I recently read a book called Stumbling on Happiness by the psychologist Daniel Gilbert that analyzes the mistakes we make when we try to imagine our personal futures. He spends the whole book arguing that imagination is an unreliable predictive tool. Then, in summing up, he prescribes his improved method (abridged below):
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In one chapter after another, I've described the ways in which imagination fails to provide us with accurate previews of out emotional futures. I've claimed that when we imagine our futures we tend to fill in, leave out, and take little account of how differently we will think about the future once we actually get there. I've claimed that neither personal experience nor cultural wisdom compensates for imagination's shortcomings.
Why do we rely on our imaginations in the first place? Imagination is the poor man's wormhole. We can't do what we'd really like to do -- namely, travel through time, pay a visit to our future selves, and see how happy those selves are -- and so we imagine the future instead of actually going there. But if we cannot travel in the dimension of time, we can travel in the dimensions of space, and the chances are pretty good that somewhere in those other three dimensions there is another human being who is actually experiencing the future event that we are merely thinking about. Surely we aren't the first people ever to consider a move to Cincinnati, a career in motel management, or another helping of rhubarb pie; and, for the most part, those who have already tried these things are more than willing to tell us about them. It is true that when people tell us about their past experiences, memory's peccadilloes may render their testimony unreliable. But it is also true that when people tell us about their current experiences, they are providing us with the kind of report about their subjective state that is considered the gold standard of happiness measures.
If you believe that people can generally say how they are feeling at the moment they are asked, then one way to make predictions about our own emotional futures is to find someone who is having the experience we are contemplating and ask them how they feel.
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I have tried this and I think it works.
Many years ago, I interviewed with AMOCO (now part of British Petroleum) near Chicago for an engineering job. I told the interviewer that I might be interested in eventually pursuing a career in patent law. The interviewer perked up at hearing this and immediately hauled me up to the corporate penthouse suite and introduced me to the head patent attorney, a corpulent man in an expensive suit. After informing me at considerable length about his prestige in the world of corporate law, the attorney gave me a road map for my career. He told me that I would work half time as an engineer and attend the University of Chicago law school at night. Within four years I would graduate and make twice the salary of an engineer. He took me over to the window and pointed out a big Mercedes town car in the parking lot. "That's my car, kid," he said. "You can afford one of your own after you graduate and join us in the legal department."
Two days later AMOCO made me the offer for an engineering job, with the option of taking the patent law path if I wished. I turned down the engineering offer. In hindsight, this was probably a mistake. However, I have no regrets about not taking the path to a patent law position with AMOCO. The head patent attorney had seemed totally lacking in vitality and enthusiasm. I didn't want my future life to feel like that.