Lookout Outlook | October 2025 | Bookkeeping Newsletter


Q4 Money Moves

Pumpkin spice is in the air, and it's your last chance to file your extended Form 1040 (aka your personal tax return) and/or your Form 1120 (aka your corporate tax return) before late filing penalties + interest start stacking up!

The fourth quarter is also the PERFECT time to make all your tax planning moves. Why? You're starting to get a good idea of what your income will look like for 2025, but because there are still three more months left, you've got a lot of flexibility in what tax planning measures you can still take. Once that ball drops on December 31st, you lose out on A LOT of tax savings opportunities, so I'd strongly recommend booking a 2025 tax planning session with your tax professional before year-end.

Speaking of tax planning, now is the perfect time to assess whether your entity type is working for your business and not against your short- and long-term goals. Thinking of filing an S election? Keep reading!

TikTok tax bros make electing to be taxed as an S corporation sound like some massive loophole the IRS doesn’t want you to know about, but they’re not some magical, one-size-fits-all tax hack. So, why all the hype? For certain business owners, depending on their earnings and goals, it can help reduce self-employment taxes.

It’s more important NOW than ever to stay on top of your finances and understand how changing tax law will impact your personal and business finances.

I’m here to help you navigate these changes. Let me know if you have questions!

New Website Design

Have you seen it?

My big project this summer was to refresh the website & branding assets.

We hope you'll take a look—and, we 've got a new offer for startup/DIY entrepreneurs! Be sure to take a look at The Advisory Vault—coming soon!

Click the link below to visit the website!


Recommended Reading

Sales tax is one of the biggest headaches for small business owners—confusing rules, state-by-state differences, and costly penalties if you get it wrong. In our latest blog post, we break down what sales tax really is (and isn’t), highlight Tennessee’s tricky rules on services vs. products, and share practical tips to stay compliant without losing your mind.

👉 Read the full post here and make sure the state doesn’t send you a letter you really don’t want to open.


This Month's Freebie!



Grab my free “Everything You Need To Know About S Corporations” guide before you make an election for a tax status that could cost you more than it saves you!


Come See Me at The Chattery This Saturday!

If you know someone who's struggling with QuickBooks Online, please send them the link to register for my class "QuickBooks Online Power Hour for Entrepreneurs."


In Closing...

Okay, I’m in the mood to bust a few more finance myths, let’s do it:

MYTH: Avoid taxes by having your clients put emojis in their Venmo memo.

REALITY: This does NOT magically hide your income from the IRS.

MYTH: Your bookkeeping is 100% accurate just because your accounts are reconciled.

REALITY: Your bookkeeping can be done incorrectly (i.e., transactions categorized to the incorrect account) and still reconcile just fine.

When it comes to your finances, if it sounds too good to be true, it probably is. When you’re ready for bookkeeping help from a bookkeeper who wants to help you save money but ALSO wants to keep you out of jail, you can find me at www.lktbook.com


Vendor Spotlight – American Express

If you are looking to add a credit card to your business, I highly recommend American Express. They have a couple of options for business owners, and I have utilized both in my business.

The first option highlighted is the Business Blue Cash Card. The Business Blue Cash Card from American Express was my first credit card in business. There is no fee, and an introductory 0.0% APR for purchases in the first 12 months. You will earn 1.5% Cash Back on purchases in the form of a statement credit each month, too.

With the Blue Card, when you spend $5,000 in the first 6 months of card membership, you'll get a $250 statement credit.

DISCLAIMER: Program benefits may change at any time.

Full disclosure: By using this referral link, you will receive $250 statement credit when you spend $5,000 in the first six months of having the card. When you signed up, I will receive a $50 statement credit as well.

Please be wise when choosing to utilize credit for your business.

The second option highlighted is the Delta SkyMiles® Reserve American Express Card. If you travel and use Delta Airlines for your flights, the perks are worth the annual fee (currently $650). You will earn SkyMiles® with all purchases as well. This is the card I primarily use in my business now.

With the Reserve Card you'll get 125,000 miles after spending $15k in the first 6 months of card membership.

DISCLAIMER: Program benefits may change at any time.

Full disclosure: By using this referral link, you will receive 125,000 Delta Miles when you spend $15,000 in your first six months of membership. Highest bonus AmEx has offered with this card ever! When you sign up, I will receive 25,000 miles as well.

The above information is subject to change at anytime with American Express & does not constitute financial advise. Please be wise when choosing to utilize credit for your business.


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


Cheering You On!


Lookout Bookkeeping

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