Many people are brought up, almost conditioned, to desire success. Unfortunately few people who desire success have much of a handle on what being successful entails. Some rely on the judgments of others as a standard, and thus using their wealth or popularity as a measure of success. Others see success as a matter of fitting in with society, and so try to be a typical as possible. And yet others measure their successes by the tasks they apply themselves to, considering themselves successful if they can be a successful X (a successful astronaut, or artist, or whatever). These possibilities, in a great many cases, have little or nothing to do with leading a successful life, and so for many people trying to be successful by one of those standards is a mistake.
To really address the question we have to decide what exactly a successful life is, and then we can reflect, on that basis, to what extent the previously mentioned approaches work. As far as I can determine the successful life means the same thing as a desirable life. To call a life successful is, as we commonly conceive of it, a recommendation to lead that kind of life. To say that someone is successful is to say that they are living well. Obviously then to say that someone is living a successful life must necessarily imply that they are leading a desirable life, because success wouldn’t be much of a recommendation if some successful lives were undesirable. And the implication seems to go in the other direction as well, it is hard to imagine a situation in which some life is desirable, and yet cannot be considered successful. And this establishes that calling a life successful is simply another way of calling it desirable.
Thus there is something confused about wishing to lead a successful life. Because a successful life is a desirable life this boils down to desiring to lead the life that is desired. And that is about as free of content as a desire can get, making it comparable in many ways to the desire to be happy. People feel that they should be happy, should be successful (because other people imply that they should), but the desires bring with them no real goals (unlike the desire to eat some ice cream). Thus people tend to invent ways to be successful or happy, meaning that they observe people who are described as successful or happy and try to be like them in order to be successful or happy as well, not knowing how to achieve these things on their own. And so they have invented for themselves objective standards for success or happiness while in reality there are no such things. Given that success and happiness both boil down essentially to desire what makes a person successful or happy depends exclusively on what they want, there is no objective criterion for success, no guaranteed way to be happy.
So the standards for success I mentioned at the beginning of this post are necessarily invented standards. From this perspective the fact that they are fictions is fairly obvious, as is their origins. Society tends to idolize the wealthy and the popular, and thus some, confused as to what success entails, might attempt to emulate them. Similarly the desire to be “average”, to have a dog, two kids, and a house with a back yard is also a product of the fact that being “average” is often held up as proper, which is reinforced by our natural tendency to imitate the people around us (once someone tells us that something is normal we naturally are drawn to try to be that way). And, again, people who are successful in their careers are described in glowing terms, and so we may be led to try to be successful in our careers in order to be successful in general.
But just because they are invented standards doesn’t mean that they don’t fit some people. Some people genuinely do desire to be popular. Some genuinely desire the life that the “average” person leads. And some genuinely desire to pursue a career that they also happen to be good at. I would, however, doubt that anyone genuinely desires wealth or the things it can buy; material desires are the fundamental desires of children not adults. On the other hand, just because such invented standards may fit some people doesn’t mean that they fit all people. I have no idea how many people end up taking jobs they don’t particularly enjoy because they are profitable or because they happen to be what they are good at. But whatever the exact number is it is too large. Invented standards are thus a trap for some people, because the life that is most desirable to them may be that of an eccentric unsuccessful artist rather than a successful accountant.
Of course the world doesn’t end if people talk themselves into leading lives that they don’t really want. Assuming they keep themselves busy and don’t bother to reflect upon their life they may not even be that troubled by it. But it seems to me like a waste. In the grand scheme of things most individual lives are relatively unimportant; from the vantage point of an observer who can take in the whole of human history almost all individuals simply don’t matter. Still, although they might not matter in the grand scheme of things, individual lives still matter to the individuals leading them. And given that we might as well make the most of them in that context, by making them the most desirable lives possible. Anything less is to end up with a life that is unremarkable from any viewpoint, a waste of potential.