Moncrieff himself never married. Before he was out of his teens, Moncrieff had "written and made money by a real book". While he attended the University of Edinburgh he wrote "A book about Dominies" (1867), Dominies being a term used for schoolmasters in Scotland. This was taken by a publisher, who published it "at his own expense with a promise of profit to the author, which proved rather a mirage in the cold light of publishing accounts." It was published anonymously with no author's name given. The book was well reviewed and went into several editions. Moncrieff followed this up with "A Book About Boys", (1868) adopting his pseudonym "Ascott R. Hope" for the first time. Moncrieff was ashamed of some of his early books and went to some expense to withdraw them from circulation. Moncrieff says that he had "have made awkward attempts at more than one handicraft, with the view of gathering straw for literary bricks". He was said to have taken up teaching briefly more with the purpose of studying schoolboys and their ways than to making it a profession. Moncrieff travelled extensively. Even his census returns in the UK show how much he bounced around:  Moncrieff not only travelled the whole of Great Britain, but he also travelled internationally. He wrote: "It has been by lot to be a good deal about the world from an early age. After a boyish visit to Paris, my travels began with a cruise in the Mediterranean and a stay in Italy, still heaving from Garibaldi's exploits." Moncrieff travelled, and visited four continents. He even tried his hand at farming in Canada, but soon abandoned it. All of his travels contributed not only to the background for his books, but also supported his books on geography and history. Moncrieff suffered from short-sightedness and this led him to favour occupations such as walking and riding. And these leisurely pursuits allowed him to make observations that he made use of when writing on topographical topics. His study of the geography of the world, "The world of to-day : a survey of the lands and peoples of the globe as seen in travel and commerce" (1905) took him five years, and was updated every two years or so. Moncrieff wrote ever word of the six volumes, bar a single page. Moncrieff was a member of first the Savile and later of the Athenaeum.