It really depends on the goal. For some goals, you never want to derail, so you set the pledge really high. For others, you want the flexibility of being able to choose whether or not to derail and pay X, and you want to set X ahead of time to maximize awesomeness.

It’s not at all clear to me that the value of X that maximizes awesomeness is the same as the value of X that maximizes revenue.

Scenario 1:

Suppose 15% of the time I want to stay up late bad enough to pay $5, but not bad enough to pay $10, and 10% of the time I want to stay up late bad enough to pay $10.

At X=5, I pay $5 25% of the time, or an average of $1.25.

At X=10, I pay $10 10% of the time, or an average of $1.

Scenario 2:

Now suppose 5% of the time I want to stay up late bad enough to pay $5, but not bad enough to pay $10, and 20% of the time I want to stay up late bad enough to pay $10.

At X=5, I pay $5 25% of the time, or an average of $1.25.

At X=10, I pay $10 20% of the time, or an average of $2.

So in the first scenario, X=5 maximizes revenue, but in the second scenario, X=10 does.

Now, which maximizes awesomeness? Looking back from outside the akrasia horizon, only a small portion of your choices to pay will seem worth it. The distortion makes staying up late seem more worth it at the time than it really is taking the outside view.

So let’s say that when I would only pay $5, I regret it 60% of the time, and when I would pay $10, I regret it 40% of the time.

Then in Scenario 1 at X=5, I stay up and regret it 13% of the time and stay up and don’t regret it 12% of the time. At X=10, I stay up and regret it 4% of the time and don’t regret it 6% of the time.

In Scenario 2 at X=5, I stay up and regret it 11% of the time and stay up and don’t regret it 14% of the time. At X=10, I stay up and regret it 8% of the time and don’t regret it 12% of the time.

Now, how do we measure awesomeness? Let’s say it’s measured by the proportion of the times you don’t regret your choice minus the proportion of times you do (i.e., weighting them equally).

In Scenario 1 at X=5, awesomeness is -1%. At X=10, awesomeness is 2%.

In Scenario 2 at X=5, awesomeness is 3%. At X=10, awesomeness is 4%.

So the revenue-maximizing value of X maximizes awesomeness in Scenario 2 but doesn’t in Scenario 1.