What builds lasting change in our lives and why is it difficult for so many people to sustain? The process of self-development happens on multiple levels and time horizons, yet much of the research on lifestyle change examines single factors or interventions. It is not only one thing, one cycle, or one process that moves someone from floundering to flourishing. This paper examines upward spiral dynamics, self-determination theory, self-actualization, and self-transcendence to identify the multi-level and multi-domain factors that contribute to lasting change. It also explores the development of vantage resources, the physiological, social, and emotional resources which allow us to benefit from positive experiences. I theorize that through the cultivation of vantage resources via intrinsic or integrated goals our potential to experience well-being grows, and through sustained effort we’re able to build lasting change. Additionally, self-transcendent experiences ranging from mild to significant reshape the schema of what is valued, purposeful and meaningful. By fostering experiences likely to trigger self-transcendence we perpetuate the cycle of self-development aimed not at narcissism, but meaningful contribution. Artifact 1 proposes a model for these cycles of change, the Upward Spiral of Self Development and Well-Being. Artifact 2 is a catalog of potential vantage resources and related multi-domain activities that potentially contribute to upward spirals.