The more you do it, the easier it gets. The more you learn and research these things the easier it gets. Here's how I go about it. But remember that I've been doing this for many years so this isn't my first rodeo. That being said, it isn't the end-all be-all either, just my way. When I first started I was a babe in the woods. I build a whole new world every few months so, like I said, the more ya do it the easier it gets.

So start out with some sort of shape, make it a big blob then start taking chunks out of it. Then add on to it in other places. Refine it. Refine it again. Refine it, yet, again. Keep refining until you like it - ie until it isn't boring. The more detailed and intricate that you can make your coastlines the more interesting it will look - within reason - so make sure to leave some areas that are not so darn wiggly, keep some parts kinda straight but not too straight. Think about fjords and gulfs and bays and coves and islands and peninsulas an isthmuses (I think that's the right plurality). Don't make all of your landmasses the same size, make some small and some medium but only 1 maybe 2 large ones. Also, try to avoid putting your continents in the same place as they are here on earth. This is hard thing for a lot of people. On the other end of the spectrum, try to avoid pangeas or a world filled with tiny islands. Okay, phew, first thing done.

Now, I was a pretty good geography and geology student so I retained a lot in my memory from my school days but not everything. In the real world, most of it is covered with forest (I'm sure there will be someone who wants to argue that point but this isn't high school debate club right now - yes, deserts and tundra have no forests, yay) so start your map thinking that everything is forest and then just take away parts to fit in other things (these are called biomes or ecosystems but we mappers call them terrain features or landforms - physiography - graphical depiction of terrain). Another term is natural geography which is opposed to human geography - cities, roads, etc. I started out making things pretty random until I realized that deserts were most often found, on our earth, at the Tropics of Cancer and Capricorn. I said most often, not always. Desert placement, like wetlands, is affected by amount of rainfall and that can be affected by many things like jet stream, trade winds, temperature, and rain shadow (mountains blocking the rains). So knowing that helped me to make sure that I never put a desert up in a place similar to Canada on my map. That's probably the first major thing you need to know...keep your deserts in hot arid places. Technically the arctic is a desert (or is it the antarctic, I always forget) since it receives a tiny amount of rainfall but deserts are hot and full of sand, right? Fuhgetaboutit, just make that the ice cap. Now you have two things done, landmasses and deserts (polar regions are a given). Now if your planet rotates top to bottom (instead of side to side like earth) then these biomes get mixed up (deserts at the point facing the sun, ice in a ring going around top to bottom, live-able area is always in sunlight unless the orbit makes night-time a long winter, etc). Also, the orbit and moon/s and other planets affect things but these are discussions for another time and probably you need to be way smarter than I am. So let's just stay with something earth-like for now.

Having a rough idea about plate tectonics helps you to set up where the mountains will be. You don't have to draw out the tectonic plates if you're doing a small region or a single continent but you should if you're making a whole world. Where any two plates collide one will get pushed down (subducted) and the other gets pushed up. Generally, oceanic plates are heavier since they have water on top and land plates are lighter because they just have air on top. Nearby the coast, somewhere inland, the one on top will wrinkle into mountains - like the Rockies or Himalayas. Other mountains are old and have been eroded for a long time so they're shorter like the Appalachians. Put your mountains into semi-wavy chains with a few branches and not willy-nilly things like rings or straight lines. Put hills around the edges to act as foothills but, really, hills are everywhere. You can also add plateaus to this area if you want. For regional maps, say like you're doing just one country or just an area around a village, you can put mountains anywhere but not scattered all around, put them into a chain. Okay, good, three things done.

Next up is the plains or grasslands - these will just go between the poles and deserts. Piece of cake, you don't really even have to draw anything for them if you don't want to but make sure to put some other terrain (forest, hills, swamp, desert) around some of the edges so folks know where the plains end. 4 done. Then you put the tundra/steppe/taiga between the plains and the poles. Again, you don't really have to draw anything here unless you want to but just know that the area is there. Some people like to put coniferous forests between the plains and the tundra. Cool, 5 done. Jungles go in hot wet places roughly around the equator up to the deserts. You can draw them as plain old forests or use palm trees or mangroves or whatever. Sweet 6 done. Swamps/marshes/bogs/fens/moors/heath/etc go anywhere where it is wetter/lower than the land around it and in any temperature zone except frozen. Great, 8 done. Whatever is left is forest. Well, that's how I go about it, shrug. Now you can add the exotic things like canyons and volcanoes and mesas and escarpments and meteor craters or whatever. Just don't go hog-wild with a whole bunch of canyons or else they won't be so exotic anymore. 9 down.

