The RetireOdds methodology

Your financial life, kept as a set of books.

RetireOdds is not a one-shot retirement calculator. It builds a source-aware annual ledger from your portfolio, income, spending, taxes, healthcare and life events, then extends those books across every remaining year.

One continuous financial recordIllustrative structure
The closing books for one year become the opening books for the next. Cash, tax character and unresolved obligations do not disappear between screens.
Ledger firstEvery deterministic year is built before results are summarized.
Sources stay separateTaxable, tax-deferred, Roth, illiquid and deferred compensation keep their own treatment.
Uncertainty comes secondMonte Carlo and historical paths replay the plan; they do not replace the underlying books.

A projection should balance before it persuades.

Most retirement tools begin with a handful of inputs and jump to a probability or chart. RetireOdds begins with the books: what you own, what kind of account holds it, what comes in, what goes out and what remains unpaid.

A retirement decision is rarely changed by investment returns alone. The same withdrawal can create a capital gain, ordinary income, no federal income, a Roth penalty, an ACA subsidy change or an IRMAA surcharge two years later. Collapsing every dollar into one balance loses the information needed to model those consequences.

The RetireOdds ledger preserves that information through time. Every modeled year has an opening position, categorized activity, source-aware settlement, a tax and healthcare record, and a closing position that rolls into the next year.

QuestionTypical calculatorRetireOdds ledger
What is modeled?A balance, growth rate and spending rule.Account books, income character, expenses, taxes, healthcare, events and obligations.
How is time represented?A start value and an ending outcome.A continuous annual record from the current year through the final settlement.
What happens to account identity?Balances are often pooled.Taxable, deferred, Roth and non-liquid books remain distinct.
What happens when cash is insufficient?The result may simply hit zero.The unpaid amount remains visible as an obligation and fails plan funding.
Can a number be checked?Usually only the assumptions are shown.Ledger cells carry facts, source references, rule versions and equations where available.
Our structural rule

A specialized feature may read from the canonical plan, but it may not invent a second financial history. Taxes, healthcare, Roth analysis, Compare and simulation must reconcile to the same resolved inputs and year conventions.

Real inputs become one canonical record.

RetireOdds does not continuously scrape your financial institutions. You control the record: enter facts manually or upload brokerage and expense files, review what changed, and confirm the books that drive the plan.

Portfolio & accountsBalances, holdings, cash, cost basis, tax treatment and valuation dates.
Household & cash flowWages, Social Security, pensions, spending, liabilities and life events.
Planning rulesRetirement age, withdrawal order, healthcare, tax residence and assumptions.
Canonical annual Plan LedgerOne resolved set of inputs · one age axis · one real-dollar frame · one closing position per year
LedgerTax PlanningHealthcareRoth analysisWhat-ifPlan successReportsiOS

Inputs carry provenance

Account classifications, basis records, as-of dates and imported positions are not decorative metadata. They determine whether a withdrawal is a taxable sale, an ordinary distribution or a Roth distribution. File imports use snapshot reconciliation: matching positions are updated, absent positions can be removed after confirmation, cash is replaced rather than added, and repeated imports are designed to be idempotent.

Missing facts stay visible

If a material input is absent, such as account tax treatment, cost basis, investment-income character or a valuation date, the product raises a review action. It does not silently turn unknown data into a confident result. Where a conservative fallback is necessary, the assumption is disclosed.

Every year must explain where the money went.

A ledger year is a cash-and-balance reconciliation, not just a return calculation. The exact rows vary by phase and enabled features, but the conservation rule does not.

Where an exact equation is available, RetireOdds calculates its residual and treats a difference greater than one cent as unreconciled. The ledger also distinguishes balances, cash flows, transfers, tax metrics and non-spendable values so a transfer cannot be mistaken for income and illiquid NAV cannot quietly pay a bill.

