up and run things while you’re gone, says Jessica Glazer, Strategic Recruitment Director/President of MindHR, a staffing and recruiting agency.

“Ensure that you have A-players, people you can rely on and trust to do the work you need done.” 

In lieu of that, sometimes you might want to find trusted colleagues who do similar work to yours and will pick up your slack without taking over your clients.

“Understand that if you’re gone for a week or two, your company will not crumble,” Glazer says.

However, you might want to be thoughtful about what tasks you delegate, says Tim Trampedach, CEO of Torqued, an importer and distributor of motorsports parts. 

“Administrative jobs or technical skills like graphic design or media are good jobs to delegate. But you can’t delegate big decision making or creativity if it’s your role,” he says. This leads to the next consideration: when to schedule your vacations.


While there might be an ideal time to hit the beach, the snow or the mountains, it might not always coincide with the ideal time for your business.

Matt Schmidt, CEO of Diabetes 365, says, “Schedule a vacation during a slow period of the year. Less work for your employees and fewer tasks to complete will allow you, the business owner, to relax a bit more.”

This may also eliminate the need for being “on” in replying to emails and texts when you’re supposed to be relaxing.

Better yet, schedule your vacations well in advance. Ben Blackmon, Chief Results Getter for One Focus Marketing will schedule his vacations as much as a year in advance.

 “I share my calendar with my clients as they come on board and email them a week ahead of time to remind them I’ll be off and unreachable.”

Paige Arnoff-Fenn, Founder and CEO of the marketing agency Mavens & Moguls has found that planning in advance method to be quite successful on a number of counts. Not only does it ensure you schedule that necessary down-time, but it allows colleagues, clients and employees time to prepare for your absence.

“No one was surprised when I left because I gave everyone ample opportunity to discuss back-up plans and raise questions,” Arnoff-Fenn said. 

Moreover, it had the added benefit of driving some of her clients who were waiting to commit to making the decision to work with her before she left. 

“Not a bad way to accelerate the sales cycle by creating a sense of urgency every now and then,” she says.


Where possible, Trampedach recommends automating any process that you can. “Many of our core business processes that we execute on a day to day basis, such as order processing or taking on new inventory are automated, or at least well documented,” he explains.

This allows employees to act more in an oversight capacity, he says, rather than having to make decisions and judgment calls. 

Additionally, depending on the nature of your business, dashboards and monitoring can make it possible to keep a distant eye on your business without having to be fully involved.


If you’ve truly set up your business to run without you, you have earned the ability to leave your technology behind. That might be the only true way that you will feel refreshed.

“Let it go and enjoy your time away,” Paige urges. “It will all be there when you get back."

Tags: business, business advice, business travel, downtime, entrepreneur, mental health, time management, travel, travel tips, vacation

Jordan Rosenfeld

Jordan is a freelance writer and author of eight books--six writing guides and two novels--most recently: How to Write a Page Turner (Writer's Digest Books). Her articles and essays have appeared in such publications as The Atlantic, Daily Worth, The New York Times, Quartz, Scientific American, The Washington Post and many more. Follow her: @JordanRosenfeld on twitter, or visit:

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