Honestly, I get what you mean about the stress relief. But as someone who’s had two fender benders in the last year, I feel like I’m always just waiting for the next thing to happen.
That’s what gets me—I thought I’d be fine with a higher deductible, but when the bill hit after my last accident, it stung way more than just paying a bit extra every month would have. Sometimes rolling the dice just ends up costing more, especially if your luck’s like mine.“could you pay that high deductible tomorrow if you had to?”
Man, I hear you on that sting. It’s easy to think you’ll never need to cough up that deductible until—bam—you do. I’ve tried both ways over the years, and honestly, sometimes paying a bit more each month just lets me sleep better. Luck’s a weird thing with cars... seems like when it rains, it pours.
Picking a deductible really does feel like rolling dice sometimes. I’ve been down this road more than a few times—especially since I’m always planning the next long trip, and stuff just happens out there. Here’s how I usually break it down for myself, step by step, when I’m deciding what to set my deductible at:
First, I look back at my own “incident history.” Like, how often have I actually needed to make a claim? For me, it’s rare, but when it happens, it’s never cheap. Had a deer run-in outside Flagstaff once—totally not my fault, but that $1000 deductible stung way more than I expected. On the other hand, I went four years before that without a single issue.
Second thing, I compare the difference in premiums. Sometimes you only save like $10-15 a month by raising your deductible from $500 to $1000. Over a year, that’s not even $200. If you have one accident in five years, you’re still out more than you saved. But if the monthly jump is huge, then maybe it makes sense to take the risk.
Then there’s the “sleep at night” factor you mentioned. That one’s hard to quantify. When I’m gearing up for a big cross-country trip, knowing I won’t be totally wiped out if something goes wrong is worth a lot to me. But during stretches when my car barely leaves the garage... yeah, I get tempted to crank that deductible up and pocket the savings.
I know some people treat insurance like it’s just a numbers game—lowest cost wins. But for me, it’s more of a gut check. What can I actually afford to pay out of pocket if things go sideways? And how mad will I be at myself if I gambled and lost?
Anyway, “luck” with cars is real... or at least it feels that way. The one time you decide to save a few bucks is always when some random nail finds your tire or someone backs into you at the grocery store. Murphy’s Law in action, I guess.
I’m not sure there’s ever a perfect answer here—it’s always some mix of math, gut feeling, and whatever kind of year you’re having.
I get where you’re coming from, but honestly, I’d push back a bit on the “gut check” approach. A lot of folks underestimate just how much the numbers can work in your favor if you look at the long-term averages. For example, if you rarely file claims and have enough emergency savings to cover a higher deductible, it really can make sense mathematically—even if it feels risky. I’ve seen people stick with low deductibles for years and spend way more in premiums than they ever would’ve paid out of pocket. It’s not all luck... sometimes it’s just playing the odds over time.
Honestly, I think you nailed it with the “playing the odds” bit. I’ve been restoring old cars for years, and I used to cling to low deductibles out of habit—felt safer somehow. But after running the numbers, like you said, it just didn’t add up for me anymore. Upping the deductible felt weird at first, but my wallet’s definitely happier now. Still, I totally get why folks hesitate... it’s not just about math, there’s always that “what if” worry in the back of your mind.