The Small Business Owners' Checklist Before Going on Vacation


I have a friend who refuses to go on vacation. It’s not that she doesn’t want---or need---a break from the office, it’s that she’s too nervous to go. She owns a small business, and she thinks the risk of leaving her baby (her company) outweighs the restorative powers of a vacation.

She compared leaving her business for a week’s vacation to that tinge of nervousness you feel when you leave your home for a few days and, an hour down the road, start to wonder if you left the garage door open or the front door unlocked. She was certain that panicked feeling would ruin her entire time away, so she just never left.

Do you know anyone who feels this way? Most entrepreneurs don’t need a reason to go on vacation, they need an assurance that, while they’re away, business won’t go up in smoke (figuratively and literally!). And guess what? With a little planning, a restful vacation is completely within grasp. Here’s are the items that should be on every small business owner’s checklist before going on vacation:

1. Strategize when you’ll take vacation time.

This is key to ensuring you’ll actually make it to your destination. Consider your business’ rhythms, and schedule to be gone during a time of relative calmness. If your business doesn’t have predictable faster and slower periods, AdviCoach CEO Brian Miller suggests “testing the waters” of vacation during holidays, when clients aren’t as likely to need you. Another bonus to planning a vacation in advance? Studies show that the mere act of planning---and subsequent waiting for---a vacation is enough to boost happiness levels for weeks. And that’s not even considering the vacation itself!

2. Prepare your employees for your vacation.

Once you’ve marked your departure date on your calendar, don’t look back---look around. Those people sitting in your office? You hired them for a reason. They can do good work, so give them a chance to shine. Start a couple months in advance (maybe ten weeks or so), preparing employees to handle the tasks you usually accomplish.

This article from the New York Times includes several tick-boxes for preparing employees, including:

  • writing and explaining detailed instructions on handling correspondence;

  • preemptive problem solving: going over potential problems with employees and providing guidance on how to handle them; and

  • meeting with staff members and reviewing all projects beforehand to snuff out potential issues.

3. Let your clients know they’ll be in good hands while you’re gone.

If your ongoing projects involve customer feedback, it’s worthwhile to keep them in-the-loop on your plans, too. With reassurance they won’t get left high-and-dry while you’re away, you’ll not only avoid panicked “where are you and what’s going on?!” emails, calls and texts, but you’ll be introducing a chain-of-command that will give you backup for the next time you are away. Some concrete ways to do this? Personally introduce the employee who will be taking care of each customer while you’re away, and include both your customer and employee on correspondence before your trip, so everyone is on the same page. If you don’t want to miss a single conversation, consider recording the calls your employees have with your customers. You won’t miss a beat, even when you’re miles away.

4. Wrap-up big projects before you leave.

Don’t leave any important tasks sitting on your desk. Finish them before your vacation, so you don’t have the distraction of a nagging to-do list in the back of your mind. Clean out your inboxes, voicemail, and physical paper piles, too, so you can come back to work with a clean desk and fresh attitude.

5. Schedule limited check-ins.

If you must, make the choice to check-in at specific times during the day or week. Some business owners choose to check in first thing in the morning and again in the late afternoon; others check once-a-day at 10 a.m. Tell your staff the parameters for when they should contact you directly, otherwise, don’t waste your regenerative time sorting through emails. Set aside the time period you’re willing to work, and prioritize the things that you must attend to. If it can wait, let it, and enjoy your time away!

With this checklist, you’ll be able to spend restful quality time away from the office with peace-of-mind that comes with knowing everything at your business is under control. And you may even find that the time you spend outside of the office improves your work inside the office!

Now you tell us, what’s the longest time period you’ve spent away from your business?