Guides

The stuff nobody tells you about tipped work.

Tip-out math. Quarterly tax deadlines. Mileage you can actually write off. Self-employment tax that nobody warned you about at orientation. Worker rights. Retirement when nobody's matching. Written in plain English by someone who's worked the floor.

Taxes

How much tax do tipped workers actually owe?

Federal brackets, state, FICA, and what your W-2 doesn't tell you. The honest version.

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First-Time

Filing taxes for the first time as a tipped worker

Reading your W-2, picking free filing software, and the rookie mistakes that trigger IRS notices.

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Records

How to track tips for taxes (the right way)

IRS Form 4070, daily logs, audit-defensible records, and year-end reconciliation with your W-2.

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Tip-Out

Tip-out explained: pools, percentages, and points

The four kinds of tip-out you'll run into and how to figure out what you actually take home.

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Quarterly

Quarterly tax deadlines for self-employed tipped workers

Four dates a year. Miss them and the IRS adds penalties. Here's the schedule and how to estimate.

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SE Tax

Self-employment tax: the 15.3% nobody warned you about

If you drive, deliver, do hair in your own booth, or 1099 anywhere — this is the tax that eats you alive.

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1099

Got a 1099 you weren't expecting? Here's what to do

Three scenarios: you forgot the gig, the amount is wrong, or you never worked for them. Different responses.

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Planning

The year-end tax checklist for tipped & gig workers

December actions, January waiting, March review, April filing. The full annual cycle in one list.

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Tip Pool

Bartender tip pool rules: who's in, who's out, what's legal

Federal law on tip pools, the 2018 rule change, and what managers cannot do with your tips.

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Rights

Tip pool violations and wage theft: a tipped worker's rights

The seven most common violations, how to document them, and how to recover back wages.

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Side Work

The 80/20 rule, sidework, and your right to minimum wage

The federal saga, the 2024 Fifth Circuit ruling, and the state rules that still protect you.

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Rights

Worker misclassification: am I really a 1099?

The classification tests, what misclassification costs you, and how to file Form SS-8 and Form 8919.

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Decisions

W-2 vs 1099: which is actually better?

The tax math, the benefits gap, and the hidden cost of "contractor" status nobody talks about.

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Rideshare

The rideshare mileage deduction, the way the IRS wants it

Standard rate vs. actual cost, what counts as deductible miles, and the records you have to keep.

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Benefits

Health insurance for gig workers in 2026

ACA marketplace, premium tax credits, HSA-eligible plans, and what subsidies you qualify for.

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Retirement

Retirement savings when you're self-employed

Roth IRA, SEP-IRA, Solo 401(k), SIMPLE IRA — limits, tax treatment, and which fits your income.

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Track the math, not just read about it.

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