The Payday journal

Notes on the practice.

Field notes, guides, and the thinking behind Payday.

  1. 01

    How Much to Set Aside for Taxes When Self-Employed: The Mental Accounting Trick That Makes It Painless

    How much to set aside for taxes when self-employed, and why a separate account beats willpower. A behavioral-science guide to never scrambling at a quarterly deadline again.

    2026-06-17

    7 min read

  2. 02

    The Safe Harbor Rule: How to Avoid the Estimated Tax Penalty Without Predicting Your Income

    The safe harbor rule for estimated taxes lets you sidestep the IRS underpayment penalty using last year's numbers — no crystal ball, no guessing this year's freelance income.

    2026-06-13

    7 min read

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