Should I Pay Off Debt or Invest? This calculator will help determine whether you should invest funds or pay down debt. You are viewing this website at a small screen resolution which doesn't support calculators. Click here to view this calculator. Have A Question About This Topic? Name Email Address Question Thank you! Oops! Related Content When Life Insurance Becomes Taxable Life insurance proceeds are generally tax-free. But not in all cases. The Junk Drawer Approach to Investing It's easy to let investments accumulate like old receipts in a junk drawer. Systematic Withdrawals in Retirement Taking regular, periodic withdrawals during retirement can be quite problematic.