I wish painting faces was like riding a bike. I used to draw portraits photo-realistically like it was my job, back when I was 10 or 12 years old. That’s when I drew all of the time, and you’re bound to conquer anything you put that much practice into. Now I’m starting over, except with paint and a brush, and the road back to decent portrait painting has been rockier than I anticipated. I’m getting there though. Each one is getting a little bit easier, feeling a little more natural, and a lot less confusing. But I definitely had to make a concerted effort and re-learn all the proportions and techniques.
The biggest challenge to painting faces is 1) symmetry (which is why doing face profiles are fairly easy), and 2) learning the difference between painting realistic faces and Barbie faces. Not every face needs to be so perfect in proportion that it looks plastic. Yet…every face does need enough proportion to render it realistic. That being said, clearly there is a lot of fabulous art that is neither realistic nor technically correct. But, there is something to be gained from first mastering technicality and then exploring what it means to break it down.
Even my little boys know that it’s inherently more meaningful to destroy a meticulously built castle in the sand than it is to destroy a crude heap. They can and will do both–but the former is always more satisfying.