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Drawing : He was attracted towards drawing and sketching. He sketches the portraits of many persons in his family, specially of Rabindranath there were numerous sketches in different styles. He drew the sketches of plain folk around him including the employees of his shipping firm. He had drawn around 2,000 sketches, which are preserved in Rabindra Bharati University museum. Some of his sketches were published in Bharati in 1912. William Rothenstein happened to see them. When Rabindranath proceeded for third time to visit England, he carried a bunch of sketches prepared by Jyotirindranath. Rothenstein was highly impressed and with his assistance the book Twenty-five collotypes from the original drawings of Jyotirindranath was published in England.
Business Venture : Jyotirindranath earned some money from indigo cultivation. He could not continue indigo cultivation due to the fall of demand of natural indigo after the discovery of chemical indigo in Germany. He became esger to switch over to other ventures. At that time, there was need for a steamer link between Khulna and Barisal (both the places are now in Bangladesh). He started a steamer service, Sarojini. But a English company Flotilla also started the same business. To meet the competition, he purchased four more steamers, Swadeshi, Bharat, Bangalakshmi, and Ripon. But after reducing the fare, Jyotirindranath incurred heavy losses. Moreover, Swadeshi hit a jetty and sank. Jyotirindranath had no alternative but to sell the steamers and opt out of the competition.
Other activities : He served as secretary of the Adi Brahmo Samaj from 1869 to 1888. He founded Adi Brahmo Samaj Sangit Vidyalaya. At his initiative a secret society Sanjivani Sabha was formed, possibly in 1876, with Rajnarayan Basu as president. This society manufactured match sticks and hand-woven cloth which could not earn any profit but did encourage swadeshi enterprise.
Marriage : He was married to Kadambari Devi on 5 July 1868. He arranged for her education including horse-riding in the public grounds of Kolkata defying the attitude of conservativbe society. Kadambari committed suicide on 19 April 1884, the cause of which was unknown..