🤔 Brainteaser of the day: I’m bought by the yard, worn by the foot. What am I?
Click here to see the answer.
✅ Today’s Checklist:
🥗 Keep dinner handled this fall with chef-crafted meals (50% off plus free Daily Greens with code ASSIST50FG).
🎁 Ohh Snap, Boss’s Day is next Friday, check out some fun gift ideas here.
🗣 Turns out daily AI users can’t spot a cloned voice either.
🛋 Game tables are moving out of the basement and into the living room.
The email from HR lands, or the marketplace notice shows up, and it’s written in a language nobody taught you. Here’s the translation, plus what’s different this year.
The five words that decide what you pay
Premium. What you pay monthly whether you see a doctor or not. The number everybody compares, and the one that misleads most.
Deductible. What you pay yourself before the plan starts covering things. Preventive care stays free from day one.
Copay. A flat fee at the point of service. Thirty dollars for a visit, fifteen for a prescription.
Coinsurance. A percentage instead of a flat fee, usually after you’ve hit the deductible.
Out-of-pocket maximum. The ceiling. Once you hit it, the plan covers 100% of in-network care for the rest of the year. The 2027 federal cap is $12,000 for an individual, up from $10,600.
Why the cheapest premium usually isn’t
A low premium almost always comes with a high deductible. That works beautifully if you see a doctor twice a year and takes a serious bite if you don’t.
Take last year’s actual usage, every visit, prescription and scan, and run it against two or three plans. Multiply the premium by twelve, add what you’d owe against each deductible and copay structure, and compare totals. A plan costing $90 more a month can come out thousands ahead if you have anything ongoing.
Then check two things. Are your doctors in network for next year, not just this year? And is every prescription on the formulary, at what tier?
If your coverage comes through work
Most employers run enrollment in October and November, effective January 1. Miss it and you’re locked in until next year unless you have a qualifying life event.
Open the comparison document even if you plan to keep what you have. Deductibles, networks and drug tiers change from year to year, and renewal doesn’t flag any of it.
While you’re there, look at FSA and HSA options. An FSA uses pre-tax dollars and mostly expires at year end. An HSA pairs with a high-deductible plan, rolls over forever, and invests, and the 2027 HSA limits are $4,500 individual and $9,000 family.
If you buy your own
Enrollment opens November 1 and closes January 15 in most states, and December 15 is the deadline for coverage starting January 1. Enroll after that and you’re uninsured through January.
This year deserves extra attention. Premiums are up around 15% at the median, ranging from under 7% in some states to 29% in Arizona. Insurers are pulling out of markets far more often than they’re entering, and hundreds of thousands of marketplace enrollees will see their plans end this year. Subsidies rise alongside benchmark premiums, so anyone without one absorbs the whole increase.
If you’re helping a parent with Medicare
Different system, different calendar, and it closes first. Medicare’s annual enrollment runs October 15 through December 7.
The document that matters arrived in September. The Annual Notice of Change is easy to mistake for junk mail and lists every change coming to their plan. Find it first.
Two things change most often. Part D drug lists reshuffle every year, so a covered medication can move tiers or fall off. Medicare Advantage networks also shift, so a doctor they’ve seen for a decade can drop out of network.
If you buy your own, don’t let it auto-renew
If a plan is ending, auto-renewal hands an algorithm the job of picking your replacement. If it’s continuing, it may be continuing with a different deductible, a different network, or your specialist newly outside it. Nobody is going to call and tell you.
Twenty minutes this fall
Whatever your situation, the move is the same: open the document, read what changed, and decide on purpose instead of by default. It’s less complicated than the to-do list item makes it seem.
You copy from one tab, paste into another, fix the formatting, send it, then do the whole thing again in thirty days.
Kat Norton (Miss Excel) is running a free class on building dashboards that update themselves, so you build the report once and after that you just refresh it.
You’ll learn how to:
✅ Build an interactive dashboard from scratch
✅ Automate the copy-paste steps you’re still doing by hand
✅ Turn messy data into something a director reads in ten seconds
She also shows you where your week actually went, down to the hours you lost to meetings that could have been an email.
Sign up and you get her new Dashboard Cheat Sheet.
📚 Read: Fruit Fly by Josh Silver
Josh Silver’s adult debut is a darkly funny send-up of the publishing world, and it’s half the TA team’s current read. A24 has already optioned it for TV, so read it before everyone else starts talking about it.
📺 Watch: Toy Story 5 (Disney+)
This time the toys are up against Lilypad, a tablet with big opinions about how Bonnie should spend her time. It’s streaming now on Disney+ and makes for the easiest family movie night of the fall.
🎧 Listen: Pink Clouding by Taylor Swift
It’s off The Life of a Showgirl: The Encore, out September 25, and it’s the track Cameron can’t stop replaying. Queue it up for your weekend drive.
The tool your team loved last year can start feeling like the wrong fit this year. The work changed, and the tool didn’t.
If the problem is app sprawl, ClickUp folds tasks, docs, chat, and goal tracking into one workspace, with an AI layer that already knows the context behind them. Five million teams run on it, rated 4.7 on G2 by more than 10,000 reviewers.
If the problem is scattered projects and manual updates, Smartsheet keeps the work moving with familiar spreadsheet-style views, real-time dashboards, and automations. Built for teams managing complex projects, it makes tracking progress, coordinating resources, and keeping everyone aligned a whole lot easier.
If the problem is visibility, monday.com puts every task and deadline on one board the whole team updates live, with AI agents that draft status reports and schedule meetings on their own. Trusted by over 60% of the Fortune 500.
All three are free to start, so you can test the fix before you pitch it to your boss.
Upcoming Events
* Smart Girl Society is our private community for women who want deeper conversations, accountability, and tools that actually make life easier. Join the waitlist to get in the next round.
Frank joined his family (and their office) this summer as an 11-week-old, 6-pound puppy, and he’s already the most popular member of the team. Between his sweet face, his curious streak, and his endless puppy energy, he’s settled right into his role as unofficial office morale manager, and nobody’s complaining.
Pssst…Lemonade Pet starts at $10/month and settles around half of eligible claims on the spot, right in the app. Add the wellness plan and vaccines, checkups, and dental cleanings come along too. Whatever’s left over from claims at the end of the year goes to a cause you pick.
👉 See your pet’s price in under a minute.
🐾 Got a cute fur baby? Submit them to be our pet of the week in an upcoming issue.
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