The Roadmap Canvas in Practice: The Roadmap That Was Meant to Be Wrong
Greta runs a print shop in Eau Claire, Wisconsin, that her grandfather opened in 1958 — the kind of business where the presses have names and half the customers knew her as a child. She had done the reading about AI; she had done, in fact, rather too much of the reading. What she hadn’t done was start, in part because the shop’s one previous AI initiative — a customer-service chatbot her son talked her into last year — had stalled into an embarrassment nobody mentioned. Clarity without structure, the book calls this condition. Chapter 11’s answer is the Roadmap Canvas: a living document, five elements, with an instruction Greta says finally unlocked her — draft version 1.0 in thirty minutes, because it’s meant to be wrong.
She drafted hers on the back of a job ticket, timed.
Purpose — why this transformation matters, not what you’ll build
Keep the shop worth inheriting. Free the craft from the drudgery — the quoting, the chasing — so the part my grandfather would recognize is the part that grows.
Plays — three 90-day experiments, hypotheses to test
An AI quoting assistant on the estimating inbox (hypothesis: turnaround from two days to two hours without losing the judgment quotes); digitizing ninety years of job files into a searchable house memory; and pairing their one designer with generative tools to say yes to the short-run custom work they currently decline.
Risks — an honest 4-Lens assessment
Gary. Thirty years estimating, doesn’t type, doesn’t deserve to be optimized out of his dignity — if quoting automates, his next chapter gets named now, with him, not discovered later. And the phone: this is a town where the shop answers. No bot answers our phone.
Rituals — anchors to purpose, not productivity hacks
Friday coffee, the week’s AI mistakes reviewed out loud, the funniest posted on what the floor immediately christened the Wrong Quote Wall — the shop’s oldest ritual, the press check, extended to a new kind of press.
Metrics — measuring meaning, not just numbers
Quotes won because they arrived same-day; hours Gary spends advising customers instead of typing; and one story a month a customer tells about the shop, collected deliberately, because that’s the inheritance metric.
Then the part the book is strict about: she shared it with an accountability partner who would ask hard questions — her father, who ran the shop for thirty years and has opinions. They review monthly. At the 30-day review the canvas did what version 1.0 exists to do: it turned out to be wrong. The archive play was the wrong first move — too big, too slow, a museum project wearing an experiment’s clothes — and it was swapped for something the quoting pilot had surfaced: an AI pass that catches spec errors in customer files before they reach the press, which the floor wanted so badly they’d started doing it unofficially.
Ninety days in: quoting turnaround is same-day, Gary conducts the assistant and has stopped calling it “the intern,” and the shop has said yes to eleven jobs it would have declined. The canvas hangs by the schedule board, crossed out and rewritten, which Greta has decided is what a living document looks like. Her summary is the book’s line, earned the honest way: the roadmap that changes your life is the one you actually start — hers started wrong on the back of a job ticket, and that turned out to be the feature.
Greta is a composite — drawn from conversations with small-business owners moving from AI reading to AI doing, with details changed. The Wrong Quote Wall is free to steal.
Try it yourself
Thirty minutes, five elements — Purpose (the deeper change, not the tech), three 90-day Plays (hypotheses, not commitments), Risks (run the four lenses, name the people), Rituals (anchors to purpose), Metrics (meaning included). Share it with someone who’ll ask hard questions, calendar the 30-day review, and let version 1.0 be wrong in the direction of started.
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