- When did Matthew commit to the life of a maritime captain? Was he following his dream? Could he have had a completely different life? Why did he choose a life at sea?
- What was Matthew’s relationship with his mother, his father?
- Matthew had to take command of the ship when he was only seventeen. Did he feel prepared to accept that responsibility?
- How did Randy Derby help Matthew cope with the responsibilities of being the ship’s captain?
- In Canton, China, a crew member breaks the rules set by the Chinese for visiting merchants. How does this affect the ship’s relationship with the local merchant community?
- Matthew is exposed to slavery in Martinique, France, Turks and Caicos, aboard a slave ship off the coast of Africa, and at home in North Carolina. How does this influence his thinking about slavery?
- When Matthew was aboard ship, there was never a time when he was ‘off duty.’ How did his visit to his friend Yoman’s village, Munduk, in Bali help him see a different way of living? Was he able to relax?
- How did Matthew’s mother support her husband, Nymphas, both emotionally and in business, even though, much of the time, they were far apart? How did Matthew’s wife, Elizabeth, support him in the same circumstances?
- Matthew suffered from depression, bouts of anger, and alcoholism. When and how did this affect his life?
- When Matthew’s ship, the Trumbull, was shipwrecked, he came close to giving up. What kept him alive?
- When Matthew was reflecting about how to reestablish his wealth and status, he thought, “The greatest rewards available to me come from the sea. It is what I know, it is pulling me with the force of a strong ebb tide.” Then he decided to run the British blockade in the War of 1812. At the time that he made the decision, was it wise?