How you all doing? Have a good holiday? Have you storyboarded 24 stunning Elf on the Shelf vignettes?

We have about three working weeks left in the  year. Hopefully, you’ve scheduled some time with your tax adviser and you’re well on your way to completing health insurance open enrollment. (If you’re holding out for extended ACA subsidies, I’m sorry – it’s not looking likely.)  

Today, I’m going to talk about something that can tank your most ambitious hopes and dreams for January 2026. You’re building your pipeline. You’re taking sales calls. You’re fully in the New Year, New You mindset. And then you get my January 14 email, and it all comes to a screeching halt. 

That’s going to be your reminder that your 1099s and W-2s are due by February 2. 

You’ll stop building your business while you chase consultants and freelancers for W-9s. You’ll be scraping year-old bank transactions and running data merges to produce teeny-tiny forms. 

But not this January, because you’re going to get organized right now.

For US-based contractors and vendors, the document you need is a W-9. In a perfect world, your partners send these with their first invoice. If that didn’t happen, start collecting them now.  

How you paid is important in this process:

• 1099-NECs are for consultants and contractors paid at least $600 by check, ACH, or Zelle. 

• 1099-Ks are for those paid at least $2,500 by Cash App, Venmo, or PayPal. 

• If you paid by credit card, you don’t have to file a report.

Summarize how much you paid each person and from what source. Here’s my 2025 article on who needs a 1099. I’ll revise this in January with guidance on how to use your beautifully organized data.

🔎 Go deeper: Who of your service providers needs a 1099?

W-2s are for employees. You’ll need to summarize pre-tax benefits, retirement savings, qualifying overtime wages, and tips. Many of the new tax rules were just clarified in November, so tax software is still catching up. But you can organize your data. If your payroll company provides W-2s by default, you can often preview the documents later in December.

Why is this important? Because you can’t take deductions if you don’t have receipts. And when you pay people, those receipts are in the form of IRS filings. No 1099s and no payroll reports means no qualified business expense deductions. Womp. Get organized.

It’s crunch time on the end-of-year checklist. How’s your progress? It’s time to get serious about your health insurance open enrollment. 

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

• December 15: Last day for January 1 marketplace open enrollment (plus first premium payment) 

• December 19: Last day to expect professional partners to be in the office

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

• December 31: Last day to open a 401(k) retirement account or make purchases for 2025 qualified expense deductions

I’ve updated my 2026 Self-employed and Small Business Health Insurance Guide, as some new policies were announced after our October 28 event. 

Ulta proves location isn’t everything. Fast-growing beauty supplier Ulta has grown to an $11 billion business in the overlooked corners of strip malls. While competitors focus on scale or prestige, Ulta does both. If you want to build loyalty and brand trust, this story is a must-read. 

My favorite free legal webinar is next week. If you do business in California, sign up for CDF Law’s annual Year in Review webinar. In one hour, CDF attorneys will bring you up to speed on news rules, regulations, and trends. This is a do-not-miss for me.

TikTok on the shop. TikTok’s store has grown by about 125% in six months, now at $19 billion in estimated sales. While US shoppers spent $12 billion on Black Friday sales (largely funded from Buy Now Pay Later financing), TikTok has been a consistent star for product sales growth.

Something else on the shelf. Elf on the Shelf is celebrating its 20th anniversary this year, inspiring…competitors? I’m not sure, but Guido on a Ledge is killing it on TikTok.