In this new drawing class, my teacher showed me how to shave down pencils so that more of the lead is exposed. Simple, but smart. Also this doesn't waste the lead like a pencil sharpener does. I also got a gum eraser (not pictured) and some fixative so my drawing don't smudge.
If you don't draw and aren't interested in drawing you may want to skip this paragraph. Or not. Whatever. With new materials, and new skills, I decided to take a slightly different approach. I tried to shade more gently. I held the pencil between my thumb and middle finger like a paintbrush. It's a method I knew about before but never took seriously because I got frustrated easily. When I tried this a few years ago, I was expecting to have the same sort of accuracy holding it like this as you would if you were holding it 'normally', as you would for writing, so when I couldn't get that I just dismissed it more or less. Not holding the pencil at the tip, near the lead, makes things smoother all round. It's also fun because it requires a lot more patience building up the tones than furiously moving the pen back and forth. Holding the pencil from far, I can push it down on it's side more easily for a darker tone, and I don't lose accuracy. It takes more patience, but it definitely works better for smooth shading. I will still hold the pencil the old way sometimes, to make more sketchy, hatched looking drawings, or just to draw lines but I'll stick to trying to make smooth tones like this. Another thing I learned was to make things darker. Makes sense, more contrast, more range help. I still didn't go dark enough in this portrait but it's a start!