Annual recordWhat it preserves
Opening positionTaxable, tax-deferred, Roth, illiquid and deferred-compensation values entering the year.
Money coming inWages, Social Security, pensions, timeline income, deferred compensation and characterized distributions.
Money going outLifestyle spending, healthcare, life events, liabilities, taxes, penalties and capital obligations.
TransfersRoth conversions, RMD proceeds and other moves whose tax character matters even when total wealth is unchanged.
Tax & healthcare factsOrdinary income, gains, taxable Social Security, ACA MAGI, IRMAA MAGI and the two-year lookback queue.
Closing positionEach source book after activity, plus any unfunded amount that must remain visible.

A dollar's source changes what it can do.

RetireOdds keeps market value separate from statutory basis and keeps liquid wealth separate from assets that cannot fund spending today.

Taxable & cash

Tracks market value, cost basis, realized-gain fraction, dividend character and cash with full basis.

Tax-deferred

Tracks pretax balances, traditional IRA basis, ordinary distributions, RMDs and conversion sources.

Roth

Separates market value from contribution basis, conversion lots, taxable and nontaxable principal, earnings and qualification clocks.

Illiquid assets

Maintains NAV, basis, debt, capital calls and explicit cash flows. NAV is wealth, not spendable cash.

Deferred compensation

Runs as a separate gross pretax sub-ledger with elections, investment return, fees, withholding and ordinary-income payouts.

Liabilities & obligations

Remain uses of cash. If the plan cannot settle them, the unpaid amount survives as a visible shortfall.

Settlement is source-aware

When cash is needed, the engine uses the selected withdrawal order and the legal character of the available source. A taxable sale realizes only its gain portion; a tax-deferred distribution creates ordinary income and can recover entered IRA basis pro rata; a Roth distribution follows contribution, conversion and earnings ordering. Taxes created by the draw are included in the amount that must be funded.

Basis survives market losses

Market value and statutory basis are different records. A decline in Roth market value does not erase historical contribution basis. A taxed dividend can increase taxable cost basis when reinvested. A return of capital reduces alternative-asset basis before later gains are characterized.

The books begin today, not at retirement.

The same annual architecture covers the current year, working years, retirement years and the final plan settlement. This prevents pre-retirement activity from bypassing tax, healthcare or source rules.

Current booksBalances, current-year income, windfalls, expenses, conversions, deferred-compensation bridges and taxes settle before the first projected year.
AccumulationWages, contributions, dividends, gains, life events, healthcare inputs and alternative-asset cash flows enter annual records while the source books grow.
RetirementSocial Security, RMDs, pensions, withdrawals, Roth conversions, taxes, ACA, IRMAA and household changes are solved together year by year.
Plan horizonOutstanding ACA settlement, commitments and ending after-tax treatment are shown separately so the last visible year cannot hide a remaining obligation.

The primary person's age is the shared axis. A spouse is represented by an age offset, so claim dates, Medicare eligibility, survivor tax status and each person's horizon remain tied to the same calendar year rather than drifting across two independent timelines.

Depth without a second set of answers.

Complex features add characterized facts to the annual record. They do not create disconnected calculators with their own balances or year conventions.

Federal and state tax

Stacks ordinary income, preferred gains and dividends, taxable Social Security, conversions and NIIT before applying progressive federal rules and the disclosed state estimate.

Healthcare

Uses full Social Security in ACA MAGI, prices marketplace support from the relevant income estimate, reconciles advance credits and bills IRMAA from the statutory two-year lookback.

Roth conversions

Moves dollars from deferred to Roth, preserves IRA-basis recovery and conversion lots, recomputes tax on the year's complete income stack and keeps tax funding visible.

Required distributions

Uses prior-year-end deferred balances, SECURE 2.0 start ages and per-owner schedules where ownership data is available. Surplus RMD cash moves to taxable rather than disappearing.

Deferred compensation

Models confirmed elections, payout timing, fees, investment of the undrawn balance, ordinary income and withholding as a prepayment rather than a second tax expense.

Illiquid assets

Keeps NAV and liquidity separate; capital calls, distributions, return of capital, sales, debt and remaining commitments conserve value and cash independently.

