LEGACY TAX BLOG

Stay Ahead With Smart Tax Tips, Updates & Insights

Stay Ahead With Smart Tax Tips, Updates & Insights

Practical tax guidance, IRS updates, planning strategies, business insights, and timely information to help you make informed decisions.

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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? Hereโ€™s what Chicago and Illinois taxpayers should gather, review, and do now before the October 15 filing deadline.

October 2026

TAX ON TIPS

IRS Clarifies โ€œNo 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

TAX PLANNING

7 Ways To Get Ready Now

YEAR ROUND TAX PLANNING

Why Year-Round Tax Planning

Matters

Read Article โ†’

SIDE HUSTLE INCOME

What Side Hustle Workers

Need to Know About Taxes

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. โ€œI looked at the number and thought, Iโ€™ve been robbed,โ€ he joked.

The real problem wasnโ€™t 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 weekโ€™s earnings for taxes.

The lesson: good tax planning starts long before the tax return is prepared.