You can try, but the truth is you probably don’t understand what you’re up against. Critical retirement decisions are complicated in the best of times. Even then, retirement planning turns some of our most cherished assumptions about investing upside down, challenges our ingrained financial biases, and necessitates a comprehensive change in our frame of reference. In the income phase, the most successful total-return “accumulator” must shift gears and focus on successful “decumulation” to spend down a lifetime of savings. In this process, managing long-term risks you’ve never faced before—longevity, capital depletion and return sequence—comes to take precedence over maximizing short-term return. Ironically, the more successful you’ve been in accumulating your wealth, the more locked in you may be to what has worked for you in the past, limiting your responses to the very different challenges you now confront. As we age we decline and, with the passing of time, personal circumstances and family dynamics change. None of these adjustments are easy. Your plan needs to look three or four decades into the future and be flexible enough to respond to all kinds of changes; your planner should be there to help you anticipate, pre-empt and prevail.