Painting is said to be a risky source of income due to generating reputation that attracts the attention of your Hunter. It is viewed as risky due to reputation, but it's really not - more on that later. Painting is always a good source of income when you've put in the effort to level up your imagination. Later you can stop physical work, although I would still do this for money from time to time unless I'm a doctor. The first time you get sick after obtaining 3 Health, leave it to get Decrepitude. You should get all the Health before studying lore, with the other two better wait for random Eruditions/Glimmerings. It's also good to have the painting skill upgraded to the point where you put 4 cards in the Work verb, although that's not necessary and might be tricky to do. The final stats you need to obtain to finish the game smoothly are: 3 Health, 5 Reason, 5 Passion. Once you get the basic painting skill, you can also turn to studying Reason.
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So your first Study priorities are Passion, until you can upgrade it, then Health. You should start with unskilled labour, because painting needs a skill to be any good. Unskilled labour gives you Vitality and painting gives you Glimmering, which you need to upgrade your Health and Passion.
You will not be making any money, but you don't need to at this point - you're not reading books yet.
In the early game you should focus on unskilled labour and painting. The main point of working is not earning money, but development (read: helping with Study) and the position at G&G only hinders that.
What I have to say is: ♥♥♥♥ these guys! You don't need to see them, ever. All the guides that deal with work I've seen deal with working at Glover & Glover and earning promotions there.