self-employment tax

Social Security COLA 2027: The 3.5% Estimate, the October 14 Announcement and the 2032 Trust Fund Cliff โ€” The 9-Move Freelancer & Digital Nomad Playbook

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The 2027 Social Security COLA lands October 14: forecasts say 3.5 to 3.6 percent, the biggest raise since 2023. The math, the Medicare bite and the 2032 cliff.

Quarterly Estimated Taxes for Freelancers & Digital Nomads in 2026: The September 15 Deadline, the 7% Penalty, and How Much to Pay

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The September 15, 2026 estimated tax deadline is here, and the IRS underpayment penalty holds at 7% through year-end. Safe harbor rules, real freelancer math, the annualized method & a nomad-specific action plan.