"Crop Irrigation" | 11x15 | Watercolor - Plein Air (Available Here) In watercolor, the natural order of things is to paint light to dark. In this case, the sky and horizon were first, with the field being second, and the dark accents in the foreground as well as the trees and irrigation equipment being last. Sometimes breaking a scene down into three value groups or steps can signigicantly clarify where to begin and what to do next. 

Recently I watch a video by renowned Australian watercolorist Herman Pekel, and I was a bit shocked to see him start his painting right at his center of interest, the most important area in the painting. I don't do that with landscapes, but I often will with portraits. As watercolorists we tend to paint the lightest things first and work toward the darker colors. In oils, most artists paint the darks in first. Often times people paint the furthest thing in the distance and then work their way forward. So which way is the best way? 

The truth is, as you may suspect, there is no right or wrong way, and it really depends on your painting style, the subject you're painting, or the medium you're painting with. 

In terms of painting style, I tend to lean more toward the painterly side of the scale, meaning that I like to leave gestural brushstrokes that embody momentum and convey the energy of an object. This type of painting style does lend itself more flexibility in terms of where to begin a painting because there is more emphasis on energy and rhythm than there is on precision and accuracy. That means when you paint loosely you don't have to worry as much about whether you're painting in the right spot because you aren't as worried about "leaving tracks" in the wrong spot. 

"Enticing Sunrise" | 11x15 | Watercolor - Plein Air (Available Here) Gestural brushstrokes tend to hide the starting and stopping that painters do while they are thinking about what to do next. Too much of it can cause chaos in a scene, but the right amount can add lots of energy, and can buy you some time to figure out what to do next. 

If you tend to paint more controlled, then you likely want to have more of a system to where you start and where you stop. I have certain work I've done over the years that falls into the "tighter" realm or style, and when working this way I think an artist tends to start with a very detailed drawing, and then picks there way through the piece. I like to start with the largest and easiest shape in the composition. It helps to get the feet wet, settle some nerves, and take a big chunk out of that intimidating white canvas or paper in front of you. 

What subject you are painting will often dictate where you start. For example, many portrait painters will work on the portrait first, knowing that it doesn't pay to spend any time anywhere else if you don't get the portrait right in the first place. Landscape painters do often work backwards to forwards, using the paint layers to create a pseudo sense of depth, in addition to the logical layering that occurs to establish overlaps and therefore an illusion of distance in a piece. 

 "Enticing Sunrise" | 11x15 | Watercolor - Plein Air (Available Here)
This piece uses the backwards to forwards method, where clearly the horizon is first, the warming house second, and the pole on the left being last. 

Whether you are working in watercolor, oil, or acrylic makes a big difference too (I can't speak to pastels as I haven't worked with them enough). Each medium has an approach that best suits its true nature. 
Watercolor is a transparent medium, meaning that each layer of paint cumulatively builds on the ones before it, and also meaning that if you want something to be light, you typically have to paint around it. For example, if you want a white cloud in your blue sky, you have to paint around it. So in watercolor, many artists will simplify their subject into three value groups: lights, mids, and darks, and then paint 3 subsequent washes that correspond to those value groups: a light wash, a middle value wash, and a dark wash. That means, they start with their light colors and work toward the dark ones. 

Oil is a slower drying opaque medium. The nature of the colors in oil make it so that it works best to put down the darker, thinner colors first, and then build the fatter, lighters colors over the top. The key phrase here is fat over lean. Lean means using solvent like mineral spirits to mix in with the paint, fat means using oils like walnut oil to mix with the paint. So many oil painters will actually draw their scene in with a bush loaded with dark paint, and then will paint in all their dark areas, followed by middle value areas, and wrapp it all up with the lights. 

 "Bathed In Warmth" | 18x24 | Oil (Available Here) Here, the light accents of the street lights and car highlights were the last things painted in the scene. The first things were the darkest areas of the building shadows and foliage. 

Acrylic is the medium that is most commonly used in both an opaque and transparent manner. This means you can kind of start and stop where you want. And since it dries quickly, it allows you to build up layers in short order to create depth and to rework areas until you're happy. The drawback of course is that you tend to end up with a lot more hard edges in acrylics due to the fast drying time, and it's also more difficult to blend colors together in a seamless, soft texture.

All three mediums have their own tendencies as to what works best to paint first, but I would say that acrylics in general are the most flexible. That can sometimes be a drawback too, because if your not carefull it can cause you paint yourself in circles, so to speak. 

A final suggestion would be to to take the wise words of a college professor of mine and work from "general to specific". Find the broadest, largest area and start there, eventually working your way to smaller shapes and finishing with details like accents and line work. It's not always the best approach in every situation, but it will give you some strategy to tackle your painting and win the stare-down with that all intimidating blank canvas. Hope this helps you a little bit and happy painting! - Dan