Why does picking a deductible feel like a weird gamble?

Title: Why does picking a deductible feel like a weird gamble?

“sometimes the lower monthly payment feels like a win, but after a couple claims, it adds up fast.”

That’s the part that gets me every time. It’s like you’re forced to play this weird guessing game with your own luck. I totally get what you mean about hitting a deer right after switching to a higher deductible—same thing happened to my neighbor, except he went years with nothing and then had two accidents in six months. The “betting on yourself not to mess up” thing is real, but even if you’re the most careful driver, there’s just so much out of your control.

I actually ran the numbers for myself last year and realized that unless I go three or four years without a claim, the savings on premiums don’t really make up for how much more I’d pay if something did happen. But then again, I drive in rush hour every day, so maybe my risk is higher than average? Hard to say.

What I find tricky is that insurance companies seem to bank on people not doing the math or just hoping for the best. The way they structure those premium differences almost feels designed to make you second-guess yourself. Like, do you take the “safe” route with the higher monthly payment, or roll the dice and hope nothing goes wrong?

I wonder if anyone actually feels confident about their deductible choice, or if we’re all just kind of crossing our fingers and hoping we guessed right. Does anyone ever look back after a few years and think, “Yeah, nailed it”? Or is it always hindsight making us wish we’d picked differently?

Honestly, I’ve spreadsheeted this to death and still feel like I’m guessing half the time.

“The way they structure those premium differences almost feels designed to make you second-guess yourself.”

- If you can easily cover a high deductible out of pocket, maybe worth the risk.
- If not, peace of mind is worth a few extra bucks each month.
- The “I’ll never have a claim” optimism always gets me... until that rogue shopping cart strikes.

I don’t think anyone’s ever 100% confident. It’s like picking lottery numbers, but with more paperwork.

The “I’ll never have a claim” optimism always gets me... until that rogue shopping cart strikes.

That one made me laugh—had a client once who swore nothing ever happened to their car, then a tree branch took out their windshield during a freak windstorm. They were so glad they’d picked the lower deductible. I always say, if paying that higher deductible would sting, it’s probably not worth the stress. But yeah, it does feel like a gamble half the time.

Yeah, it’s wild how those “it’ll never happen to me” moments catch up. I used to think the same until a valet clipped my bumper—didn’t see that coming. I get the logic behind higher deductibles, but honestly, peace of mind’s worth a bit more for me. Sometimes you just have to hedge your bets and hope for the best...

Man, I hear you on the “never happen to me” thing. I used to roll my eyes at all the stories about random accidents, but then I got rear-ended twice in the same year—once at a stoplight, once in a parking lot. Neither was my fault, but both times I ended up paying out of pocket because my deductible was higher than what it cost to fix. That stung. I picked the higher deductible thinking I’d save money, but it just felt like a bad bet after that.

I get why people want peace of mind, but sometimes I wonder if insurance companies are just banking on us being too optimistic or too cautious. Like, are we really saving anything in the long run? Or is it just a psychological trick? I’ve thought about switching back to a lower deductible, but then I look at the monthly premium and start second-guessing myself again.

Has anyone actually done the math on this over a few years? Like, factoring in real-life claims versus what you pay extra for lower deductibles? I feel like every time I try to figure it out, something unexpected happens and throws off my calculations. Maybe that’s just life... or maybe it’s the universe telling me to stop trying to outsmart insurance.