Small Business Owner’s Guide to Getting Ready for Vacation

Entrepreneurs and small business owners are notorious for not taking vacations. Sixty-six percent of small business owners find it difficult to take vacations, according to the June 2015 Office Depot Small Business Index.

And that’s a shame, because a relaxing vacation is good for your business. You’ll come back with fresh ideas and a new, positive attitude. What seemed like crushing problems or ever-present worries get put in perspective.

Your personal life will benefit, too. So many business owners make sacrifices and put in long hours each week. A vacation is an opportunity to reconnect with your spouse and kids.

Benefits of Taking Vacations as a Small Business Owner

Top Tips for Getting Ready for Vacation as a Small Business Owner

The trick to a worry-free vacation is proper planning. Follow these tips to get ready for vacation and you will soon be slipping into a pair of flip flops:

Preparation Strategy Description / Key Points
1. Assign a Deputy – Designate a person to be in charge during your absence.
– Accept that mistakes might occur.
– If no managers, clearly define authority limits to employees.
2. Clear Your Plate – Avoid leaving unfinished projects.
– Work an extra hour or two in the lead-up to your vacation.
– Start with easy tasks to build momentum.
– Deliver projects early to maintain client trust.
3. Let People Know – Notify key contacts like clients about your vacation.
– Send reminders a few weeks and days before departure.
– Personal connections can be made when discussing plans.
4. Update Your Messages – Set up auto-reply email messages.
– Change voicemail to inform callers of your absence.
– Remember to revert to normal messages upon return.
5. Plan for Problems – Anticipate potential issues.
– Brief your team on how to handle various scenarios.
– Assure the team they can contact you for major issues.
6. Specify Emergency Numbers – Provide your personal contact for emergencies.
– List other contacts like insurance agents, attorneys, etc.
– Clarify preference between texts or calls.
7. Write Down Procedures – Document critical business procedures.
– Have employees practice procedures before you leave.
– Consider recording a video of critical tasks for reference.
8. Pay Your Bills – Ensure all upcoming bills are paid.
– Make arrangements for any bills or payroll that might come due during your vacation.
9. Clear Your Calendar – Check calendar for any upcoming events.
– Cancel or reschedule meetings and events that coincide with your vacation.
10. Don’t Be Available (Much) – Try to truly disconnect from work.
– If necessary, limit work-checking to a specific time slot daily.
11. Pack Light Tech – Opt for lighter tech options like tablets.
– Pre-download necessary apps.
– Use cloud storage or thumb drives for important documents.
12. Share The Memories – Share your vacation experiences briefly with the team.
– Consider bringing back small gifts for the team as a gesture of appreciation.

1. Assign a Deputy

getting ready for vacation

You’ll need someone to be in charge when you’re gone.

If you have managers in your company, they know their roles already. If you have more than one manager on your team and they are peers, it may help to designate one of them to be the main person in charge, in case of emergency.

Accept that mistakes will happen. Be sure your deputy knows he or she has your full confidence.

But what if you don’t have managers? That’s when you have to be clearer with your employees. They may need special instructions as to their authority and how far that authority extends. Make sure they know when to reach out to you.

2. Clear Your Plate

getting ready for vacation

You won’t like thinking about that stack of unfinished projects when you’re digging your toes in the sand, with sunscreen in one hand and a margarita in the other.

If you haven’t got a staff to delegate to when you’re inching out the door, here’s how to clear some of this stuff off your plate before you leave. Simply log an extra hour or two each day for a week or two in advance, whittling away those projects. That’s much better than pulling an all-nighter just before you’re due to drive 12 hours to the beach.

If you are a procrastinator, start with the easiest task first. Finish it — and the feeling of accomplishment may just get you fired up enough to tackle another project. And another.

Projects delivered before deadline make clients happy. And happy clients are less likely to fill your email box with missives or bug you by phone while you’re trying to decompress in paradise.

3. Let People Know

getting ready for vacation

Tell key people, such as clients and others who are used to dealing with you personally, that you’ll be away. It sets expectations. Knowing that, most people will not make urgent demands just before you leave.

Notify them a few weeks before your departure. Then provide another reminder a few days before you pack your bags. Here’s an example of a “going on vacation email” to send to clients and other key people:

“Just a short note to remind you that I will be on vacation  August 10 – 25, enjoying the sunny ocean at Myrtle Beach. For any product or service issues, Joe can assist you at [phone / email]. For anything else, please contact Mary in my absence at [phone / email].”

There’s another benefit to keeping clients in the loop. Discussing your vacation plans makes you a bit more human in their eyes. You’re no longer just the owner of a business. You and the other person may find you have a common interest in snorkeling, for example, and can better connect.

4. Update Your Messages

getting ready for vacation

Some people like to create an auto-reply message for their email. That way, when a new email comes in, the sender gets an immediate response back that they’re out of the office. Simply adapt the message in Tip 3 above.

For Microsoft Office 365, set up the Automatic Replies feature. Or use the Rules and Templates functionality for Outlook desktop versions.

GMail and Google Apps email have an out-of-office reply feature that is easy to set up.

