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This suggestion only makes sense until it doesn't. Suppose everyone actually took that advice. Then you'd have an entire population of overqualified people who cannot find jobs that are appropriate to their skill level and who still have to take crappy jobs. Paradoxically, maybe even you are one of them. Then what?
Now consider that this upleveling actually does happen for many people, and yet the issue of risk of financial ruin continues to exist for the bottom rungs in perpetuity.
Also, the point about deserving feels a bit myopic. Does someone deserve to be so poor that their family ends up resorting to tax funded programs like unemployment benefits, or worse, they turn to stealing, landing in jail and imposing a $40k tax burden per head on the rest of the population?
If the money flows from big corps to privileged highly paid workers pockets to the IRS to govt-run programs, why not just route the money directly to the less privileged so govt programs are less needed in the first place? The status quo is really not that different from Omelas[0]
[0] https://en.wikipedia.org/wiki/The_Ones_Who_Walk_Away_from_Om...