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Lookout Outlook | June 2025 | Bookkeeping Newsletter

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...

Lookout Outlook | May 2025 Tax season is over... what’s next? There are three types of people post tax season: those who filed their returns, those who extended, and those who are panicking… If you find yourself in the panic crowd, we can assist with historic bookkeeping to get your 2024 financial reports together! Click here to get started. If you’re in the first two buckets, you can’t get too comfortable! One of the sneakiest tax deadlines of the whole year is the second quarter due date...

Lookout Outlook | April 2025 No April Fools, Taxes Are Due! It's officially coming down to the wire, Tax Day is on April 15th. Let's recap everything that’s due: Individuals: Your Form 1040, or individual tax return, is due. You can file Form 4868 for an automatic 6-month extension to file your return, but your tax payment is still due on April 15th. Failing to pay your taxes owed by this date can result in penalties and interest. If you’re required to pay estimated taxes, your first quarter...

Lookout Outlook | March 2025 Are you suffering from tax-iety? The upcoming March and April tax deadlines have everyone feeling a little nervous... What happens if you can’t get all your documents together and get everything filed on time? Easy answer—you just extend your tax return! While the form you’ll file for an automatic extension changes depending on which type of tax return you’re extending, the process is pretty much the same. You can file electronically or mail your extension form....

Lookout Outlook | February 2025 Roses are Red, Violets are Blue… There are only 68 more days until your individual taxes are due! It's time to ask yourself these questions: FOR BUSINESS OWNERS: Are all my income and expenses entered and categorized for 2024? Have I reconciled my accounts (including any payroll and loan balances)? Have I sent all required 1099s and W-2s? Have I organized additional tax info, including my mileage log, home office deductions, retirement contributions, and...

Lookout Outlook | January 2025 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...

Bookkeeping Newsletter | December 2024 Wrapping up 2024... Whew, what a year! You’re in for a treat today, I’m letting you in on a little behind-the-scenes action of what we we're up to at Lookout Bookkeeping in 2024. Here are the greatest hits from our official Spotify Wrapped: Lookout Bookkeeping Edition! In 2024, Lookout Bookkeeping: Served over 70 clients. Most popular genre (a.k.a industry) was home service providers. Most played songs during work hours was definitely anything from Max...

Bookkeeping Newsletter | October 2024 Here’s what you need to do this month for your taxes: If You Extended: File extended individual tax returns (Form 1040) File extended corporate tax returns (Form 1120) Prepare for next year so you don't have to file an extension To Prepare for 2024 Filing: EOY tax planning with your professional Start planning any EOY charitable donations Collect W-9s from all contractors What happens if I just don’t file? Failure To File Penalty: If you haven’t filed...

Bookkeeping Newsletter | September 2024 Ready to tackle your extended tax returns? September means the kids are settling back into school, football season is kicking off, and you’ve got some pretty important tax deadlines coming up! Let’s go over what’s due on September 16th: Partnership and S Corporation tax returns: If you extended your Form 1065 or Form 1120-2, your tax return is due. Third quarter estimated tax payments: Individuals and corporations need to make their third quarter...

Bookkeeping Newsletter | August 2024 TTYL, Summer! It’s super depressing that summer’s coming to an end (but maybe not so sad that the kids are going back to school!). If you’re anything like me, you’re already looking forward to the extra time to plan your fall marketing campaign. Here are some marketing expenses your business might be able to deduct: Marketing Write-Offs Facebook/Google Ads Branding Photoshoot Copywriting Services Website Design Branded Merchandise Event Sponsorships...