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 Encore Careers: Push Your Boundaries Ready for retirement? Find out why many are considering encore careers and push your boundaries into something more, here. IRA Withdrawals that Escape the 10% Tax Penalty The list of IRA withdrawals that may be taken without incurring a 10% early penalty has grown. Self-Employed Retirement Plans Estimate the maximum contribution amount for a Self-Employed 401(k), SIMPLE IRA, or SEP.