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Planning the Perfect Working Vacation

In this day and age it's almost impossible not to bring electronics with you on a trip ... even on a vacation. This isn't a good or bad thing. It just is. The reality is that many of us live in a world where our bosses, our peers, our customers, our partners and oftentimes even our own families expect us to be reachable. So, what's a vacationing professional to do? How can you plan a working vacation?

When done right, it's less stressful to have a connection back to the office. An electronic leash, if you want to call it that. It's tough not to think about checking in at work while you are on vacation when you're carrying your office around in your pocket. Kudos to those who can turn it all off. However, this post is for those who want to fit in a little work with their vacation. Below are a few tips and tricks.

The Electronic Leash

As maligned as it might seem, there is often a benefit, if not a need, to having an electronic leash. When used wisely they can be effective for both personal and professional needs. Personally, tablets, phones and laptops are good for staying in touch, video conferencing, storing and sharing pictures, providing entertainment, exploring social media and using weather apps, among other things. Professionally, you can use these devices to check email, look at your calendar, have Web access, participate in conference calls, look at travel apps, track expenses, take notes and more.

Some of these functions are useful if you're traveling alone, with your spouse or with kids. They are especially useful for staying in touch and sharing what you are up to while away.

As you begin to think about, plan and execute a successful working vacation here are a few things to keep in mind.

1. Set expectations. You need to set expectations with your family, your co-workers, your boss (everyone has one), your customers, partners and with yourself.

Tip: Be realistic. People will understand.

2. Think about the tools you'll need. You may need to improvise. You might be used to having a lot of resources at your fingertips. When traveling you might not have them handy. So, think about the tools you can bring with you and plan accordingly.

Tip: Practice with them before you leave.

3. Delegate effectively. While you're on your working vacation you should assign someone to fill in for you or otherwise attend to tasks you will not be able to handle directly.

Planning is NOT Overrated

As you plan your working vacation, take time to think about the things that can go wrong. Also, think about the things you want to make sure go right. If you have a specific thing you want to do, plan around it.

When you don't have your electronic leash you may:

-- Worry about what you have left behind.

-- Wonder how big your inbox will be when you get back.

-- Question if your customers are being taken care of properly.

The simple answer here is ... Don't. Delegate wisely, set expectations and trust the processes you have setup beforehand.

Some points bear repeating, and some are common courtesy and shouldn't be ignored.


1. Set boundaries. Let people know when you will be available. And by implication, let them know that you won't be available at other times.

2. Delegate. Assign someone to act for you. Empower your delegates to solve problems. If needed they can contact you in an emergency.

3. Get to know the hotel staff. You may be surprised at what a kind word can do. You might find out a conference room is magically available.

Tip: Also make sure you tip the people who help you.

4. Know how to use your out-of-office message. Every email system has this option. Learn how to use it.

Tip: Within the email you should clearly delineate hours and days you will be available. List your delegates, what they can help with and their contact information.


1. Be the guy yelling into his phone. Or worse, into his PC's microphone while sitting in the lobby of the hotel.

Tip: Bring a good headset if you know you will be on conference calls. One that has a good microphone.

2. Waste your whole vacation in front of a screen.

3. Bemoan that you are working on your vacation. Embrace it. Own it. Execute wisely.

A working vacation is not the worst thing. In fact, if done right a working vacation may help you learn how to manage your career more effectively and efficiently. Your time management skills, ability to delegate and let go can be improved. With practice you might find every vacation becomes a working one.

With a little planning you can create, plan and execute a successful working vacation. Now, get planning and don't forget the sunscreen.

Jeff Shuey is a contributing author to the Personal Branding Blog. He's a veteran in the Enterprise Content Management industry, and over the past 20 years he has worked with customers and partners to design, develop and deploy solutions around the world. Shuey is currently Director of Strategic Alliances at Winshuttle, and has worked for Microsoft, FileNet (IBM), K2, Captaris, Open Text, Kofax and Kodak. He speaks and blogs about ECM and the intersection between social, mobile and cloud computing.

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