If you haven't sent in withholding taxes on a quarterly basis, but you have the money in the bank, often the IRS will accept an annualized payment much like your annual income tax payment as an employee, except that you are paying all of your taxes. If you haven't the money, the IRS may consent to an installment payment plan if you meet its criteria. All in all, they're actually pretty nice about these extenuating circumstances, especially if you're confronting the rules for the first time.