Knowing where you go seems very simple at home but while traveling in a country where you do not speak the language and sometime cannot even read the signs can become overwhelming. The good news come in 3 letters GPS, for few hundred US dollar you can buy a nice unit from Garmin or other reputable GPS maker. I use the 76CSX, waterproof and with micro SD card on which you can load large maps. I will recommend to make copies of your map just in case one of them fail on you, you can find maps online already on memory card or on some great websites, many are even free. Once you have chosen your GPS, load and try your map prior departure.
The paper maps are still my favorite to prepare the trip and even while on the road, just to get a general idea of where you go and what will be the terrain. You can also mark your track on it so you will be sharing it at your return. Be very careful to do not trust paper map too much in some developing countries: they often mark the road they plan to build, not the ones which are already existing (google map is not much more accurate in that matter).
Ok, now that you have your equipment and that you tested enough to know how very well all the possibility it offer, you need to realize that sometime you will need to ask for direction, even macho guys get lost so learn the basic in the language of the country you are in or at least write some phrases somewhere easy to find. Now very important… never point in any direction when you ask for direction, just ask “do you know where this road go” or ask “where is the road to…”. If you point in specific direction and they do not know the response they most likely will say is “yes” because they do not want to upset you or they do not want to look stupid. When you travel by motorcycle or 4X4 always remember that some locals do not have a vehicle themselves and they cannot see why you will not be able to drive on a goat trail or across a deep river so be aware. Same thing goes for time to destination, for example in south America they will often tell you “its 4 hours by car but with a motorbike no more that 2:30“, yes right if you are a race driver and know the road maybe. If you want to get a good idea of how long it takes to go to the next town just ask how long it is by bus, this should be pretty close to what it will take you. Another good tip for you is when you are in a very busy city, lets say Calcutta, the GPS is not working well enough to go to your hotel before you know it you are lost and tired, the night is coming, you start swearing… Ok you have a solution : stop a taxi and ask them to go to the hotel while you follow him and no worry he will not loose you since he want to be paid. One last tip today, if you are in a big city and are afraid to get lost when leaving it, go the bus station and follow a bus going in the direction of your next adventure, slow but efficient. I almost forgot, for the travelers with family and friends at home who want to know where you are at all time there is an inexpensive solution called spot tracker http://www.findmespot.com/en/index.php?cid=101. This will show them on a map where you are almost live and almost everywhere in the world.
For the global organization of your trip, you can read this post.