It might be that the only way to truly be comfortable with uncertainty is to have confidence in one's ability to gain objective knowledge at all.
This page is a stub, created on 2020-04-11. Its contents are notes on the issues and angles I want to address about this topic.
Being comfortable with uncertainty, and more, being comfortable with admitting uncertainty (or ignorance!) were not things that came easily to me. By disposition, I am very drawn to wanting to understand, being able to see patterns and connect them to new experiences/observations, and having confidence and certainty in the logic and truth of my conclusions. For someone passionate about knowing the truth about things, especially if that truth is sometimes (or often!) controversial or bucks convention, it can be difficult to admit the limits of one's knowledge.
Personally, I'm remembering many arguments I've had over the years about politics and my unpopular political views. Even many years later, everything I've learned and all the ways in which I've grown have only reinforced and refined my understanding, but I recall feeling back then that I had to be able to answer every challenge. I felt obliged to deal with a great deal of "whataboutism". I could never say "I don't know about that; I'll have to learn/think about it further. Tell me what you know about that and why you think it's relevant.". Needless to say, that was all unpleasant and combative, and that's a subject for a different post.
The important part here is that I felt that my certainty, justified though it may have been, would only be credible if I could answer every objection. (The feeling of needing to be persuasive is maybe also a topic for a different post.) And while one of the benefits of this phase of my development was that it actually challenged me to engage with all those objections to my views and learn more, the point is that I had a profound discomfort with uncertainty and ignorance.
I don't want to recapitulate the Objectivist Epistemology (for that, feel free to check out Introduction to Objectivist Epistemology), but the short of it is that I do still believe that objective truth and knowledge are possible. Knowledge is contextual, and it's limited by the range of observations and experience that it's based on. But to say that knowledge is contextual is not to void it of power; by contrast, it equips us to differentiate between knowledge that is acquired by a logical inductive process and beliefs that are based on wishes, errors, willful ignorance, or some other irrational / detached-from-reality process.
With all that said, what I want to explore more is where comfort with uncertainty can come from. I have a feeling that true comfort can only come from understanding that objective knowledge is possible, even if one has not achieved it on some particular issue. (And a related topic to explore is how admitting uncertainty actually builds credibility.)
I suspect that true comfort can only manifest in the feeling of "I know what I know; I am confident in that. I am okay not knowing all the things right now; perhaps I can come to know them later.". In a way, I think there's a connection to self-esteem, where one can only practice true compassion and care for others when one has compassion and respect for oneself.
Another possible parallel is how feeling security in the sanctity and respect of one's rights and property is what enables generosity and charity, whereas we see that when rights and property are not protected, the expressions of generosity and charity in a culture tend to decline. (Think about that one for yourself: Do you feel more or less generous when what you might otherwise share voluntarily is demanded from you as a right or entitlement?)