Should You Ever Retire? A growing number of Americans are pushing back the age at which they plan to retire. Or deciding not to retire at all. Related Content Healthcare Costs in Retirement Without a solid approach, healthcare expenses may add up quickly and potentially alter your spending. Retirement Questions That Have Nothing to Do With Money Things to consider before retirement. Yours, Mine, and Ours: Estate Strategies for Second Marriage Second marriages are a trigger event to revisit any existing estate strategies.