At some point he began working for a cobbler and became interested in the making of shoes. At that time more than half of the shoes produced in the United States came from the small town of Lynn, Massachusetts. Still unable to speak more than rudimentary English, Matzeliger had a difficult time finding work in Lynn. After considerable time, he was able to begin working as a show apprentice in a shoe factory. He operated a McKay sole-sewing machine which was used to attached different parts of a shoe together. Unfortunately, no machines existed that could attach the upper part of a shoe to the sole. As such, attaching the upper part of a shoe to the sole had to be done by hand. The people who were able to sew the parts of the shoe together were called “hand lasters” and expert ones were able to produce about 50 pairs of shoes in a 10 hour work day. They were held in high esteem and were able to charge a high price for their services, especially after they banded together and formed a union called the Company of Shoemakers. Because the hand lasters were able to charge so much money, a pair of shoes was very expensive to purchase. Hand lasters were confident that they would continue to be able to demand high sums of money for their services saying “… no matter if the sewing machine is a wonderful machine. No man can build a machine that will last shoes and take away the job of the laster, unless he can make a machine that has fingers like a laster – and that is impossible.” Jan Matzeliger decided they were wrong.

After working all day Matzeliger took classes at night to learn English. Soon, he was able to read well enough to study books on physics and mechanical science. This enabled him to a number of inventions. Lacking sufficient money, he was unable to patent these inventions and watched helplessly as other people claimed to have created the devises and received the financial rewards they brought. Matzeliger did not despair over these situations because he was already thinking of a more important invention – the shoe laster.

Watching hand lasters all day, Matzeliger began understanding how they were able to join the upper parts of a shoe to the sole. At night he sat devising methods for imitating the mannerisms of the hand lasters and sketched out rough drawings of a machine that might work in the same manner.

Although he attempted to keep his invention a secret, people found out, including the expert hand lasters he was trying to “compete” with. These people criticized and ridiculed him and tried to dissuade him pursuing his goal. He considered on, however, and decided to try to raise money in order to improve his working model. He was offered $50.00 to sell the device he had created up to that point but turned it down, knowing that if people were interested in buying, he was on the right track.