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A simple explanation for why “estimations” and timeline-based “roadmaps” don’t work, is that product development isn’t a scheduling problem but an explore/exploit problem.

Time isn’t the constraint, but knowledge.

Knowledge that isn’t currently “priced in” to the market.
Product development is closer to stock trading & epidemiology than manufacturing or traditional pure software dev.

🤷‍♂️ What confused me when first starting out in product management is learning techniques rooted in manufacturing or software dev, then struggling w them in practice
Took a long time to realize I should be reading Taleb, Hayek, Judea Pearl, Donella Meadows, Ray Dalio, etc.

Instead of what is usually recommended reading for product managers like Toyota Way, or Marty Cagan.
I should also clarify (since a lot of people have pointed out that explore/exploit also includes an element of time) that this does not mean product development does not employ scheduling methods. Quite the contrary. You schedule efforts to negotiate the explore/exploit trade off
You can “split the difference” by opting to do equal parts exploring and exploiting, treating them as categorically different types of work. This is the “dual track” method.
Or you can make incremental bets into various areas of exploration, where exploring and exploiting lies along a continuum, and you’re maintaining a portfolio of bets at any one point in time.
In practice this often looks like a scheduling problem: you’re dealing with the finite resource of time and the mechanics of flow. But this is where the similarities end.
A follow up train of thought: graphs as a way to represent opportunities, and graph traversal as a means to explore / exploit:
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