how you fall down the insurance rabbit hole
January 27th, 2026 at 11:08 pmDrum roll please. My DK1 gets her license today. Woot Woot! I am so excited yet at the same time TERRIFIED. I am scared and nervous all in one. Anyone who has kids knows the feeling. It happens when you give birth and the world falls away from your feet and you are free falling into parenthood. NOTHING and NO ONE can prepare you. She turned 16 on sunday (my world changed in moments of a push). The unreal feeling of a baby moving became real in an instant. Your heart stops when you realize the dr says we need a vaccum or we're doing a c-section. You panic and are desperate. She was born in the middle of a snowstorm and there was a big snowstorm in the northeast this past weekend as well. 4 weeks early and she was gorgeous (not really but i was dazed and confused). 7 lbs at 4 weeks early!

Anyway that same sweet baby is driving today. I am petrified. I cannot believe it! I blinked and suddenly we're on the 16th hole of 18 and the game is almost over.
Anyway three weeks ago I started shopping for new auto, home, and umbrella insurance obviously. I am about to add a teen driver. So i started calling around to all the mass market chains and was told "we can't underwrite you, you have no relationship wtih us." I was like but I've been with american family connect (costco) since 2019. I have a clean driving record and no blemishes on our home and I have a $2m umbrella policy.
Well I talked to state farm, all state, progressive geico, liberty mutual. They were all expensive to be expected but each one said well we don't write $5m umbrella for people we don't know. Lesson number 1 have a relationship with a company who underwrites more. Lesson 2 - use a broker because it turns out they can advocate for you and lean on their relationship with the insurance underwriter if they know you.
So though I had referrals of state farm and all state from friends I couldn't get more insurance coverage. I could get matching but what was the point? I was happy with am fam. So I decided time to find a different broker and I went on FB groups and found people talking up their agents.
I contacted one agent (Broker A) who told me that we were underinsured (yeah i knew that) and told me they could do it Wedesdnay 1/14. But they were going on vacation and we could chat in two weeks 1/28. But if I was nervous I could call their agency and discuss it. I was stressing out so Tuesday (1/20) after MLK I called two more brokers and explained the situation. I also called broker A company and ask they move me along. A coworker said no problem for Broker A and that she would have it when she got back Monday 1/26.
Broker B got back to me the next day (wednesday 1/21)and told me I had a lot of touchpoints. My clue rating was 8 and i couldn't be underwritten easily. I had to switch to him for a year with no claims and then he could shop me around. You can imagine this shot my stress through the roof. I was beside myself. Realizing we were not exactly great risk analysis was stressful. But he got me quotes from Safeco but at a lower more expensive level.
Broker C got back to me Friday 1/23 and told me they got someone to underwrite us could we answer a few more questions. I did and then the quote came back that afternoon and we were underwritten for what I wanted for an expensive price but at the level i wanted.
I touched base with the Broker A office who assure me she'd get backt o me on Monday with notes. Monday came and no updating on the quotes which she said couldn't be done until 1/28 wedensday. So last night I decided no more waiting and pushed forward with broker C.
I'm not sure if rude but i felt under the gun. I really wanted to get everything sorted asap as my kid was driving today. I was going to hold her off and still might for a day. But the realization how expensive it was and how much i really wanted higher levels of coverage made it stressful.
I decided to go with broker C. She made it happen fast and efficiently. I stayed with our old company for 7 years and I suspect we'll be permenantly with broker C. She made it happen with the new company and I have no desire to really change. I know maybe we could shop around but knowing what I know about us. That we have "touchpoints" 8 to be exact in 5 years. That we have a teen driver and are getting a second, I think I prefer staying with the known instead o the unknown.
Anyway moral of the story? After a certain point it might be worth paying for a broker to help you instead of trying to do it yourself.