Open enrollment is coming. I haven't looked at mine yet. Here's what we're both probably missing.

We're in the gap.

School starts in two weeks. Sports are already running — soccer everyday, gymnastics every Monday, Wednesday, and Friday evenings — but the school schedule hasn't kicked in yet. The house still has that loose summer feeling where nobody has to be anywhere at a specific time in the morning and the dog is getting walked more than usual because the kids are still home.

It's a good week. A quiet one. The calm before the September schedule takes over and everything gets loud and structured again.

Work has been busy — the kind of busy where the days disappear and you surface at 5pm slightly confused about where the time went. Which is exactly why I haven't done the thing I'm supposed to do this time of year.

Open enrollment is coming up. I haven't looked at it yet.

That's a slightly embarrassing thing for a guy who writes a family finance newsletter to admit. I work in finance. I literally wrote an entire issue about employee benefits earlier this year. And I still haven't opened my own enrollment portal.

If you're in the same boat — haven't looked at yours, planning to auto-renew, or didn't even know it was coming — this one is for you. And also for me.

Most employer open enrollment windows run two to three weeks between September and December. Most employees spend less than 20 minutes on it. Most auto-renew whatever they had last year without comparing anything.

That's an expensive habit.

Here's what's actually at stake when you auto-renew without looking:

The families who win open enrollment aren't the ones who spend the most time on it. They're the ones who ask four specific questions before they click confirm.

Question 1 — Did anything change in our family this year?
New baby. Kid graduating and leaving the household. Spouse starting or stopping work. Change in income. Any of these changes the optimal benefits elections. My oldest graduated in June — that's a household change that affects my coverage needs. A spouse getting their own employer coverage may mean you can drop to a cheaper plan. Don't auto-renew a life that changed.

Question 2 — How did we actually use our benefits this year?
Pull up your Explanation of Benefits statements from your health insurance. How many times did your family see a doctor? Did you hit your deductible? Did you use your FSA funds fully or leave money on the table? Last year's actual usage is the best predictor of what plan makes sense this year. Most people ignore this data entirely.

Question 3 — Are we maximizing the free money?
Your 401k match. Your employer's HSA contribution. Your employer-paid life insurance. These are the benefits that pay you to use them. Before you look at anything else confirm you are getting every dollar of employer match and contribution available to you. Leaving a 401k match on the table is the most expensive financial mistake working parents make.

Question 4 — What's changing in the plans themselves?
Premiums go up. Networks change. Deductibles shift. The plan that was right last year may not be right this year — not because your situation changed but because the plan changed. Read the summary of benefits for any plan you're considering. It's two pages. It tells you everything that matters.

The open enrollment checklist — do this before you click confirm:

Log into your benefits portal this week — before enrollment officially opens — and find last year's summary of benefits and your EOB statements. Just pull them up. You don't have to do anything with them yet. Having them in front of you when enrollment opens is the difference between a thoughtful decision and a rushed one.

Note: This is financial education not personalized advice. Your specific situation is unique — consult your HR department or a financial advisor for decisions specific to your family.

If your employer offers a Dependent Care FSA and you have kids in after-school care, summer camps, or any childcare — you should be using it.

Here's how it works: you contribute pre-tax dollars up to $5,000 per household per year. You use those dollars to pay for qualifying childcare expenses. The pre-tax treatment means you save 22-32% on every dollar depending on your tax bracket.

On $5,000 of childcare spending that's $1,100-1,600 in tax savings. Every year. Just by running the same money you're already spending through a different account.

Most families with kids in sports, camps, or after-school programs qualify. Most families never sign up because nobody explained it to them during enrollment.

Check the box this year. It takes thirty seconds and the math is straightforward.

Two weeks until school starts. Sports are already running but the mornings are still loose. Nobody has to be anywhere at 7:15am yet. The summer isn't quite over even though it sort of feels like it is.

My youngest two are soaking up the last of it — sleeping in a little, staying up a little later, squeezing the final days out of a summer that included a cattle ranch in Montana, the Grand Tetons, and the Snake River in Wyoming.

Not a bad summer. Not bad at all.

In two weeks the alarm goes off early, the lunches get made, the school schedule takes over and the quiet mornings disappear until next June. That's how it's supposed to go. That's the rhythm of this life.

But right now it's still the gap week. The dog is getting walked. The kids are still home. The house is still summer.

I'm going to enjoy the next two weeks before September takes over.

And I'm going to open my benefits portal. Probably this weekend. Definitely before enrollment closes.

The holiday spending trap — most families overspend by $500-1,000 every November and December on purchases they didn't plan for and don't fully remember by February. We're building the Four Kids Later Holiday Budget System before the Christmas creep starts. October is the right time to do this. December is too late.