Retirement

New here? Start with the big picture — why retirement is three problems rather than one, what the five parts cover, and how to read the guide alongside the calculator.

Part I picks the accounts you build the pot in; this section is about the habits and principles that decide how big that pot gets in the first place — the groundwork underneath the tax rules. How much to save and the discipline to sustain it, whether to steer spare cash into the mortgage, the handful of investing principles that quietly beat most professionals, and what a century of market returns shows about compounding and patience. The first three are told myths-and-facts style so the common traps are easy to spot.

The years before retirement are about two things: building the pot, and building it in the right accounts. Each pillar here has its own tax treatment, contribution limits, and rules — and using them in the right order (capture the match, fill tax-advantaged space, then taxable) and the right mix (pre-tax vs. Roth) sets up every decision in the rest of the book. The recurring ideas: tax-advantaged compounding, the free money of an employer match, tax diversification across buckets, and the inflation-protected foundation that Social Security and Treasury bonds provide.

This is the harder, less-taught problem: turning a pile of savings into a paycheck that lasts the rest of your life. It's dominated by a system of interacting risks — inflation, healthcare, taxes, Medicare surcharges, market sequence, and longevity — and by the levers you finally control: which account to tap, when to claim Social Security, when to convert. These chapters cover safe withdrawal rates and the sequence-of-returns risk that shadows the fragile early years, the retiree-specific risks of inflation and healthcare, the guaranteed lifetime income you can add through pensions, annuities, and your home equity, the deliberate use of low-rate debt to fund a bad year without selling into it, the earned income of part-time work and how it ripples through Social Security, payroll tax, and Medicare, and the tax levers you finally control: bracket-filling, IRMAA-aware withdrawals, Roth conversions, Social Security timing, sequencing, the required distributions that eventually force your hand, and the state that taxes it all — closing with longevity, the master risk that stretches every other one.

Retiring before 59½ means bridging two different gaps: getting at your money without the 10% early-withdrawal penalty, and covering your own health insurance until Medicare begins at 65. Three routes unlock early access to your accounts — the rigid 72(t) schedule, the flexible Rule of 55, and a pre-planned Roth conversion ladder (alongside the Roth contributions you can always reach) — each powerful and each carrying a classic mistake that quietly forfeits it — and a fourth chapter tackles the pre-Medicare coverage bridge and the income-based ACA subsidies that make it affordable.

Whatever you don't spend passes to others — and two separate questions decide how well. First, how it's taxed: with the federal estate tax now irrelevant for nearly every family, the real game is income-tax character and the step-up in basis, so leave the step-up and tax-free assets to your heirs and spend down or convert the pre-tax accounts yourself. Second, how it's transferred: beneficiary designations, payable- and transfer-on-death registrations, deeds, and a revocable living trust decide whether it reaches your heirs privately and in weeks — or crawls through public, months-long probate.

The whole guide in one place — the durable ideas that run through every chapter, and a do-this action plan by part with the 2026 numbers that matter. Read it last as a recap, or first for the big picture.

The money is only half a retirement. This closing part covers the half a spreadsheet can't — the purpose, relationships, and health that most predict a good late life; the housing continuum and long-term care that decide where and how you'll live; and the directives, simplification, and legacy folder that let someone step in when you no longer can. Non-financial by design, and meant to be read as a coda to the plan.

Seven quick-reference appendices and the glossary — the ages, the numbers, the tax tables, how each account is taxed across its life, the life-expectancy tables, a full guide to the calculator, which investments belong in which accounts, and the vocabulary, in one place.