He managed it, rather frequently, I think. "Whoa, Sam Gamgee; your legs are too short, so use your head..."
He talked himself into it. Frequently. Not always, but often enough.
Besides, Sam was Frodo's servant; strictly speaking, he was under Frodo's direct command, not Gandalf's or Aragorn's except by chain-of-command. His default choice of of loyalty to Frodo was obvious and appropriate.
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...down to the water to see the elves dance and sing upon the midsummer's eve.
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