The goal of this dissertation was to explore how self-directed learners assess their learning in informal contexts. Self-directed learners experience high intrinsic motivation and learner control, so studying these learners’ experiences provides valuable insights into learning. I pose four questions: 1) How do self-directed learners in informal contexts satisfy their need for a) autonomy, b) relatedness, c) competence, and d) prioritize the satisfaction of these needs? 2) How do self-directed learners in informal contexts self-regulate their learning? 3) What affordances are perceived by informal learners during self-directed learning? 4) What relationships exist between the satisfaction of learners’ basic needs, self-regulation, and perceived affordances during self-directed, informal learning? I employ multiple methodologies, including interviews (N = 19) and an open-ended survey (N = 154), and based on this evidence, theorize a Lanes of Learning model to explain how learners regulate learning, assess competence, involve others, and use tools to meet their needs. Participants’ needs also influenced which learning tools they integrated and, from those, what they perceived as possible, including accessibility, personalizability, and adaptability. Evidence shows learners in 1) Lane A prefer efficiency, collect confirming cues, involve others to meet a goal, and use tools that provide a set of correct steps; 2) Lane B prefer structure, collect confirming cues and add affirming cues, involve others for functional purposes, and used tool that resemble the real thing; 3) Lane C prefer depth and chase information as it becomes relevant, collect affirming cues, involve others for emotional reasons, and use tools that provides more information to chase; and, 4) Lane D prefer innovation, collect affirming cues and add confirming cues, involve others to build a network, and use tools that are inspirational, not educational. I argue people are motivated to learn when that learning is on their terms, and this motivation manifests in the strategies and processes taken by individuals during learning.