Painting portraits for a living is a tough business.  For one thing, most people don't know what they actually look like so your job to replicate someone's appearance is already a losing proposition.   Every facial feature puts you at crossroads.  He's got heavy eyelids.  Why?  Too much sleep?  Too much wine?  Bad parenting?  Well never mind all of that - you can't paint those lids as is or he'll look like himself and trust me, no one wants that.  Make the eyes brighter - always do that.  Add flicks of light no matter that there were none to be found in your photo reference.  Everyone should peer out from glistening eyes - it's a trade secret.  Don't mind telling you since we're already here talking art.    

An arm and a leg ...

Know where that saying comes from?  Portrait painters used to charge more for adding limbs to their paintings.  Want that hand of yours resting on the captain's chair?  It'll cost ya.  Lose those legs - save some dough.

As I finish up one of my tougher portraits I'm left with the feeling that it matters less that the work captures the patron and more important that they look amazing sitting in that wing-backed chair staring blankly at us with a smile that looks like an iron-on decal.  What's most important is to keep in mind that these paintings are heirlooms and people want to look back on Uncle Jimmy as having great hair and the lightest of eyelids.  We're selling idealized memories here, nothing archival  -- these works are eulogies and eulogies don't speak of smile lines.

The worst thing that can happen with a portrait that doesn't please the patron?  You're stuck with it.  What the hell can you do with that double portrait of that woman with the thick frizzy hair and her calico? No one wants someone else's portrait - that's like buying a diary with words already scribbled in it.  Unless you're famous and troubled in which case a portrait of anyone you might paint will sell, you probably need to gesso over the work and reuse the canvas as a tiny sail on some boat.