If you have your “head in the clouds” you’re fanciful and out of touch, but if you “reach for the stars,” which are impossibly far away, you’re an ambitious go-getter.
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Also if you “reach for the sky”, you’re in trouble with sheriff woody.
Arguably, you could reach for the stars while still being super grounded (and not having your head in the clouds) if you just had really long arms.
Clearly, that’s what the advice is suggesting, no idea why people don’t get it. /j
Alternatively, having your head in the clouds might just mean you have a big head