Editors' pick: Originally published Dec. 8.

What will you do the first Monday after you retire?

That's the question Indiana financial planner Warren Ward throws at his clients who are preparing for retirement. What's the right answer? Ward elaborated: "We really don't care what their answer is, but often there simply isn't one. Instead we get a blank stare, sometimes even a look of terror."

Just that is the very wrong answer - but ask retirement planners where their clients go wrong, and they will tell you usually wrong turns aren't about about money, they are about emotional readiness - or the lack thereof.

This just may be becoming a crisis, as 10,000 Baby Boomers turn 65 every day - and many are absolutely unprepared emotionally for what lies ahead. Their 401(k)s may be stuffed with dough. But the emotional aspect of retirement is for many much harder, said Tom Foster, a spokesperson for MassMutual Financial Group. "The people who are happiest in retirement have planned for it," said Foster, who added that he means real planning. "For at least five years. Those are the people who really enjoy their retirement."

Yes, Foster means it takes five years - not months or weeks or days, but years - to get ready to retire. It makes sense too, after a working life that for many is 40 plus years.

What's not to like about retirement? No boss. No clock. No hectic to-do list.

Chuck Underwood, founder of consulting firm The Generational Imperative in Ohio, said what's not to like: "Most retirees badly underestimate the severity of the impact of awakening each day without a major purpose. Retirees who feel grandparenthood, volunteerism, travel, and just 'relaxing' will fill the purpose void consistently learn this hard lesson: for decades, their jobs have guided their entire lives, claimed the most vital eight hours of their weekdays, and been the source of most of their thinking. For decades."

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