In 1885, he passed the Diplomatic Service examination, and was assistant private secretary to the Earl of Carnarvon as Lord Lieutenant of Ireland before being attached to the British Embassy in Rome. In 1888, he arrived in Berlin as the embassy's third secretary, and after retiring from the Diplomatic Service four years later, he was made assistant private secretary to the Earl of Kimberley, the Foreign Secretary at the time. Howard was a talented linguist who would spoke 10 languages and chose to retire from the diplomatic service in 1890 out of boredom. For the next 13 years, Howard lived a life of irregular employment, spending his time prospecting for gold in South Africa, working as a researcher for the social reformer Charles Booth, making two lengthy trips to Morocco, working as the private secretary to Lord Kimberley in 1894–1895, frequently visiting his sister at her estate in Italy and running unsuccessfully as a Liberal candidate in the 1892 election.