How to Take a Guilt-Free Summer Vacation

Author: Stephanie Taylor Christensen | June 13, 2016

Planning a summer vacation is often one of those pivotal moments where entrepreneurs realize the pros and cons that come with being the boss. While you technically have more freedom to take a vacation than an employee on someone else’s payroll, disconnecting as a business owner presents real costs. Not only must you trust that your employees can handle your duties in addition to their own during your absence (if you have a team at all), days you’re not working can mean days you’re not getting paid.

If the summer vacation struggle sounds familiar, you’re in good company. More than 66% of business owners who responded to an Office Depot study agreed that finding the time to get away was indeed a challenge.

While carving out vacation time does take strategy, advance planning, and self-discipline on your part, it can be done without shortchanging your business revenue, disappointing your clients, or stressing out your staff. Here’s how.

1. Establish virtual access

Inexpensive tools designed to help business owners stay connected to their operations—whenever and whereever—are plentiful. Use them to gain control over your vacation, including when you check in with business and when you disengage, without disrupting your staff or confusing your clients.

  • Google Voice. This free tool forwards business calls to your cell phone, while the caller remains none the wiser. You can see who is calling in real-time to determine if you want to take the call, or send it to voicemail, which gets transcribed and delivered to your email.
  • Cloud-based file access. Cloud computing systems like Dropbox, Evernote, and Google Drive make it easy access the latest versions of shared files remotely without requiring you to call someone back at the office or log into email to download them.

2. Set summer vacation expectations in advance

The more detail you can add to your out of office email and voicemail notifications, the better you set expectations for clients, prospects, and peers who message you during your trip. Establish a schedule for when you will and will not check messages and respond to calls and emails (if you intend to at all). Include those times in your auto-responder, and stick to the times you’ve agreed to be available. When you do work while you’re away, set a timer to keep yourself honest about start and stop times.

3. Empower those you leave behind

Few things are more disruptive to your summer vacation plans than unplanned calls and business “fire drills.” Assign one point person on your team who will tend to emergencies in your absence. Before you leave, define what constitutes an emergency and what can wait until you return. Establish a plan for how and when that person can reach you, including agreed-upon times when you will call to check in to provide consult on urgent needs.

4. Automate as many tasks as possible

Whether you have a support team on payroll or you hire a virtual assistant to step in while you’re away, summer vacation is easier to manage you when you minimize the workload you leave behind. If you use productivity tools like Evernote, Slack, Trello, or Dropbox in your business, the app IFTTT (short for “if this, then that”) integrates with all of them (and 300+ other popular apps) so you can sync your activity with the push of a button. (You can even use the app to organize business expenses from your trip, turn on your lights at home, water your lawn, and control your thermostat).

5. Define what needs to be done

Set priorities for your team at least five days before you depart for your trip to make sure all hands are stacked and to give yourself peace of mind that critical business functions won’t get neglected. Likewise, make a list of daily tasks your team can temporarily suspend, like daily sales reports you likely won’t review during your trip or marketing campaigns to pause while you’re out.

6. Set up an alternative email for VIPs

Checking work email while you travel instantly transports you out of a summer vacation mindset. Set up a private email account whose address will be shared only with employees who will act as your direct point of contact during your trip and key clients or partners with whom you want to maintain a direct line of communication. You’ll be less stressed knowing that you’re in touch with the urgent needs without the stress of seeing a packed inbox.

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