Count the cost of learning. When you choose a path towards a goal, it's absolutely critical to optimize for the cost of learning. Often, with software, it is easier to learn by a series of smaller steps, even if they start out as random, rather than take on the major risk of a large step possibly going the wrong direction. This isn't always true; sometimes, the cost of learning is greater with small steps. Determining which is true in your situation can make or break your plans.
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