Instead of planning not working as well as people in the past thought, as a society we’ve become worse at technological planning

The hypothesis goes: in the past 30 years, software and finance has created a disproportionate amount value, especially based on mindshare. Both software and finance are domains where the returns to doing a good job developing a precise, multi-year technical plan are low compared to not developing that plan. In fact, detailed technical plans in those domains can possibly even lead to worse outcomes. This low-or-negative return to long-term technical planning led to the individual and institutional ability to do long-term technical being selected out - ie. culturally we’ve become worse at long-term technical planning. I suspect that the failure of plans to create value both in domains where they could potentially create value and also in domains where they can’t create value injected an attitude that ‘plans don’t work’ into our culture.

This narrative runs counter to a different narrative that we’ve always been just as bad at long-term technical planning and over time the alternatives have become more feasible. In this scenario, we develop both better alternative processes like agile development and technologies that make iteration cheaper and faster.

In other words - is roadmapping a lost art or is it a myth?

In a way this is a facet of Peter Thiel’s indefinite/definiteness thesis.

The decline-of-planning-ability narrative depends on four core pieces of evidence:

  1. There was a high return to technological roadmapping compared to not roadmapping in the past
  2. The returns to good technical planning have decreased
  3. Plans are valuable compared to not planning for a certain class of problem

It’s also important to disentangle “long-term technical planning” from the many other kinds of planning. Many ideas and actions have gotten lumped under the term ‘planning.’ For example, there is evidence that management practices have contributed massively to productivity over the past few decades and those practices in large part involve effective planning. I would call this ‘firm-level strategic planning.’

During the 20th century (and still today), “planning” connoted “government planning” specifically “government planning economies.” Fighting for or against the idea took on a philosophical and ideological tone. American economists who argued against planning were no longer just arguing for what was the best economic policy but instead fighting by proxy against the Marxist ideology. This conflation of idealogical battle and policy debate has been forgotten As far as I can tell there is pretty strong that government economy planning has poor results. However, people generalize from this to “therefore planning doesn’t work and is bad in general” which is not necessarily true.

There’s also the specter of “Big Design Up Front.” Are roadmapping and big design up front the same thing? I don’t think so. Roadmapping is concerned with constraints, dependencies, and sequencing. Big design up front is concerned with constraints and dependencies, but it’s less worried about sequencing and feels more rigid. ::This needs more work::

What is the relationship of technological roadmapping with systems engineering

In short - we should be open to the possibility that planning works well in some situations but not in other and instead of making universal statements about planning, we should instead try to tease apart the situations where it does and does not work and why that is the case.


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