To escape the problems and make a better life for his son, Henson's father moved the family to Washington, D. C.. While Henson's father worked, Matthew took care of the elderly uncle they lived with. While they lived in Washington, Henson's father died, leaving his son in the care of his uncle.

Henson's uncle was mean and abusive to the point that it caused him to run away from the only home he had. Finally, he came to a small restaurant. The owner hired Henson to sweep and mop the floors, clean the kitchen and wash the dishes. Since he had nowhere else to stay, the owner allowed Henson to sleep on the floor of the restaurant after closing.

One day, Henson saw a sign advertising a ship captain looking for young men to go to sea. Henson figured he had nothing to lose and signed up. That was the beginning of Matthew Henson's sailing career.

For the rest of his teenage years, Henson sailed around the world. He learned mathematics, navigation, the operations of a ship and how to read books and maps. By the time he was 21, Matthew Henson was an experienced sailor.

Between his terms at sea, Henson would sometimes work to earn a little money. One job he had would change the course of his life. The year was 1887, the place was a fur and supplies shop in Washington, D. C. where Matthew Henson had been working as a clerk. It was a family owned shop so the owner knew Henson quite well.

One day, as Henson was working, a man visited the store to buy some supplies. He was an engineer and explorer named Robert Peary. Peary needed supplies and a servant to take with him on a trip to Nicaragua. He was working for the government to chart the Nicaraguan jungle in hopes of building a canal there. The store owner told Peary that Henson was "bright and strong. He's only 21, but he's already been around the world."

The trip to Nicaragua was the changing point in Henson's life. He used his mapmaking skills from his sailing experience to help Peary chart the Nicaraguan jungle. Peary was so impressed that he made Henson his trusted assistant and fellow explorer.

Peary's dream was to reach the North Pole. He wanted to be the first man in the world to reach it and he wanted Matthew Henson to be right there with him. Henson was there every time except for the first attempt.

Over the course of the first five trips, Henson learned everything he possibly could from the Eskimo about surviving in the arctic. He learned to break trails, build camp, repair sleds, drive a dog team, hunt polar bears, and even make clothes out of animal skins. Henson was so skilled and strong that Peary remarked "I couldn't get along without him."

On his last trip to reach the North Pole, Peary took Henson with him. Peary was almost fifty, and more determined that ever to reach the North Pole before he died. Conditions in the arctic favored the expedition. It was spring and the winter storms had passed. The men had just enough supplies to take a single trip to the site that Peary had calculated to be the North Pole. April 9th, 1909, six men made a mad dash for the North Pole.

They were (in order from first to last) Matthew Henson, followed by four Eskimos pulling Robert Peary on a sled (his feet were frostbitten.) Henson out ran them all, becoming the first man in the world to reach the North Pole. Peary handed him the American Flag, which he planted at the site, in the snow. He then posed for a picture with the four Eskimo guides who led Peary and Henson to the top of the world.

Henson never received full recognition for being the first man in the north pole. Only after joining the Explorer's Club, he received his well deserved recognition. In gratitude for what they had done for Matthew, after his death, his family donated half of his insurance money to the Explorers Club.