Returning to Norwich, Repton was apprenticed to a textile merchant, then, after marriage to Mary Clarke in 1773, set up in the business himself. He was not successful, and when his parents died in 1778 used his modest legacy to move to a small country estate at Sustead, near Cromer in Norfolk. Repton tried his hand as a journalist, dramatist, artist, political agent, and as confidential secretary to his neighbour William Windham of Felbrigg Hall during Windham's very brief stint as Secretary to the Lord Lieutenant of Ireland. Repton also joined John Palmer in a venture to reform the mail-coach system, but while the scheme ultimately made Palmer's fortune, Repton again lost money.