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. Related Content It Was the Best of Times, It Was the Worst of Times All about how missing the best market days (or the worst!) might affect your portfolio. Retirement Income and the Traditional Portfolio Experiencing negative returns early in retirement can potentially undermine the sustainability of your assets. Trends in Charitable Giving Some people may want a more advanced gifting strategy that can maximize their gift and generate potential tax benefits.