Money Lessons with Andrew Temte, PhD, CFA

Self-Employment Tax, Estimated Payments, and the Side Gig

October 3, 2026·15 min
Episode Description from the Publisher

In this episode of Money Lessons, Andy turns to the earners the pay stub episodes left out: the self-employed, the independent contractor, and the side gig.  He defines the five terms that matter — self-employed, the 1099, net earnings, self-employment tax, and estimated payments — and works through the tax bill on the same $50,000 last week's employee earned, so listeners hear what happens when both halves of Social Security and Medicare land on the self employed.  A trip back to 1943 explains why the self-employed still pay the way every American once did, and why the IRS wants four payments a year instead of one. The episode closes with Andy's rule for anyone earning without a pay stub: set the tax money aside the day the payment arrives, and put the four dates on the calendar. AndrewTemte.com

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