Breaking the Jump explores how people navigate “jumps” - moments when they must move from what they know to an unfamiliar state without a clear path. Our design argument is that technology should not simply break the jump for the user. While current AI systems can often provide an immediate solution, doing so can remove the learning, agency, and problem-solving ability gained from experiencing the jump independently. Instead, we explore how technology can help users break the jump themselves by making possible paths, intermediate steps, and reflection more visible without taking ownership of the process away from them. We are identifying how people experience and respond to jumps and translating these findings into potential technical interventions. Ultimately, Breaking the Jump asks how technology can help people overcome uncertainty and shift paradigms without taking away the value of overcoming it themselves.