Thankful for YOU!

November is the unofficial kickoff for year-end prep at Lookout Bookkeeping, and one of the things we’re turning our focus to is 1099s!

Whether I prep your 1099s or you do them yourself, it’s time to check that you have W-9s on file for all contractors you paid $600 or more to in 2025. A W-9 has almost all of the information you’ll need to prepare your 1099-NEC filings, and you can be subject to penalties if you file with missing or incorrect info. So, I’ve prepped a quick script you can copy + paste to make your life a little easier:

“Hi [Name], it’s been a pleasure working with you this year! I’m updating my records for year-end tax reporting and need a quick Form W-9 from you. This form helps me issue your 1099 in January (and keep both of us in compliance with IRS rules). You can fill it out here [the official W-9 form] and send it back via [your preferred method]. Thanks so much for helping me get this squared away before year-end!”

I know that’s A LOT of financial talk when you’d really just like to wind down for the holidays, so as a literal palate cleanser, I’m sharing my must-make holiday recipes at the close of this newsletter. Keep reading and scrolling to find them below!

Advisory Vault | New offer from Lookout Bookkeeping

Do you know a business owner who is just getting started, or in the beginning of their journey as an entrepreneur? Our new offer includes:

• QuickBooks set up, with guidance on which level is right for your business
• Ongoing support in our Membership
  • Zoom meetings twice a month for coworking with other business owners on your bookkeeping—with a “bookkeeper in your pocket” during our calls so you can ask questions
  • Heylo Community where you’ll be kept up to date with tax/bookkeeping things, can ask questions, and interact with your fellow members
  • Access to a library of information on best practices and bookkeeping information

If you know someone who is struggling in their current solution of spreadsheets, who isn’t sure how to do their books, but not yet ready for done for you services, this is for them! We are excited to connect with budding business owners with this offer.

Recommended Reading

This November, don’t just count your blessings, count your balances, too. 💛
Gratitude isn’t just good for the soul—it’s good for your business.
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Learn how reflecting on your books can help you see progress, celebrate wins, and finish the year with clarity and confidence.

👉 Read the full post: Counting Blessings (and Balances)​

This Month’s Freebie! ​ ​ 1099 prep isn’t the only thing you’ve got to worry about before 2026. Check out my “6 Tax Planning Moves To Make Before 2026″ guide as a reminder of a few things you might want to ask your tax accountant about before the ball drops. ​ ​ ​ Get the Freebie!

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In Closing…

Enjoy these recipes, from my family to yours, this holiday season!

This recipe is one of my favorite desserts. I’ve shared this recipe with friends and family alike, and now I’m sharing it with you…

Chocolate Chip Cheesecake

• 2 packages cream cheese
• 1/2 cup white sugar
• 2 eggs
• 1 tsp vanilla extract
• 1/2 cup mini chocolate chips
• 1 pie crust (store-bought)

Mix cream cheese, sugar, eggs, and vanilla extract together using a stand or hand mixer, then pour into pie crust. Top with mini chocolate chips. Bake in oven at 350° F for 45 minutes or until it sets. Refrigerate after cooling down.

This recipe is a family favorite since I was a young girl. My mom would often put this chip dip out to hold us over before the main meal was ready to eat. It was the perfect little snack to keep our hunger at bay!

Chip Dip

• 8 oz. cream cheese, softened
• 8 oz. sour cream
• 1 tsp cumin
• 2 tablespoons picante sauce
• 1 can (4.25 oz.) chopped olives
• 2 tomatoes, chopped
• 1 bag of shredded lettuce
• 1 bag (8 oz.) shredded cheddar cheese
• Doritos

Mix cream cheese, sour cream, cumin, and picante sauce in a stand mixer or use a hand mixer until blended. Spread the mixture on a 13 x 9 shallow dish or pan. Top with tomatoes, olives, shredded cheese, and lettuce. Enjoy the dip with Doritos!

Got a recipe for something your family makes EVERY year around this time? Send me the recipe for the Thanksgiving food your family can’t live without, and I’ll share my favorites throughout the month on my Instagram stories (follow me @lktbook so you don’t miss out!).

Wishing you and your family a wonderful Thanksgiving, I am SO grateful to be your trusted advisor & bookkeeper.

Vendor Spotlight – Gusto Lookout Bookkeeping partners with Gusto for payroll processing. If your next step in business is to hire employees, we are here to assist you in getting payroll set up. We are Gusto Payroll Certified. Would you like to see how compliant your payroll & employment practices are? Use Our Checklist!

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Looking for a DIY Solution?

Look no further than our Small Business Bookkeeping Tracker! For the start-up side gig who just has a few transactions a month, this tracker will be your BFF for tax filing. You can enter your transactions each month and this tracker will produce monthly and annual reports. The best solution for any business until you need to partner with a bookkeeper to provide done for you services.

$97.00 Small Business Bookkeeping Tracker | Lookout Bookkeeping This Small Business Bookkeeping Tracker in Google Sheets helps you keep track of your business income, expenses and… Read more Get it now!

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