More thoughts on this that started as thinking out loud in a daily beemail (prompted by @mary making an incisive counterpoint):
Derailing early and often until you reach your Motivation Point is great but then won’t you just continue at Peak Awesomeness without ever derailing again?
I think there are different ways it can play out. My personal favorite, and perhaps the one most compatible with this “everyone should derail as much as possible” thesis, is where you settle on an amount of money that motivates you during normal circumstances and when anything unusual happens you pay to derail and are happy about that.
It’s like a natural way to define the right amount of flexibility without having to worry about fine print (which I personally kind of dislike). The criterion is simply “are these circumstances extenuating enough that I’m ok paying this pledge?”
Of course there’s still a balancing act – you have to make sure you don’t akratically decide to derail too often.
The point is, there’s not a single Motivation Point. It depends on a million things and changes over time. But, so I claim, more derailing always correlates with Beeminder doing more motivating.
PS: And now I’m thinking about a follow-up essay about “Motivation Points vs Success Spirals” since @nick has a philosophy of beeminding that might be pretty incompatible with this whole derailing-is-not-failing thing…