User Guide

1 Welcome to RetireOdds

RetireOdds turns the messy question "will my money last?" into a clear, year-by-year picture you can actually inspect and change.

You bring the basics of your financial life into one place — your net worth, your accounts and holdings, what you spend, your taxes and healthcare costs. RetireOdds uses those inputs to build a Ledger: a year-by-year projection of your retirement, from today through the end of your planning horizon, showing how each year is funded.

Then it runs the numbers the honest way. Instead of assuming one smooth average return, RetireOdds runs a Monte Carlo simulation across 1,000 randomized market paths and reports your Chance of Success — the share of those futures in which your plan never runs short. A plan "fails" if any year, including the last, can't be funded.

From there you optimize. Dedicated views help you lower lifetime taxes, plan Roth Conversions, model Healthcare and Medicare costs, and line up your Year-End Moves — and every edit instantly recalculates your odds.

RetireOdds works right in your browser and as a native iPhone app, so your plan travels with you. It never links to your bank or brokerage; you stay in control of what goes in.

2 Create your account

Signing up takes a few seconds, and there's no password to invent or remember.

RetireOdds uses passkeys instead of passwords. When you create an account at /signup, your device makes a passkey and you approve it with Face ID, Touch ID, your fingerprint, or your device PIN — whatever you already use to unlock your phone or laptop. There's nothing to type and nothing to leak in a breach: the secret key never leaves your device, and a passkey only works on RetireOdds, so it can't be phished onto a fake site. Apple, Google, and Microsoft back your passkeys up to your other devices automatically.

Later, once your account holds real data worth protecting, RetireOdds gives you one-time backup codes in the app. Save these somewhere safe — they let you get back in if you ever lose access to your passkey device.

Every new account starts with a free 30-day trial — no credit card required. You get full access to every feature for those 30 days. When the trial ends, you can keep going with lifetime access for a one-time $199 (a limited-time deal, until September 30, 2026) or an annual plan at $69/year. Either way every feature is included, and there's no lock-in — you can export all of your data at any time. Full details live on the Pricing page.

3 The setup interview

After you sign up, a short guided interview collects the essential facts behind your first Ledger — four sections, saved as you go.

The wizard moves through Your plan, Income & wealth, Spending, and Retirement & income, then ends on a Review screen. You can move between sections freely; your draft is saved before each jump, so nothing is lost if you step away and come back.

Here's what each part asks:

• Your plan — whether the plan is just you or you and your spouse, your current age and a planning life expectancy, your state of residence, and (if married) the same details for your spouse.
• Income & wealth — your annual income before tax, your tax filing status, and your current balances split across three tax buckets: taxable investments, tax-deferred accounts (401(k), 403(b), traditional IRA), and tax-free accounts (Roth IRA, Roth 401(k)). Rounded balances are fine.
• Spending — a single monthly household spending number, using what you actually spend today.
• Retirement & income — your retirement age, your annual Social Security benefit at full retirement age and the age you plan to claim it (usually 62–70), plus an optional expat destination country if you expect to retire abroad. Married plans also set each spouse's timing and a survivor-spending percentage.

Why split balances by bucket? Because taxes work differently in each. Money in a tax-deferred 401(k) is taxed when you withdraw it; Roth money comes out tax-free; taxable accounts are taxed as you go. RetireOdds needs to know which dollar is which to project your taxes — and your real chance of success — accurately.

Choosing a destination country sets simplified currency, inflation, and cross-border tax assumptions; it does not change the spending number you entered. On the Review screen, RetireOdds flags assumptions worth a second look (for example, a plan with no Social Security), then runs your first 1,000-path simulation. Nothing here is permanent — everything is editable later in your Profile.

4 Your household profile

Once onboarding is done, your Profile is home base — every plan input lives here, organized into sections you can revisit anytime.

