How to Retire Early Retiring early sounds like a dream come true, but it’s important to take a look at the cold, hard facts. Share | Related Content 18 Years’ Worth of Days The average retirement lasts for 18 years, with many lasting even longer. Will you fill your post-retirement days with purpose? Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit? Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.