I have worked with hundreds of retirees in my 10 plus years as a financial advisor.  One theme is constant.  Prior to retirement, money is the worry.  After all, we all are creatures of habit.  We work, we get paid, we work, we get paid, we work, we get paid.  Naturally, when it's time to stop working the fear of the unknown of where the money will come from is a natural fear.  What I have found though, is that after a few months in retirement the money issue is fine.  What isn't fine, is what to do with all the free time. 

A job, for many, provides much more than a paycheck; it's an identity, a social setting, a purpose.  When retirement does come, certainly make plans for your investments, but also, do not fail to focus on what activities will be needed in order to have a fulfilling retirement.  Sleeping until noon and watching "Andy Griffith" reruns may sound nice now, but trust me, this will get old fast.  Take time to identify clubs, hobbies, and groups you will want to be around once you are retired.  Also, finding somewhere to volunteer often provides a deep sense of purpose.  You have gained a lot of valuable experience over the years, retirement can be a time to share that experience on your own terms.  Don't discount this opportunity.