I read an interesting book within the past couple years called "The Paradox of Choice: Why More Is Less", by Barry Schwartz. I realize that it has actually had some influence on how I live my life, which is rare for a book.
When we face a problem, there are two ways to approach it: As an "optimizer", who seeks the best solution, and as a "satisficer", who seeks a solution that is good enough. Many of us, much of the time, feel obligated to optimize, by educating ourselves on the alternatives, reviewing them thoroughly, and choosing the best one according to our criteria. To the extent we fail, we feel guilty. Other people may let us know that we missed some great bargain, or the even better restaurant, and we cooperate with them in feeling that we failed.
It's worth optimizing about the big things in life: what city to live in, what house to buy, what job to take. It is worth optimizing money when it concerns large amounts -- bargaining carefully for the best price on your home or the best salary at your job. We can sometimes regret not having devoted as much attention to these questions as we should.
But for the less important aspects of life you can often find a solution that is good enough.
Consider driving to an event in a city where parking is an issue and you may have to park at some distance from the event. The density of cars parked beside the road increases as you near the event, but there are other reasons than your event for local concentrations of cars. You can't see by peering ahead where the last space is you could park in (think fire hydrants, driveways). You are likely to go just a little farther. Often you get it pretty much right. Less often you find you have passed the last available space and need to turn around and go back to those spaces you passed. Often when you get there the previously closest space is taken and you have to go back a little bit farther. This is frustrating. The satisficing solution is to park at the first space that is good enough, and not let yourself feel incompetent if as you walk towards the event you see an empty space that was significantly closer. You may have saved yourself the possible frustration of having to turn around. More importantly, you have saved time of your life spent looking for a parking space. You could be walking instead, something we generally find inherently more relaxing and in line with our values. This is especially relevant if you are the sort of person who regularly runs several miles for exercise.
Consider driving with a friend to a place you have never been before and will probably never go again. You know one way to go, but there might be a better way. You can study a map for some time, determine the route you want, and spend your trip verifying you are following the path you have charted. Or you could spend the entirety of a slightly longer trip talking with your friend.
At the supermarket you can look at the different brands and different package sizes and spend considerable time finding the best buy. Or you can just pick one and spend less of your life in the activity known as shopping.
When you vacuum your house you can dig into every corner, every time, and chase every last bit of dust. Or you might reflect that within a day or so the natural accumulation of dirt will have rendered the benefit of your more thorough cleaning imperceptible. The goal could shift from having a house that is (periodically) "extremely clean", to having one that is "not very dirty", or in other words "good enough".
Now, for all the caveats:
For some people, optimization habits are just a part of the fabric of their life and define "how one ought to live".
Successful optimization shows competence and mastery, and for many people such opportunities are not abundant.
Some people just really enjoy shopping, including getting the best deal on small items. Some inherently enjoy feeling that their house is extraordinarily clean, even if briefly. Enjoyment is good.
Finding the best route to a particular destination could increase one's knowledge of the lay of the land, allowing faster trips when time really is important.
Sometimes it really is important to optimize on even small amounts of money, since they do add up. But it might be prudent to look at one's budget as a whole to see where larger amounts of money are at stake. You could feel that you are living a frugal life by checking out the brands, whereas ten times that amount of money is at stake in what you might have to admit are luxuries if you were forced to think about it.
For some people, it may be hard to make a mix of optimizing and satisficing decisions. Perhaps they are not only on a tight budget, but if they relaxed their buying habits in one area of life it might spread to areas that are more important. My mother, a child of the depression, sometimes washed lettuce by using a small stream of water and shutting it off after finishing each leaf before picking up the next one, though I don't think water was ever expensive or in short supply in her life. But it was part of an attitude of frugality.
There can also be an instance of the "free rider" problem. If few people were engaged in careful comparison shopping, the stores could gradually raise their prices. Being confident that all prices are "good enough" depends on optimizers who do pay attention to which store has milk that is five cents cheaper. People who carefully compare prices are doing a service for the rest of us, even if as individuals it may not be in their immediate self-interest to do so. I wonder sometimes to what extent Whole Foods is an entire chain built on customers who are satisficers with regard to price. I'm not actually feeling guilty about the "free rider" problem, since there is no looming shortage of comparison shoppers.
The next step is to be willing to go public: tell your friends that you aren't troubled that you spent a few extra dollars on something because it's not a priority for you. What you paid was good enough.
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