Lookout Outlook | January 2025 | Bookkeeping Newsletter

January 10, 2025

Lookout Outlook Archives

Cheers to a stress-free tax season!

Happy 2025! To celebrate the new year, I’m gifting you a personalized New Year’s resolution: Never miss a tax deadline in 2025!

Let’s start with what’s due this month:

January 15th:

  • The final installment of your 2024 estimated tax (Form 1040-ES) is due.

January 31st:

  • Employers must file W-2s and send a copy to each employee.
  • Form(s) 1099-NEC must be filed and a copy sent to recipients.
  • Form 940 (Federal Unemployment Tax, for payroll) is due.

This one isn’t an official tax deadline, but it’s still something you need to do in January: Close out your books for 2024!

Lookout Bookkeeping will be hard at work to wrap up all of your 2024 bookkeeping items. Be on the lookout for questions in the client portal for EOY loan statements, and other documents we may need, to get things boxed up and ready for your tax professional.

Recommended Listening

Going into business with someone? Avoid the partnership trap! In “Keep What You Earn” podcast episode 715, Shannon explains the importance of having guaranteed payments that match the effort of the work you’ve done—aligning equity with effort. You don’t want to get to tax season and not have enough money to pay your portion of the partnership tax return, so ensure your ownership share matches what you deserve in comparison to your partner(s).

To hear more of Shannon’s advice, like how the best partnerships have complementary skill sets, follow this link!

Know a friend who could use our help?

We would love to support them!


The biggest compliment is that you trust us with your bookkeeping.

The second biggest compliment is when you send your friends our way!

Refer a business owner who signs up for monthly services and receive a $100 cash referral gift. You can send this intake link to your friends: bit.ly/LKTLead

Your support of our small business makes all of this possible, thank you!

In Closing…

It’s officially the new year, and here is what’s changing around Lookout Bookkeeping.

  • We will continue to advise and connect clients with excellent payroll services, but we are no longer offering payroll processing services for new clients. NOTE: current clients will enjoy these services through 2025 with Lookout Bookkeeping & we will help you to transition in January 2026.
  • NEW SERVICE: Lookout Bookkeeping has partnered with Clockwork.ai to bring you more insights and information to your numbers. If you’re looking for a better understanding of your cash flow & want to look at some scenarios—like, “Can I hire another employee? What will that do to my numbers?” THIS is the perfect new service for you. We are offering this for 50% off for the first three months to try it out and see if it is a service that benefits your business.
  • For the first time in two years, Lookout Bookkeeping has adjusted pricing. Most of our clients have received their new proposals, and the rest will go out in the next 7-10 days. We look forward to continuing our partnership with you.
  • Last, if you are a current client, you’ll notice that emails from the client portal will transition to “donotreply@lktbook.com” — We are continuing to streamline our services and keep communications in the client portal. If you have a time-sensitive issue, we always ask that the request is entered in the client portal and a text or phone call is made to our business number 423.497.4144 so we can assist you. We made this change not only to streamline our communications, but also to ensure that your messages don’t get lost in Melissa’s inbox!

One of my New Year’s Resolutions is to help even more service providers and real estate investors have tax-ready books and monthly reports to empower you in your business. If you know someone who could use my help, I would love for you to make that introduction.

Vendor Spotlight – Clockwork.ai

I’m extremely excited to announce I’m now offering Business Advisory Services in addition to the best-in-class bookkeeping you already know we provide. A few of the services are listed below:

● Cash flow forecasting and financial modeling with CFO level accuracy

● Custom Metrics Dashboard to manage all KPIs important for your business in real-time

● Scenario modeling based on all your “what if” questions

● 24/7 access to custom metrics and reporting packages, plus monthly reporting

If you’ve been wanting to get more information from your numbers, see projections on cash flow, and put in scenarios to estimate what changes with income and expenses will do for your business, this is the answer!

There are three tiers of service within advisory & I’d be happy to chat with you in order to find which one is a good fit for you and your business.

This month’s freebie!

Tax Season Survival Guide

This tax season I don’t want you to just survive, I want you to thrive! I’ve set you up with everything you need for a stress-free filing season.

Cheering You On!

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

Would you like to add the tax deadlines to your calendar?

Check out our Add Event Calendar – you can add this to any calendar & keep up with all the important tax dates!

PO Box 2475, Chattanooga, TN 37409
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