Using RetireWell

Getting started

From the menu, choose "Run projections." You can fill the form in by hand, or upload a CSV to populate it automatically — either way you can review and edit everything before running.

Nothing is saved anywhere unless you check "Save this profile for next time." If you leave it unchecked, your numbers exist only for this one run and disappear when you close the tab.

Personal details

Your name, date of birth, state, and marital status. If you're married with a living spouse, a second set of pages appears for their information — most of it (income, work history, Medicare) is asked separately per person, since it's used to calculate each of your Social Security benefits independently.

• US citizen / legal permanent resident (5+ years): required to qualify for Medicare at all — defaults to yes.
• Legally blind: adds an extra amount to your federal standard deduction and, in California, an extra tax credit — see the tax guide for the exact amounts.
• Dependents: a single household count (not per-person), used for California's dependent tax credit.

Work and retirement

Target retirement age is when your regular income stops in the projection. Life expectancy caps how far out the projection runs for you personally.

For Social Security, you can enter "years worked so far" (RetireWell assumes you'll keep working — and keep accumulating Social Security credit — up until your target retirement age), or upload your actual SSA earnings statement (the XML file you can download from ssa.gov) for a much more accurate estimate. Without a statement, RetireWell assumes you earned the maximum taxable Social Security wage every working year, which is an optimistic upper bound, not a real estimate.

Income, tax, and expenses

• Self-employed: changes how the 0.9% Additional Medicare Tax is calculated — self-employment income and W-2 wages are treated slightly differently under that rule.
• Tax filing status: Single, Married/Registered Domestic Partner (RDP) Filing Jointly, Married Filing Separately, or Head of Household.
• Yearly income: your regular wages or self-employment income today. It grows every year by the increase rate you set, unless you've entered a specific override for a given year under "Projected income by year."
• Projected income by year: an optional table for when you know a specific future year's income exactly — a planned raise, a phased retirement schedule. Whatever you enter there replaces the compounding estimate for that exact year only.
• One-time income: not the same as the above. This is a one-off amount on top of everything else — an inheritance, a bonus, an asset sale — added to your taxable income only in the specific year you list it. Enter it separately for yourself and, if applicable, your spouse; each side's entries only affect that person's page.
• Estimated monthly expenses: your household's regular living costs, excluding mortgage payments (those are captured separately under Loans and Mortgage).
• Yearly charitable contributions: household-shared. Counts toward your federal itemized deductions alongside mortgage interest, property tax, and medical expenses — see the tax guide for how RetireWell decides whether itemizing beats the standard deduction.
• Investment growth split (QD/LTCG % and OD/STCG %): the share of your investment growth each year taxed at the lower long-term capital-gains rate versus the share taxed as ordinary income. If you're not sure, a conservative default is fine — this only affects the tax estimate, not your account balances.

401(k) and HSA contributions

Asked separately for each working person in the household, once income is entered. Fill in what your actual plan supports — not every employer offers all of these (Roth 401(k), after-tax "mega-backdoor" contributions, or an employer match) — check your own plan documents if unsure.

RetireWell fills your elections in a fixed order: traditional (pre-tax) first, then Roth, then after-tax, up to the annual limits the IRS sets (which RetireWell keeps current and grows with inflation each future year). Only traditional 401(k) and HSA contributions reduce your taxable income; Roth and after-tax contributions don't, since you've already paid tax on that money.

Employer match is genuinely new money added to your retirement savings on top of your own contribution — it doesn't reduce your income the way your own pre-tax contribution does, and self-employed profiles don't get one (there's no employer).

Medical insurance and Medicare

If you have medical insurance, RetireWell asks for your premium and deductible while working, and again for the gap between retiring and turning 65 if you plan to retire before then — those are genuinely different cost phases and both get asked for separately when they apply.

From age 65 on, everyone is asked about Medicare separately: whether you'll enroll in Part C/D (Medicare Advantage or a prescription drug plan) and what you expect your premium and deductible to be. Leave the deductible blank to use a reasonable default.

Household step (shared items)

Once your and your spouse's personal pages are done, one more step captures everything that belongs to the household rather than one person: real estate, loans and mortgages, insurance policies, and one-time expenses.

• Real estate: mark each property Primary or Rental. Only a primary residence accepts a property tax entry; only a rental accepts a monthly rental income figure. Enter your real property tax if you know it — RetireWell only estimates one for you when you leave it blank.
• Loans and Mortgage: covers mortgages and other loan types (auto, student, personal, other) together. Link a mortgage to the property it's on for an accurate interest-deduction estimate — a mortgage on your rental is excluded from your household expenses entirely, since rental expenses are already accounted for through your rental-income percentage above.
• Insurance policies: life insurance or annuities with cash value, a death benefit, and optionally an income stream that starts at a chosen age.
• One-time expenses: a major future cost tied to a specific year — a wedding, a renovation, a big purchase — added in full in that year only.

Accounts and debts

List your savings and retirement accounts by balance and type, and any other debts (credit cards, etc. — not mortgages, which live in the household step). Accounts and debts can each be tagged to you or your spouse individually.

Running your projection and reading the results

Click "Run projections" and RetireWell calculates three parallel scenarios — average, conservative, and aggressive market conditions — from the same inputs, so you can see a range rather than one fragile number.

The results page shows a year-by-year table and chart, a retirement timeline of key milestones (Social Security start, Medicare eligibility, when income stops), a tax and Roth-conversion strategy, and an AI-written advisory report that reads your specific numbers and calls out cash-flow risk, debt payoff timing, insurance gaps, and concrete next steps. The advisory report can take a little longer to appear than the numbers — it's generated separately.

Keeping a copy

Download your results as an Excel workbook, or save directly to Google Drive, from the buttons above the results table. See the "Understanding your export" guide for what each sheet and column means.