When to abandon something you have already built
Four cases where the question was not whether the work was good, but whether continuing it was the right use of the next six months.
We killed a feature after six months of build. The reasoning held; the timing did not.
Adoption sat at 4% of target after two quarters. Four options on the table, three rejected. The decision to discontinue was defensible on the evidence available — the error was waiting two months longer than the criteria required.
Rewriting the billing system instead of patching it for another year
The estimate was five months. It took nine. Whether that counts as a failure depends entirely on what the patching path would have cost, and that number is unknowable.
We ended the contract with the client that was 41% of our revenue
No board, no runway, no second opinion. The decision took eight months to execute and the replacement revenue arrived four months later than the plan assumed.
We took a down round instead of an acquisition offer. Eighteen months later the company closed.
An offer on the table at roughly half the last valuation, against a bridge at a 60% markdown. The reasoning was documented at the time. It did not survive contact with the following year.