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Six Tips for Planning an Extended Adventure Trip

Taking off for an extended, leave-it-all-behind, adventure trip is a darn sight more complicated than planning for your annual week-long beach holiday. The world is not set up for people who decide to have no fixed address, no job, and no itinerary.

Taking off for an extended, leave-it-all-behind, adventure trip is a darn sight more complicated than planning for your annual week-long beach holiday. The world is not set up for people who decide to have no fixed address, no job, and no itinerary.

The planning process is such a marathon that just making it to the airport feels like a triumph. And that's where Jane and I are now, sitting in the airport, about to embark on a bike trip around the world, and feeling like we've already accomplished a miraculous feat.

When it comes to planning your own extended getaway (you are planning one, aren't you?), here are five key tips that will help you get to the airport on time.

Start Earlier

How long do you think it will take to plan your dream escape? Three months? Double it. Six months? Double it. A year? Yup, now you're in the ballpark. Completely dismantling one life while simultaneously preparing for a new one takes time.

About six months ago, we started seriously planning to cycle from Rome to Russia – though we'd been tossing the idea around for a while before that. Six months sounds like plenty when it's all ahead of you, but when you're running out of days, your house is full of furniture, your cars are still in the driveway, and no one wants your prize-winning fern, you realize six months is just a blip.

The truth is, no matter how much time you give yourself, some things just cannot be done until a few weeks before you leave. And by some, I mean hundreds. If at all possible, quit your job early enough that you can spend two to three weeks being a full-time furniture seller, house cleaner, packer, mover, and travel agent on your own behalf.

Things Will Go Wrong

No matter how deftly you've orchestrated the transition from 'normal' life to transitory life, things will definitely go wrong. Even the simple things can be difficult, so be prepared for unexpected stress, especially in the final month or so before departure.

Our most stress-inducing moment came less than a week before we were supposed to leave. For simplicity's sake, we had gone to a used car mega-store to sell off our cars. We already had an offer, so we were expecting to hand over our car and be given a check.

What we got was a refusal to buy our car on the grounds that our official paperwork said it was owned by Bank of America. This was news to us, since we had paid cash for the car more than five years before. All of a sudden, what should have been easy – drop off the car, get paid, rent a truck, go home – became a stress-inducing scramble to get the correct (notarized and official) paperwork.

After many frantic (and rather angry) calls to banks, department of motor vehicles, and the dealership where we bought our car, the initial estimate of several weeks to get the paperwork was whittled down to a few days. We couldn't have done it without some amazing customer service from all involved.

When you're dealing with difficulties like this, the best way to get people in your corner is to tell them about your crazy trip. Everyone loves an adventure story and they really don't want to be the ones to ruin your plans.

Everything Has A (Cheap) Price

If you're going to be gone for six months or more, sell everything you own. No seriously, sell it all (or at least everything you can stand to part with).

Getting rid of excess stuff greatly simplifies the moving process and gives you more, cheaper storage options. This time around, we sold, gave away, or threw away so much stuff that we were able to move everything ourselves, into a friend's basement, in a matter of hours.

More importantly, you just don't know who you're going to be when you get back. Sure, your Beanie Babies collection means a lot to you now, but once you've experienced foreign lands and tested your mettle against the elements, maybe you'll wonder what you ever saw in those fuzzy little fellows in the first place.

On our first big trip, when we left Vancouver to go backpacking around Europe, we kept huge piles of clothes and CDs. Though we had planned to be gone for only six months, we ended up settling in London and didn't come back for that stuff until nine years later! A lot those CDs seemed pretty ridiculous after almost a decade and the clothes were downright hilarious. We would have been much better off selling them and using the money to treat ourselves while away.

While you're selling stuff, remember that nothing is worth what you think it should be. Most of our furniture went for a third, or less, of what we paid for it. Records and books are generally worth pennies and household items are hard to shift at all.

Sell what you can and be prepared to give the rest away.

Prepare for Mixed Emotions

For months before you leave, people will constantly ask if you're excited. You will look at them blankly, think for a minute, and realize that no, you are not excited in the least. You're exhausted, frustrated, and stressed out. You're sad to be leaving your friends and your home. You're not sure you'll ever get everything done.

You may be so unexcited that you'll wonder exactly what the heck you were thinking when you decided to take this stupid trip. You'll worry that it's the biggest mistake of your life. There will be days when the only thing keeping you on track is that it's too late to go back; there's no way to break it to your friends that you're just going stay home and watch TV after all.

These feelings are normal. They come from fear, inertia, and plain laziness all mixed together. Ignore them and keep plugging along. There is plenty of excitement in store after you leave.

Don't Plan Too Much

It's tempting to treat an extended trip much like a typical weekend holiday, with every destination mapped out, every night accounted for, and every piece of clothing carefully coordinated into at least three possible outfits.

Don't get obsessed with having exactly the right pieces of equipment.

You may think that if you get all the perfect things, nothing will ever break, the sun will always shine, and you'll never be cold, tired, or hungry. The truth is, no matter how ideal your socks are (and trust me, I spent a lot of time trying to find the perfect socks), there will be bad days. So take it easy, pick something that seems about right, and replace it if it doesn't work out.

Similarly, you can get bogged down in the details of which sights you'll see, where you'll go each day, and which roads you'll take to get there.

When applied to a long-haul trip, this kind of route planning falls somewhere between Herculean and impossible. Besides, all plans are guaranteed to go haywire before you're even a week in. If things don't go wrong, it probably means you're spending so much energy trying to stick to your itinerary that you'll forget to have any fun.

Remember Why You're Doing This

Every once in a while, when you're surrounded by piles of boxes and seemingly insurmountable difficulties with no end in sight, sit back, pour a cup of tea, and think about the reasons you started this whole crazy project in the first place.

What do you want to get out of it? What are you trying to change? Who do you want to be at the end of it?

A few focused moments of reflection will go a long way to keeping you moving forward, dreaming big, and heading towards your adventure of a lifetime.