The Profile opens on an Overview that shows how many of its eight sections are ready and which still need review, with a one-click path to the next item and a button to open your Ledger. From there you can jump into any section:

• Household & horizon — who the plan covers, filing status, state, retirement country, and the ages that set how far the projection runs. Married plans add spouse ages, a survivor-spending percentage, and optional lifespan uncertainty.
• Income & benefits — employment income and Social Security amounts and claiming ages for you and, if applicable, your spouse. Entering $0 asks you to confirm it explicitly, so a blank field is never mistaken for a real zero.
• Spending — a manual monthly baseline, or a figure derived from your tracked Expenses.
• Portfolio, Taxes & withdrawals, Healthcare, Assets & obligations, and Life events & destination — specialist sections that link out to the fuller views for accounts, tax and withdrawal strategy, coverage and Medicare, illiquid assets and debts, and future income or one-time events.

Each section has its own Save section button. When you save, RetireOdds confirms "Your Ledger uses these values" and recomputes everything downstream — your Ledger, your taxes, and your Chance of Success — so the number you see always reflects the inputs you just changed. Edit, save, and watch the plan update: that's the whole loop.

5 Add your portfolio

Your accounts and holdings are the balances the simulation draws from. RetireOdds never links to a bank or brokerage — you type accounts in or import a CSV you export yourself, and every change flows straight into the Ledger.

Open Portfolio. Accounts are grouped down the left rail by their tax treatment, because how an account is taxed decides how withdrawals, Roth conversions, and RMDs are handled later. There are four buckets:

• Taxable — selling can realize capital gains.
• Tax-deferred — withdrawals are ordinary income, and RMDs may apply.
• Tax-free — qualified Roth withdrawals come out untaxed.
• Cash — available without selling a position.

Click + Add to create an account with a name, a tax treatment, and an optional cash balance. If you turned on household planning, you can also mark whether an account belongs to you or your spouse.

Adding holdings

Use + Add holding to enter one position by hand: ticker, an optional name, quantity, and a cost basis (leave it blank if you don't know it — you can fill it in later from the table). ↻ Live prices refreshes market prices, and ↓ Export CSV saves your positions back out.

Importing a brokerage statement

↑ Import CSV / XLSX loads a statement you exported from your brokerage. An import is treated as the complete current snapshot for one account, so RetireOdds shows you a preview — how many positions it will add, update, leave unchanged, and remove — before anything is saved. If the file's layout is unfamiliar, you map its columns once and can save that mapping for next time; only the column names are remembered, never the statement's values. When a file holds several accounts, you route each one to a destination.

Each holding also has an Income button, where you can classify the dividends or interest a position already pays (asset class, tax character, annual yield, and whether it's reinvested or spendable). These describe distributions that are part of total return — RetireOdds never adds them as extra growth.

Illiquid assets, deferred comp, and debts

Three companion pages round out your balance sheet:

• Illiquid Assets — private funds, real estate, a private business, private credit, or collectibles. Their net equity (NAV after debt) counts toward total wealth but can't fund spending; only cash flows you enter explicitly, such as a distribution or a sale, become spendable.
• Deferred Comp — a confirmed, fully vested account-balance NQDC plan, entered manually or from the RetireOdds CSV template. Undistributed balances stay gross and can't fund spending until they're paid out.
• Liabilities — credit cards, auto and student loans, medical debt, or a mortgage. Each debt subtracts from your net worth and shows an estimated payoff date.

6 Track your spending

Your tracked spending becomes the average that drives the retirement simulation, so the closer it matches real life, the more honest your odds.

On Expenses, add a transaction with the inline bar (or the + button): a date, payee, category, currency, whether it's an expense or income, and an amount. Categories range from Rent and Groceries to Travel, Health, and Taxes. Mark a large purchase as a one-off and it still shows in your history but is left out of your average monthly spend.

Quick add: receipts and voice

On a phone, the + button opens a dedicated add screen with two shortcuts:

• Scan a receipt — opens your camera or photo picker and reads the receipt on-device, then prefills the amount, payee, and date for you to confirm.
• Dictate — in the iOS app, when on-device voice is available, a mic button lets you speak your expenses and review the parsed rows before saving.

