You will need:

Paper to draw on - I used newsprint
A writing utensil - I used a black Sharpie
A hard surface

You'll also need someone to draw. You can use a live model, a mirror, or a photograph.

I used a picture of my cute wife. To make it easier, I edited the photo to make it black and white. It's best to use dramatic lighting to create contrasting colors. This not only makes the model interesting, but also easier to draw.

Step 1: Create Your Outline

Draw a quick line across the middle of the eyes and down the nose to make your guidelines.

Step 2: Understand the Four Points of the Face

There are four areas on the face that are vital.

Underneath the eyebrows
Underneath the nose
The top lip
Underneath the bottom lip

There is always some sort of shading that must occur in these areas. Steps 3 - 6 will walk you through placing these points.

Step 3: Underneath the Eyebrows

Imagine two parallel lines running vertically from the inside corners of the eyes. Use this to estimate the distance between them. Sketch in the darkest areas beneath the eyebrows. Use your guideline to find the corners of the eyes.

Step 4: The Nose

Use your pen to match the angle from your model to your paper to find the right spot to begin the nose. Imagine a triangle forming with a corner on each of the outside corners of the eyes and one at the tip of the nose. Mark this point by shading the dark areas beneath the nose.

Use your pen to find the position for the sides of the nose. Measure the distance from the inside corner of the eye. Ask yourself, is the edge of the nostril lined up to the eye or is it more narrow or more wide?

Once you have the position, sketch in the darkest areas around the nostrils.

Be aware - Often, the nose is drawn too long. This is why the triangle is important. When in doubt, move it up.

Step 5: The Top Lip

The lips are always a shade darker than the rest of the face.

Use your pen to find the corners of the mouth in relation to the eye. Ask yourself, is it below the pupil or more narrow or more wide?

Sketch the shading of the top lip while keeping in mind the extent of the bow of the lips.

Step 6: Underneath the Bottom Lip

It's not necessarily the chin that you're focusing on, though sometimes it can be. The bottom lip sticks out and creates a cast shadow along the skin. The shading here will give your portrait realistic depth.

Start with a simple, short line underneath the center of the bottom lip. Follow this line to create the cast shadow.

My model had some definitive shadows that shaped her chin in this area so I went ahead and shaded those in.

Step 7: The Eyes

Begin adding the details to the eyes: the pupil, the iris, and any deep shadows.

A few warnings when detailing the eyes:

Don't be confused by the whites of the eye. The eye is a sphere and will still have shading around the iris.
Be wary of the highlight. It will be in the exact same spot in each eye.
Don't try to draw individual lashes. Use dark shading instead.

Step 8: The Darkest Darks

Find the darkest darks. This includes the negative space surrounding the face. This darkness will likely have you framing the face.

Don't be afraid of the dark. Determine the shape of these dark spaces and fill them with bold strokes. Make adjustments as needed.

Framing the face may also bring you to the ears. My model has hair covering her ears. These don't have to be fancy. Compare the tops of the ears with the eyes to find the position and mark it. Use the bottom of the nose, or possibly mouth to position the lobe of the ear. Fill in the dark spaces and be done.

Step 9: The Lightest Lights

Find the highlights. Create a contrast with the surrounding area by making the edges of the highlight dark. This will contour the face.

My model has light coming off her hair. I used my pen to create a dark contrast with the negative space to bring it out.

Step 10: Contouring

Your darkest darks and lightest lights should be in place. Now is the time to shade in the rest of the face. If your model has dramatic lighting, one half of the face may be darker than the rest.

Don't make it complicated. Find 2-3 different shades of light. Put them in and be done.

Step 11: Completing the Portrait!

Step back.

Close up, you may think your portrait is a mess. Leave it alone and step away to see it from a distance. Compare your model with it to make any finishing touches.

Art always looks better from further away.

You're done!