IRS
He Drove for Uber to Keep the Lights On. Then the IRS Sent Him a $1,800 Bill He Didn’t Expect
A Little Rock Uber driver expected a $2,100 tax refund. The IRS had other plans.…
self-employment tax
9 articles
IRS
An Uber Driver Expected a $3,400 Tax Refund. The IRS Sent Him a Notice Instead.
Roughly 33 million Americans work in the gig economy, and according to the IRS Gig…
IRS
Deshawn Parker Cleared $36K Freelancing Last Year — Then His 2025 Tax Return Showed a Bill He Never Saw Coming
The conventional wisdom about tax refunds goes something like this: file your return, wait a…
IRS
My Partner Earns $140K and I Earn $18K — Here’s What That Does to Our Joint Tax Return
Most financial planners will tell you that filing jointly is almost always the smarter move…
IRS
She Expected a Tax Refund After Leaving Corporate Work — The IRS Had Other Plans for Her $18K Yoga Income
Have you ever built a life around a set of values — simplicity, presence, purpose…
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…
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…
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…