Importing and currencies

Import CSV pulls in a file exported from a tool like Quicken or Simplifi; pick which currency the rows are in first. You can set a base currency for the page, and amounts in other currencies are converted to it. Export CSV saves your transactions out.

At the top of the page, Tracked average (from your logged spending) sits next to your Current plan figure, so you can see how what you actually spend compares to the assumption behind your plan. Review your categories before you publish a spending baseline.

Monthly Close

The Monthly Close page is a short monthly ritual for the complete liquid books. Review account balances, amounts owed, the month's recorded cash flow, and the spending source currently used by the plan. Closing the month freezes an immutable, reconciled record; a later correction creates a new version without rewriting the original.

7 Watch your net worth

The Net Worth page rolls everything up: what you own, minus what you owe.

Four figures sit across the top — Net worth (assets minus liabilities), Assets, Liabilities, and Annual growth. The Net worth over time chart is drawn from snapshots recorded as you hold real securities; add holdings or import a brokerage CSV and it tracks from there, while cash-only balances stay flat.

Below it, a flow diagram toggles between Balance (assets against liabilities) and Allocation (how each account maps to US stocks, international stocks, bonds, and cash). A liabilities panel lists your debts alongside the income and spending figures currently feeding your cash-flow view.

8 The Ledger: your retirement, year by year

The Ledger is your home page and the heart of RetireOdds. It lays your whole plan out as a table with one row for every year from your current age through the end of your plan, so you can see exactly how each year is funded — where the money comes from, where it goes, and what balance you carry into the next year.

Every figure on the Ledger is in today's dollars (inflation-adjusted), so a number in your 80s is directly comparable to one today. Reading a year top to bottom, the rows are grouped the way you'd actually think about a year:

• Opening position — the balances you start the year with: taxable, tax-deferred, and Roth accounts, plus any illiquid asset value and deferred compensation, and your total opening liquid portfolio.
• Money coming in — employment income, household Social Security, other taxable income, required minimum distributions, deferred-comp and illiquid-asset distributions, post-tax cash added to the plan, and any income surplus reinvested.
• Decisions and transfers — Roth conversions you've scheduled (a move between buckets, not new money).
• Money going out — lifestyle spending, healthcare (net premium and care), one-time and timeline expenses, ACA reconciliation, Medicare IRMAA, total modeled income tax, penalties, and the total spending need for the year.
• Funding — how much cash your income covered, how much the portfolio had to provide, and any unfunded amount left over.
• Growth and closing position — real investment return, then your closing account balances and total modeled net worth, which become next year's opening line.

Open any cell and the Ledger explains how that number was produced and links you to the page where you'd change it — spending sends you to Expenses, taxes to Tax Planning, a conversion to Roth Conversions, and so on. Expandable detail rows break out the tax character behind the totals, like which slice of a draw was taxable versus Roth.

If you're already retired — your retirement age is earlier than your age today — the Ledger doesn't start in a year that has already passed. It anchors at your current age and projects forward from there.

Above the table, the Ledger | Situation toggle switches the same plan between the table and a node map: Situation draws each year's income, obligations, and balances as connected nodes, which some people find easier to follow than rows and columns. It's the identical plan, just visualized differently.

9 Chance of Success: the Monte Carlo simulation

The Ledger shows one path through your retirement. Markets don't move in a straight line, so Chance of Success replays your plan across many possible futures and reports how often it works.

By default the simulation runs 1,000 randomized market paths. The returns aren't guesses pulled from nowhere — they're lognormal real returns calibrated to your own stock and bond mix, so a more aggressive allocation produces a wider spread of good and bad years and a conservative one produces a narrower band. Each path walks the same life stages as your Ledger and re-solves withdrawals, taxes, Social Security taxation, healthcare, conversions, and RMDs against that path's balances.

A path succeeds when every modeled year is fully funded, and fails if any year comes up short — including the very last one. (A path can even reach a zero portfolio and still succeed, if outside income like Social Security covers every remaining obligation.) The headline percentage is simply the share of paths that made it, and alongside it a safe-spend figure estimates the spending level your plan can sustain.

