LEGACY TAX BLOG
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Featured Tax Insights
Timely guidance to help you prepare, plan, and make informed
financial decisions throughout the year
TAX DEADLINE
October 15 Is Almost Here!
Filed an extension? Hereโs what Chicago and Illinois taxpayers should gather, review, and do now before the October 15 filing deadline.
October 2026
TAX ON TIPS
IRS Clarifies โNo Tax on Tipsโ Rules for Workers
New IRS guidance explains how eligible tipped employees and some self-employed workers may deduct qualified tip income. Good reporting and recordkeeping will be key.
September 2026



A Chicago rideshare driver thought keeping up with weekly earnings was enough. Tax season told a different story
FEATURE STORY
Missed Deductions Leave Uber Driver
Paying More Than Expected
CHICAGO โ Marcus Reed, a 38-year-old rideshare driver, thought keeping track of his weekly deposits was enough. Between fuel, maintenance, tolls and long evenings driving passengers across the city, taxes rarely crossed his mind until filing season arrived.
That changed when Marcus learned how much of his rideshare income could be subject to income and self-employment taxes. โI looked at the number and thought, Iโve been robbed,โ he joked.
The real problem wasnโt that someone had taken his money. Marcus had driven thousands of business miles but never maintained a consistent mileage log. He had also paid for parking, phone service, vehicle supplies and other work-related expenses without keeping organized records.
Some of those costs could potentially reduce taxable business income, but without documentation, determining and supporting eligible deductions became much harder.
Marcus left with a new plan: track mileage, save receipts, review his rideshare tax documents and set aside part of each weekโs earnings for taxes.
The lesson: good tax planning starts long before the tax return is prepared.






