Jeffrey Levine CPA/PFS, CFP®, AIF®, CWS®

For many, correctly answering the question, “When should I begin to take my Social Security benefits?” is a critical step toward making sure their retirement income and savings last at least as long as they do. For others, who perhaps are lucky enough to have accumulated a more substantial nest-egg, the decision may have less of an impact on their ultimate chances of a “successful” retirement (as they may have enough income and/or other assets to overcome a poor choice). But let’s face it … nobody wants to leave Social Security dollars on the table because of a less-than-ideal claiming decision.

Unfortunately, making the right choice for you and your specific life and financial circumstances is often much easier said than done. Consider, for instance, that there are literally thousands of rules governing the Social Security system and nearly a dozen different types of Social Security benefits.

As if that weren’t bad enough, choosing the best time to claim Social Security benefits also means trying to guestimate how long you will live, which just complicates things further. Factors such as health, family history and even income can all be helpful predictors, but they’re far from perfect. Healthy people sometimes die young, while those with poor health sometimes live beyond even the most optimistic estimates.