Lookout Outlook | September 2025 | Bookkeeping Newsletter


It’s tax time...again!

Remember back in April when you extended your tax return and then proceeded to totally forget about it until now? Yeah, this newsletter is for you! But WAIT - before you close this because you have already filed, there’s still a deadline you need to know about in September (more on that in a bit).

Okay, listen up extended filers: you could have due dates this month AND in October, depending on the type of return. What’s the due date? September 15th for extended partnership and S corps.

Now, back to the part of this newsletter that could apply to everyone (regardless of whether you extended your tax return or not), your Q3 estimated tax payments are also due on the 15th.

If you expect to owe at least $1,000 in taxes when you file your return (after withholding and credits), you probably need to be making estimated payments. You especially need to be aware of this if you’re self-employed, earn rental or investment income, or have any other sources of significant income not subject to withholdings.

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

🙃“It connects to QuickBooks, so it must make my life easier.”
…famous last words. I can’t tell you how many times I’ve seen integrations turn a clean set of books into a dumpster fire:

  • POS systems dumping in thousands of line items
  • Project management tools double-invoicing
  • Payment processors creating “mystery income”

Here’s the rule: if it makes your books messier, don’t connect it. Your books should show financial reality, not become a junk drawer for every tool in your tech stack.

👉I broke down the biggest headaches with these "simple" integrations in my latest post. Read it here!


This Month's Freebie!

Systems = Freedom.

After helping dozens of business owners clean up their books and streamline their operations, these are the 3 vendors I recommend every time:

✅ Gusto for stress-free payroll
✅ Relay Financial for a Profit First banking platform
✅ Anchor for seamless proposals and payments

The right tools don't just make life easier — they keep you PROFITABLE.

📈 Want to know how these tools fit into your business? Click below!


Come See Me at The Chattery!

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...

We’re entering one of the busiest times of year (for you and me both!), and I want to make sure everyone gets the support they need without the last-minute stress. If there’s a service you’ve been thinking about, or you’re not sure what you need but know you need something, just hit reply and let me know. I’ll send over the details and help you figure out the next steps!


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.


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

Read more from Lookout Bookkeeping

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Lookout Outlook | July 2025 In your Summer Slowdown era? A slower season in your business gives you uninterrupted time to focus on those back-office business tasks that you've been neglecting! Here's what I'd focus on during a slowdown: Client Onboarding + Offboarding: Create (or revise) a set of standard operating procedures to ensure you follow all the steps on your onboarding and offboarding checklists. Sales Funnel Walkthrough: Walk through your sales funnel yourself and make sure there...

Lookout Outlook | June 2025 Your Official Summer To-Do List If you’re self-employed, part of a pass-through entity, or have other sources of income not subject to tax withholdings, mark your calendar for the Q2 estimated tax deadline on June 16th. If you'd like to add these tax deadlines and more to your calendar, feel free to grab my tax calendar here. Pro Tip: If your income has grown in the first half of 2025 (yay!), your original estimated tax payments from April may no longer be...