What does it mean to retire, not just financially but personally?  Retirement can bring a lot of transitions into a person's life, and it can also be a time of heavy grief and loss.  Some retirees have a hard time spending money after decades of saving.  But when you have a plan for your money and how you'll spend your time in retirement, it's a lot easier to adjust to the big transitions in your life while ensuring that you're focusing on what matters most to you.