Reach for the Stars, Land on the Moon
Sketch the ideal end-state journey, then work backwards and ship it in measurable pieces.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 90%
Katie Dill's antidote to the organizational fear of bold ideas. Because big changes are hard to measure and incremental ones feel safe and quarterly-shaped, teams incrementally optimize their own scope and never make the whole thing better. The fix is vision work that maps the full ideal journey — but vision work with teeth: you work backwards from the North Star, split ownership across the org, and ship pieces sequentially so you can still study, learn, and validate data as you go.
Origin
Katie Dill's framing. She explicitly links it to Brian Chesky's 11-star experience exercise at Airbnb (which Chesky himself credits to a conversation with Paul Graham) as the method for sketching the ideal version.
Core principles
- 01Fear of bold ideas is rational and therefore dangerous — increments are measurable, quarterly-sized, and career-safe.
- 02If you don't know what the ideal looks like, the chance you increment your way to it is near zero.
- 03Vision work that ends in a beautiful deck on a shelf is worse than none — it discredits vision work.
- 04You do not have to ship the whole vision at once; you have to know it.
- 05Big risk-taking can be measured and thoughtful if the path back from the North Star is explicit.
How to run it
- 1
Name the incrementalism trap
Recognize when the org is choosing small, measurable, quarter-shaped bets because they feel safe — and note that users judge quality across products, surfaces, and time, so scope-local increments will not make the whole thing better.
Watch out Performance management often actively rewards the incremental choice. Check whether your rubric is producing the timidity.
- 2
Sketch the ideal version of the whole journey
Do comprehensive vision work across the entire experience — not the five-star or six-star version, the 11-star version. Make it concrete and visual, like the architect's drawing of the finished house.
Pro tip Chesky's 11-star exercise is the tool: deliberately overshoot the plausible to find the shape of the ideal.
Watch out This is not licence for a decorative vision deck with no owner and no path.
- 3
Work backwards from the North Star
Ask: if this is what the product looks like in two years, how do we get there? Decompose the path into pieces and assign ownership of each piece to the parts of the organization that must build them.
Pro tip The vision is a team effort by construction — if only one team can build it, it was not a whole-journey vision.
- 4
Sequence shipping so each piece is learnable
Ship one piece first so you can study it, learn from it, and make sure the data is good before committing to the next. The North Star governs direction; the sequence keeps the risk measured.
Pro tip This is what makes the bold bet defensible to metrics-driven leadership — the boldness is in the destination, not in the release plan.
Watch out If you try to get to day-one perfection, you will likely give up.
- 5
Keep the vision visible so progress feels real
Because each shipped piece maps to a known destination, the org experiences visible progress rather than a series of disconnected bets.
In the wild
Rather than a typical e-commerce grid of outlined squares, Stripe's website team asked what a great experience for discovering books would be — modeled on browsing a bookstore, seeing the spines, picking a book up and turning it around — and built a teaser site with design and engineering working side by side.
→ A distinctive, widely-shared site experience, and a Stripe Press reissue of Poor Charlie's Almanack that expresses the company's 'ideas of progress' mission rather than its core business.
You would not build a house by letting the roofer, deck builder, and siding contractor each optimize their own piece without a drawing of the finished house, an architect, and a GC — and a house is less complex than most software products.
→ Establishes why the ideal-state picture is not a luxury but the precondition for coherent incremental work.
Common mistakes
Vision work that dies on a shelf
A beautiful deck nobody builds is the reason vision work gets a bad name. Vision without a backwards-worked path and named owners is decoration.
Incrementing without a destination
Small measured steps within your own scope will not compose into a better whole experience, because the user's experience spans surfaces and time that no single team owns.
Trying to ship the entire vision at once
Big-bang delivery makes the bet unmeasurable and unlearnable, and increases the odds you abandon it. Ship pieces, validate the data, then proceed.
Is it for you?
Best for
Product and design leaders whose roadmap has become a queue of safe quarterly increments and whose end-to-end experience is drifting.
Not ideal for
Teams in a genuine short-term survival or crisis mode, where the correct horizon really is this quarter.
From the transcript
“for the stars and land on the Moon”
“I think Brian chesky talks about it I think it was like the 11 star experience”
“if you don't know what that is like what are the chances that you're going to increment yourself to the right outcome”
“I'm not suggesting you have to ship the whole thing at once”
“they make a beautiful deck and then it gets like seated on a shelf and nobody ever builds it”
From the episode
Building beautiful products with Stripe’s Head of Design
Katie Dill (Stripe, Airbnb, Lyft)