The decisions that shape your life deserve a coach and a thinking partner. Now you have one.
Life Charted helps you think through what matters most: your money, your career, the big moves, where your life is headed. It gets you to a plan you trust, remembers your situation as it grows, and leaves every decision to you.
Works inside the Claude or ChatGPT app you already have. Setup takes about two minutes.
What it does
A real thinking partner, on the things that matter.
Sees what you hadn't thought of
A thinking partner widens your view: the angle you missed, the option you hadn't considered, the question under the question.
Gets you to clarity
It doesn't rush to an answer. It draws out what you actually want and where you really stand, until the picture is clear.
Turns it into a plan
You come out with something real: the call, the next moves, and the signals that tell you it's working.
Remembers, so your thinking builds
It keeps your context as your life grows and connects the dots over months, so you never start from zero.
How it works
It walks you to a plan, one question at a time.
Underneath every conversation is a simple sequence, the kind used for an organization's biggest decisions, pointed at your life:
What do you really want?
What would success actually look like?
Where are you right now?
What are the gaps?
How are you going to get there?
How will you keep track over time?
How do you adjust as life changes?
Your answers become the plan, and the plan grows with you.
What to bring it
Bring it the big stuff.
What to do with your life
When the direction isn't obvious yet.
Your career
Which path, when to move, how to grow into it.
Your money, for the long haul
Building the foundation, not just getting through the month.
A big move or a leap
A city, a degree, a change you keep weighing.
The person you want to become
And how you actually get there.
What matters to you
Your own principles, settled before the decisions pile up.
Why I built it
I've spent almost twenty years helping people think through what's next.
Foster homes, the Big Brother program, family, friends, people I've worked with. By trade I work in security: I'm the Family IT Guy, and I've spent nearly thirty years protecting people's data and systems, some of it for the defense and intelligence world. Along the way I learned a planning method built for an organization's biggest decisions, and I kept noticing it worked just as well on a person's own life. Almost no one is ever taught it.
So I built the private version of it, and built it the way someone who works in security would: a coach and thinking partner for your real decisions that helps you see what you hadn't thought of yet, and keeps what you tell it locked down.
Ben GillenwaterFamily IT Guy. Builder of Life Charted.
Your data is yours
Structured, encrypted, and yours to keep.
When you talk things through with a regular AI, it disappears into a chat history you can't really use. Life Charted turns what matters into clear, organized records that are yours. Pull up your full picture anytime, take it with you, and trust it won't get lost or quietly rewritten. Your records are encrypted, and Life Charted never sells them or trains a model on them.
Your conversation itself runs through your own Claude or ChatGPT account, so what you type there follows that app's rules, and you decide whether they use it to train. The setup guide shows you how to turn that off. Your saved records stay yours either way.
You chart your course. Life Charted helps you see the map clearly.
Life Charted is invite-only while it's in early access. If you've been invited, you're two minutes from your first session.