There is another way...

Among caricaturists, there is ENDLESS debate and controversy about what should be emphasized, whether quality or speed. And there's much noble talk about balancing these two elements. On one extreme is the artist who demands a "studio" type piece on each drawing, and seems to take FOREVER on each drawing. The other extreme is the FAST artist, who will draw very similar-looking faces over and over, very quickly, while being a real salesman and, even, a clown/comedian or something, entertaining and laughing and grinning. I suppose the second type is closest to what is expected of the contemporary caricaturist, but, boy, you're starting to move a long way from ART in that scenario. Then again, some interesting things happen in those pressure-packed, crazy, spontaneity-filled sessions of caricaturing at retail stands and at private gigs. The IDEAL caricaturist is the one who can draw great, and quickly. That ideal is, simply, phenomenally difficult, and rare.
...In nearly four years in Florida, I do think I've fully explored the normal approaches to caricaturing.
...But there is another way to approach retail caricaturing, I believe, and for aspiring artists, it may the best. Here it is: retail caricaturing should emphasize neither speed nor quality, but, instead, LEARNING. That is what I'm doing now. Of course, I want to maintain a reasonable speed, and I want the finished work to be neat and fair. But, before that, I can learn.
Here's how it works. You go into a shift at a retail stand. You set-up, and there is no one to draw. Well, sit down and begin sketching. Maybe bring reference material. Sketch, sketch, sketch. And then color, color, color. Now, since you're at a caricature stand, the professional thing to do is to sketch and color cartoon-like material. But what am I doing, exactly, with all this sketching? I'm CREATING. I'm exploring. I'm thinking of a certain character design, maybe a flowing movement THIS WAY, or THAT way, and I grab my pencil and I sketch it out. Wow, that's cool, let's try it like this. ...What you're doing is flexing your creative mind, and your VISUALIZATION. Try to SEE the image on the paper before you draw it.
But what about customers? Here's what I do these days. I'm happy! I look at the model and I visualize his/her face in a "cool" way or angle. What cool features does he have? What does he want to be? Basketball player? Well do you want to be dribbling, or shooting, or dunking? Dribbling? OK. ... So I draw the face, using marker-only at first, then using a pencil to guide me for a lot of it. And then the body. Hmm, I've done dribbling basketball players before, but maybe I can come-up with something NEW. I look at the model. Is he skinny or fat? Or muscular? Or is the model a pretty female teenager? Are her breasts small? Are her arms long? Or is she a little chubby girl? ...You see, instead of drawing the same little body over and over, which I'm guessing is probably kinda lame anyway (be honest!) you let the WHOLE person guide your creativity, and you come-up with something original and cool. (You must use a pencil for this type of creativity, by the way, before inking.)
And you can extend this to the use of watercolors (if you're at a location that uses watercolors) or whatever coloring method you use. Experiment, mix creatively. Although, to be honest, most of the experimenting with color should be done at another time. But what CAN be done is OBSERVATION. Use your color knowledge to match the model's hues/complexion. I mean, just yesterday, my buddy Brian told me he uses a madder (pinkish) color to mix with his naples yellow-red, and when I tried it, WOW, it was SO much better than the red I was using (for many faces).
My roommate Wayne had told me that when he worked with our friend Joe (Bluhm), that Joe told him to "make every picture different." And that was the insight which got Wayne on the way to phenomenal improvement. Caricaturing ended-up not being Wayne's "thing," but my point is his artistic improvement, which was crazy-good.
And that's the whole point. That's the "other way" to approach caricaturing. You see, caricaturing is a TEMPORARY activity for most of its artists. They will either move on to other art and be successful, or they'll leave professional art behind altogether. I'm speaking to those who want to "move up" to other art and be successful. That's what I'm trying to do myself. Now, that "other" art may be, simply, studio caricaturing, or it may be illustration, or fine art oils, or even sculpture. Whatever. The main thing is that you use your many hours "in the trenches" as a valuable tool in increasing your artistic skill. It IS possible. Anyway, it's a lot more satisfying than cranking out the same crap over and over. And you can still make a sustainable living.
Good luck!

[One last note: For those who wish to continue caricaturing in retail and at gigs, I recommend the same approach. But you MUST be able to "change gears" and go REALLY fast. There's really no other way. If there's a line of people, you MUST knock 'em down quickly. That's how the game is played. And that's fine. It's intense, it's crazy, it's like an athletic competition. BUT, I plead with you, avoid this: DO NOT become one of those guys who apparently doesn't care. That's the only way I can describe it, in a sense. This is the guy who never improves, and cranks out pic after pic, and it's all crap, really, and it all looks the same, and the guy often will make lots of dollars. And the caricaturing companies "love" this guy, simply because he makes a lot of money for them. They really do WISH he drew better quality stuff, but they have only so much control. (Heck, if I owned such a company, I'm sure I'd feel a similar way.) But, unfortunately, it comes down to paying the bills, and this artist will indeed be rewarded. He has reached a certain point, where the average customer is generally satisfied with the experience. But this is NOT art. It is an assembly line, it is entertainment and salesmanship. These artists talk and sing and dance and joke and, sadly, never improve and do not respect art. They respect their sales numbers. ...Sales numbers. Gosh, that's all I ever hear anymore! I did THIS much here. THAT much there. I BEAT so-and-so, hooray! ...It's low-brow competition among friends, but it's not art. ...In general, I'd say this is a Crap Stage we all go through, but you MUST move beyond it. I'm trying, myself, to move beyond it. And while fast crap may pay the bills, you satisfy only your wallet, while the other artists furtively snicker, and while the artist inside of you regrets ever giving you talent. How can that be satisfying? You may as well be selling used cars.]