dude_on_chair_phoneThe average American leaves one-sixth of their vacation days unused, Expedia reports. If you know you need a vacation to recharge the batteries but your boss demands your time on an upcoming project, you may still be able to keep up with the team from your by telecommuting from a island with white sand and clear blue ocean water. Sound too good to be true? Read on to find out how you can make this work-from-vacation dream into a reality.

Convincing Your Boss it’s Cool

Forbes suggests first feeling out your boss on the topic of telecommuting. If your boss comes back with something extreme, like saying upper management is firing anyone who asks to telecommute (unlikely but it could happen), you’ll know you won’t be able to extend that vacation. If your boss critiques the idea, saying people just don’t work well outside the office, you’ll know how to craft your argument.

Review Company Protocol

Review any ‘Bring Your Own Device’ (BYOD) and telecommuting policies your workplace may have. On vacation, you’ll be relying on your personal phone, tablet and laptop to check in — and mixing personal and work information can be problematic. After you convince your boss it’s cool, convincing the IT department to Invest in a security tool and device management aid such as mobility management by BlackBerry is the next step. These tools allow your IT team to remotely lock and wipe your device if you lose it and they also keep personal and work information separate, which may put your company at ease when it comes to device security while telecommuting.

Plan it Out

Next, make a plan. Maybe you’re hoping to spend your vacation in a remote location off the coast of Maine and your boss’ main concern is connectivity. When you can point out the library offers free wireless every day, your seaside cottage has free Wi-Fi and the ferry runs hourly and delivers mail, you’ll be better able to convince him that you can always be in touch.

Keeping Your Promises

While your requirements will vary by job duties and workplace culture, there are many ways you can stay in touch remotely. Pick and choose from the tactics below to build a comprehensive list that works for your vacation getaway:

  • Smartphone: Respond to email, text message, review product PDFs and call to check in from your mobile device; a necessity for any telecommuter. If that’s not enough, you can listen to meetings podcast-style and schedule face-to-face talks.
  • Skype: Speaking of productivity, Skype lets you video chat, phone chat and screen share. With a little planning, you can walk your boss through your workflow by sharing documents, PowerPoints, mockups and more.
  • Hightail: Get around file size limits when sending email with Hightail (formerly YouSendIt), a secure file manager that lets you email oversize PDFs, JPEGs and other files. You can get started with a free membership, and upgrade to a paid membership if the file size limits are too small for you.
  • Productivity apps: When possible, use apps to remain productive. You might use a Kindle app to read and mark up the latest white paper from your phone, for example.
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