Should You Ever Retire? A growing number of Americans are pushing back the age at which they plan to retire. Or deciding not to retire at all. Related Content Systematic Withdrawals in Retirement Taking regular, periodic withdrawals during retirement can be quite problematic. Should I Pay Off Debt or Invest? This calculator will help determine whether you should invest funds or pay down debt. Will Power Preparing for the eventual distribution of your assets may not sound enticing. But a will puts the power in your hands.