I want to revisit individual health insurance, as many of you will be choosing your 2025 plans this week.

It’s been quite a week for health insurance. I was on my last corporate renewal call when the news of the UnitedHealthcare CEO’s murder broke. Murder is wrong, and I’m also not begrudging anyone their feelings based on lived experiences with insurance companies.

If you aren’t eligible for a subsidy or Medicaid, health insurance will likely be your largest annual expense until you reach age 65 and qualify for Medicare. In states where it’s allowed, many of you will flirt with skipping coverage. Things to consider first:

• Out-of-pocket maximums. When I’m thinking about wealth management, I also think about downside risks. And healthcare costs are the most likely reason you’d find yourself filing for bankruptcy. (In 2023, 66.5% of bankruptcies were directly tied to medical debt.) Marketplace insurance plans have a federally-enforced maximum cap for what you can be required to pay for in-network care in addition to your premiums. In 2025, that’s $9,450 for an individual or $18,900 for a family. (Higher cost plans may have lower maximums.) Even if you get the cheapest high-deductible health plan (HDHP), these caps are still in force.

• Network. Please look at the resources available to you beyond your planned care. National carriers like Anthem BCBS, Blue Shield, Cigna, Aetna, and even UnitedHealthcare / Oxford are widely accepted across the US by most providers. You may be tempted to get an EPO because of the low cost. An EPO offers the smallest network of providers and may not cover any travel beyond your region, even within your state.  

• Portability. If you have a PPO or POS plan, you can see providers outside your home area or health system. While all health plans must cover emergency care regardless of network, that requirement does not clearly extend to subsequent hospitalization. If you travel regularly, or live in a place where access to routine medical care is legally restricted, portability is important. 

If you have $18,900 in emergency reserves, buying the least expensive HDHP Bronze PPO plan with a wide network could be a smart financial move. If you don’t have reserves, or you want to cap your personal exposure to out-of-pocket health insurance costs, balance your financial risk with your actual costs. Personally, I know that I’m less likely to go to the doctor when I get a bill every time, so I invest in a Silver PPO plan with a great network. While my out-of-network costs aren’t capped, they are at least negotiated by my insurer and subject to a co-insurance cost sharing arrangement.

About those out-of-network costs. In 2020, Congress passed the No Surprises Act, which guarantees you the right to use out-of-network hospitals and ambulances in an emergency if you did not have a choice in your care, and a defined process for settling the related bills. In a recurring theme that I call “Texas vs. Everybody,” that law has been successfully challenged in a Texas federal court, partially overturned on appeal in October 2024, and is now a hot mess of provider compliance. But, it still exists.

If you skip health insurance, there are federal limits on how much you have to pay per year before you can deduct it on your taxes, about 9.2% of your income. However, those rules do not limit the total amount of debt you can accrue. They just reduce your taxes when you have high healthcare costs. Not ideal.

The system we have stinks. It’s unfair, it’s expensive, and you can pay a lot and still have to fight to get the care and coverage you should be guaranteed. Insurers look for reasons to not pay and force you to navigate multiple appeals. Unfortunately, given the incoming Republican control of Congress and a wildcard president who has tried multiple times to repeal the ACA, we’re not likely to see significant reform in the next two years. 

The rules for 2025 are locked in, though. Take advantage of what we have, while we have it.

BOI, you trippin’

After pummeling you for a solid year about filing your BOIs, two things are true:

1. 75% of required LLCs and S-corps still haven’t done it.

2. A Texas judge decided the law that created the BOI requirement was unconstitutional, thanks to a business called Texas Top Cop Shop, and now the requirement is on pause. 

So there’s an injunction on the law, meaning you’re currently not required to file a BOI. But the appeal moves to a court not in Texas, which means you could be required to file at a point in the future.

If you’re Team Kick the Can, congratulations. The bottom line is, if you’re operating legally, most business advisors (including me) suggest voluntarily completing your BOI filing. File for free on the FinCEN website. Or don’t, and continue to watch this space.

Last Chance Dates to Know

Despite the BOI hiatus, we still have plenty of deadlines to keep your adrenaline pumping in the next few weeks, starting with Sunday’s health insurance enrollment deadline. Here we go.

December 15: Last day for individual and family health insurance plans from healthcare.gov and state exchanges, if you want to start on January 1. Remember, enrollment requires both choosing a plan and paying the first month’s premium. No pay, no January coverage. If you need help, join this month’s AMA, check out my free 2025 guide, or download my 2025 health insurance event replay on-demand. 

December 20: Last day you should reasonably expect timely help until January 6. Between the “circle back in the New Year” attitudes and the out of office notifications, you’ll be hard pressed to get folks to respond in the last 10 days of the year. If you must have something done, especially if it involves you getting paid, fight through the cringe and use your hand computer to make a phone call. 

