Vacations are awesome and most often necessary. But, busy overachievers can't always take a complete vacation. Especially entrepreneurs, who often lack the systems and support to truly take off without worry or repercussions back at the office.

I am a big fan of work-cations. I like to set up a trip, potentially for work reasons and then take plenty of time off while I am away. It takes a bit of coordination, but the rewards are worth it. As I write this column, I am on a 2 week work-cation in Spain and Portugal. Here are my tips for making your next work-cation perfection.

1. Plan out the work.

Work-cations work best when you don't spend the whole time working. Before I left, I scheduled my columns, schoolwork and client work so I could keep them to a maximum of 4-6 hours per day. Much of the time I spend at home watching TV or socializing will go to the enjoyments of travel so I still have plenty of time for focused work and solid rest. If I work efficiently, I get more time in my day to enjoy the sites.

2. Do plenty of travel homework.

My wife and I are visiting several cities on this trip. We are open to where the adventure takes us, but we don't want to waste valuable time searching for things. So we researched the cities, made contacts, brushed up on a little Spanish and took off. Our first day was dedicated to getting time adjusted and oriented and now we are ready for fun and productivity.

3. Generate new opportunities.

I enjoy the work I do and I gain a great deal from meeting new people in other lands. So I always reach out through my network to meet up with people of similar interest. For this trip, I am speaking at the Entrepreneur's Organization (EO) Barcelona Chapter retreat. I will then have dinner with more EOers in Madrid. Sure it'll be fun, but I will also learn a lot about the business climate in Spain and probably inspire a few columns as well.

4. Make sure your connectivity is perfect.

Work-cations are not possible without connectivity. The Internet can keep you from being left alone, but it also allows you to work virtually anywhere. Make sure you have your Smartphone, Skype and email fully functional. If it wasn't for this column and my newsletter, most people wouldn't even know I left.

5. Set boundaries of time.

There is a time for work and a time for play. It's easy to get distracted from your workload, which causes stress and takes away from the much needed vacation part of the trip. I make sure I set aside uninterrupted time blocks and commit a high level of productivity. The reward is almost immediate when I get to move on to more fun daily activities upon completion.

6. Set reasonable expectations with your travel partner.

Everyday my wife and I agree on 3 things that we might do that day but are perfectly fine if we only accomplish one great experience. The goal is to spend fun relaxed time together. We are not competing in the Amazing Race.

7. Stay flexible.

We are perfectly happy to constantly amend the trip to accommodate responsibilities. And we remain open to any unexpected adventures that may occur along the way. After all, that's what a vacation is for, fun and relaxation.

8. Have a reliable contact at home.

I couldn't possibly take a trip like this and maintain my work schedule without excellent support at home. The people that help me keep on track are invaluable and I do what I can to make things easy for them when I am away. It's really thanks to them that a work-cation can be as relaxing as a vacation, more so since I have little worry and still feel productive.

Published on: Nov 4, 2014
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