Justin - now is the cheapest time to break things; bring every go-faster option to Peter and Bjorn, even the ones you would veto

October 21, 2026 at 5:30 PMstrategymedium

Situation

On the 8.10, 9.2 and 10 product-identity changes Brady wants, Peter told Justin there will never be a time with fewer customers, so do it now and do not wait on Peter reading the risk doc. Justin standing order to his team is to surface go-faster-by-breaking options and veto the too-big ones; Peter changed the filter: options Justin would veto still come to Peter and Bjorn, flagged as too big.

Reasoning

Breakage cost scales with the number of customers touched and that only grows, so deferral makes the same change more expensive. A small benefit with three years to pay is still worth it. A lead-level veto was hiding options from the people who own the trade-off.

Additional Context

Bjorn independently gave Justin the same do-it-now answer.

Observed Evidence

I will read the doc, but do not wait on me. Now is the time to go faster. Time is long; a benefit that is small but has three years to pay is still a thing.

Matching Patterns

30%
Time Over Cost(time-horizon reasoning, fixed cost vs compounding benefit)

Confidence Breakdown

32/35
Evidence
10/30
Pattern
18/20
Source
12/15
Corroboration

Reasoning Depth Analysis

Org Signal:RAT has explicit license to break things while customer count is low
Who Affected:Brady and Product, customers on affected streams, Bjorn as co-approver
Precedent:Spend low-customer windows on breaking changes; escalate above-threshold options rather than vetoing them
Consequences:Peter does not gate the change on his doc review
Timing:Customer count is starting to climb

Source

reflection

AI Confidence

72%

Related Context

🎥
Justin <> Peter 1:1 10/19

fathom

There is not going to be a better time in the future. There is not going to be time where we have fewer customers, so do it. If it seems too big, make sure you are letting me and Bjorn know.

Outcome

No outcome recorded yet.

Decision ID: abc72e02-d43d-41a3-a83e-9ebc073ea122