Because the result comes from a random sample of paths, it carries a small margin: at 1,000 paths a mid-range success rate is accurate to roughly plus or minus three percentage points, before any uncertainty in the assumptions themselves. So read the number as a range, not a precise reading — an 84% and an 86% are effectively the same plan.

Where this plan fails makes the unsuccessful share visible. It shows the exact failed-path count, when those paths first leave an obligation unfunded, the typical cumulative gap, and selected actual failing trials from the same simulation run. When very few paths fail, RetireOdds shows the observed cases without claiming a stable pattern.

Open Why this result? on the Chance of Success page to see behind the number:

• Sensitivities — a ranked view of which assumptions move your odds the most, and by how many points.
• Robustness — whether the result holds up across the three engines (Monte Carlo, historical, and block-bootstrap), labeled Robust, Assumption-sensitive, or Fragile.
• Assumptions disclosure — the full list of inputs behind the estimate, so you can trust it or push back on it.

A few advanced tools build on the same engine:

• Timing & Strategy lets you test how you draw money down — Constant Dollar, Percent of Portfolio, Dynamic SWR, Guyton-Klinger guardrails, the 95% Rule, Yield-anchored, Sensible Withdrawals, and Vanguard Dynamic Spending.
• Compare Plans puts two versions of your plan side by side.
• Life Events lets you add income, expenses, and windfalls at specific ages and watch your odds respond.

Curious what one of these simulations looks like from the inside? The Scenario library walks the same year-by-year loop against every real retirement start year since 1928 — one page per historical scenario, pass or fail.

10 Plan your taxes

Getting cash to spend in retirement is not income — it's a sale, and where the dollars come from decides the tax. The Tax Planning view turns that idea into a year-by-year picture so you can see the tax bill your plan creates and where it can be softened.

Open Tax Planning and you'll see a lifetime timeline of income tax plus IRMAA (the Medicare surcharge covered next), the tax your plan saves by drawing accounts in a sensible order, and your balance split across three tax "buckets".

The three buckets and the draw order

RetireOdds sorts every account into one of three tax treatments:

• Taxable — brokerage and cash. Selling realizes a capital gain, and only the gain is taxed, at lower long-term rates.
• Tax-deferred — 401(k) and traditional IRA. Every dollar withdrawn is ordinary income.
• Roth — qualified withdrawals are tax-free, and there are no forced withdrawals.

By default the engine funds each year's spending from taxable first, then tax-deferred, then Roth — spending the taxed-lightly money early and letting the tax-free bucket keep growing. It always takes any forced withdrawal first (see below), then covers the rest in that order.

RMDs: the withdrawals you don't choose

Starting at age 73 — or 75 if you were born in 1960 or later — the IRS forces a Required Minimum Distribution out of your tax-deferred accounts each year, whether or not you need the cash. Each year's amount is the prior year-end balance divided by an IRS life-expectancy factor. RMDs matter because they can push a big slug of ordinary income into a single year and lift you into a higher bracket, so the tools before this one exist partly to shrink that future forced income.

Why Social Security taxes are tricky

Social Security is only partially taxable: depending on your other income, either 50% or 85% of your benefit becomes taxable — or none of it. Because the taxable share of your benefit depends on how much you withdraw, and your withdrawal has to cover the tax on that benefit, larger draws can quietly drag more of your Social Security into tax. RetireOdds models this loop (sometimes called the "tax torpedo") rather than ignoring it.

Year-End Moves

The Year-End Moves view is the December checklist: concrete actions you can still take before the calendar closes. It lets you test a Roth conversion, a long-term capital-gains harvest, or a Qualified Charitable Distribution against a single shared estimate of your tax, ACA subsidy, and IRMAA tier — so you can see how one move ripples across all three before you commit to it.

11 Healthcare before and after 65

Healthcare is often a retiree's largest controllable expense, and how much you pay is driven less by your age than by your income. The Healthcare view projects that cost across two very different phases.

