Topics

Every guide on the site is filed under one of these topics. Open a topic for an overview, the guides to read first and its calculators.

• Roth conversions

  Moving pre-tax savings into Roth accounts: how much to convert, when, and what the extra income does to everything else.

  Start with: Roth ladder: how a Roth conversion ladder works · The three 5-year rules of Roth accounts · Roth conversion tax calculator (2026)

• Medicare & IRMAA

  Enrolling on time, the income-based IRMAA surcharges and their two-year lookback, appeals, and where an HSA fits.

  Start with: IRMAA: the Medicare surcharge with a two-year memory · Working past 65: Medicare, IRMAA, and employer coverage · Medicare Part B late enrollment penalty calculator (and Part D)

• Social Security

  When to claim between 62 and 70, how benefits are taxed, what a survivor keeps, and the rules for working while claiming.

  Start with: Social Security break-even calculator: claim at 62, 67, or 70? · The Social Security tax torpedo · The widow(er)’s penalty: same money, single brackets

• ACA & early retirement

  Retiring before Medicare: health coverage, the ACA subsidy cliff, and penalty-free ways to reach savings before 59½.

  Start with: The early-retirement money bridge: Rule of 55, 72(t), Roth basis, and the ladder · The ACA subsidy cliff after 2025 · One MAGI budget: why Roth conversions and ACA subsidies fight

• RMDs, inheritance & giving

  Required minimum distributions, giving from an IRA, and what heirs face when they inherit retirement accounts.

  Start with: The RMD bomb: how pre-tax savings become forced income · Inherited retirement accounts and the 10-year rule · RMD exceptions and fine print: still-working, aggregation, Roth 401(k)

• Taxes in retirement

  How retirement income is taxed: brackets and deductions, capital gains, the 3.8% surtax, estimated payments and state tax.

  Start with: The 0% capital-gains bracket is real: LTCG stacking explained · The many MAGIs: one income, five different tests · NIIT: the 3.8% surtax with the frozen threshold

• Withdrawal strategy & market risk

  How much you can spend, what a bad market early in retirement does, and the rules that adjust spending as markets move.

  Start with: Monte Carlo vs “the number”: why your plan is a probability · What a 2008-style crash at retirement actually does · Why an 80% 'success rate' leaves millions unspent