How to Calculate Quarterly Estimated Taxes for the Self-Employed
The four-step process for estimating your quarterly tax payments, plus the safe-harbor shortcut that avoids an underpayment penalty.
1099 & Quarterly Taxes
Everything about self-employment tax, 1099 forms, and paying the IRS in quarterly installments instead of paycheck withholding.
What Counts Toward Your AGI When You’re Self-Employed
Quick answer: Your Adjusted Gross Income (AGI) isn’t your Schedule C net profit — it’s that number after a few more subtractions, most notably half your self-employment tax, your self-employed health insurance premiums, and any retirement contributions. AGI is usually meaningfully lower than your net profit, and it’s the figure that determines a lot more … Read more
Schedule C, Line by Line: The Freelancer’s Walkthrough
Quick answer: Schedule C is where every 1099 contractor and freelancer reports business income and expenses to the IRS. It has five parts — income, expenses, cost of goods sold, vehicle information, and other expenses — and the bottom line feeds directly into your self-employment tax and income tax. Part I: Income This is your … Read more
What Really Happens If You Forget to Report a 1099
Quick answer: often, yes — because whoever paid you may have already told the IRS. If a client, platform, or payment app files a 1099 in your name and the income doesn’t show up on your return, an automated system is likely to flag it, sometimes a year or more later. How the mismatch actually … Read more
Does the IRS Actually Know About Your Venmo and Cash App Income?
Quick answer: Yes — if you’re receiving business payments through Venmo, Cash App, PayPal, or Zelle, the IRS can see it, either through a 1099-K these platforms issue once you cross the reporting threshold, or through their own records even below that threshold. The 1099-K threshold, and why it’s not the whole story For 2026, … Read more
Married Filing Jointly Tax Guide: How to Handle Withholding When One Spouse Is Self-Employed
How mixed-income households can cover a self-employed spouse’s tax bill — through extra W-4 withholding, quarterly payments, or both.
How to Pay Social Security Tax When You Are Self-Employed: A Step-by-Step IRS Guide
Why self-employment tax exists, how the 15.3% rate splits between Social Security and Medicare, and how to calculate what you actually owe.