The starting point for any analysis on whether you can afford to retire is a look at how much money you currently spend.

BBC: Fergus Muirhead

Determine the cost of your various financial goals (e.g. college for your children, if you have them, your retirement living expenses, etc) and help you decide when you can afford to retire.

FORBES: Sudden Loss: Financial Advice For Widows

It's hard to agree on when to retire if you aren't sure you can afford it.

WSJ: How Couples Decide When to Retire