 Yu Shiji was considered knowledgeable and quiet in his youth, and was particularly good at calligraphy.The high-level officials Kong Huan (孔奐) and Xu Ling (徐陵) were both impressed with him, and Xu was so impressed that he compared Yu Shiji to Pan Jun and Lu Xun, and gave a niece to him in marriage.He initially served on the staff of Chen Shuyin (陳叔英) the Prince of Jian'an—the brother to Chen's last emperor Chen Shubao, and later served in the imperial administration as well.