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The Boring Newsletter, 6/14/2025

Hi Friendos, Today I am going to share a little tax “trick” that could help some people avoid an underpayment penalty if they did not make quarterly estimated payments on schedule. Maybe it will help you out. The scenario: You received some income where taxes were not withheld, like self-employment income or interest income. You […]

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Pay As You Go, or You Will Owe

Or…why do I have to pay more money in April when I’ve been paying all year long? The U.S. income tax system is pay-as-you-go, meaning, the IRS expects you to pay taxes on your income as you earn it throughout the year. In fact, if you owe too much at tax time (relative to your […]