There isn't a clear philosophy of life-planning in the literature. So let's start from scratch. What do we need in order to make a plan for any temporally extended project?
- An assessment of the outcomes we want to bring about
- An assessment of the likely workings of the natural and social environment in which action will occur
- A theory about how to achieve those outcomes -- strategy and tactics
- An assessment of the likelihood of negative interactions among various aspects of the plan
- An assessment of the riskiness of the environment
- A backup plan if things go off the rails -- plan B!
We know what it is to be rational about limited choices like choosing a new car, picking a vacation destination, or investing retirement savings. Each of these decisions falls within a broad degree of certainty of assumptions for us: we know that we enjoy the beach more than the opera, that we want a fair degree of security in our retirement accounts, or that we need a car that is good in wet weather. That is to say, we know a lot about our tastes, our future needs, and our current circumstances. So small-gauge choices like these depend fairly simply on locating a solution that serves our tastes and preferences in our current and near-future circumstances. With these conditions fixed, we can then go about the information gathering that allows us to assess how well the available sets of alternatives serve our tastes, needs, and circumstances.
Sometimes we can even reduce our choice situations to a simple set of cost-benefit tradeoffs: I'll get a 20% improvement in crash-worthiness by paying an additional $10,000 for the car I choose; I'll have a chance on a 10% annual return on an investment if I accept a greater degree of risk; etc. And I might find that I like the tradeoff for one set of costs but not for another -- more safety is worth $10,000 to me but not $50,000. Or I will accept the greater investment risk when it means moving from 1% chance of losing everything to a 3% chance, but not to a 10% chance.
A life plan isn't like this, however. Consider the space of choices that confronts the 20-year old college student Miguel: what kind of work will satisfy me over the long term? How much importance will I attribute to higher income in twenty years? Do I want to have a spouse and children? How much time do I want to devote to family? Do I want to live in a city or the countryside? How important to me is integrity and consistency with my own values over time? These kinds of questions are difficult to answer in part because they don't yet have answers. Miguel will become a person with a set of important values and commitments; but right now he is somewhat plastic. It is possible for him to change his preferences, tastes, values, and concerns over time. So perhaps his plan needs to take these kinds of interventions into account.
Another source of uncertainty has to do with the future of the world itself. Will the economy continue to provide decent opportunities for young people, or will income stratification continue to increase? Will climate change make some parts of the world much more difficult for survival? Will religious strife worsen so that safety is very difficult to achieve? Is Mary Poppins or William Gibson the better prognosticator of what the world will look like in thirty years? A plan that looks good in a Mary Poppins world may look much worse in the Sprawl (Gibson's anti-utopian city of the future).
And then there is the difficult question of akrasia -- weakness of the will. Can I successfully carry out my long term plans? Or will short term temptations make it impossible for me to sustain the discipline required to achieve my long term goals? (Somewhere Jon Elster looks at this problem as a collective action problem across stages of the self. Is this a reasonable approach?) For that matter, how much should future goods matter to me in the present?
It is worth asking whether life plans actually exist for anyone. Perhaps most people's lives take shape in a more contingent and event-driven way. Perhaps guided opportunism is the best we are likely to do: look at available opportunities at a given moment, pursue the opportunity that seems best or most pleasing at that point, and enjoy the journey. Or perhaps there are some higher-level directional rules of thumb -- "choose current options that will contribute in the long run to a higher level of X". In this scenario there is no overriding plan, just a series of local choices. This alternative is pretty convincing as a way of thinking about the full duration of a person's life, as any biographer is likely to attest.
Consider an analogy with the life of a city or state: decisions and policies are established at various points in time. These decisions contribute to the life course of the city; monuments established in 200 BCE continued to inform Roman life in 300 AD. But Rome was indeed not built in a day, and its eventual course was not envisaged or planned by any of its founders and leaders. A city's "life" is the complex resultant of deliberation at many points in time, struggle, and contingency. And perhaps this describes a person's life as well.
This point of view has a lot in common with Herbert Simon's 1957 concept of bounded rationality and satisficing rather than maximizing as a rule of rational decision-making (Models of Man). Instead of heroically attempting to plan for all contingencies over the full of one's life, a bounded approach would be to consider short periods and make choices over the opportunity sets available during those periods. And if we superimpose on these choices a higher-level set of goals to be achieved -- having time with family, living in conformity to one's moral or religious values, gaining a set of desired character traits -- then we might argue that this decision-making process will be biased towards outcomes that favor one's deeper values as well as one's short-term needs and interests.
This approach will not optimize choices over the full lifetime; but it may be the only approach that is feasible given the costs of information gathering and scenario assessment.
So what about a rational life plan? At this point the phrase seems inapropos to the situation of a person's relationship to his or her longterm "life". A life is more of a concatenation of a series of experiences, projects, accidents, contingencies -- not a planned artifact or painting or building. A life is not a novel, a television series, or a mural with an underlying storyboard in which each element has its place. And therefore it seems inapt to ask for a rational plan of life. Individuals make situated and bounded deliberative decisions about specific issues. But they don't plot out their lives in detail.
What seems more credible is to ask for a framework of navigation, a set of compass points, and a general set of values and purposes which get invested through projects and activities. The idea of the bildungsroman seems more illuminating -- the idea of a young person taking shape through a series of challenging undertakings over time. Development, formation, values clarification, and the formation of character seem more true to what we might like to see in a good life than achieving a particular set of outcomes.
Where, then, do thinking and reasoning come into the picture? This is where Socrates and Montaigne seem to be relevant. They look at living as an opportunity for deepening self-knowledge and articulation of values and character. "To philosophize is to learn how to die" (Montaigne) and "The unexamined life is not worth living" (Socrates). The upshot of these aphorisms seems to be this: reasoning and philosophizing allow us to probe, question, and extend our values and the things we strive for. And having examined and probed, we are also in a position to assess and judge the actions and goals that are presented to us at various stages of life. How does a college major, a first job, a marriage, or a parenting challenge frame the future into which the young person develops? And how can practical reflection about one's current values help to give direction to the future choices he or she makes later in life?
Practical rationality perhaps amounts to little more than this when it comes to constructing a life: to consider one's best understanding of the goods he or she cares most about, and acting in the present in ways that shape the journey towards a future that better embodies those goods for the person and his or her concerns.