5 Ways to Plan a Vacation as a Small Business Owner

5 Ways to Plan a Vacation as a Small Business Owner

5 Ways to Plan a Vacation as a Small Business Owner

Summer’s a short hop and skip away! But that doesn’t mean the same thing when you’re running your small business as it did when you were in school, does it? As a small business owner, you don’t have the luxury of working part-time, spending 90% of your paycheck on parties, and taking spur-of-the-moment vacations. Of course, that doesn’t mean you should give up altogether on taking a break from work and going on a vacation.

We reached out to small business owners around the world to get their advice on how to keep your business thriving, even when you’re on vacation. Here are five ways to get ready for a vacationbut you don’t have to take our word for it:

Choose a time when business is slow. 

Depending on your field, taking a week (or even just a long weekend) away when your clients are off as well can maximize your fun while minimizing your stress.

Jeff Moriarty of Moriarty’s Gem Art said, “My family owns a small jewelry business in Crown Point, IN. We take two weeks off per year. For any small business it really depends on when your ‘season’ is. For example, right after Christmas our main season is over and it is very slow, so we take a week starting the day after Christmas off. For the other week off, we look at the slowest weeks from the past 5 years and take that week off. Usually in mid June, when kids are getting off school and families are going on vacation.”

Max Robinson of Turnbull & Scott Industrial Heating had this to add: “Whenever I’m planning to take time off, I always choose a time that I know will be quiet for the business. For us, this is usually the summer months (more issues arise with heating systems during the winter). You’ll always be missing out on business when you take time off, but you can minimize the impact by choosing a generally quieter period to take your vacation.”

Don’t keep it a secret. 

Well in advance (we’re talking a month or two), let your employees know of your plans. Business owners who are planning to close up shop during their absence will want their customers to know ahead of time.

Steven V. Dubin, President of PR Works, responded, “Plan well ahead. This offers ample time to have a plan and relish the anticipation. Alert your client of when you will be unavailable. No surprises. No procrastination.”

“In order to have a stress free relaxing vacation you must plan ahead… Also, let your customers know in advance when your business will close so they have time to prepare for their shopping,” said Lisa Chu, owner of Black N Bianco.

Alana Rivera, founder of Etta + Billie said, “Turn this into an opportunity to connect with customers! I always let both my B2B and B2C customers know when I’m going to be away and where I’m going via our newsletter. This sets the expectation for how accessible I am and how the business will be operating while I’m gone (i.e. orders will ship out per normal or things will ship a week later). Not only does it strengthen our business relationship, it’s also an opportunity to connect on a more personal level. When I went to Portugal last summer, I let my wholesale partners know a few weeks ahead of time that I’d been gone for a couple of weeks and asked for any suggestions of places to eat or see. Not only did I get an influx of orders but I also got wonderful recommendations and well wishes!”

Alternatively, owners who are keeping their business open during the interim, or online-only shops, may choose to keep their vacation on the down-low. Efuah Faler, co-founder of Devoted, said “We run an online business so we don’t have to physically shut up shop. We prepare any blog posts or marketing material to go out while we’re away.”

Over-prepare in advance. 

Alana Rivera of Etta + Billie had plenty to share on the subject: “Over Prepare! After a five day trip to NYC a few years ago, where I spent more time on the phone with employees then I did exploring the city, I decided things had to change. At least a month before any trip, I sit down with staff to go over as many potential issues and situations that may come up while I’m gone and how to handle them. This turns into a document that I share with everyone. We discuss who is taking on what tasks while I’m gone and who to contact in case of emergencies. A week before the trip, we go over these items again. I confirm that everyone has a contact sheet, email scripts, knows who is responsible for what, and where I’ll be while I’m gone (and how accessible I am). It can feel a little overzealous but it makes a huge impact in how comfortable everyone is while you’re away and, I promise, will reduce the amount of frenzied phone calls you’ll receive.”

