People usually want to draw the outline of a mug first, the one that outlines the rim, handles, and outside edge. They want to draw the outline of a leaf first, the seemingly simple outline of shape until the curve takes a strange tilt. They want to draw the outline of a key first, the outline of those small teeth that feel important in the moment. And yet before the pencil starts going around that outline, the eye needs a moment to process what it is seeing.
Find one simple object and set it up with even lighting. Do not draw. First look for the biggest outline in the image. Is the outline of your object portrait or landscape? Is it oriented upright, leaning left, or tilted to the top right? By seeing the biggest outline, you can avoid a common sketchbook problem where the outline is neat, but not the biggest outline.
Then look at the space around your object. The empty space inside the mug handle, the empty space in between those two leaves, and the empty space underneath those two scissors. It can be easier to measure the empty space than the object itself. This is negative space, and it will give you more clues to your scale. If you see narrow empty space in your real object, but it’s drawn with wider empty space in your sketch, the outline could be off, even if it’s a nice line.
And lastly look at the edges, the points where your outline ends. Some parts of the object’s outline will have sharp edges, while other edges can be lost in shadow, a change in plane or change in angle. Maybe the pot has a crisp side edge, but the bottom edge is more subtle, like the curve of its bottom. Maybe your shoe has a strong bottom outline where it meets the ground, but a more subtle curve on top. You can avoid drawing every edge at the same line weight.
It’s easy for a new artist to get distracted by the small details. You may want to draw the pattern on a cup, the veins on a leaf, or the little holes in a key before you draw the larger forms you see. That’s OK, that detail will be added later, just use light construction lines for now to block in the height, width, angle, and the largest curves first. Start with a simple box, oval, or cylinder, and use your reference object to see if your drawing looks about right for size and proportion.
After you have your initial outline, do not judge, compare. Look at your object, then look at your drawing, then ask a very focused question. Is the top of the drawing too wide? Is the side too tall? Is the bottom too narrow? Is the handle too low? Answer that one question, fix that one mistake, then go back to your reference. This makes fixing your outline more practical, and helps avoid erasing the majority of the drawing.
The final outline will be the choice made after you’ve done the most observation. With your biggest outline, most important negative space, and all the key edges checked, it will be a much more straightforward task to draw your darker outline. You will not be trying to discover the drawing, you will just be tracing what you’ve already seen.