Stumbling On Happiness by Daniel Gilbert

Despite the title, Gilbert actually describes the major problems people have with Imagination. Granted, Happiness certainly involves imagining our future selves, but the strengths of this book lie in the enumeration of Imagination's failures.

We first realize that our brain fills in details (or leaves them out) in order to facilitate comprehension. Since the mind likes comprehension, a facility with randomness makes life much easier (much easier to say than do ;). Regardless, just knowing our brains will try to smooth things over can lead one to better decision-making.

Secondly, we have problems with creating mental imagery for time's passage. Hollywood's chronological films use devices like calendars flipping by or clocks with the RPMs of a racecar. In our minds, we can do X, Y, and Z axes for a spheroid, while adding a T for time to show the motion of that ball over time. Although, if you ask us to imagine us vacuuming our abodes next week versus next month, the imagined cleanings do not differ.

Finally, we fail to consider our brain's defenses in imagining how things will feel. Imagine how you would feel were you to be judged by a single person or a group of people. Usually, people say the imagined result does not vary that much. In reality, having a roomful of people say we suck hits us much harder than having a single judge say we suck. We can easily rationalize the judge's verdict ("Great, I got Judge Marion "Crackhead" Barry), while the diverse crowd's presents a challenge ("Good thing I brought my AK-47. Say Hello to my Little Friend, you fucks!").

Gilbert's literally solves this problem by proxy. He suggests finding people who have gone through your imagined sequence, and then ask them how they feel. Aggregating people's feelings should indicate roughly how we will feel. With the 'Net, this can be easily done, we just need to implement that solution more often.

Better ask people who are at least somewhat similar to you in personality and interest otherwise you may end up sitting through a lot of crappy movies.
Yeah, he doesn't attempt at quantifying or qualifying his solution. He just makes the conjecture that your best estimate of future happiness will be worse than your social average. Untangling that one requires another book. -- Patrick.
We already sit through crappy movies. Pre-frontal cortices and all.
I still haven't forgiven you for 'Black Dog'.