This Episode provide a comprehensive overview of U.S. federal income tax obligations, primarily focusing on estimated tax for individuals and withholding for various income types. The IRS documents, specifically excerpts from Form 1040-ES and Publication 505, detail who must pay estimated taxes on income not subject to withholding—such as self-employment earnings and gig work—and offer instructions on calculating these payments, including updated standard deduction amounts for 2025. Other sources, including articles from a tax center, a law firm, and a financial services company, further explain the complexities of managing taxes for multiple jobs and self-employment, emphasizing the need for accurate Form W-4 completion, proper business expense deductions (like home office and mileage), and the use of financial tools to track income and make quarterly tax payments to avoid penalties. The consensus across the texts is the critical importance of organization and utilizing IRS resources, such as the Tax Withholding Estimator, to ensure compliance.