Deductibles and premiums—what's the real deal?

I get the peace of mind angle, but I’m not sure the math always works out. You mentioned,

“if you go three years without a claim, maybe it works out... but if you have even one incident, all those ‘savings’ are gone in a flash.”

I’ve seen folks regret going with the lowest deductible after a couple years of no claims, but then again, I’ve also watched people get hit with a big bill and wish they’d played it safe. Personally, I lean toward higher deductibles too—just gotta be ready for that “what if” moment. City driving is a gamble, no doubt.

City driving is a gamble, no doubt.

That’s the truth. Nothing like weaving through city traffic to remind you how unpredictable things can get. I used to go with a super low deductible, thinking it was “safer,” but over time, those higher premiums really started to sting—especially when I went years without a single claim. Switched to a higher deductible last renewal and just keep a little emergency fund stashed away in case something wild happens (like that one time a rogue shopping cart tried to take out my bumper).

Honestly, I get why folks stick with lower deductibles, especially if they’re not comfortable with surprise expenses. But for me, I’d rather keep my monthly costs down and roll the dice a bit—just makes those road trips feel a little less expensive, you know? Still, every time I parallel park downtown, I do wonder if I’m tempting fate...

Parallel parking downtown is like an extreme sport—one wrong move and it’s “hello, mystery scratch.” I hear you on the deductible switch. Here’s the thing: higher deductible = lower premium, but only if you’re cool with coughing up more if disaster strikes. I always tell folks to ask themselves, “Would I actually have that cash handy if a rogue cart (or, let’s be real, a runaway scooter) takes out my fender?” If yes, then you’re probably playing it smart. If not… maybe stick with the lower deductible for peace of mind. City driving keeps us humble, that’s for sure.

Deductibles and premiums—what's the real deal?

“Would I actually have that cash handy if a rogue cart (or, let’s be real, a runaway scooter) takes out my fender?”

That’s the question right there. I’ve been burned by both sides of this—once had a low deductible and felt like I was overpaying every month, but then when I switched to a higher deductible to save some cash, I found myself scrambling after a not-so-gentle tap from someone parallel parking behind me. The savings on the premium felt great until I was staring at a $1,000 bill.

Here’s how I break it down for myself now:

1. First, I look at my emergency fund. If I don’t have at least the deductible amount set aside (and not earmarked for something else), I just can’t justify going high. Life in the city is unpredictable—one day it’s a shopping cart, next day it’s a food delivery bike.

2. Next, I check how much I’m actually saving on the premium by raising the deductible. Sometimes the difference isn’t as big as you’d think. If it’s only $10-15 a month, that adds up slowly and might not be worth the risk.

3. Then, I consider how often I’ve needed to use my insurance in the past few years. If you’re like me and your car seems to attract trouble (I swear my bumper is a magnet), it might make sense to stick with a lower deductible just for peace of mind.

4. Finally, I try to factor in stress. For some folks, knowing they won’t have to cough up a big chunk of change if something happens is worth paying more each month. For others, saving every dollar is key.

One thing I’ll mildly disagree with: sometimes people focus so much on the “would I have that cash handy” part that they forget about how often incidents actually happen where they live or park. If you’re in an area where dings and scrapes are basically guaranteed, it might be smarter to play it safe—even if you technically could cover a higher deductible in an emergency.

City driving really does keep you humble... and maybe just a little bit paranoid about scooters.