Don’t forget your voicemail, either. Consider leaving a recorded message alerting people that you’re out and will be returning messages more slowly than usual. Here’s a sample vacation voicemail message:

“Hi, this is [me]. Thanks for calling! I’m out of the office until [date]. If you have an urgent matter, please call Brittany at [number]. She will be glad to help.  Otherwise, please leave a message and I will get back to you when I return.”

Important: put a reminder in your calendar to swap out those messages as soon as you get back. Don’t be the person who still has that old vacation voicemail message playing weeks later.

5. Plan for Problems

getting ready for vacation

Don’t automatically assume everything will go wrong in your absence — it won’t! But as you’re getting ready for vacation, do try to anticipate potential scenarios that might blow up.

Brief your team. Explain what you would do in each situation.

And assure them it’s okay to contact you if they feel the situation is beyond them. It’s better to interrupt your vacation for an hour, than to spend days fixing a mini disaster on your return.

6. Specify Emergency Numbers

getting ready for vacation

Make a list of two types of emergency numbers to give to key employees.

The first set of emergency numbers is your own, for employees who might need to reach you.

A mobile phone number is best. Give an alternate, too, just in case yours is turned off or the battery is dead — perhaps your spouse’s mobile phone.

Specify whether you want texts or calls. A short text message exchange can be less intrusive than a voice call, yet more immediate than email.

Next on the emergency contact list, designate people who may be able to answer questions in your absence. This list could include your business insurance agent, attorney or IT consultant.

7. Write Down Procedures

getting ready for vacation

Go over important business procedures that you will be delegating in your absence. For example, someone other than you may need to open the shop in the morning or close the office at night. Typical procedures that trip people up include:

  • setting the security alarm or turning it off in case it was accidentally triggered,
  • running credit card transactions,
  • processing payroll,
  • rebooting servers,
  • logging in as an admin to key software systems, or
  • anything the person is not used to handling.

Ask the employee to perform the procedures for you a couple of times before you leave.

Always write down the procedures as a backup, too. (Memory is a tricky thing.)

A quick video of you performing key procedures may be even better. Ask the employee to use his or her mobile phone to record it, so it can be a convenient refresher.

8.  Pay Your Bills

getting ready for vacation

Unpaid bills have a way of nagging and intruding in our minds. Who needs that?

Leave for your vacation with a clean slate of accounts payable. Pay invoices, credit card statements and bills that will come due while you’re gone. Make sure payroll is set up to be processed while you’re gone as well.

9. Clear Your Calendar

getting ready for vacation

This might seem obvious, but the problem arises when people try to go by memory. Or they forget about recurring teleconferences and standing meetings that don’t appear on their calendar.

Actually check your calendar — before you leave. And take a moment to consciously think about those standing meetings and calls, so you can tell people not to expect you.

10. Don’t Be Available (Much)

getting ready for vacation

Resist the temptation to take work with you. If you are glued to your laptop or phone, it not only will spoil your time but your family’s time, too. Imagine the grumpy faces of your family as they sit around waiting for you to get off the phone, so you can all go hiking.

Still, most business owners do want to stay in touch. They just don’t want to involve themselves so much that it stops feeling like a vacation. Seventy-six percent of business owners check their phones and email on vacation, according to the Office Depot Small Business Index survey.

If you must stay in touch with your business, limit it to a specific time slot each day. For example, you could set aside one half hour each morning at 9 a.m. to field messages that can’t wait or check in with staff. Once the 30 minutes are over, give yourself permission to go play with a clear conscience.

11. Pack Light Tech

getting ready for vacation

Luckily, technology has made it easier than ever to stay in touch remotely. For those who don’t have staff, but still need to handle a few critical tasks while on vacation, mobile devices are a godsend.

A tablet or even a smartphone can substitute for a laptop while away. Just take the time to download a few key mobile apps in advance if you need to. A good app can make mobile transactions faster and easier.

Documents stored in the cloud can be accessed from a smartphone or tablet.  If you don’t use the cloud, take a few minutes before you leave to transfer critical files to a thumb drive.

12. Share The Memories

getting ready for vacation

Remember:  a little R and R can bring some ROI (return on investment).

Upon your return, share your memories with your team for a few minutes. Not to bore them or make them feel bad that you were on vacation and they weren’t — but to reveal your human side. It strengthens staff relationships.

A nice touch is to bring something inexpensive back for team members, if practical. Boxes of saltwater taffy, T-shirts or coffee mugs all around show you thought about your team and you care.

Bonus Tip: Avoid The Social Media “Dead Giveaway”

It’s good planning to let “almost” everyone know you are leaving on vacation. But today there’s a big exception: social media sites. Here are some pointers for the security conscious:

  • Resist the urge to tell everyone on Facebook that you’ll be gone for two weeks. You don’t want to take the chance someone might break into your home — or your place of business if you don’t have a regular staff — while you’re away. Burglars have been known to monitor sites like Facebook.
  • Don’t use “check-in apps” such as Foursquare that show you at the airport or having dinner in a far-off place.
  • Avoid uploading fun family photos from some far off destination to Instagram or Twitter while you’re away. Save those photos and picturesque descriptions of that perfect beach on Maui until your return. The photos and the memories will keep. Your colleagues, clients, friends and extended family will love hearing about your adventures just as much when you’re safely back home again.

Vacation Photo via Shutterstock

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