PurpleScissors' Sketchbook

[Punk-A-Cat]

I don't think it's psychological, I think it's because he's so familiar to you that it needs to be /perfect/ - whereas someone you don't know, you can get a likeness of, and you won't feel it's wrong because you don't know them so well.

I also think it's harder to draw someone you know well because you've reduced their face into a symbol in your mind. You could try using a photo reference and turn it upside down, so you are drawing what's /there/ not what you think should be there - just as an exercise to see if it helps.

I think sometimes facial expressions really make a face more familiar too - so if someone is sitting for you, and they are holding a pose, they might not be displaying an expression you normally associate with them, which might be messing with that feeling of it looking right.

Just keep working at it - use the putting in the mirror/ flipping the canvas upside down tricks and try and see what it is that's not feeling right. Putting it down and leaving it for a week can also give you fresh eyes, as can taking a photo of it if you are working traditionally.

If you are working from reference, getting someone else to look at it alongside the reference might also help.