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 | Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content You May Need to Make Estimated Tax Payments If… Have income that isn’t subject to tax withholding? Or insufficient withholdings? You may have to pay estimated taxes. 401(k) Plans Are Not Just for Big Businesses Many small businesses are one person businesses. RE: Retirement How does your ideal retirement differ from reality, and what can we do to better align the two?