Quarterly Tax Strategies for Small Business Owners

Weekly Tax Tips

January 26, 2026

Weekly Tax Tips

Trivia Question❓

Which expense category is most commonly underreported by small business owners, despite being fully legitimate?

Answer at the bottom of the newsletter

Quarterly Tax Strategies for Small Business Owners

Quarterly tax planning is one of the most effective ways small business owners can stay in control of cash flow, reduce surprises, and make smarter financial decisions throughout the year. Instead of scrambling when deadlines arrive, a quarterly approach allows you to adjust in real time and make decisions while they can still have an impact.

One of the most valuable habits is revisiting estimated tax payments each quarter. Because business income often fluctuates, relying on last year’s numbers can result in underpayments, overpayments, or unnecessary stress. Reviewing year-to-date income and expenses alongside prior-year performance helps ensure estimates stay aligned with how the business is actually performing.

Quarterly reviews also create an opportunity to tighten up expense tracking. Small, overlooked purchases can quietly add up, and missed deductions often stem from inconsistent categorization. Taking time every few months to reconcile accounts and clean up records keeps books accurate and reduces last-minute guesswork at tax time.

Timing plays a critical role in tax efficiency. In stronger quarters, accelerating certain expenses—such as equipment purchases, software renewals, or planned professional services—may help reduce taxable income. During slower periods, it can make sense to delay spending or income when appropriate. These decisions are most effective when they’re considered before the quarter closes, not after.

Payroll and contractor payments deserve regular attention as well. Ensuring workers are properly classified, withholding is accurate, and payments are reported correctly can help avoid penalties and administrative headaches later. This is especially important for businesses that rely on independent contractors or seasonal help.

Retirement planning is another area where quarterly reviews can pay off. Many small business retirement plans allow flexible contribution timing, making it possible to increase contributions during profitable periods while still supporting long-term financial goals.

Quarterly planning isn’t just about compliance—it’s about clarity. Regular financial check-ins create space to evaluate performance, identify opportunities, and address potential issues early. Sharing these updates with a trusted tax professional before a quarter ends often leads to better outcomes than waiting until year-end.

When done consistently, quarterly tax planning transforms taxes from a once-a-year burden into an intentional, strategic part of running a successful business.

💼Is Your Retirement Really Protected?


Your IRA or 401(k) may be tax-deferred, but it’s not tax-free, lawsuit-proof, or safe from future rule changes. Learn how to protect your retirement savings, create tax-efficient income, and reduce future tax exposure...all in this free educational webinar hosted by CPA and tax coach Gary Heldt.


🎓100% educational. Nothing will be sold.

Want to Sell Your Real Estate Without Paying Capital Gains?


Join our free webinar on Thursday, Jan. 29th at 2PM ET to learn how our Real Estate Diversification Trust can help you legally sell appreciated land or property, eliminate capital gains and estate taxes, and unlock lifetime income...without DSTs, CRUTs, or IRS red flags.
 
Plus, attend live for a chance to win a luxury 5-star resort stay!

Legacy Webinar - Inspiring Family Generosity

Stories connect us...and generosity defines us.

In this free one-hour session, estate planning expert Stan Miller will show you how to preserve your family’s stories to pass on values like generosity, connection, and purpose.

Register now to preserve the generosity that defines your legacy.

📋 Event Details:
Date: Thursday, January 29th, 2026
Time: 12PM–1PM Eastern
Location: Zoom (link provided after registration)

📣 Bonus: One lucky attendee will win a 3-night, 4-day stay at a 5-star resort...but you must attend live to be eligible!

💡 Answer to Trivia Question:

Small recurring expenses like software subscriptions and professional tools.

Watch this 6 minute video about how to import anyone else's social media networks and turn them into leads for your business: Watch HERE!

Watch this 7 minute video about how to direct message anyone who interacts with your online ads, or your competitor's ads: Watch HERE!

Want to Grow Your Business with a Podcast? Grab a copy of my new book here: Ultimate Podcast Book

Get ready to level up your trading game with Troy Noonan!

Step Into The Backpack Trader Life is your weekly podcast hosted by Tory Noonan, dedicated to unraveling the real stories behind the trading world. Whether you're a beginner or a seasoned pro, this show dives deep into the strategies, tools, and mindset needed to succeed in the fast-paced world of trading. Each episode features insightful conversations, actionable tips, and inspiring stories from both new and experienced traders. So grab your backpack, step into the life of a trader, and join Tory as he navigates the highs and lows of trading, entrepreneurship, and personal growth.

Listen now on Apple Podcasts: Step Into The Backpack Trader Life