Chuck Smith emphasizes the transition from the wilderness to the promised land, urging believers to take a step of faith despite the obstacles that lie ahead. He reflects on the struggles faced in the wilderness, including doubt and strife, and contrasts this with the abundant life that awaits in the promised land, which is rich and filled with God's blessings. The sermon highlights the importance of faith in God's Word as they prepare to cross the Jordan River, symbolizing the challenges that must be faced to experience a deeper relationship with God. Smith encourages listeners to dare to get their feet wet, trusting in God's promises as they move forward.