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Everything you never thought you’d read about 🧑💼 Businesses & Gigs, but here you are.
🧑💼 Businesses & Gigs
February 6, 2026
The Gig Worker’s Retirement Crisis (And Tax-Smart Solutions)
The gig life feels great until you realize you’re your own HR department and there’s no employer throwing free money into a 401(k). Most gig
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🧑💼 Businesses & Gigs
January 30, 2026
Employee (W-2) vs. Contractor (1099): Know the Rules
W-2 = employer control, benefits, and half your taxes paid for you. 1099 = you’re a business with freedom, full tax responsibility, quarterly payments, and
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🧑💼 Businesses & Gigs
January 24, 2026
The Great 1099 Schism: A Tale of Two Forms (And Why You Should Care)
Learn the key differences between the 1099 NEC and 1099 MISC, new thresholds, deadlines, and easy rules to file correctly.
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🧑💼 Businesses & Gigs
January 19, 2026
Estimated Tax Penalties: The Most Expensive “Oops” in the Tax Code
In 2026, underpaying estimated taxes can trigger steep interest penalties, even if you report everything correctly. The safest way to avoid them is to pay
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🧑💼 Businesses & Gigs
December 22, 2025
Estimated Taxes: The Quarterly Subscription You Didn’t Sign Up For
The US tax system is pay-as-you-go. The moment income hits your account, the IRS effectively owns a slice of it. Hold onto their share too
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🧑💼 Businesses & Gigs
November 20, 2025
Don’t Let Taxes Kill Your Brand
It takes years to build a brand. It takes one envelope from the IRS to make it feel like it could vanish overnight.
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🧑💼 Businesses & Gigs
November 20, 2025
Profit Motive: How to Convince the IRS Your Side Gig Is a Real Job
You've done it. You've turned your passion into a side hustle. Now it's time to convince the IRS you're legit. Learn what you need to
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🧑💼 Businesses & Gigs
November 19, 2025
“I’ll Just Work from the Beach,” and Other Fun Tax Fantasies
Tax agencies don't care about where your company's fancy headquarters are. They care about where your feet are planted while you're typing away at your
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🧑💼 Businesses & Gigs
November 16, 2025
What Uber and Lyft Don’t Tell You About Your Taxes
When you sign up to drive, they sell you the dream: Be your own boss. Set your own hours. Earn great money. What you don't
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