Retirement is about
so much more than the money.
It's about giving the rest of your life the same depth of plan you've given your wealth: your health and the years it buys, the people who fill your days, the place that helps your plan or quietly works against it, the passion that still gets you excited, and the purpose that tells you why you're here. Do that, and you can be confident you're doing everything you can — for a longer life, and a happier one.
Why this exists ↓A sample readiness profile
academic research and the best of modern thought leadership
a written assessment today, a plan you work tomorrow
a private link, no password, nothing to download
The Retirement Strategy is so much more than a questionnaire.
Not a quiz score — a written assessment, and a plan you keep working.
The Assessment — a written readiness document
The Plan — a worst-first, sequenced plan
Not a chatbot — an expert on one subject.
Most retirement tools hand you a static form. This one adapts to you in real time, reasons across six messy human dimensions, and remembers what you said — made possible by the engine underneath.
Built on Claude, Anthropic's most capable AI — the same frontier models, pointed at a single job.
It reasons from a curated library of retirement research and expert frameworks — not generic answers off the open web.
Not a general-purpose chatbot — shaped specifically to assess readiness across Health, Wealth, People, Place, Passion, and Purpose.
It carries your context for years, and gets sharper as the models advance and the research library grows.
It surfaces the quality of your own thinking. It never gives financial or medical advice.
Why this exists
There's a pattern that shows up about six months into retirement. People who spent decades performing at a high level — who planned meticulously for the financial side — find themselves disoriented. The calendar is empty. The identity that came with the title is gone. The friendships that felt deep turn out to have been built on proximity.
It's not a rare outcome. Research suggests retirees face higher rates of clinical depression than working adults, and the effect is strongest among high achievers who drew their sense of purpose from their careers.
What's striking is how little exists to help people plan for it. The financial-planning industry is a trillion-dollar machine. But the questions that actually decide whether retirement is fulfilling — Who am I without my work? Where do my relationships come from? What gives me energy on a Tuesday in October? — have almost nothing rigorous behind them.
The Retirement Strategy was built to fill that gap. It draws on academic research and the best of modern thought leadership, and delivers it as a structured conversation that pressure-tests your readiness across every dimension that matters.
How it works
Have a conversation
About 30 minutes, sometimes more. The assessment asks the questions a thoughtful advisor would, across all six dimensions — not how much you have, but how clearly you've thought it through.
See where you stand
A written readiness assessment scores each dimension and names the gaps — usually not the ones you expected.
Work the plan
Turn the assessment into a sequenced plan you keep working — worst-first, one move at a time, up to and well past the day you retire.
“Absolutely brilliant — quick, insightful, and gave me real, tangible things to address.”
Greg
Retiring within 3 years
“I genuinely think everyone thinking about retirement should do this.”
Barry
Recently retired
“It's cathartic to go through that structured thought process — and the results are spot-on.”
Michael
5+ years from retirement
Two kinds of writing
The research behind the assessment — and the story of building it.
Each piece unpacks the findings and research behind a dimension. Also a weekly newsletter on LinkedIn.
A weekly essay on what it actually looks like to build with AI after a long career — written as a retired solo founder, in real time.
Read on Substack →