Should you wait to buy health insurance?

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2026 Health Insurance Updates

The US government is eeking toward re-opening. However, it’s looking very unlikely that extended ACA subsidies will be revived before December 15. That means we need to make choices based on what we know today, even if the options are cringe. 

These tips from my health insurance event might help: 

  • ACA subsidies still exist, but end at about $60,000 AGI for individuals and $120,000 AGI for a family of four. The upper limit is 400% of the federal poverty line.

  • The OBBBA restructured premium subsidies. There are no $0 plans anymore. Everyone has to pay something, and at higher incomes, you may be required to pay up to 10% of your household AGI as a premium. 

  • On the marketplace, only Silver plans qualify for subsidies. Bronze plans may now cost you more than Silver plans. 

  • Subsidies are based on AGI, not household income. Estimate for 2026 after business expenses and retirement savings, especially if you expect your AGI to be lower next year.

  • If you’re renewing through an employer or union, make sure you review the details thoroughly. Employers can reduce coverages or raise out-of-pocket costs to maintain premium levels.

If you choose to explore options beyond the exchange, your options are off-market, medically underwritten, association, and catastrophic coverage plans. If you want to go this direction, consider an individual broker or an insurance concierge to help you identify options.

  • Off-market: direct from insurance companies, ICHRAs

  • Medically underwritten: through a broker or directly with an insurance company

  • Association: try your Chamber of Commerce and professional organizations

  • Catastrophic coverage: likely a fraternal order or local insurance company

If you get an off-market plan, please read the fine print. I cannot stress this enough. Make sure you understand which providers you’re allowed to use and which coverages are excluded, like preventative services and anything related to your reproductive organs.

(Note that in CA, DC, NJ, RI, and MA, you must have an ACA- or MEC-complaint plan or request a waiver.)  

If you missed the event, watch the replay here and check out my updated blog post, 2026 Health Insurance Guide for Self-Employed & Small Business Owners, on my blog or in this formatted, printable PDF. Both are free, shareable, and ungated. Pop them into your AI of choice in support of your specific questions.

Important Dates

We have about seven weeks left in the year, and they’re chock-a-block with deadlines. This can be a lot to track, so I made you an end-of-year checklist, walking through each week’s critical tasks. Make your own copy in Google Sheets or export a PDF. 

The checklist links my blog and video resources for choosing a retirement plan, checking your S-corp compliance, deciding who needs a 1099, and running a test close for your year-end accounting meeting.

Important dates:

  • Now: health insurance open enrollment for individuals and businesses

  • November 27: Thanksgiving federal holiday

  • November 29: Small Business Saturday

  • December 1: the last day your very accommodating vendor might be able to add a small group plan

  • December 7-10: small group open enrollment deadline (yours may be earlier)

  • December 15: Marketplace open enrollment deadline for January 1 coverage

  • December 26: Last day for most payroll runs with direct deposit

  • December 31: Last day to open and minimally fund a 2025 401k

A Heads-Up

I’ve gotten lots of requests this year for an easier way to work with me than a strategy engagement. I’m working on something for early December -- you will hear about it first. I still get the icks at the idea of feeding a never-ending marketing funnel to sell programs. But if you’re interested in working with me 1:1 for 2026, watch this space after Thanksgiving.

Media Kit

All things retail: Ever wondered about the origins of Two Buck Chuck? Or who named the guacamole “Avocado’s Number”? Check out this epic podcast episode from Acquired about the origins and growth of Trader Joe’s. It covers market research and differentiation, supermarket economics, private labeling, the rise of California wine, employee stock ownership programs, the feud between the Aldi brothers, and probably more because it’s still going. Ready-made for passing 3.5 hours of holiday travel.

Pennies from heaven: America has minted its last penny. While 300 billion pennies remain in circulation, retailers are already complaining of shortages and reassessing prices for a world without exact change.

Thank you for reading! If you have suggestions or feedback, hit reply or email me at [email protected]. See you next week.

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PPS -  Need a strategy sanity check? Book a free 20-minute Strategy Session with me.