The idea behind pairing these ideas is that the amount of care we exercise in preventing bad outcomes can, under some circumstances, be translated into an unrealistic and ominous assessment of what those outcomes could be.
I have had a lot of opportunity, lately, to prevent bad outcomes.  I get a lot of leeway just for being old. Failures that in a younger person might be chalked up to lack of effort are passed over because I am old. I’m not sure that is good for me, but I am sure, as W. S. Gilbert says, that “these attentions are well meant.”
I am often in settings where I am a customer and customers are notoriously under-criticized. As an academic, I spent a lot of time in settings where disciplinary rivalries were well established and anything said by a member of the psychology department, for instance, might be objected to, just as a matter of habit, by a member of the sociology department. But where I live now, I am “an academic” by contrast with the other residents, who were were in business or in other professions. In this setting, I am granted the kind of space academics are given by people who don’t really appreciate how narrow academic specialties really are.
So, all in all, I am in the very fortunate position of not being criticized very often except by people who really know me.
The downside of being that fortunate is that I have become less adept at dealing with difficult experiences. I have become, to say it more briefly, less resilient. I am going to tell about a recent experience in a moment, but before I do that I want to pause to resuscitate the verb “resile,” which really ought to be more popular than it is.
It seems odd, when you stop to think about it, that the adjective resilient is so common and the noun resilience is pretty common, where the verb resile has to be put in quotation marks (as I did in its first use, above) so people will know you said it on purpose. 
I had an experience recently that surprised me. I went out for a medium-sized bike ride after surveying the weather and concluding that it was going to be a day of drippy Portland weather. I begin this route at the point furthest from home, so when I started, I didn’t have half the route to go; I had the whole route to go.
And I had no sooner started than it began to rain really hard. I had several backup plans in place, but as I approached the site of each one, it seemed to me to be not much better than just continuing. And as I continued past these checkoff points, I began to get the sense that it would be kind of like the old days to just allow myself to get good and soaked (I wasn’t cold) and just finish the route as planned.
And that is what happened. I was soaked through by the time I got home and I was feeling absolutely exultant. I could have felt bad for failing to predict the weather accurately or for failing to use the backup plans, but I didn’t. I felt really good about getting through it and really paying very little attention to my discomfort. That part felt really good and it called to my mind a lot of times I had made that choice as a younger man and had felt really good about it.
There is a time, when you are young, when you are curious about just how much you can take. The goal in that phase is not to prevent the hard knocks but to ignore them. You just endure them and take the discomforts for granted and draw conclusions about how resilient you are. A part of this phase is that it happens at a time when you are much less able than you will be later to think through and therefore to prevent, those outcomes, but that isn’t all of it. Part of it seeks those discomforts as a way of testing just how strong you are, which is something you really need to know when you are young.
So…in this model, you tend to ignore (or undervalue) prudence when you are young and to appreciate (or overvalue) resilience. When you are old, you tend to overvalue prudence  and, as a result, lose your sense of how resilient you can be when it is really called for.
Agency is fundamental
Why does it work that way? It turns out that one of the most fundamental questions we ask ourselves is, “Why am I doing this?” “Agency” in the sense I used it above, can be understood as “doing-ness.”
I remember my first look at how powerful this question is. In a well-known psych experiment, students were given a really boring job to do, then asked to come back later in the week and do it again. Some of the students were paid to do it the first time and others were not. When they were asked to come back and do it again, it would be for free. No one would get paid. The proportion of students who were not paid the first time and who volunteered to do it the second time was larger. Why?
In the view of the experimenters, the people who were paid the first time said, “Why am I doing this?” and answered, “Because they are paying me.” So then next time, when there would be no pay for anyone, they asked, very sensibly, “Why would I do that?” and then refused.
But the students who were not paid the first time were in a very different situation. When they asked, as everyone does, “Why am I doing this?” there wasn’t any obvious answer. Many of them answered the question, “I must like it.” That was the answer to the question. It wasn’t accurate, but it was accepted and it accounted for the larger proportion of these students who volunteered to do it again.
Ever since I read about that experiment, I have had a real appreciation for the power of the question, “Why am I doing this?” It is a question we can’t stop asking and the answer guides our behavior whether we are aware of it or not.
I am arguing here that when I exercise excessive prudence  I am answering this unavoidable question in a way that affects me. When I am “excessively careful” about being on time, I am teaching myself that it would be really awful to be late. When I am excessively careful not to offend anyone, I am teaching myself that it would be really awful if anyone were to take offense at what I am doing. Or, succinctly, I am “awfulizing.”  I am overstating the seriousness of the consequences of my actions or the seriousness of a threat.
I don’t have the need, as an old man, to find out how tough I am the way I did as an adolescent. And I have the means, as an old man, to avoid a lot of the difficulties I could not avoid as a young man. I can avoid having an ill-tempered boss for instance, or having to fight through tiredness to complete my workday, or being hungry (or eating junk-food because I didn’t have time to eat.) I don’t have to do any of those things now. And if I think of those as occasions for practicing my resilience, I now have a dearth of those occasions.
As a young man, I treasured the occasions that demanded resilience because I wanted to know if I could resile adequately. As an old man in very favored circumstances, I am in a good position to avoid those occasions. And when I do, I teach myself that it would be really really awful to be tired or hungry or or to have an unreasoning obedience demanded of me. I take the commonplaces of my youth and I awfulize them. And because they are so awful I exercise “excessive” levels of prudence to avoid them and in that way, I come to imagine that I have very little resilience.
I look at the strenuous efforts I make to avoid these challenges and I say, “Why am I doing that?” That is, I argued above, an unavoidable question; everyone asks it whether he or she is aware of it or not. A common answer to the question is, “Because it would be really awful if that happened.”
And that’s how I lose my resilience.
Resilience is a good thing because it helps you recover from the bad things that happen. Knowing just how resilient you are is also a good thing because it keeps you from worrying about how you will manage when bad things happen.
And prudence is a good thing. It keeps you from acting like a young man when you are, in fact, an old man. You have less flexibility, less strength, a less effective immune system, poorer vision, and poorer hearing. You have “positions” you have taken over the course of your life that you are reluctant to change unless there is a good reason, and hardly anyone is left in a position to require that you change them.
It would be foolish to pretend that those things are not true and to take them into account when you decide just what kind of an action will count as “daring.” On the other hand, trying too little and staying too safe and being too prudent will deprive you of your resilience—you do, after all, have to hit something to “bounce back”—and losing your resilience is a catastrophe. And losing your awareness that you can bounce back is disabling as well because it pushes you into unnecessarily prudent choices that whatever “muscles” resilience requires will atrophy.
So it turn out that unnecessary “prudence” is not prudent at all. It leads to awfulizing, which leads to atrophy which leads to life in a very small place.
 In everything that follows, I make an exception for physical difficulties, which are more common among my peers than they are among younger people.
 And not, as all my kids said when they were little, “on accident.”
Here, as is so often the case, the etymology of a word is helpful.English gets prudence from the Latin prudentia, which emphasizes sagacity or practical judgment; but prudentia is a contraction of the Latin providentia, which points us in the direction of seeing (vide-) ahead of time (pro- as a form of pre-)
 There must be, in principle, some “just the right amount” of prudence; not too much and not too little. The description “excessive prudence” means only that more prudence is exercised than this hypothetical “just the right amount.”
 Awfulizing is a term coined by psychologist Albert Ellis. It refers to an irrational and dramatic thought pattern, characterized by the tendency to overestimate the potential seriousness or negative consequences of events, situations, or perceived threats.