Shilling joined the Nikolai Cadet Corps in 1888 and the 1st Pavel Military School in 1890.
He served in the elite guard, the Izmailovsky Regiment, between 1888 and 1913, and reached the rank of colonel in 1909.
After the signing of the Brest-Litovsk Treaty, Shilling entered in the service of the German-controlled Ukrainian State of Pavlo Skoropadskyi until its collapse in December 1918, when he joined the White Russian Volunteer Army.
He was widely criticised for the disastrous evacuation of the city on 6 and 7 February 1920, when thousands of White soldiers and civilians were left behind to fall into the hands of the Red Army and the Cheka.
When Anton Denikin was replaced by Pyotr Wrangel at the head of the AFSR, Shilling was retired and emigrated to Czechoslovakia, where he temporarily led the Foreign Union of Russian War Veterans.