The owner said that he had a vacancy and offered to take Henry on, on a trial basis. After some discussion, they decided that Henry would craft one pair each of men’s and women’s shoes, and they would then seek to reach an agreement on the terms of employment. Choosing the design of Philadelphia’s latest styles, Henry quickly fashioned the shoes and presented them to Mr. Carlyle with a smile. He had to acknowledge Henry’s skill and offered him a job as a regular employee, to be paid by the week as were his other workers. The young man politely declined this offer and said he would prefer to work with a fixed payment for each pair of shoes. After some careful assessment of how much he was actually paying his current shoemakers for each pair they produced, Mr. Carlyle made an offer, based on Henry’s shoes being examined for quality before payment was made and the terms of their agreement not being revealed to the other shoemakers.

Henry accepted, pleased by an arrangement that would give him independence from the strict control of his employer, remove any limit on his maximum earnings, and permit flexibility in his working hours so that he could travel around the city during the daytime to learn about aspects of the leatherworking trade with which he was not acquainted.

To minimize his living expenses, Henry made arrangements with a nearby family to share two simple but ample meals each day, and got permission from his employer to set up a folding cot at night in the shoemaker’s storeroom, where he would serve as something of a night watchman. When necessary, he worked there by candlelight to maintain an acceptable level of shoe production. Henry pleased his employer by producing shoes of good quality at a surprisingly high rate, sometimes more than two pairs a day.

He was able to work part-time at a large tannery, where he learned how to cure, dye, and finish the hides of cattle, unborn calves, deer, and horses, and the skins of sheep and goats. He accumulated a careful list of supplies he would need to produce leather for heavy belting for drive pulleys, saddles and harnesses, work shoes, and the finer grades used for jackets, hats, dress shoes, and other light apparel.

On his cot at night, surrounded by the reassuring odor of cured leather and sometimes the stench of the tannery left on his own clothes, Henry planned for his future in North Carolina. As he worked in the shop, he constantly accumulated information from customers who were familiar with the social and political situation in the western regions of the southern colonies.