For the rivers, start at the coast where you find a bay or gulf or cove and just draw a squiggly line inward towards the mountains. As you get further inland add branches and make sure that they go towards the mountains and not the coast. Think of a river like a tree growing from the coast. This part usually takes me the longest amount of time as I'm a real stickler for rivers...plus I like to draw squiggly lines Don't make them too straight but also don't make them impossibly squiggly. It's hard to say, really, it either looks right or it doesn't. Looking at real maps helps a lot here so that you can learn how to draw rivers with the right "feel". You can put in as many or as few as you like. Alright, 10 things done. Now plop down some lakes, large and small, anywhere - it's not a major thing just don't plop down too many or it looks kind of silly. Also, it helps if you connect them to the river system. A word of advice, don't put too many in deserts or tundra regions because, while totally plausible and acceptable, it looks odd to our earth-bound eye - something about preconceptions is probably at work there. Lastly, don't make them round 'cuz that looks too man-made or fake. Unless, of course, it's a crater lake then, by all means, make it round. 11 done.

Lastly, if you're obsessive, like me, then you can put in bathymetry - underwater topograply - such as the Marianas Trench, Challenger Deep, and seamounts but also esoteric things like reefs and smokers. 12 things done, finally, and now on to the human geography.

I start placing country/nation/kingdom borders pretty much according to the terrain - this is a primitive world after all so they don't have GPS but they do have wars so you don't always have to stick to the terrain...it just makes things easier to start with. Follow the mountains and rivers until you start getting story ideas about wars and other things which might move the border beyond the natural topography. If you're countries are all about the same size then break a few of them up into smaller things and these small countries will either be weak countries or strong trading or seafaring cultures with no need of vast lands for crops and herds. Not all countries are human - some are halfling or dwarf or orc or goblin or whatever. Also, not all borders are absolute as they are hard to patrol like mountains, forests, swamps, tundra, and deserts. Some territories don't have any real border at all - just some area like the elfin forest or the dryad forest or the ogre hills or swamp of the head-hunters. 13 done.

Start placing cities and towns along the coast where a river hits. Inland, put them where major rivers intersect. This is all for commerce and trade hubs are essential. Next, think strategically and place them near mountains (for mining), near forests (for construction timber), at the edge of a jungle (for spices and medicines) and so on. Then think of some cities as forts and place them near choke points or where they can control territory. Pick one of these places to be the capital and then pick a couple to be where the dukes live (these are major cities), a few more for the earls (towns), barons (villages), and so on. You can make this as detailed as you want or as simple as city/town/village = king/dukes/barons. Being obsessive, I have a list of some 16-20 divisions of hierarchy for the various nobility cross-referenced to merchant class, military, criminals, and clergy. Gotta have some towers so put some in for the mages to hermit themselves away to study their books. Put in some old lost shrines and ruins of towns from long long ago. These places need to be far away from towns or else they won't be special or "lost". Caves and dungeons need to fairly close to all of the small villages since major cities have armies to go clean them out. But you can put them wherever you want out in the wilderness. For non-human town placement use your best judgement as to how you think the particular species might think or behave. 14 done.

Draw in the trade routes between major cities and capitals and ports. Put some roads between medium-size towns and put some trails between small villages. Connect the smaller routes to the more important routes and make sure that there are fewer main routes and many minor routes. All cities and towns should be linked up. Try to connect most of the villages but you don't have to connect them all. Places connected by river don't necessarily have to have a road since they already have a river. 15 done. This next part takes almost as much time as river placement (for me) and that is coming up with names for all of these towns. There are many name generators online but they all seem blatantly fake to me so I just use generators to spark my imagination into coming up with real and good names. But when all else fails just go with a generator. 16 done. Now start naming other things like mountains, lakes, swamps, etc. 17 done.

Put a compass on the map to indicate north and then come up with a scale (distance meter). 18 done. Put on neat lines - a border - whether fanciful and swirly or just an extended scale bar. 19 done. If you want to get fancy then you can add latitude and longitude lines, rhumb lines (those angled lines you see on old maps - there is a reason for them but I'll let you research that), inset maps, decorations, and illustrations. 20 done. Lastly, put your name or logo or watermark on it and if you make it public anywhere (like say post it online or in a blog or your own website) make sure that you state some sort of usage/copyright (you can look that up in the guild as well).

Placing things in a city is a whole other can of worms so we'll discuss that elsewhere.