Optimistic Skepticism
[Optimism] inhibits lucid thought, it shuts down core reasoning centers and seems to inflict terrible damage on memory. It is optimism that continually causes us to lose our respect for limits and to have unrealistic expectations of what we can achieve, which leads us to set ourselves up for failure and disaster by encouraging us to overreach and believe that we can find a solution to every problem.
Larison above is talking about optimism with respect to foreign policy, but I think much of the critique can be extended to optimism in general. On a personal level, I suggest that the appropriate response is to replace unqualified optimism with optimistic skepticism.
While optimism thinks that the best will happen, optimistic skepticism thinks the best probably won’t happen, and that therefore one can prepare for the various non-optimal scenarios that most likely will result. That is, because one is appropriately skeptical, one can create plans that will actually work.
With governmental policy, the optimist will think that this governmental program will work (even though most or all of the ones in the past aimed at fixing this problem have not or have made the problem worse). The optimistic skeptic will think that this governmental program will probably not work, and therefore one can plan and calculate based on that premise - which in itself can be quite useful.
On a personal level, it’s similar. This plan (for example, an exercise plan) probably will not work - unless there is an extreme level of effort, skill, time, external pressure, and so on, brought to it - much like project plans in business where you double (or triple or quadruple) the time to completion and half the features. At that point, your chances of having a realistic plan increase significantly, and therefore any plans you have that depend on this plan have a greater likelihood of also going to completion.
Here is a practical example. Tomorrow, the optimist in me thinks, I will get up at 6am, go to the gym, and then get in 4 hours of high-productivity work. “Right,” thinks the skeptic. The optimistic skeptic’s role is then to figure out a plan that will actually make that happen. “I will pay my neighbour $5 every day for a week to bang on my door at 6am until I answer it. I will then arrange to meet someone at 6:30am at the gym (with some sort of social cost if I don’t show up on time). Finally, I will meet a friend at Starbuck’s at 8 for a quick chat, and then work there until 12:30pm.” Now the chances of the plan completing are starting to go up. Repeat until you think you have just a silly amount of effort being brought to bear.
Now you probably have a plan that will work.