The Best-Laid Plans


The best-laid plans of travelers often go awry…a truth you will most definitely learn on the road. Traveling long term is different than a vacation. In a vacation you normally have to maximize your short time very carefully; transportation, lodging, tours, and sometimes food is often planned. However when you are roaming from place to place over the period of 3 to 12 months, planning each detail becomes much harder.

Here are some things to consider when trying to plan:

You Will Change

One of the most rewarding things about extended travel is that you have time to learn; not only about other cultures, but about yourself. You may be surprised what you learn about yourself. The knowledge you gain will likely effect your plans, so consider leaving yourself open to new opportunities.

Seeing the Whole World

You can’t get to every ‘must-see’ in the world. We know it’s tempting to look at the globe and know that you have more time off then you ever have before in your life and want to do EVERYTHING. But really…do you want to do everything? If you do, then what’s left? One of the biggest benefits of taking a career break and traveling is that you will infuse travel into your life from this point on. We’ve never met anyone who traveled the world and didn’t want to go back out again. Travel and exploring will become a part of your life, you will have more opportunities to get back to places you didn’t get to on this trip.

You Don’t Know Until You Get There

Many times you plan to go to a place and have something specific that you want to do there or see. But once you hit the ground, you’ll meet locals and other travelers and bond with them. Soon you learn of other things that you want to see and do that they recommend. If you have everything already planned, then you may miss out on these new places/experiences that you just learned about.

Oh – The People You’ll Meet!

Whether you are a solo, couple, or family traveler you will meet hundreds of new people while you travel. Each person brings a new possibility; one which you will never be able to predict or control. You may decide to travel with a new friend, you may fall in love, you may get offered a job, or you may decide to stay and help someone. Remain flexible & open and you will most likely end up in a place that you never knew about – and certainly wasn’t according to plan.


Sometimes when you plan too much in advance, the universe has a way of laughing at those plans. That’s what happened to Stephanie and she shares how she now travels at a different pace.

You Will Get Tired

At some point in your extended travels you will get tired. You won’t want to move any longer, pack any more, see another museum, or ride another bus. If you plan everything in advance, then you’ll wear yourself out with no time to recover. Remember you don’t want to return home as tired and stressed out as you were when you left!

Overall we recommend to build a structure and foundation, but know it’s ok to fill in the details as you go. If you are the planning type, then we recommend to get the first few weeks or months planned with transportation and an itinerary, but leave the remainder open ended. It’s good to have a few core ideas, but fight the urge to connect them until it gets closer to the time in which they will occur.

Basic Training

We cover more on how to plan for your time in Career Break Basic Training, as well as other topics related to your On-the-Road experiences.

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Career Break Guide Table of Contents