Nobody sits new business owners down and says: hey, you might owe the IRS four times a year now, not once. So let’s have that conversation before the penalty notice does. When you work for someone else, taxes get taken out of every paycheck automatically. You barely think about it. When you work for yourself, nobody’s withholding anything — which means the responsibility for sending that money to the IRS throughout the year now belongs to you. That’s what quarterly estimated
