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Small withdrawals from IRA
Yes, it really will hurt you to keep pulling your money from your IRA. Your best bet is to set up a payment plan with the IRS, and pay the taxes you owe now, as well as adjust your withholding (with a new W-4 to your payroll department) so that you don't have a large tax liability next year. These tax advantaged plans really are designed to penalize you if you pull the money out early to give you incentive to keep the money for retirement. Your best bet is to make a monthly budget that includes your tax payments for taxes owed this year, as well as higher deductions from your paycheck to properly withhold taxes for next year.