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I would think that this is just a me problem, like I'm particularly inflexible (and, maybe that's true) but after spending much of the last month on public transit getting whacked in the arm by people awkwardly struggling to do this with their normal 2-strap backpacks as they scrunch up their arms to shrug them off and then get them back on, on public trains and buses, so no, it's absolutely a you problem, not a me problem.