Vincent van gogh painted over 30 self-portraits between van gogh self portrait the years 1886 and 1889. his collection of self-portraits places him among the most prolific self-portraitists of all time. van gogh used portrait painting as a method of introspection, a method to make money and a method of developing his skills as an artist.in a letter to his brother theo in july of 1888 van gogh wrote, "besides, i think i have spoken the truth, but if i should succeed in replacing in goods the money spent, i should only be doing my duty. and then, something practical i can do is portrait painting." van gogh did not have money to pay models to pose for portraits nor did he have many people commissioning him to do portraits, so van gogh painted his own portrait. van gogh did not see portrait painting as merely a means to an end; he also believed that portrait painting would help him develop his skills as an artist. in a letter to his brother theo dated september 16, 1888, van gogh writes .