Household and survivor

Models spouse age, Social Security streams, filing-status changes, survivor benefit step-down, Medicare enrollment and the longer household horizon.

Expat retirement

Coordinates U.S. and host-country tax character, FTC baskets, FEIE-eligible earned income, local cost inflation and FX. Unsupported countries stay explicitly simplified.

Life events

Adds dated income, windfalls, expenses and recurring commitments to the same timeline. Relative events re-resolve when their retirement anchor changes.

Expense management

Turns tracked spending into a planning baseline while keeping one-time purchases and premium-versus-care healthcare distinctions explicit.

Every consequential number should have a receipt.

Click an underlined Ledger amount to open its explanation. The side panel is generated from the selected cell's typed provenance, not generic help text.

Why is closing liquid wealth formed this way?year.2037.closingTotal · deterministic-taxproj
Result carried to the next yearClosing taxable + deferred + Roth
Formula
closing taxable + closing tax-deferred + closing Roth = closing liquid portfolio
Equation reconciles within the one-cent tolerance

A trace can include the output cell ID, financial phase, treatment, source facts, source-page links, input references, decision references, rule ID, model version, exact unrounded result and downstream cells. Where an exact formula exists, the panel shows the terms, result and residual. Where detailed provenance is not available, RetireOdds does not show an empty “breakdown.”

This makes review practical. You can move from a tax number to Tax Planning, from spending to Expenses, or from an account balance to Portfolio, change the underlying fact and regenerate every downstream year.

A scenario is a temporary second set of books.

What-if analysis is useful only when the alternative keeps the same accounting discipline as the baseline.

Saved baselineYour confirmed portfolio, plan and events remain unchanged.
One temporary overrideRetirement age, spending, country, return, one-time expense or Roth conversion.
Rebuilt resultThe same ledger generator recomputes affected years and shows baseline deltas.

The preview request is allowlisted and never writes back to your saved plan. Changed assumptions re-resolve dependent ages, healthcare, taxes, life events and horizon values instead of editing one headline in isolation. A country preview, for example, reprices living costs, healthcare, inflation, FX and coordinated tax assumptions as one server-owned bundle.

Withdrawal-strategy comparisons are different: the annual table remains the deterministic reference plan, while paired stochastic runs compare market-path outcomes under the selected strategy. Both runs still begin with the same resolved plan and common random seed.

Monte Carlo sits on top of the ledger.

The deterministic books explain one internally consistent plan. Simulation asks how often that plan remains funded when market returns, longevity and other enabled uncertainties change.

Monte Carlo

Draws positive lognormal real gross returns calibrated to the selected allocation's geometric return and volatility.

Block bootstrap

Resamples five-year blocks of historical stock and bond returns to preserve clustered sequences.

Historical

Replays only complete historical start-year windows without wrapping the end of history to its beginning.

Monte Carlo and bootstrap run 1,000 paths by default. Each path walks the same life stages and re-solves source-aware withdrawals, taxes, MAGI, healthcare, conversions, RMDs and enabled cash flows against that path's balances. A path fails when any after-tax obligation remains unfunded, including in the final modeled year. A zero portfolio is still successful when outside income fully covers every obligation.

The Chance screen also preserves the other side of the percentage. Where this plan fails counts the exact paths that left an obligation unfunded, groups their first-shortfall ages into real five-year bands, and shows one to three actual failed trials selected deterministically from the early, middle and late ranks of failure timing. The ages and gaps are conditional on failed paths only. These examples come from the same run as the headline success rate; they are not forecasts, causal diagnoses or synthetic percentile paths.

How to read the results

  • Plan success is the share of paths in which every modeled year is funded. It is not a guarantee.
  • P10, P50 and P90 are the 10th percentile, median and 90th percentile ending balances for each future year.
  • Median funded spending reports what the paths actually funded, which matters when a strategy flexes spending.
  • At 1,000 paths, a mid-range success estimate has roughly a ±3 percentage-point sampling margin at 95% confidence, before model uncertainty.

