What quadras do you identify with?
Just do it....
That analyzer voice sounds like E-type 1, doesn't it? Remember this: that voice is not more right than you are. It's just another opinion. Some people will agree with you, some with that voice... At least that's what I'm telling myself.
But I know exactly what you mean about analyzing. What about you paint that portrait only for yourself, without thinking about showing it to anyone? Then you could enjoy the painting process, and ruin the portrait afterwards if you feel like it, or show it only if you want. I guess it's better to make a "you" painting than to make a perfect painting. Or? At least I can't make "me" if I listen to hard to that analyzer voice. In my world
perfect is OK,
"me" is better,
perfect and
"me" is the best. I paint myself, and I have decided to never feel the need to "show" my paintings to anyone, as I paint only for my own pleasure. Once I feel the need to show off, the analyzer takes control over me, and it's not recreation anymore. Painting is for me and for me alone. I have a lot of other areas of my life where I feel the need to be "perfect", so I don't want art to be an area of perfection, it's for expressing myself... I'll show you some of my paintings if you'd like. They are all weird, haha. Do you sell your paintings?
It's very similar to me then. I also recognize some 3 and a little piece of 5 in myself. Read this about type 9:
We have sometimes called the Nine the crown of the Enneagram because it is at the top of the symbol and because it seems to include the whole of it. Nines can have the strength of Eights, the sense of fun and adventure of Sevens, the dutifulness of Sixes, the intellectualism of Fives, the creativity of Fours, the attractiveness of Threes, the generosity of Twos, and the idealism of Ones. However, what they generally do not have is a sense of really inhabiting themselves—a strong sense of their own identity.
Ironically, therefore, the only type the Nine is not like is the Nine itself.