"If you fail to plan, you plan to fail." This maxim, often attributed to Benjamin Franklin and likely the cause of many a teenage eye-roll when enduring a lecture about the evils of procrastination, is so ubiquitous you'll even hear it on a Taylor Swift single. That doesn't mean you shouldn't pay it any heed, particularly when you're thinking about retirement. Dr. Rui Yao, Director of Graduate Studies and the Director of International Financial Planning Initiative at the University of Missouri, stresses that failing to plan is the biggest mistake most people make. "People love to dream about what they will do when they finally do not have to work, but they hate to do the math. Ironically, retirement is too important a financial goal for people to make mistakes on. We can put off a vacation if we make a planning mistake, but once we retire, it is impossible to start over." According to a recent survey from the Transamerica Center for Retirement Studies, many workers report having a financial strategy in place for retirement, although nearly half of them (43%) don't have that plan written down on paper. Only 34% of surveyed workers say they have a contingency plan if their original one fails for any reason. The whimsical nature of fate is not to be underestimated, according to several experts. Nearly 40% of workers are forced into retirement, says New York University clinical assistant professor Dr. Colin M. Slabach.

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Phil Stuczynski, assistant teaching professor of finance at Penn State Behrend, agrees. "The biggest mistake is being certain that everything works out from a timing point of view," he asserts, "whether that is realizing how long it takes for the Social Security office to process your application and send you the first check, or it is understanding how to make money last with a fixed, consistent income, but with unexpected and unplanned events or celebrations in the 'real world' continuing to arise." When pondering just where to retire, many potential retirees will consider a location that will permit them to stretch their dollar without having to sacrifice too much of their accustomed lifestyle. To help facilitate that decision, WalletHub investigated the retiree-friendliness of 182 U.S. cities. To compile this study, they compared each city across four key dimensions: Quality of Life, Health Care, Affordability, and Activities. Those dimensions were broken down into 45 metrics and graded on a 100-point scale.

Coming in dead last on the ideal cities list: Stockton, CA, with a score of 35.33. Stockton scored particularly low for health care and activities. Newark, NJ, follows with a score of 37.68. The top five is rounded out with Bakersfield, CA (37.90); San Bernardino, CA (38.29), and Detroit, MI (38.55). Detroit also ranked second on the list of cities with the lowest percentages of employed population 65 and over. (Gulfport, MS, took the lowest spot.) Bakersfield may not have done well overall, but it ranked third on the list of cities with the mildest weather, topped only by sister cities Riverside and Glendale. See our slideshow above for WalletHub's top 10 best cities to retire, and click here to read the full study.