How to Go On Vacation: A Checklist for Small Business Owners
When you’re a small business owner, to say that you have your hands full is an understatement. But study after study has shown that taking a vacation will, in the end, make you healthier (read: better able to work productively and consistently), and it’s important that you treat yourself like a human, not a machine.
Here are a few tips to help you rationalize your vacation. You deserve it!

Set your vacation responder.
It’s tempting to “forget” to do this, but it’s important.
There are two reasons small business owners tend not to set a vacation responder:
- They don’t want to make people feel like they have to wait for a response.
- They fully intend on checking in every day.
Of course, the logic here is flawed:
- The world will not implode without you in your absence.
- The whole point of a vacation is to not have to check in for a few days.
The people likely to send you emails either need your direct attention, or they need immediate attention. Let them know when you’ll be back and ready to address their concerns, and give them the contact info of someone prepared to handle things in your absence. Nothing kills the magic of “getting away from it all” like giving yourself the extra pressure of needing to check in throughout the day.
Plan a good strategy for your absence.
With careful planning, you can minimize the degree to which your business depends on your every word. Sure, it feels great to be needed. But it feels even better to unplug and tune out—even though your ego might take a slight hit when you realize your team can get along without you for a few days.
Try this: instead of handing your cellphone number out willy-nilly and telling your team to contact you whenever they need to, if it’s really not possible to completely disconnect yourself, consider scheduling a fifteen-minute daily phone call—strictly for matters that absolutely require your input (nothing that can wait until your return). In most cases, that phone call might take only 30 seconds. (“Everything good? Alright? OK, keep up the good work!”)
Tell everyone about your trip.
Customers, vendors, employees, affiliates—anyone you might expect to try to contact you in the time that you’re gone, give them a call or send them an email alerting them to your vacation plans.
While many small business owners are hesitant to do this, thinking it sends the wrong message, this is a win-win-win situation: your customers and affiliates know what to expect, and they’re given ample opportunity to wrap up any immediate business with you; your team won’t be crushing anyone’s hopes and dreams of speaking with you immediately, thus avoiding potential frustration on the part of your customers; and you’ll be rewarded for your careful planning by a thinner inbox than you might have otherwise expected.
Empower your team.
If a typical workday finds you scurrying from one desk to the other authorizing every little discount your sales team offers and making all of the smaller decisions yourself, it’s possible that you’re shooting yourself in the foot in more ways than one. Not only are you creating work for yourself by giving yourself all of the responsibility, but you could be micromanaging your sales team right out of any genuine enthusiasm they might have for the job itself—and nothing sucks away sales like an unenthusiastic team!
If you’ve got great employees, trust them to make good decisions, both in your absence and when you are around. (And if you don’t, what are they doing there?) You’ll save yourself time making decisions, and your team will appreciate the vote of confidence and the opportunity to gain your approval by doing a great job all on their own!
Come back a day early.
Or, more accurately, tell everyone you’ll be gone for longer than you really are. This gives you an opportunity to get home, collect your bearings, and start digging through your inbox and memos without anyone expecting an immediate response. (The last thing you want at 9:00 a.m. on your first official day back in the office is to be bombarded with phone calls and voicemails from people expecting you to be available rightnow.)

While the workaholic in you may find vacations acceptable for other people, but not necessarily you, it’s important for you to give yourself these mental breaks. Think of it as a benefit, not a detriment, to your focus on your business: when you’re able to turn your mind off, you’re open to new ideas and fresh perspectives. You’ll likely come back to the office rejuvenated, refreshed, and more ready than ever to push your business forward.
So turn off that laptop, get your shades, and spend your vacation focusing on your family and loved ones. And try the fresh lobster—I hear it’s delicious!
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