Given your DDK level, here are a couple of rules of thumb, which you can apply unless you think you shouldn't. Go has many rules of thumb that have many exceptions. Don't worry about the complexity. Just violate a rule of thumb if you want to. You may be right.
The following rules of thumb are based upon go history, the accumulated wisdom of experience over centuries of play. They are also based, in part, upon the example of AlphaGo, who may know something no human does.
The first rule of thumb is when you are pincered, don't panic.
If you approach a corner and your opponent pincers, you have prevented an enclosure with sente. Pat yourself on the back and play somewhere else, if you want to. If your opponent attacks your lonesome stone, you may be able to sacrifice it and play somewhere else again.
So the first thing to think about when pincered is to play somewhere else. Top players had figured this out centuries ago.
The second thing to think about is jumping out. Why? Because by doing so you may threaten the opponent's stone in the corner or the pincering stone. You are not just running out. Just running in order to run is in general a bad idea, something that top players also knew long ago.
The third thing to think about is playing to make life or a base. The base may not be alive without running, but that may be better than nothing.
Edit: Oh, yes, something I forgot to mention. I don't know where to put this idea, whether it is more important than making a base or not, but it is definitely something to think about, and that is to make a counter pincer. Typically your opponent will attack the pincered stone and then you can extend from your counter pincer. This is a common pattern of play.
To pincer or not to pincer, that is the question.
Centuries ago, when other top players ignored their pincers, top players figured out that not pincering, but playing somewhere else might be better. So the first thing to think about instead of pincering is to play somewhere else, if you want to.
Now, remember the second rule of thumb for the pincered stone, to jump out, threatening either side. That leads us to the second rule of thumb for whether to pincer. Think about extending from the corner instead. AlphaGo does that a lot. If you do that and then pincer, the pincered stone cannot jump out and threaten either side, because you have already strengthened one of the sides. You are not just strengthening the corner in order to make territory or to make a base, but to threaten a pincer.
AlphaGo frequently replies in the corner and then follows up with a pincer.
Edit: Extending from the corner prevents a counter pincer, as well.
Sometimes an unsupported pincer is right, but it is the third thing to think about.
Good luck!