Our expert says:
The spendthrift and the workshy never deserve any financial assistance from others. Of course he'll never find "the big one" by jumping around from job to job - and if he accidentally came across it, they wouldn't dream of employing someone with such a lousy work history.
By "helping him out" financially, you are only encouraging him to spend stupidly and to be foolish about money - so long as he knows youguys will always bail him out, why should he bother to work hard, earn well, and save sensibly ? That pit is, indeed bottomless.
That sort of help is the precise opposuite of empowering someone. Check the web and read up about co-dependency, and about Tough Love.
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