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Late adolescence was a difficult time in Barry's life. He returned to England in the summer of 1900 and was confronted immediately with the question of his career. By this time it had been decided that Barry would not go into the family business, that privilege having been secured for his young step-brother. Whether this was Barry's own decision, or whether – as family lore decrees – his step-mother used his adolescent illness to have him removed in favour of her own son, remains unclear. Certainly Sonny was assumed to be taking over the family firm from an early age. In a letter from 1904 Francis' stepmother writes: 'poor little Sonny must hurry up and grow and go on with the works. It is lucky he is made that way and really loves work of any mechanical sort' Sonny was only nine at the time while Francis was approaching twenty-one.

Having decided his son was not fit for diplomacy, the services, or the cloth Barry's father was vexed about his prospects. Barry's own determination to pursue his painting met with opposition. Though his parents had encouraged his early works, they balked at the idea of him actually becoming an artist. To a family of industrious entrepreneurs the idea of a career in art must have seemed dangerously indulgent.

Barry's tutor Mr. Prentice, a keen horticulturalist, proposed a career in gardening. Barry's friend Beresford-Hope wrote of the possibility of army life. The Boer War which had started in 1899 was beginning to take friends and relatives. But then, as ever, Barry exhibited a notable lack of interest in politics and patriotism. Eventually, Barry prevailed and was allowed to study art.

Alfred East, a fashionable painter, was engaged to oversee Barry's work. East might well have been a family friend; an Associate of the Royal Academy, a successful landscapist, he was certainly as acceptable an image of the artist as Barry's parents could hope to find. When East was knighted in 1910 they must have felt vindicated in their choice.

Barry maintained a warm relationship with Alfred East throughout his life; indeed he dedicated his later treatise on painting 'with lifelong gratitude, to the memory of my beloved master and friend, Alfred East.' East's main influence on Barry's work was in his approach to landscape. East taught Barry to simplify; to concentrate on the overall form rather than the detail.

In the summer of 1900 Barry spent some months at Bournemouth Art College, against his parents' advice. Bournemouth was a small municipal institute set up to train professional artists and art teachers. Though it offered classes in figure, landscape and still-life drawing, it specialized in practical crafts such as etching and lithography. It might well have been here that Francis Barry first developed a taste for etching.

After returning from his European tour in 1900 Barry was prohibited from living with his family. Although he begged to come home on several occasions, his parents maintained that it would be detrimental to his health. Until he was old enough to be on his own, Barry lodged with various doctors. Perhaps his parents genuinely felt he would be safer under the eyes of professionals; a more sinister explanation suggests that he was being disenfranchised from the family. During these difficult years Barry turned to his maternal grandparents for comfort. He visited them often and enlisted their support. Disputes arose and in October 1900 Barry's father forbade him to write to any members of the family, particularly his Bicknell grandparents. Concerns about his mental state feature in the family correspondence at this time, although there is no evidence to suggest that he was ever unstable.

While studying at Bournemouth Art College Barry lodged with Mr. Prentice and his mother in Ringwood – a small town north of the city. He remained with the Prentices for several years – not all of them happy. When Barry wrote to his father asking to go away for a short break, his father insisted on 'talking the matter over with Dr. Prentice'; regarding his censorship of his son's correspondence he stated: 'I do not feel inclined to make any alterations at the moment, but I will talk the matter over with Dr. Prentice next time I'm in Ringwood.'

In 1901 Barry wrote to his father saying that he hated where he was living, it was full of elderly invalids, he was lonely and found it difficult to paint; but as late as 1903 Barry's father was still insisting that he remain with Mr. Prentice. As a consolation he offered his son a regular allowance of £400 per year to be paid in quarterly instalments, 'the same amount as your Grandfather allowed me when I was your age.' By today's standards that would amount to about £24,000, but the gift was not without conditions: Barry was admonished to keep careful accounts which his father would periodically inspect. His father also lifted the ban on letters, claiming: 'I am going to show my confidence in you by allowing you to write to anyone you like without showing the letters to anyone, either to Mr. Prentice or to me.' But the problems continued.

In 1903, when he was not yet twenty years old Francis Barry became engaged to a fellow artist, Doris Hume-Spry. Despite her impeccable ancestry – she was descended from the Dukes of Rutland – Barry's family opposed the engagement; Doris seems to have had no money behind her and Barry had demonstrated no ability to support himself. Barry's parents refused to receive Ms. Hume-Spry. Mr. Prentice was drafted to meet the young lady. Barry was counselled to wait till his twenty-fifth birthday. Doctors were consulted. Ms. Hume-Spry's mother was informed of his medical history. The engagement was broken several times – by Doris who found another chap, by Francis who found another girl – but somehow the relationship survived.

In 1904 Barry broke free of Mr. Prentice and moved in with a Dr. Sells in Guildford who later attested: 'When Mr. Barry came to me as a resident guest in July 1904 I considered that he was suffering from overwrought neurosis due to the conditions and surroundings in which he had been for a long time living. All these effects have passed away and he has gained in self confidence and character – in fact he became a perfectly normal young man it is my opinion that when he attained the age of 21 he was fully competent to assume the responsibilities of his age and therefore fit to manage his own affairs and take his proper place in life and this opinion has been fully justified by subsequent events'

For reasons which remain unclear Barry's father did not approve of Dr. Sells. When, in 1905, Barry decided to follow Alfred East to Cornwall to study at the Newlyn Art School, for once he had his father's full approval.
 

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