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. Share | Related Content 18 Years Worth of Days The average retirement lasts for 18 years. Are you prepared to fill that many days? Social Security Benefits: How Much Will I Receive Calculating your potential Social Security benefit is a three-step process. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.