He stayed in Smyrna for a few years before he settled in the city of Volos in about 1897, searching for occasional work and painting in houses and shops of the area.
As well as painting, he was also involved in organizing popular theatrical acts for national ceremonies, and in the carnival period he had a major role, sometimes dressing as Alexander the Great, with pupils in Macedonian phalanx formation, and sometimes as a hero of the Greek Revolution, with gear and costumes made by himself.
Legend states that he left Volos because of an incident in a kafeneio (coffee shop) where someone played a joke on him in front of others and threw him down from a ladder where he was painting.
In Mytilene, despite the mockery of the people, he continued to draw, painting many murals in villages for little payment, usually for a plate of food and a cup of wine.
In Mytilene, the renowned art critic and publisher Stratis Eletheriadis (Tériade), who lived in Paris, discovered Theophilos and brought him a great deal of recognition and also international publicity, though posthumous.