Imagine that you’re going to take the trip of a lifetime. You’ve got the time, you’ve got the money, and you’re finally going to experience that dream trip.

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Would you enjoy planning that trip? Would you browse the Web with relish, looking at hotel reviews, airline guides, destination websites, and whatever else you can find? Would you browse the bookstore for guidebooks and maps? Imagine yourself sitting with your travel companion in your living room stashed with books and maps and telephone and computer, planning that trip. It’s a good thought, right?

The heart of your plan is a combination of where you want to go, what you like to do, how, and with whom. The flesh and bones of your plan is a collection of concrete details: dates, flight numbers, hotel reservations, tour plans, and so on.

What would your travel plan look like? Where would you keep it? How would you share it?

You probably wouldn’t write your trip itinerary out as a formal document with a prescribed outline, table of contents, and appendices. You probably would keep it where you could get to it quickly as needed, whether that was on your phone, on your laptop, or in a collection of papers in your carry-on bag.

And you probably would work with your plan as you take the trip. For example, as you travel, things happen. Flights get cancelled or delayed. You miss connections. The article in the in-flight magazine recommends a hotel or a restaurant you wouldn’t have thought of otherwise. Hurricanes close airports. Hotels close for remodeling.

What do you do with your trip when things happen, and circumstances change? You change your plan, you revise your schedule, you plan as you go. You sit somewhere with your travel companions, and go back over guidebooks and schedules and possibilities, and revise accordingly. You don’t dump the core of your plan, but you might change the flesh-and-bones details.

You certainly wouldn’t keep going just because that original plan said so, right? You wouldn’t try to fly into the hurricane or charter a plane to substitute for the one that was cancelled. You wouldn’t sneak into the hotel that was closed for remodeling. You wouldn’t ignore that great tip you got from the in-flight magazine.

When assumptions change, you don’t just run your head into a brick wall, because that’s what your plan said; you change your plan.

You enjoy the travel plan as you build it, and you revise and correct and improve the plan as you go. Take some guidebooks and maps and a laptop along, so you can change things later. Listen to people you meet who offer new ideas. Expect to revise your plan as things happen and assumptions change.

Planning is part of the journey. It makes it better.

You might call that plan-as-you-go traveling.

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Tim BerryTim Berry
Tim Berry

Tim Berry is the founder and chairman of Palo Alto Software and Bplans.com. Follow him on Twitter @Timberry.