This week’s email is about health insurance. Yes, it’s that time again, and yes, I felt your collective skin crawl. 

TL;DR: live help

This year, I’m offering direct help. On November 12, I’m hosting a 90-minute webinar, Decoding your 2025 Health Insurance Choices. This webinar is specifically for the self-employed and small business owners. I’ll review the highlights of individual and small business plans and take live questions for 30 minutes. The cost is $27 and includes the replay. It’s open to anyone who wants to attend, you do not need to be on my list. Learn more and register here. 

And please share the invite! This is a public event.

In 2018, I moved my family to Spain for a year. One of my core memories is taking our kiddo, then three, to visit the pediatrician. We saw a lovely doctor for 20 minutes, the kiddo got a shot for something exotic, and we were sent on our way. 

Being a well-trained American, I stopped at the nurse’s station to check out. “What is my co-pay?” I asked in my elementary Spanish. The nurse said, “We don’t have that.” We went around several times before she said, “If you paid for your insurance, that’s all you have to pay.”

It was literally all we had to pay for unlimited medical and dental care for a year. Just the premium. Which was about US$2,200 for three people. And Spaniards were aghast at how expensive it was.

Which brings me back to the United States, where we are rapidly approaching the annual dance we call health insurance open enrollment. The Center for American Progress reports that about 10% of Americans are self-employed, and most of us must provide our own health insurance. 

Buying health insurance is one of the biggest financial decisions you’ll make each year, with family premiums over $1,000 per month for even the most high deductible plans. If you’re new to buying your own medical and dental insurance, it can be downright tear-inducing. 

So, where to start?

Each year, I write a guide to self-employed and small business health insurance. The 2025 Guide is now available on my blog. The article reviews the basics of public, individual, and small business options, with guidance on how to understand what you qualify for and tips for choosing the right approach for you.

This year, I also created a separate glossary of health insurance terms. If you’re new to health insurance, start here. Keep it handy while you’re evaluating coverage.

Key Dates and Deadlines

November 1: Marketplaces open. Public marketplaces for individual and SHOP small business plans open enrollment on November 1. You can check your estimated subsidy without providing personal information using healthcare dot gov's calculator. (You may be referred to a state exchange.) If you have under 25 employees, you may qualify for a Small Business Health Insurance Credit applied to SHOP plans.

November 5: Election day. We get the health insurance choices we vote for. One presidential candidate wants to reinstate discriminatory practices against those with pre-existing conditions and eliminate the ACA. The other wants to expand subsidies and coverages, including reproductive care. Make a plan to vote.

November 12: My self-employed and small business health insurance webinar. Register now.

November 14: My free monthly subscriber AMA. Bring your questions for live support. Submit questions here.

December 10: Group plan deadline for January 1. If you currently offer a small business plan, you should receive renewal information any day now from your existing carrier or broker. You typically have about one week to review your choices before your employees are asked to start open enrollment. New and existing plans close open enrollment by December 10, if not earlier. Please let your team know as soon as possible if you’re offering a group plan, before they pay a nonrefundable premium for individual coverage.

December 15: Coverage deadline for January 1. With a marketplace plan, if you want your coverage to start by January 1, you must select your plan and pay your first premium by December 15. 

January 15 or 31: All marketplaces close. Some states offer extended enrollment and allow February plan start dates. Check your state rules here. 

I know this is complex, but please don’t just skip it. As an individual, if you do not opt into a plan during open enrollment, you won’t be able to join one until next year barring a qualifying life event. While health insurance is expensive, unexpected and uncapped healthcare costs are an even bigger risk. One in 12 Americans has significant medical debt, and medical debt accounts for about 40% of all personal bankruptcy filings. 

Please reach out if you need support.

Ten Weeks to Close

Health insurance choices are your first assignment in closing out 2024. Next week, I’ll provide a detailed summary of priorities for the next ten weeks to help you finish the year strong and enjoy a drama-free last week of the year. Well, at least business-wise.

Media Kit

Marketplace: This week, we celebrate 50 years of women having access to personal credit. (Business credit happened in 1988.) Marketplace reported a lovely story about NOW’s efforts in the early 1970s to help women understand that they were being discriminated against, as most thought it was fine for the mans to run the money. As a person with eight credit cards, two mortgages, one loan, and zero husbands, I fully approve your economic empowerment. Not very long ago, you would have needed a male relative’s permission to have Apple Pay. Think on that.

The Hollywood Reporter: Sick of keeping up your brand on social media? Just try being a content creator. THR reported this week that 90% of influencer / creators are suffering from burnout and 70% have considered quitting. While market demand for content creators continues to grow, and establishing an audience-based content channel is now a proven path to building IP, more and more creators are deciding it’s just not worth it.

CNBC: The IRS has released 2025 inflation-adjusted tax brackets and an updated standard deduction of $15,000 for individuals, $22,500 for head of household, and $30,000 for joint filers. Federal tax brackets are adjusted annually to make sure you’re not paying higher tax rates strictly due to inflation. Individuals earning more than $626,351 (double it for joint) will pay the top marginal bracket of 37% on incremental earnings. For context, the top marginal rate peaked at 94% in 1963.

City of Los Angeles: If you’re an LA County-based business and would like to be considered for services contracts related to the 2026 World Cup, 2027 Super Bowl, or 2028 Olympics / Paralympics, now is the time to complete your vendor certification. The City of Los Angeles has set up a small business-specific agency to help these event organizers meet their goals for spending with qualified, diverse local entrepreneurs. Attend an info session with PACE / ProcureLA to learn more.