A Lot of Free Life Models
Here is what you can do to do to increase your time working from live models:
First, make sure you can draw well enough so that you don't thoroughly embarrass yourself the first day. I am assuming you have been drawing objects over and over and over again for years. Specifically, draw over and over again the oval shape of the head, where the eyes are on a line in the middle of the face, the location of the ears, etc. etc. in the full face (and easiest ) pose. (If you can get the location of the features right and add big eyes (for children) and pouty lips (for women) you will be halfway home in your drawings for many people. Incidentally, caricaturists frequently do this.) Then, buy a Planes of the Head cast and try this at home with a light in the classic portrait setup.
Secondly, set yourself up somewhere with your charcoal setup and inexpensive paper, two chairs, a timer and a portable light. Put your subjects in the same full face position, where you can see both ears and be lit from above, so there is a shadow on the nose that doesn't hit the upper lip. Make a big sign that says "Free Charcoal Drawings" and settle down for a few hours. (You can also try this with your oil paints but maybe not your first time out there.)
Take time figuring out where the "somewhere" should be. One of my favorite artists did this in a busy shop that his friend owned, one Saturday a month and the friend promoted the artist and put out flyers. The line of willing models went out the door.
I suggest that you take the position that you are creating free sketches - don't sign them with your signature. Be prepared to take some hits to the Ego of Vous. At first you will have only be successful with, oh, maybe one out of ten but in a short while this ratio will get much better and most importantly you will gain confidence.
If you're going to work in a park or on the street be sure you research the local ordinances against vagrancy and solicitation. Even if you aren't selling anything you can still be hassled for sidewalk obstruction, and then you'll be pushed into the gutter where you may be taking up valuable parking space.
What you should NOT do is take along a photo and show everybody how skilled you are at copying it. You will be ridiculed by passersby who snipe, "Oh, he's just copying a photo", and you will deserve it.
Your goal is to live and breath making art, to let seeing and drawing or painting flow seamlessly from you into your art. Get tough about criticism and rejection - all it means is that certian people are not with you on your planet, which is fine - others will enjoy you, and nobody is for everybody. (Nevertheless, get better, for heaven's sake, and seek out artists who can help you grow to be a better artist.) You must get your confidence level up - winning awards doesn't do it, DOING the work does it.
Remember that you are a drawing and painting machine! When somebody asks you to paint him, you don't say, "Oh, wait until I take the photo and go Photoshop it and then I'll get back to you." YOU PAINT. You're an artist, that's what you do.
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