Retirement 20/20 is the Society of Actuaries initiative to find new retirement systems (focusing on tier II) that meet the needs of stakeholders better than the existing DB/DC models. The first steps in the initiative were to identify characteristics of a successful new retirement system, by identifying the needs and risks of stakeholders in the system. What has emerged is an understanding of the tension that exists today between investment and insurance, choice and default (including how choices are structured). In addition, the Retirement 20/20 initiative has constructed a Measurement Framework that can be used to analyze how well plan designs meet the needs and risks of stakeholders in the system; in the analysis of several plans, we have brought out other features that lead to successful retirement systems. This paper summarizes what we’ve learned to date about the balance between investment and insurance, choice and default, highlight roles for stakeholders and suggest new ways of bringing people together to prepare for their retirement.