IRS
The IRS Hit This Detroit Freelancer With a $4,200 Tax Bill After He Quit His Warehouse Job — He Never Saw It Coming
The first quarter estimated tax deadline — April 15, 2026 — is now two weeks…
quarterly estimated taxes
5 articles
IRS
Grace Nakamura Earned $18K Teaching Yoga in 2025 and Owed the IRS $2,400 She Didn’t Have
Roughly 16 million Americans who work as independent contractors or freelancers fail to make quarterly…
IRS
He Left His Warehouse Job for Freelance Design — Then the IRS Sent Him a $3,400 Bill He Never Saw Coming
The first thing Deshawn Parker showed me when I sat down with him at a…
IRS
His Auto Shop Revenue Fell $54,000 in Three Years — Then the IRS Sent a Notice He Didn’t Expect
Roughly 16 million self-employed Americans are responsible for paying their own federal taxes through quarterly…
Tax Refunds
He Left a Warehouse Job to Design Full-Time — Then a $14K ER Bill Wrecked His Credit Before Tax Season Even Started
The IRS deadline for self-employed filers to submit their first quarterly estimated tax payment for…