One Tool Becomes a Roadmap
When I built the Retirement Runway Snapshot, the most useful thing I gained wasn't the tool itself — it was the pattern. A clean set of questions, an AI layer with strong guardrails that stays on the right side of the line, and a plain-English result that points you toward a professional. Once that pattern exists, every new tool is mostly a matter of choosing which knot of pre-retiree anxiety to untangle next.
And there are a lot of knots. The years approaching retirement are full of questions that feel too small to bother a professional with, but too murky to just sit with. That's the exact gap these tools live in. Here are the ones I most want to build — a roadmap, and an open invitation to tell me which you'd actually use.
1 Retirement Runway Snapshot Live now
The one that's already here. Answer a few questions about your timeline, rough savings ranges, and what's weighing on you, and get a plain-English read on your runway plus five things worth thinking about. No scary number, no jargon, no advice — just clarity. It's the template everything else builds on.
2 The Fee Reality Check
Fees are the silent tax on a retirement. The trouble is that an expense ratio of "0.8%" sounds like rounding error, when over a couple of decades it can quietly eat a meaningful slice of your nest egg. I want a tool where you enter a fund or two and a rough balance, and AI explains — in plain English, in ranges, never as a prediction — what those fees actually mean over time and what questions to ask about them. Not "switch to this fund." Just: "here's what this is costing you in human terms, and here's what to ask."
3 The Pre-Retiree Question Builder
The single most valuable thing you can bring to a financial professional is good questions. Most of us show up with a vague sense of unease and walk out having forgotten half of what we meant to ask. This tool would take your situation and what's on your mind and generate a personalized, organized list of questions to ask — grouped by income, healthcare, taxes, and legacy. It turns a stressful meeting into a productive one. It's the tool that most clearly hands you off to a human, which is exactly the point.
4 The Healthcare Bridge Explainer
The number-one concern I see from people in their fifties isn't running out of money — it's healthcare, especially the gap between retiring early and Medicare at 65. It's genuinely confusing, and the confusion itself causes people to delay decisions. I'd build a tool that takes your target retirement age and walks you, plainly, through what the "bridge" years could involve and what to learn more about. Education, not enrollment advice — but enough clarity to replace dread with a to-do list.
5 The Income Picture Sketch
Going from "a pile of savings" to "a monthly paycheck in retirement" is a mental leap a lot of pre-retirees never quite make. This tool wouldn't project a precise dollar figure — that's exactly the kind of false precision I avoid — but it would help you think in the right shape: what sources of income tend to come into the picture, how people often sequence them, and what trade-offs are worth discussing with a professional. A sketch, not a blueprint.
The Thread Running Through All of Them
Notice what every one of these has in common. None of them tell you what to do. None invent a number for your future. Every one takes something intimidating, makes it legible, and points you toward a real professional better prepared than you were five minutes earlier. That's the whole philosophy: reduce the dread, raise the questions, respect the line.
I've become a little obsessed with this audience — people roughly a decade out, smart and capable, who've been handed scary calculators and dense content but very little plain-English clarity. The more tools I build for them, the more convinced I am that this is where small, well-guarded AI tools do their best work. It's a space I plan to keep building in for a long time.
🧭 Start with the one that's live
The Retirement Runway Snapshot is tool number one and it's ready right now. Run it, then tell me which of the others you'd actually use — your answer genuinely shapes what I build next.
Run My Snapshot →Your Turn
This is the part where I need you. I have a roadmap, but the order should be set by the people these tools are for. If you're somewhere in that ten-year window, which of these five would actually earn a spot in your week? Is there a sixth I'm missing — some specific knot of confusion that's been nagging you that a plain-English tool could help untangle?
Tell me, or just run the Snapshot and reply to the email. Every bit of that feedback is what turns a roadmap into the right roadmap. Building in the open only works if the people you're building for keep talking back — so please do.