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Small Business Owner's Checklist for a Stress Free Vacation


Running a small business is no small task. With limited staff and a never ending list of things to be done, having vacations stress free can sometimes feel impossible. Here are some of the tricks you can use and hopefully make your upcoming vacations stress free and relaxing.

Before the vacation

Here are the things you should do before the vacation -

1. Put all your most important deliverables on the Calendar

As a small business owner, you probably have a never ending list of things that are needed to be done. If you are serious about having a stress free vacation, you will need to focus on only the most important things and leave the rest for "after vacation". Important things for me are anything related to the promises that I'd have made to my customers, important project deliverables, etc. All internal and personal work can be pushed to after vacation.

Also, check with your family and know the dates that are equally important to them. Just like you, your spouse might have some important work related dates. Your kids may have some important dates. Perhaps important wedding or anniversary dates of loved ones that just can't be missed.

Note all these dates on the calendar. This will give you a good idea of when you can be "off the grid" and when you can't.

2. Setup a backup & action plan with your employees

Everyone loves to take some time off during the holidays. But things can go wrong and may need your immediate attention. Websites crashing, orders misplaced, important support inquiries left unanswered, water pipe bursting, electrical outage; there are just unlimited things that can go wrong while you are "out". Make sure you have a strong "back up" plan, there's someone to cover for the most important things, and that person is well trained to handle the situation. A good backup & action plan ensures that the problem is handled professionally and resolved in a timely manner without creating chaos. It clearly defines the procedure one must follow with respect to communicating everyone involved.

Doing this early on will help you take into account your employees' important dates and holiday plans as well. Ask all your employees when they plan to take time off during the vacation and have them assign "backups" for each other. Review all backup plans and make sure everyone is on the same page.

3. Inform employees, customers and vendors

Once your vacation dates have been finalized, communicate it to your employees, customers and vendors. Each employee must know who their backup is while they are gone, and who they are backing up in return. Each customer must know who will be supporting them during the vacation (that is the backup person's name and contact information). Vendors must know who to contact to while their primary contact may be on vacation.

4. Setup email auto-reply and phone greeting

Make sure to set up email auto-reply so that the sender knows you may not be able to respond back immediately. Also update your phone greeting. While doing so, you don't need to lay out your entire vacation itinerary; the most important thing to mention is name and contact information of the alternate person they can reach out to in case of an emergency.


During the vacation

Here are the things you should do during the vacation -

1. Avoid checking work emails and phone calls, except from "your backup"

Many small business owners are good at planning their vacations, but still have a hard time enjoying them! The single most important reason behind this is their habit of constantly checking work emails and phone calls. Avoid the urge of responding immediately to any email that has you in the "TO" or the "CC" list; instead focus on enjoying the time with your friends and family. Only respond when "your backup" person asks for help. And keep the communication limited and focused.

2. Avoid (virtual) work meetings

Internet and virtual meetings have made it possible for anyone to work and collaborate from anywhere. That's great! Unless if you are on a vacation! Avoid joining meetings if weren't personally informed by the host that you have to, have to, be there at that meeting. Let your friends and family know about such exceptions that you will need to make during the vacation. Keep these as limited as possible.


After the vacation

And here are the things you should do after the vacation -

1. Remove email auto-reply and update phone greeting

Removing email auto-reply and updating your phone greeting will help avoid any unnecessary confusion that may occur as a result of the sender receiving two responses - one from your auto-responder, and one from you!

2. Notify your backup, employees, customers and vendors

Make sure to notify your backup person that you are back and can take over from where he/she left. Setup a "handover meeting" with the backup person so that he/she can bring you up to speed with whatever happened while you were on vacation. Prepare a communication plan to be sent out to rest of the employees, the customers who were working with your backup person and vendors.


Plan for your next vacation!

Lastly, vacations are amazing stress relievers. Spending time with friends and family helps build strong bonds and improves overall happiness. Just because you are running a small business doesn't mean you should spend little time planning vacation. Hopefully this small checklist will help you get started in planning your next vacation, and enjoying it as well! Happy Holiday Season!

Tags: cover-story,vacation,stress,tips,checklist

Gautam Tandon

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