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 Retirement Income and the Traditional Portfolio Experiencing negative returns early in retirement can potentially undermine the sustainability of your assets. When Life Insurance Becomes Taxable Life insurance proceeds are generally tax-free. But not in all cases. A Primer on Dividends A company's profits can be reinvested or paid out to the company’s shareholders as “dividends."