In summary, the three questions you must answer before you choose to retire:
1) Do You Have A Reliable Cash Flow Plan?
2) Have You Accounted for Healthcare and Unexpected Costs?
3) How Will You Spend Your Time And Stay Fulfilled?
Will these three questions really determine 99% of your retirement success? Who knows (it did catch your attention, though, right?). Regardless of the actual percentage, there’s no doubt in my mind that these are the right questions to ask as you approach retirement (I think my old boss would be proud 
).
More important than the questions are your answers. If you’re not comfortable answering them yourself, this is one area where it pays to hire an expert to help.
Spend the necessary time to answer the questions well.
Your retirement success is riding on it.
Source: 3 Questions That Determine 99% of Your Retirement Success - The Retirement Manifesto