I got back from a trip to find it waiting on the counter: the open enrollment package. Is it just me, or do we all dread this every year? Even in the years when nothing changes for us, we still have to sit down and work through all the scenarios. Now, granted, our family is somewhat medically complex. (Hi, it's me. I'm complex.) But after nearly 20 working years of doing this, it hasn't gotten any easier.
Except now, with AI, maybe it…has?
Let's be extra clear: AI should not be making decisions for you, and you shouldn't be handing it all your personal information. What it can do is break things down Barney style, which, let's be honest, is one of my favorite uses of AI. Is there anything more confusing than comparing three health plans, with terms you don't understand and numbers that don't mean much, for things that haven't happened yet but might? I say no.
The real problem is that the benefits handbook is written for everyone, which means it's about nobody in particular. Nowhere in it does it say which plan is right for your family, your kids, and your medical needs, how much life insurance is enough, or how much disability coverage you might need. (Do I need disability coverage? I'm still not totally sure.)
So we went looking for what families tend to overlook, plus how people are using AI to get through it. And we turned the best of it into three copy-and-paste AI prompts: one each for health insurance, life insurance, and disability insurance.
In this issue:
✅ The one word on your health plan summary that can cost you thousands
✅ The life insurance mistake that's a five-minute fix (if you have kids, check this tonight)
✅ The work benefit that might be paying for maternity leave
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(It goes without saying, but we're not financial or insurance advisors, just parents passing along what we found. Please, please check anything that matters with your HR team or a licensed professional.)
🤖 Health insurance: check one word before you compare anything
👉 If your family is on one plan, find your plan summary and look for the word "embedded" (or its opposite, "non-embedded" or "aggregate") next to the deductible. It decides when insurance starts paying for the one person in your family who has a big year.
Say a plan has a $4,000 individual deductible and an $8,000 family deductible:
Embedded: once one person's bills hit $4,000, insurance starts paying for that person, even if nobody else has used a dime.
Non-embedded: nobody gets coverage until the whole family has spent $8,000 combined. So a $7,000 year for one kid can be all yours.
An embedded deductible is generally the better deal if one family member tends to have high medical expenses (a kid in ongoing therapy, a planned surgery, a baby on the way), because insurance kicks in for them at their own limit instead of waiting on the whole family's.
Then log in to your insurance provider and look up what you actually spent last year. Plan summaries are full of hypotheticals. Your real number is the best guess at next year you've got.
Now that you have that number, use it. We found a few people using AI to do the plan math for them (like Tom's Guide's Amanda Caswell and StretchDollar's Marshall Darr) and compiled the best of it into one free prompt. Give it last year's numbers and the plans your company offers, and it runs the scenarios for you: what each plan would actually cost your family in a good year, a normal year, and a bad one.
💸 Life insurance: check who gets the money (and don't forget the parent at home)
👉 Most of us picked a life insurance beneficiary once, probably in a hurry, and never looked again. Tonight, log in to your benefits site and check yours. Two things to look for:
Is it still the right person? (Your mom from 2014 is a lovely choice, just maybe not the current one.)
Did you name your kids directly? It feels like the obvious move, but insurers generally can't pay money straight to a minor. As Everplans explains, it first has to go through an adult, and if you haven't named one, a court may have to appoint a guardian, which is slow and costly. Their fix: name a guardian in your will, or set up a trust and name that as the beneficiary.
And if one of you stays home (or earns a lot less), make sure there's a policy on that parent too, not just the one with the bigger paycheck. The question isn't their salary, it's what it would cost to replace everything they do. Ramsey Solutions, citing Care.com, puts infant daycare at about $225 a week and a nanny at about $700, roughly $11,700 to $36,400 a year for one kid.
As for how much: you've probably heard "get 10 times your salary." CFP Daniel May at Money Guy calls that a rule of thumb, and says a young family without much saved may need enough to cover closer to 30 years of expenses. (I beg your finest pardon!)
Our prompt based on the these sources walks you through what actually raises or lowers your number (your spending, your debts, what you already get through work), so you can figure out the right ballpark for your family and walk into a conversation with an agent informed.
🧘♀️ Disability insurance: the coverage that might be your maternity leave
👉 Disability insurance replaces part of your paycheck if you can't work for a while, and not just after a dramatic accident. Think throwing out your back and being out for three months, a cancer diagnosis, or a rough recovery after having a baby.
That last one is the part a lot of us don't know. Not every job offers short-term disability (about half of full-time private-sector workers have access, per the BLS). But if yours does, it likely covers your recovery after giving birth. Under federal pregnancy discrimination rules, employers with disability benefits have to treat pregnancy like any other temporary disability. Employer plans often pay 50% to 70% of your income for up to about eight weeks after birth.
So during open enrollment, check:
Do you have it? Some plans are automatic. Others you have to opt into (and pay for), and open enrollment may be your only chance this year.
Does it exclude a pregnancy that started before your coverage did? Some plans do. If another baby is even a "maybe" for next year, sign up now, not after the positive test.
Not sure if you even need it? Our free prompt helps you do that homework. Paste in the disability section of your benefits guide and it explains, in plain English, what your company offers, what's automatic vs. what you'd have to sign up for, how long you'd wait for a check and how much it would be, and whether your savings would cover the gap if you were out for three months.
Listen, if you open only one of our AI prompts, let it be this one. It walks you through open enrollment like a patient friend, so you don't slam the laptop shut and deal with it on the last day. Run the scenarios, avoid a costly mistake, and go in knowing what you're signing up for.
And then still please talk to your HR team, financial advisor, insurance agent, or other licensed professional. 😘
Which one had you never checked?
K that's all. You're the best and we love you.
-CK "Certified Complex" Fuller (Editor) & the JB Crew 🫡
P.S. Next week: the sneaky days off school and daycare you forget about until the morning of. Consider it your heads-up before the "oh sh*t" moment.
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