Why long-term plans don't work and how to fix them

Long-term software plans promise certainty but deliver misaligned incentives and inevitable failure. They assume nothing will go wrong, that developers know exactly what to build, and that effort can be predicted perfectly. In practice these assumptions collapse the moment a bug appears, an employee calls in sick, or customer feedback forces a pivot, yet the plan still rewards sticking to the schedule over delivering value.

When a bug forces a task to be delayed, the team either cuts scope or cuts corners to stay on schedule, which compounds technical debt and creates a vicious cycle of broken features. Estimating effort for novel design work is fundamentally stochastic; unlike manufacturing, software design cannot be timed with precision. The article shows how each additional task multiplies the chance of delay, turning a modest overrun into a disaster for multi-month projects.

The result is a product that may launch on time and on budget but provides no profit or user value. The plan rewards conformity, not usefulness, and it blinds teams to feedback that could steer the product toward real customer needs. By ignoring the cost of fixing broken assumptions, organizations waste time, money, and morale.

The remedy is to shrink the planning horizon. Short-term plans let teams test ideas quickly, incorporate feedback, and abandon dead-end work before it costs too much. This approach aligns with the Agile principle of responding to change over following a plan and removes the false need for detailed long-term roadmaps. Teams focus on delivering small, valuable increments instead of chasing an immutable, multi-year schedule.

A narrow exception exists for agencies that are paid to deliver on a fixed scope regardless of product success; there the incentives line up with long-term plans. Even then, the article argues for hourly billing and continuous product-management support to de-risk the business and improve outcomes for the client.