phrasal verbs with up and out -- up と out の複合動詞 (updated)

(I will try to translate and annotate, later. It's 1:00 AM, and I need to sleep.)

Dropping out:

You know, it's hard to think of things you can't drop out of. You can drop out of a race or a school or a class, or just about anything with a course. You can also drop out of most things with a place to be in and a place to drop to.

You can't simply drop out of jail. They don't let you.

You can't drop out of a finish line, although you can drop out of a race at the finish line.

It's hard to drop out of the ocean, because there's no place to drop to.

And it's hard to drop out of exams, because they come at the end of the course. It's possible, but the expression is not often used.

Breaking up with someone:

You can break up with any kind of partner -- a friend, a spouse, etc.

It's hard to break up with a relationship or a marriage, because that would mean that your partner was the marriage or the relationship.

You can break up a marriage, but it's not considered nice to cause a divorce.

You can break up a relationship, but breaking it off feels a little less violent.

Making something up:

You can make up after breaking off a relationship, but that's a different meaning than we are talking about here.

By definition, you can make up an excuse or a story, of course. So you could also make up a song or the plot of a play.

So you can also make up a story and act it out, as a play.

But if you make up acting, it seems like the acting is not real, is not acted. And that is confusing.

Working something out:

You can work out an answer. Figuring an answer out of a problem takes work.

And you can work out a problem, because when you are finished the problem is no longer a problem.

You can work out what a problem is, because the nature of a problem is a problem in and of itself.

You can work out at the gym or the spa, but what your are doing is working soreness and weakness out of your muscles.

A plan or a project can be worked out, right or wrong. And it seems a little strange, but it has become normal English to say that plans or projects work out right or wrong, as if these things worked themselves out. That way we can avoid assigning the blame when things work out wrong.

People can work out wrong, but what we mean when we say that is that the person in question couldn't make things work right in the role he or she was given. The role didn't work out right for that person.

A group of people can work out wrong, too, but that means that the relationship didn't work very well. Anyway, in these cases we are no longer talking about work as effort, but work as function.

But, usually, we don't like to blame people when things don't work out very well. So, rather than say

We worked out wrong. 

we would prefer to say,

Things didn't work out [well] between us.

Picking something up:

You can pick up a piece of paper or a pencil. No problem, right?

You can pick up Spanish, you can pick up information, and you can pick up a habit or a technique. Even though you can't get your hands on them, these are things that can stick to you.

A haircut is rather less tangible than even information. It's more something that someone does to you, more than something that becomes part of you. And your hair grows out, so the cut does not stay with you. So we generally don't talk about picking up a haircut. (Some people might, in their own personal dialect.)

Running out of something:

You can run out of milk, money, and things to do. That's what happens when there is not enough.

But when you say you've run out, you are implying there was not enough. So it's a bit redundant to say you've run out of enough of something. It's not the enough that is lacking, it's the thing there is not enough of.

So, either you want to say

We ran out of milk.

or

There was not enough milk.

Catching up with something or someone:

You can catch up with studies and you can catch up with another person.

("Catching up your studies" is a short way of saying "catching up with your studies," by the way.)

Now, can you catch up with yourself? Are you chasing yourself?

Actually, there are times when my thoughts get ahead of me. I find myself thinking things faster than I can understand them. And, when I come to an understanding of my thoughts, I might say I caught up with myself. But it's a poetic or philosophical expression, and not so commonly used.

Ending up doing or being something:

The expression "end up" usually means to come to a particular end. So you can end up working as a doctor, or you can end up living with someone, or you can end up in a place, like Warsaw, Poland.

"End up" can also be used as an expression for "finish", but it is not very commonly used. But "ending up work as a doctor" would mean changing jobs from being a doctor to something else. Which is quite a different thing from "ending up working as a doctor." Almost opposite.

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(Up and out is an idiom for escape by ascent. But that's not really relevant here. Well, anyway, ...)
（ここでは関係のない話なのですが、　"Up and out" とは、登って外へ出る脱出的な移動の熟語です。では、…）