Ok, excellent example.
You're pretty smart, right? So tell me: are you confident that you are getting the best-possible deal on insurance? Do you understand all the ways the companies compete (and don't) and exactly how high you should have your deductible be, to get the "best" premiums vs risk mitigation? Have you actually read your whole policy, and researched every term that you thought might have a technical meaning other than its superficial meaning?
And are you tuning it every year, as the insured object depreciates?
Maybe you've got this nailed, but you'd be exceptional. Getting some aspect of this sub-optimally, wouldn't signify to me that you're stupid. You might be lazy, you might have enough income that you don't give a fuck about an extra $20/year, etc.
Now if someone else points at a guy who has a $100 deductible on his car, and says "we're idiots," you're gonna say something like, "Hey, I don't have all my shit perfectly together, but that fuckwit isn't representative of us all!" and that's really all I meant to say about gambling. If you had to gamble, you'd probably get it about as right as you get your insurance.
And you probably get your bullshit-detecting about as well, very roughly. That you miss sometimes, doesn't mean you're an idiot. We're not idiots; we're just in zero-sum competitions with people who are experts in their fields.