2026
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What is the ‘safe harbor’ rule, and how do I avoid underpayment penalties?
Let’s talk about something that stresses out almost every self-employed person: “What if I didn’t…
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What You Actually Need to Prove an Expense to the IRS
Let’s clear something up right away: The IRS does not require you to live in…
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TaxHakr for 1099 Workers: Real-Time Tracking, Smart Strategies & Less Tax Stress
If you’re living the 1099 life as a freelancer, contractor, or gig worker, you’ve probably…
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I Started 1099 Work in 2026—Now What? A beginner’s checklist for first-time taxpayers
First of all… congrats. Whether you picked up a side hustle, left your W-2 job,…
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The Standard Deduction vs. Itemized: Which Saves 1099 Workers More?
If you’re a freelancer, contractor, or self-employed human trying to survive tax season, you’ve probably…
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Do Estimated Taxes Use Last Year’s Income or This Year’s?
If your income changes in 2026, should estimated taxes be based on last year or…
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How to Pay Your Kids Under 18 and Get a Legal Tax Write-Off (Even If You’re 1099)
Let’s clear something up right away: Paying your kids through your business can be a…
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Running a Cash-Only Business? Here’s How to Stay IRS-Safe
Cash-only businesses get a bad rap, but using cash isn’t illegal. In fact, many legitimate…
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What Does the IRS see as the Difference Between a 1099 and a W-2 Job?
If you’ve got a side hustle, freelance gig, or creator income on top of a…
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Why “Just a Side Hustle” on Etsy Still Counts as Taxable Income
Let’s get this out of the way first: If you’re making money on Etsy, it…