Theo feels a little left out, because he is the only guy in the group who was not a star athlete in high school. He admits he often pushes himself very hard so that he will be as athletic as Laterrian and James. This leads to a problem in the next mission, free diving in Key West.
There, the gang meets Meghan, the US record holder in free diving. She informs them that they will attempt to free dive, although it could be dangerous. Even though some of the Road Rulers are afraid, they all successfully dive. James dives the farthest, 29 feet, with Theo second at 22 feet. That's not the end of the mission, though. Meghan tells them that they will also be diving the next day, and then they will have to dive at least three feet further than they did the previous day. She asks them each to tell her how far they think they can dive, and then flags will be put up as markers. A successful dive means grabbing your assigned flag, and when all the flags are put together, they will form the clue to the Road Rulers' next mission. Everyone decides that they will just dive the minimum three feet extra, except for Theo. He thinks he can dive to 35 feet, but everyone urges him against that--it's impractical, and he could get hurt. He eventually decides on 30 feet, even though the rest of the Road Rulers beg him to choose a shorter distance. Everyone is upset at this decision, but their only choice is to cheer Theo on the next day.
The next day, everyone successfully dives the additional three feet, and Theo dives to 30 feet without any problems. When everyone reaches the surface, they put together the flags they collected, and find out their next destination is South Africa. They put aside their hard feelings for Theo and celebrate the news of their next destination.