- Complicated plans don’t work.
- “Spraying energy into the vortex of failure” doesn’t work.
- Your boss really doesn’t care.
There is obviously a lot more context behind these blanket statements, but he does have an interesting point. I've written about the first element in another guise, Planning is very important ... it doesn't work. Essentially, you need to plan but don't expect everything to follow the plan. This tells me that a complicated plan is only good before the project gets going. Articulate what you need to do, and then start moving. Learn something. Retrench. And move toward the goal. You know what the goal is, right?
As I read Michael's comments, I see the 2nd element is really about risk management. He ties it to overly-complicated plans too. If the project starts going haywire, it's going to be more difficult to re-plan when the plans are overly complicated and full of spaghetti logic. Plan from the goal to where you are today, rather than from today to your deadline.
And the 3rd element is pure Dilbert. Sadly, it is often true, unless the organization embraces a different mode of managing their portfolio of projects, where it is everyone's problem when projects get stuck.