Before 65: the ACA marketplace

If you retire before 65 you're too young for Medicare, so you buy coverage on the ACA marketplace. The key lever is your MAGI (modified adjusted gross income): the lower your income, the larger the premium tax credit that nets against your premium. That creates a counter-intuitive result — a year where you pull a lot from tax-deferred accounts, or convert to Roth, can raise your MAGI and shrink your subsidy, raising what you pay for the same plan.

At 65: Medicare and IRMAA

At 65 you move to Medicare, with base premiums for Part B and Part D. Above certain income levels you also pay IRMAA — an income-related surcharge added on top of those premiums. If you have a younger or older spouse, each person transitions to Medicare at their own 65th birthday, and the view handles that.

The wrinkle with IRMAA is timing: your surcharge tier is set by your income from two years prior. So a high-income year at 63 can raise your Medicare premiums at 65. Both cliffs — the ACA subsidy phase-out before 65 and the IRMAA tiers after — are the reason Roth conversions and large withdrawals need to be planned against your healthcare costs, not just your tax bracket. A conversion that looks cheap on income tax alone can cost you subsidy dollars or bump you an IRMAA tier.

12 Roth conversions

A Roth conversion moves money from a pre-tax account into a Roth: you pay income tax on it now, and in exchange it grows and comes out tax-free later — and it shrinks the future forced withdrawals that would otherwise be fully taxed. The Roth Conversions view projects that trade year by year.

What a conversion ladder is

A "ladder" is simply a series of partial conversions spread across several years instead of one big one. Spreading them out keeps each year's added income inside a lower tax bracket. The classic window is the low-income stretch between retirement and RMDs — after your paycheck stops but before Social Security and required distributions fill your income back up. In those years there's room to convert cheaply, and every dollar converted is a dollar that won't be forced out and taxed later.

The optimizer and its guardrails

You can convert a fixed amount each year, fill up to the top of a chosen tax bracket, or let the optimizer search for a schedule. Under Practical guardrails you can tell it to keep your taxable cash above a floor, cap the tax in any single year, or stay under an ACA or IRMAA MAGI ceiling — so it rejects mathematically attractive schedules that would strain your cash or push you over a cliff. The view reports the lifetime tax saved, the reduction in future RMDs, and the total amount converted.

The trade-offs

Converting is not free. You pay real tax now, and that added income in the conversion year interacts with everything in the last two sections: it can raise your ACA MAGI and cut your pre-65 subsidy, and it counts toward the IRMAA tier that hits your Medicare premiums two years later. The view exists to weigh "tax paid now" against "tax and RMDs avoided later" so you can see the whole picture rather than optimizing one number in isolation.

13 Going further

You've now seen the core of RetireOdds. A few remaining views round out the plan and let you export, relocate, and secure it.

Plan Report

The Plan Report is a full, printable audit of your plan: every assumption laid out with a chip showing whether the value was set by you, left at a default, or derived automatically, plus data-quality warnings where an input looks thin. It's the page to read before you trust a result — and the one to download or print when you want a record of exactly what your plan assumed.

Destination

The Destination view models retiring abroad. It ships with planning baselines for the most popular countries for American retirees — monthly cost of living, local healthcare costs, currency, retirement-visa income floors, and a note on each country's tax regime (for example, whether it taxes Roth withdrawals). Every figure is an editable estimate, not advice, so you can adjust it to your own situation and see how the move changes your plan.

Activity, Settings, and data security

The Activity log records the actions you take in the app, and Settings is where you tune the assumptions and preferences that drive every calculation. On the privacy side, RetireOdds is file-based and user-controlled: it never connects to a bank or brokerage and never asks for bank credentials — you upload CSVs you export yourself, and your data is stored privately. You sign in with passkeys instead of a password, with a one-time recovery code as your backup, and you can export or permanently delete your account and data at any time.

The iOS app

The RetireOdds iOS app is the same planner on your phone, so your Ledger, Chance of Success, and every view here travel with you.

Where to next

For specific questions, Help is a searchable FAQ. To understand exactly how the numbers are produced — the Monte Carlo engine, the tax model, and the assumptions behind them — read the Methodology.