Real quick, before I get to other stuff: TL;DR I am hosting a free, live event on self-employed and small business health insurance options on October 28 at 12 PM PT. I’ll be joined by two benefits pros. Registering gets you the Zoom info and replay. Get your spot now.

October is National Women’s Small Business Month. The SBA partied so much, they needed two weeks to recover.

I kid. But at this precarious time, SBA lending and supportive services have been paused by the federal government shutdown. As has the Bureau of Labor Statistics, which limits our view into unemployment, inflation, and the overall function of the economy. And we’ve got some new tariff noise after China levied fresh restrictions on rare earth minerals.

Thankfully, the Census Bureau is holding us down with a year’s worth of small business data, released in late September. They have this fun tool called the Census Business Builder, a free data visualization that will show you demographic data and business ownership stats down to the ZIP code.. 

From the Census Bureau, I learned that women continue to start over half of all new companies, and own 43% of solopreneur firms. The uptick of company creation that started in the pandemic has continued annually. Whether as side hustles or main sources of income, gigs or companies, American women are becoming increasingly self-employed in businesses they own. 

I think a lot about what it means to own a small business now. It’s easier than ever to start a company. For a few hundred dollars, you can set up an LLC or a dba, buy a domain name, make a logo, and even generate a basic business plan. You can contract with people literally anywhere to do work for you.

And then comes running the company. That part is increasingly complex. Up until 2018, you could toss up a web page, take some payments, and file a pretty simple tax return. Now, small business owners have similar management considerations to professional athletes, but without the elite team of agents, business managers, and tax accountants. There’s sales tax tracking and filing, labor laws, financial management, multistate compliance, access to health insurance, not to mention the ever-changing economic and political environment. 

Staying in business is the tough part. Writing down your goals and plan can help your company grow 30% faster. And, Brené Brown’s new research in Strong Ground reinforces that getting clear on what you value is critical to your success as a leader. 

Next Tuesday is my annual planning day. I will reaffirm my centering principles, research some new service ideas, adjust my operating budget, benefits, and wages, reprice and repackage my offerings, and build out a monthly sales and revenue plan. 

I know it’s tempting to wait until January, but any amount of organization you can do now will pay off. It’s a busy time of year, but also a critical one for resetting prices, sunsetting outdated products and services, and researching what comes next. With that in mind…

This is the time of year when we start moving from strategy to execution. We need to lay the groundwork for 2026 while finishing a bunch of time-sensitive operations, people, tax, benefits, and compliance decisions that can only be done, of course, at the busiest and most stressful period of the year. 

To ease our collective pain, next week, I’m bringing back my annual 10 Weeks to Close series. Watch this space for a checklist-style summary you can download or put on your desktop. 

Each week, I’ll walk you through what to evaluate, fund, file, communicate, and clean up before December 31 — so you’re not scrambling during school breaks or hunting down receipts over your holiday leftovers.

We start with health insurance, the champagne supernova of challenging tasks. Whether you’re buying for yourself or providing benefits to your team, your plan, budget, and partners need to be in place by November 1. 

To support your decisions, on October 28 at 12 PM PT, I’m hosting a free live event with expert guests who will help you review exchange, small business, and nontraditional options. Get your spot here and don’t gatekeep -- share this series and the live event with your friends!

TODAY (October 15)

• 2024 extension tax filings are due for individuals, sole proprietors / solo LLCs, and C-corps

• FEMA tax amnesty expires for areas impacted by January’s LA County fires

October 22:  10 Weeks to Close newsletter tips are back

October 28: Join my live self-employed and small business health insurance event

November 1: Healthcare.gov health insurance open enrollment begins

November 11: Veterans Day federal holiday

November 28: Thanksgiving federal holiday

She sips the COLA: While 2026’s standard deductions and marginal tax brackets were released on time last week, the federal government shutdown has delayed next year’s cost of living (COLA) adjustments. Between layoffs and furloughs, the Bureau of Labor Statistics cannot process the inflation data needed for the announcement. Further delays could impact the timely annual adjustments Social Security, Medicare, and Medicaid benefits. 

A legit Millennial gripe: Friends, in a few months, I will turn 50 and will qualify to make extra pre-tax contributions of $7,500 to my 401k, up to $77,500 as a business owner. Or, I will for the next two years. Beginning in 2027, the longtime “catch-up contribution” scheme will be restricted to post-tax Roth contributions only for those earning over $145,000. This rule is per person and applies to highly-compensated employees. On the flip side, if you are age 60-63, beginning in 2025, you may be able to make super catch-up contributions of an extra $11,250. If you are using your 401k to manage your tax bill, it’s extra important that you talk to your tax advisor in November about your 2025 strategy.

A sartorial dare: Time marches on, but the fashion cues are from 2008. Are you wearing…the Chanel boots? No, you’re not. But boots with the frrrrr are back, courtesy of Crocs and T-Pain. This unlikely collab was announced in a cheeky intro video that has some of my team saying, um, probably? If knee-high squishy boots and insane calf sweat are your winter dream, the Unfurgettable tall boot becomes available on October 23.