Ajai Kapoor has a nice piece on LinkedIn Pulse where he says Please STOP planning ... Really. He recounts the familiar challenge of plan / don't plan. Plan because we want to direct our efforts into the right places to achieve some goal. But don't plan because plans never survive contact with the enemy.
Ajai goes an interesting direction with the discussion. The underlying problem he sees in the challenge is that we often get too attached to our plans. We believe they are an accurate representation of reality. And when things go awry (which they will), there is a natural frustration. Depending on how deep this frustration, we may dive further into planning and perfecting the forecast. Or we might give up entirely. Neither direction leads to happiness.
Instead, Ajai suggests we do enough planning to understand what is the key limitation within the project in question. What is the constraint? With that understanding, the direction would be to protect and monitor the constraint. That is where we have the largest leverage to make the project really sing. Don't get attached to absolutely everything happening as expected. Rather, monitor from a healthy distance and pivot when necessary.
Here's his closing statement, which summarizes much of this.
There is joy and creativity in being present now. In trusting that we can act in accordance with our conscience and intuition. We can plan, but not rely on these plans to always work to get us to the goal, but to reveal constraints. With that knowledge we can be focused on the now. The plans are small enough compared to our ambitious goals that failure is acceptable. A certain level of fatalism in accepting the results can set us free.