Before your pencil makes contact with the paper, take a moment to really look at the object. A few seconds of real attention. Not a long study, not a dramatic pause, just enough time to stop guessing. The outline might seem like where you should start, but the perimeter is merely a portion. It helps to see how big, how slanted, how simple, and how placed the object will be within the page before you draw the perimeter.
Notice first, the big shapes in which the objects would fit into. It could be that a mug would fit into a tall rectangle or a rounded cylinder. A book would fit into a wide block. A pair of shoes would fit into a wedge that’s long. This “outer” shape will not be your final drawing; it’s a guide to see if you will be making the subject too broad, too shallow, or if you will have crowded the subject into one side of the sketchbook.
Take a look at the main lines that define angles. It’s common for beginners to make a subject drawn more upright than it really is because our mind prefers “iconic” or “symbol” shapes. A handle will dip down. The side of a box will tip down. The rim of a flower pot might appear to be a flatter ellipse than a circle. If you see this angle, you’ll be more likely to have the first construction lines align to the subject.
Negative space will be another good idea. This is the empty spaces on, and inside, the object. The space inside a handle, the space between chair legs, the space between a plant and the edge of a pot. It’s easier to see the space accurately than the object itself because you are less likely to name it from memory.
Next, think about where the drawing will end up on the page. It can be jarring if the subject ends up high, low, or near the edge by the time you’ve seen where you’ve drawn it. Mark the boundaries of the top, bottom, and sides, lightly so it’s easy to change. It seems insignificant, but page placement is important.
Now outline. Build it from what you’ve seen. Outline lightly, especially for lines that may bend or shift, for example, the contour of a cup might need to be curved. If the outline of a cup isn’t curved, look back at that cylinder. If the edge of a book isn’t straight, see how it compares with other edges of the book. Outline shouldn’t constrain the sketch from getting started, but it’s meant to confirm the larger decisions that have already been made.
A useful self-check is to pause when the first outline is complete but before adding hatching, shadow shapes, or small details. Does the object have the right width? Is it leaning correctly? How is it on the page? If you can make a good change after you’ve outlined, that’s better than putting more ink on the page. You’ll find the outline more helpful if you wait until you’ve looked, and not the other way around.