> Eventually, I decide I’ve done enough planning. How? I stop at the point where I’m happy with the risks I’m taking, or unable to mitigate them further. There

> Eventually, I decide I’ve done enough planning. How? I stop at the point where I’m happy with the risks I’m taking, or unable to mitigate them further. There are other important places to stop. An important one that planning-eager folks neglect is complexity. The high-level estimation needs to be light enough that you will redo it, perhaps entirely, if the facts on the ground change. You will need to assign some risk to the plan itself since it will cost some time, energy, money, communication bandwidth, political capital, etc. to change the plan. How much planning risk depends on a few things, but how much the details of the plan are exposed is an important thing to factor in. If you've signed contracts with 1000 people promising that you will complete step M on exactly the week of April 8 and it will be entirely free, you have made it hard on yourself to change many things in your plan.