All primary planning values use real, today's-dollar terms. Explicit nominal return assumptions are converted through the Fisher relation: (1 + nominal) / (1 + inflation) − 1.

The architecture is designed to expose drift.

Financial software becomes unreliable when each screen assembles a slightly different version of the household. RetireOdds uses mechanical constraints and parity tests to make that divergence visible.

One option builderEvery simulation consumer resolves the plan through the same server-owned assembly path rather than hand-building partial inputs.
One year conventionThe year ending at retirement age is the final working year; retirement withdrawals begin the following year across engines.
One financial framePrimary projections use real dollars with a common current-age anchor; nominal modules explicitly index or translate values.
Conservation testsCash, tax basis, transfers, NAV, commitments and closing balances are tested so money cannot silently appear or vanish.
Deterministic parityZero-volatility Monte Carlo fixtures are compared with deterministic projections for taxes, healthcare, balances and failure state.
Canonical hashesThe Plan Ledger has a stable content hash and model version so equivalent inputs produce a reproducible record.
iOS parityThe native simulation bundle is generated from the shared financial libraries and guarded against stale builds.
Data ownershipBulk updates are file-based and user-controlled; RetireOdds does not collect bank or brokerage credentials.

A complete model still has boundaries.

RetireOdds aims to make material simplifications explicit. The Ledger is planning-grade financial software, not a tax return, legal opinion or promise about markets.

Important current limitations

  • State income tax is a simplified planning estimate. It does not implement every state deduction, credit, locality or special rule.
  • The portfolio return model uses a blended stock-and-bond allocation. It does not project each individual security, trading cost or future rebalancing decision.
  • Traditional IRA basis is applied across the combined deferred bucket when the source account of a draw is unknown; actual tax filing aggregates IRA basis separately by spouse under Form 8606 rules.
  • The standalone Roth optimizer uses a same-age spouse simplification for some age-65 deductions and Medicare enrollment. Core household projections use the entered spouse age.
  • Detailed Roth qualification requires the first Roth contribution year. Legacy records without it remain conservative.
  • Early-distribution penalties and statutory exceptions depend on account type and circumstances. RetireOdds does not determine eligibility for every exception.
  • ACA advance credits are modeled and reconciled, but the graduated repayment cap below 400% FPL is not implemented; the full difference is used.
  • The optional Medicaid cost is a planning assumption, not an eligibility determination. State-specific expansion and eligibility rules are not fully modeled.
  • A person working past RMD age does not yet receive source-account-specific still-working exception treatment across every employer and IRA account.
  • Supported expat countries receive characterized U.S./host treatment. Unsupported countries retain a clearly labeled simplified higher-of estimate.
  • Illiquid valuations, employer credit risk, future tax law and personal behavior can differ materially from entered assumptions.

No model predicts the future. A success rate measures robustness across the assumptions and paths that were modeled. It does not measure every risk and is not a recommendation to buy, sell, convert, claim or retire.

Planning software, not professional advice

RetireOdds is a comprehensive personal money tracker and retirement planning tool. It is not a substitute for a certified financial planner, registered investment adviser, accountant or tax preparer. Review consequential decisions with a qualified professional.

The rules are tied to published sources.

Tax, healthcare and retirement constants are pinned to a stated model year and updated together. Primary authorities take precedence over summaries or memory.

AreaPrimary reference
2026 federal taxIRS Revenue Procedure 2025-32
ACA applicable percentagesIRS Revenue Procedure 2025-25 and Form 8962 instructions
IRMAASSA POMS HI 01101.030
IRA and Roth distributionsIRS Publication 590-B
Early distributionsIRS exceptions to tax on early distributions
Withdrawal researchBengen (1994), Determining Withdrawal Rates Using Historical Data; Cooley, Hubbard & Walz (1998), The Trinity Study
Market valuation researchRobert Shiller's historical market data

Put your retirement on the books.

Bring your portfolio, income and spending. RetireOdds will build the annual record, show what changes it, and carry it through the rest of your financial life.