Young Henry's time in school was brief. He was very bright and was mostly self educated. He had an especially good head for figures and it was no surprise that he followed his father and older brother into accountancy.
He started as a clerk with the firm Young and Co. in 1846. His father was probably instrumental in Henry's appointment. It was just a couple of years earlier, at the age of 15, when Henry wandered into a coffee house and saw men there playing chess. He later described his very first experiences in chess:
After about three months looking on at chess play in 1844, at Raymond's Coffeehouse near the City Road Gate, where Dr. Michaelson of the Morning Post, and Mr. Finlay, a farrier, were the respective giants, and a cup of coffee the usual stake, I learned moves at chess, and receiving the odds of a Queen for a few games, I happened one day to hear with astonishment that the gentleman conceding me the odds was not the champion of the world, but that better players could be found at Goode's, Ludgate Hill, and Simpson's in the Strand...