Sometimes it’s difficult to know how to landscape an open piece of land because there’s no context. Even though the land may appear blank to you, it’s not blank to the sun, the wind, and the plants. Instead of visualizing shapes and selecting plants, walk the property throughout the day. Observe the sun, shade, wind, and eddies around and through buildings. You’ll gain much more insight than you will from an artistic sketch in your living room.
First, observe how the yard reacts to rain or watering. Water that gathers in little pools, or areas where the ground stays wet for a long time or moss is growing, is a sign of an area with poor drainage. Dry areas where the ground is cracked could be areas where the water runs off too quickly. You can stick a finger or a small stick into the ground in various places to get a feel for what is going on beneath the surface. These factors will influence where you place a path or a garden or a patio, long before you start thinking about color or style.
Another critical thing to note is circulation. Follow a person’s spontaneous path through the garden, rather than prescribing one. The desire paths that people make through lawns will tell you a lot about the preferred routes. When the layout of a garden defies these paths, it can feel frustrating to use, regardless of how good it looks. A frequent error is to position interesting items so that they are directly on the path. They are so interesting, in fact, that people will step out of their way to get around them, and they wind up with an attractive little path edging around them. The solution is to position interesting items along the path people already use, not the path you think they ought to be using.
Don’t rush to judge the light. Observe it at different times of the day and in different seasons if possible. Take a few minutes in the morning, noon, and late afternoon to notice where the shadows fall and where the sun shines. Just 15 minutes on two or three days will help you decide where to put which plants. If you still can’t decide between two spots, think about where you’d like to sit and rest for 10 minutes. It’s probably where you’ll most enjoy that part of the garden over time.
Once you have observed all of these things, draw a rough plan of the plot and note where the sun is, where the shade is, where the wet spots are, where any existing paths are and any view you want to accentuate or screen. This doesn’t have to be an accurate or scale drawing. You just want to record your observations in a way you can refer back to them. I think it helps to make the initial design seem less arbitrary and more dictated by circumstance. And with practice, I think you become more comfortable with the process and it becomes easier.