I think I could give both of you the same answer, since your questions more or less relate a lot to each other.
When you feel overwhelmed of starting with a new area, you get easily frustrated and rarely satisfied with your first tries.
May I remind you that it took me over half a year to progress through lots of tries and fails. It’s not until recently that i’ve started to feel a bit more confident in my environmental paintings.
You can actually just dig through my archive in my blog to look for yourselves more or less.
When you are frustrated, and you are really really fighting with this picture but something doesn’t look right but you don’t know what and so on - just stop working on it. If it only makes you feel art-blocked, then start a new, different environment painting.
If you worked on a forest, then the next one could be a snowy tundra. Snowy environments are btw pretty easy and fun to paint. Since you can really play around with cool, blueish shadows and warm lights.
Since environment paintings for games or illustrations, are all based more or less on real places and the real nature here on earth, it’s recommended that you try out painting regular places like a taiga forest, a mangrove swamp, a sunny beach and so on. They are basic and there’s plenty of references.
I’d suggest you spend about 20-30 minutes on each environment. You can use either a photograph to do a very rough study on. Or use your own imagination from what you know how that particular environment looks like.
I dug through my old archives and found some old paintings I never finished that might show other techniques I used at the start:
I remember when I made this one, I was inspired by a color scheme from a painting I saw online. This kind of painting isn’t really so much of an environment - it’s just a mountain, but I think it’s not a bad idea to actually take your time and draw common nature objects separately. Just to get a bit familiar with how they look like and try out different techniques on how to paint them until you find the one that suits you.
Also, I think it’s really really fun to paint clouds. You have no idea how incredibly fun it can be if you just throw in some colors!
This one was one of my very first tries at buildings, without having to use vanishing points (aka “cheating” LOL). For nature and landscapes, starting with overlapping silhouettes as shown in this painting is not a bad start. Dontrast and backlight always looks good.
Remember to not be afraid to do very cliché paintings in the beginning, if you don’t get those cliché little nuggets down on the canvas first, they will take up space in your brain where you could’ve store more original ideas for later! :D
This one is also one of those paintings I never really finished. I think this was gonna contain airships and stuff like that, but I got bored before I even added that stuff.
However, as you can see, I used air perspective and overlapping silhouettes for the mountains. Also note that the colors are darker and more saturated as they are closer to the “camera”.
And also the most important one to do:
Do either life drawing studies of environments if you live in such a cool area.
Or do studies of photography, I strongly recommend you to go take your own photo references if possible.
A photo study I never really finished on. heh.
but I’m happy I at least tried and got started even though I rarely finished so many of the studies and thumbnails I worked on.
I hope these sort of help you peeps out!
Jack Hamm’s Drawing Scenery: Landscapes and Seascapes