tgoorden

Good point. It took me some time to rethink the relevant strategy.

OK, so a workable strategy might actually be a slight variation on the proposed system. Let's head back for a second: why do we sometimes feel uncomfortable requesting something?

I was thinking about this and I believe it might come down to our dread for getting a "no". In a sense, when people respond positively, there seems to be no problem with the appropriateness: it was appropriate to ask*. It is only when you get a reluctant "maybe..." or a "no" that things get really uncomfortable.

This changes the problem into a matter of being able to predict the outcome of the request.... (read more)

Don't worry about it, seriously. There is nothing awkward about being poor and it definitely is no reason to feel guilty, it just sucks. You've probably also experienced that people won't necessarily help you out under these circumstances, even if you specifically ask for help and if you know they have the money. So, dignity is all you have going for you.

Also remember, there is wealth in other things as well besides money. Besides buying rounds when I could, I've always made a huge point out of volunteering and helping people in other ways. Throw your time, smarts and skills around like some people spend their money. Learn how to cook. Learn... (read more)

I don't think this is a true (or healthy) approach. Consider helping a total stranger who you can be fairly certain off you will never see again. E.g. an old lady having trouble loading her groceries in a city you're visiting as a tourist. (To keep it simple.) By your rational (long-term account balance between you and the lady) one should never help her! This seems like a pretty depressing approach to life.

Secondly: what about situations where there is a potential for a long-term friendship, but you don't know yet? I often make good friends just by helping them out in a pretty intense way right off the bat. (E.g. someone new... (read more)

When "flipping the role", it is important to keep all the parameters identical! In other words: you have to be able to empathize enough with the other person to be able to incorporate their needs/wants/capabilities in your "mental model" of them.

A practical example: when I'm having beers with someone who is studying (and very low on cash because of that), I very frequently pick up the entire tab. Why? Because I can still imagine what it was like as a student myself and sort of even imagine that that person will hopefully do the same when they eventually start making money. Vice versa, I would never expect them to pay more than... (read more)

OK, I'll try and answer with fairly straight-forward points, as you seem to be in need of practical ways of judging these kinds of decisions:

1) When thinking about "things that need changing", it is very important to know two things first: a) How important is it to you? b) How easy is it to obtain?

You then decide if or not the combination of the two surpasses your "internal threshold". Or, if you're so inclined, think of it as an equation: if (difficulty / importance) > threshold: go for it.

In human language: If something is important to you, but it is extremely/impossibly difficult, you might want to just let it go. This... (read more)