Simon Slade, CEO and co-founder of SaleHoo, added: “The key to continuing a smooth-running operation while you’re away is to build a detailed wiki to document how to perform business tasks and to include input from all staff members. By encouraging your employees to document their actions as they complete assignments, and you do the same, a blueprint of all your business’ daily operations will emerge that team members can refer to while you’re on vacation to limit the contact necessary while you are gone. This wiki also serves a fantastic introductory resource for new staff members.”

Finally, taking advantage of online payroll, HR, and accounting systems is just one more way that your business can be automated while you’re gone. Make sure you don’t miss a beat while you’re away by integrating these services into your everyday routine.

Decide whether to keep your business open, closed, or online-only. 

Every business is different, and you’re the only one who knows what’s best for you. With that in mind, here are three distinct approaches that can work for you:

1. Keep your doors open: Wendy Gorrie, General Manager of BAASS Business Solutions Inc., had this to contribute: “I would never fully close the shop, if it is an unplugged with no communication vacation preparations include:

  • Prepare the high need customers prior to departure to see if anything was on their mind that they may need during my absence.
  • Prepare a one line out of the office response for email and a short voice mail response stating when you will be responding to requests.
  • Put a trusted employee in charge of personal email, empower them to make certain kinds of decisions and act on your behalf, define the boundaries as best you can, ie: do they have decision making authority, what spending approval do they have.

If the vacation allows some contact with customers and employees I would do all of the above except handing the email over to an employee.”

2. Close up shop: Carrie Seibert is the founder and owner of Soap Commander, LLC, and is a big fan of closing shop while on vacation. “We are a completely online business and have chosen to “close” when we are away on vacation. We keep our site running, but put a notice on the landing page specifying the dates we are closed and encouraging them to browse while they’re waiting for us to return. We give advance notice of our vacation time across all social media boards and find that many of our return customers are encouraged to hear that we are taking time off for a break. It actually increases their affinity for our brand, rather than detracting from sales.”

3. Online only: Finally, Marina Manasyan, co-founder of Barcelona Eat Local Food Tours, conducts her business online and plans ahead when on vacation. “I am also an avid traveler, plus my husband works abroad, thus I do travel often for long weeks. The sales for my business are made 100% online, while the experiences happen on the ground. When I am not in town, I organize things with suppliers by phone/email in advance as much as I can, and our tour-guide is the one that controls the day to day, which apart from the tour itself implies managing issues with customers and suppliers (change in dates, dietary restrictions…).”

Hire a virtual assistant. 

Mickey Swortzel, CFO of New Eagle, made it a point of business to hire a virtual assistant to make sure things went smoothly while on vacation: “This year, for the first time in 9 years, I was able to take 9 day consecutive days off. This was made possible by making a few key changes 45 days in advance of my trip. The first was hiring a virtual assistant to manage my email and calendar. That allowed me to know that any urgent issues would be appropriately handled. In addition, I looked at the information sources I had sole access to (i.e. banking) and worked to provide appropriate permissions to the systems so team members could have access apart from me. This left very few things where I was the bottleneck and allowed the team to effectively serve our customers in my absence.”

Lastly, Melisa Smith, founder of The PVA, a virtual assistant staffer company (and the author of a bestselling book, Hire the Right Virtual Assistant), had this to contribute: Start acting immediately as if you are on vacation. What can and should be automated? Remember now it’s a vacation, but what if it were an illness or family emergency? Whatever cannot be automated should be outsourced. You are the brains of your company—what are you physically doing that you shouldn’t be or at least have the option of delegating to someone else? Find a point person who can answer questions in your absence. Coming back to a ton of emails is no fun and will make you think twice about taking another vacation, which shouldn’t be the case.”

Just remember to time your vacation correctly, leave nothing to chance, and enjoy your time off! Vacations are an essential part of life, and can provide you with many opportunities to learn, grow, and return to your business with a new lease on life.


This article was originally written on March 29, 2017 and updated on January 27, 2021.

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