104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

Released Wednesday, 30th July 2025
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104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

104. From W-2 to 1099: Everything You Need to Know About Self-Employment Taxes

Wednesday, 30th July 2025
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Transitioning from W-2 employment to receiving 1099 income fundamentally changes your tax situation and officially makes you a business owner, even if you're doing the same work as before.

• Self-employment tax means paying both the employer and employee portions of Social Security and Medicare (15.3%) on top of income tax
• Business expenses can be deducted against your 1099 income, reducing your taxable income significantly
• Opening a separate business bank account is crucial for tracking income and expenses correctly
• You can simply transfer money from your business account to your personal account as needed
• Estimated quarterly tax payments are required to avoid penalties from the IRS
• Consider setting aside 25-40% of income for taxes depending on your tax bracket
• Health insurance and retirement planning now fall entirely on your shoulders
• Once netting over $50,000 in profit, consider forming an LLC and electing S-Corporation status
• S-Corps require more complex paperwork but can save significant money in self-employment taxes
• Higher-earning contractors should work with a CPA rather than trying to handle everything themselves

Check out our guides for new businesses and S-Corp owners in the show notes if you need step-by-step assistance navigating your new tax situation.


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