He then for a time acted as auctioneer's assistant, subsequently becoming partner in the firm of Willoughby & Scoones at Maritzburg, where he resided.
After a short period with a theatrical company, he raised and commanded an irregular troop, "Willoughby's Horse", which saw service in the Basuto Gun War of 1880.
[1] In January 1884 Willoughby went to Madagascar, where, gaining the confidence of the Queen Ranavalona III and her husband Rainilaiarivony, the prime minister, he was appointed on 18 May general commander of the Hovas, the kingdom's armed forces (18 May).
[1] The mission involved the negotiation of a loan; but when Willoughby returned to Madagascar, belatedly, he was charged with the misuse of funds, and expelled from the country.
On the outbreak of the Second Matabele war in March 1896, he formed part of a council of defence at Bulawayo, under the acting administrator of Rhodesia.