December 27: Last day for direct deposit transactions to clear through payroll systems on a two-day payment window. Authorization on Friday means payout on Tuesday. If you miss your payroll system’s cutoff, you can still process payments until the 31st, but you will need to pay the funds by direct transfer (fast ACH, wire transfer, Venmo, etc.).

December 31: 

• Last day for W-2 payrolls. Looking at you, S-corp owners.

• Last day for 2024 qualified business expense tax deductions. If you want the deduction, the purchase must be fully cleared from your account on or before the 31st. Charges and ACH transactions may take up to three days to clear. 

• Last day to open a 2024 401k. While you can wait to fund the 401k until next year, you must establish the account on or before December 31 if you want your contributions to count toward 2024. This applies to 401ks only; a SEP or SIMPLE IRA can be set up later.

January 15: Last day for 2025 health insurance open enrollment in most states, for a February 1 start. If you do not choose a plan by your state’s deadline, you will not be eligible for ACA-compliant health insurance for a year unless you have a qualifying life event. A few states allow you to sign up through January 31.

My final AMA of the year will be Thursday, December 12 at 10 AM PT. That’s just a couple of days before the December 15 exchange health insurance plan deadline. Submit questions here.

For 2025, we’re keeping the same standing date, the second Thursday of the month at 10 AM Pacific. Add all of my 2025 AMAs to your calendar using this link.

For reference, here’s the checklist. If you’re following along, you’ve got just a few tasks left before you enjoy the holidays. If you haven’t started yet, here’s the condensed 5 Weeks to Close version. It assumes you’ll be doing some catch-up work between December 23 and 31.

• Nudge on payments. Companies with weekly or semi-monthly payment cycles have just one or two opportunities left to process your invoice. If it’s important to you to get the cash in 2024, be a squeaky wheel. If it’s just going to add to your tax bill, you can ask if they’re okay with paying you after January 1. Same with checks -- if it doesn’t benefit you to deposit the money this year, hold onto the check until January 2. It’s nice to start the year with some booked revenue.

• Meet with your tax advisor: Review your test close, confirm end of year tax and compliance transactions, and estimate your January 15 taxes. Investing in 30 minutes now can save you thousands of dollars next year, as there’s no “oops” button for deadlines. Chase that November close.

• Finish your health insurance enrollment. Dot the i’s, cross the t’s, make sure all the open enrollment forms are in and your payments are scheduled. If you haven’t done your individual exchange enrollment yet, you have until Sunday evening.

• Reuters: TikTok on the clock. Last week, a panel of three federal judges upheld the law that would shut down TikTok in the US after January 19. On Monday, TikTok threw up a legal Hail Mary to pause the ban until the Supreme Court can review the case. The law requires that TikTok divest its US operations to a US owner due to national security concerns. To keep operating, TikTok would need the Supreme Court to decide the law is unconstitutional, a new owner, or an executive order to not enforce the law. Meanwhile, Australia has banned all social media for kids under age 16. What remains true: if you build your audience on someone else’s platform, you don’t own an audience. Commit to building your own list. (And thank you for being on mine!)

• Freddie Mac: If you’re thinking of buying a home next year, the government agency that sets “conforming” loan rates has announced its 2025 guidelines. If you qualify -- meaning you have two years with healthy AGI on your tax returns and some W-2 income -- you can now take loans of at least $806,500 for single unit homes (and up to $1.2 million in higher cost areas), and more for multi-family investment properties of 2-4 units, backed by the full faith and credit of the US government. If it’s time to buy a home, it’s also a good time to show more business profitability and taxable income. Something to consider before you make those final purchases.

• Ars Technica: Earlier this year, I mentioned that Tyler Perry had cancelled an $800M expansion of his Atlanta studio after seeing OpenAI’s Sora AI video generation software. This week, Sora was released to paying OpenAI users, with limited access to the general public. ChatGPT Plus users can use text prompts to generate up to 50 low-resolution videos per month, of up to 20 seconds. It’s also time to step up your ability to spot a fake.

• Fast Company: If you’re considering a 2025 car purchase, check out the Telo EV, a truck with the footprint of a Mini Cooper that charges in 10 minutes. Manufactured in Southern California, the Telo would qualify for a full EV credit (should they persist), with a base price of $41,500. Deposits are $152 and delivery is scheduled to start in Q4 2025. It’s a super cute delivery vehicle that you can park in a teeny space.

• NYT Wirecutter: Need more holiday shopping ideas? Check out these top-rated gift baskets, many of which are offered by small businesses. I DIY’d the first one over Thanksgiving, enjoying Torres patatas fritas with The Fishwife’s smoked rainbow trout. I have eaten potato chips on five continents, and I stand by Spain’s being the best. Separately, I also recently discovered these cool portable, rechargeable stick-on makeup lights from Leopara. Hint hint, family. I can see that you read this.