More Breaks Are Better

All the surveys say Americans take too few vacation days. I'm a big fan of taking more days, but, no matter how many days you have, why blow them all on one big summer holiday? It's ludicrous to think that a single long vacation can offset all of the stress that develops in today's 24/7/365 business environment.

The better strategy is to take more, albeit shorter, breaks. A getaway during the dog days of August is fine, but won't you need some time off during the dark days of February too? Don't you want some time in the spring and in the fall as well? Periodic getaways, even if they are shorter, will break up the work periods and make you more creative and productive.

Bottom line: Don't bank your physical and emotional well-being on one long holiday a year. Plan out a series of holidays that allow you to enjoy downtime when you need it most.

Go Your Own Way

The problem with a traditional summer vacation is that everyone else wants to go where you're going. Worse, everyone who lives and works where you're going is probably on holiday too. Which means a lot of the places you want to visit are not at their best.

The perfect example is Europe. Americans make this mad rush to visit the continent in July and August and they quickly learn that Europe is lousy with tourists and the Europeans themselves have gone on holiday. Besides, if you're interested in visiting the Southern Hemisphere, now's not the time. It's the middle of winter there, and, unless your goal is a ski resort, the weather is inclement at best, rotten at worst.

The better time to visit any urban area anywhere in the world is usually in the spring and fall. The social and cultural life of the city is in full swing, the restaurants are all open, and there are fewer holidaymakers waiting on lines and clogging the streets. The Caribbean in October and November is just as warm—and much less costly—than it will be in February and March.

The bottom line: Find out when the "shoulder season" for your destination is. That's the period between the high tourist season and the so-called off-season. The shoulder season is probably the sweet spot for good times at reasonable prices.

Don't Disconnect From Life

I chuckle when I hear supposed "experts" who advise entrepreneurs and other businesspeople on holiday to shut off their mobile phones, stop checking email, and leave laptops behind. Do these people live in the real business world?

You know what will happen if you stop reading your email while you're on holiday: You'll return to thousands of them and spend weeks trying to play catch-up. You'll be exhausted by the end of the first day back.

A better strategy is to devote a set amount of time each day on holiday to deal with the business life you've temporarily left behind. Read your email, check in with your staff, whatever you need to do. It'll not only quell the voices in the back of your head saying you're out of touch, it'll guarantee a smooth transition when you get back to work.

Work From Somewhere Else

If you're like most entrepreneurs, you may not have the time to take as many holidays as you'd like. Or you might be one of those who live to work and just can't imagine doing anything but work.

That doesn't mean you can't take a vacation of sorts. Why not work from somewhere else? Pack up what you need, go somewhere else—Rome, Bali, Hong Kong, Buenos Aires, wherever—and continue to work as usual. You'd be surprised how relaxing and invigorating it is to live your usual life in some other place. Different lunch joints, new shopping experiences, and new tunes on the radio or newscasts on TV make it feel like a holiday. And even if you work all day, you have evenings and weekends free to wander a new city and take in new cultural events. It may not be a traditional "vacation," but you'll find that your creative juices are flowing.

The Fine Print…

What makes me happy on holiday? Trying to live like a local. To me, living someone else's daily life is fascinating. I always make it a point to visit the local photography studio to see what holidays people celebrate and how they dress. I walk through the local market to see how they butcher meat, what vegetables natives love, and which packaged goods they prefer. I take long, random walks and watch the locals at play, at dinner, and going about their normal routines.