Retirement planning, with AI

Plan the road to retirement, one question at a time.

I asked AI to build a retirement dashboard around our own data and the questions we actually have. It answers with our own numbers: when to claim Social Security, how much to convert to a Roth this year, and what that does to your Medicare premiums later.

A personal tool for now. I’m exploring opening it to others.

The questions that matter

Retirement is a chain of decisions, not one number.

Most of the hard questions interact. A Roth conversion this year changes your taxes, which can change your Medicare premiums two years later, which changes the best year to claim Social Security.

“When should we each claim Social Security?”
“How much can we convert to a Roth this year?”
“Will our income at 63 raise our Medicare premiums at 65?”
“What if we retire at 62 and need health coverage until 65?”

Why AI

What AI changes about retirement planning.

Simple calculators ask for a few numbers and return one projection. Advanced planners go much further, and many already model taxes, Medicare cliffs, and market risk. Where AI makes the real difference is in how the planner adapts to you, and in keeping every number honest.

	Simple calculators	Retirement Planner
Adapting to you	You get the features the app ships, and wait for the rest.	With AI writing the code, the planner itself changes as our needs change: a new rule, a new calculation, a new kind of question.
Your questions	A fixed set of inputs and screens.	Built around the questions you actually have, including “what if we…” scenarios.
Showing its work	A result, with little explanation.	Every answer lists its assumptions and the dated rules it used.
Your situation	Averages and simplified assumptions.	Your household: both spouses, ages, accounts, income, and home.
TaxesAlso in many advanced planners	Often a single flat tax rate.	Real federal and California brackets, applied year by year.
CliffsAlso in many advanced planners	Smooth curves that hide sudden jumps.	Flags when income lands near a Medicare premium (IRMAA) tier or an ACA subsidy cliff.
MarketsAlso in many advanced planners	One average return.	Monte Carlo runs over a tax-aware, year-by-year cash-flow model.

A general comparison, not a review of any specific product. Advanced planners and professional tools cover parts of this too; the first three rows are where Retirement Planner is different.

How it spends

No fixed 4%. Spending that follows your life and your markets.

The 4% rule assumes you spend the same, inflation-adjusted amount every year, whatever happens. Real retirement doesn’t work that way, so Retirement Planner never uses a fixed rate. Instead it combines three periods of life with three spending levels.

Three periods: spend more early, then settle

Travel yearsThe active early years, when health and energy are highest. Spend more here.
Slowing downTravel and big plans taper off, and spending eases.
SettledSpending stabilizes at a steady, comfortable level.

Three levels: adjusted every year

LuxuryThe full plan, extras included, when markets have been kind.
ComfortThe normal level most years.
ProtectedEssentials only. This floor is never cut.

Each year the plan checks how your assets have grown. Guardrails suggest stepping up when there is room and stepping down when markets fall, so you adjust a little, early, instead of a lot, late.

These are well-known ideas from retirement research: spending that declines with age (often called go-go, slow-go, no-go) and guardrails that adjust withdrawals to the portfolio. Some advisor tools and planners offer one or both. Retirement Planner builds them in from the start, together with real taxes and Medicare cliffs.

How it works

AI builds it. Tested calculators do the math.

AI is great at turning what you need into working software, and bad at doing tax math in its head. So AI builds the dashboard, and the numbers always come from tested calculators, never from the AI.

01 / DESCRIBE

Describe what you need

Tell AI your situation and the questions you want answered. It builds them into the dashboard.

02 / CALCULATE

Calculators do the math

Purpose-built calculators run on your profile and on rules taken from official sources, each dated and checked for staleness.

03 / EXPLAIN

Answers show their work

The dashboard shows comparisons, with the assumptions and rule versions listed, so you can check them.

11rule files from official sources, each dated

4core calculators: Social Security, Roth room, income projection, scenarios

224automated tests check the calculators, so answers never rely on the AI’s math

0numbers made up by the AI

How it started

I built it to plan our own retirement.

In July 2026 I started using AI to work through our retirement: Social Security timing, Roth conversions, Medicare enrollment, and health coverage before 65. The answers were only useful once every number came from a real calculation, so I built the calculators, with AI writing the code.

That also made it flexible. When a new question comes up, like a home sale, a foreign pension, or a change in the rules, I can adjust the planner to fit our needs instead of working around what an app happens to offer.

Along the way it became clear the same approach could help other people facing the same decisions. It is still a personal tool, built around our situation as a California couple, and I’m exploring whether it can become something others use too.

Status

A personal tool today. Exploring what comes next.

Retirement Planner currently runs for one household and covers federal rules plus California specifics. Opening it to others would mean supporting more states and situations, and making it easy to set up. I’m exploring whether that makes sense. Interested? alex@i80.com

Not financial advice. Retirement Planner is decision support: it compares scenarios under stated assumptions. For annuities, insurance, long-term care, estate planning, and other decisions outside its scope, talk to a licensed professional.