After finishing school, he joined the service of British India as Chief Interpreter to the Commissioner of Raj Shahi Division and was posted to Buxaduar which was then part of Bhutan.

During his stay in Bhutan, he became a pupil of a learned and ascetic lama, Lopen Tshampa Norbu (Slob dpon Mtshams pa Nor bu) d. 1916 of Punakha from whom he received initiation and instruction.

(Of the three younger half-brothers he took care of, the first would later become a lecturer of Calcutta University, the second would be the prime minister of the king, and the third, "Sikkim Mahinda", joined the Buddhist priesthood in Ceylon[2] and was an important figure in the Sri Lankan independence movement, and a well-known Sinhala poet and author.)

At that time the Chogyal of Sikkim, Sir Thutob Namgyal, was looking for a headmaster, who could teach both Tibetan and English, for the state Bhutia Boarding School for boys at Gangtok and Kazi Dawa Samdup was proposed for this post by the Crown Prince Sidkeong Tulku.

In 1911 he accompanied the Maharaja of Sikkim to Delhi for the coronation Durbar of King George V. In 1912 Sidkeong Tulku Namgyal entrusted his "confidante and spiritual sister" Alexandra David-Néel to Kazi Dawa Samdup to be her a guide, interpreter and teacher of Tibetan.