The Mid-Year Tax Checkup Every Business Owner Needs

Don’t wait until the last minute to start tax planning. Mid-year is one of the best times for business owners to review their tax situation. Most business owners wait until year-end to ask, “How can I lower my tax bill?” But by then, some of the best opportunities are already gone. Instead of making proactive tax-saving moves, you’re left doing damage control.

In this episode, Mike walks through a simple mid-year tax checkup every small business owner should do before December. He covers how to review your income, estimate your tax liability, clean up your bookkeeping, evaluate your entity structure, plan retirement contributions, think through major purchases, and identify tax strategies you still have time to implement before year-end.

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Chapters

01:00 Why Mid-Year Is the Sweet Spot for Tax Planning
Mid-year gives business owners two major advantages: enough real financial data to review and enough time left in the year to implement strategies.

03:00 Grade Your Tax Planning Progress
Business owners should evaluate whether they’ve only learned about tax strategies or have actually started implementing them.

04:00 Review Your Bookkeeping Before It Becomes a Problem
Accurate bookkeeping is the foundation of good tax planning. Mid-year is the time to catch missing transactions, miscategorized expenses, personal charges, payroll errors, and missed deductions.

05:20 Review Your Entity Structure
Your business structure should match your current income, profit, and tax strategy. This includes reviewing whether an LLC, S corporation, or multi-entity setup makes sense.

07:40 Review Retirement Contribution Opportunities
Mid-year is a good time to look at retirement plan options, contribution goals, employee benefits, and whether your current plan still fits your business.

09:30 Analyze Big Purchases Before Making Them
Buying equipment or vehicles just for the write-off is not a good strategy. Business owners should review whether the purchase is needed, how it will be paid for, and whether this year or next year makes more sense.

11:10 Look for Missed Tax Strategies
Mid-year still leaves time to implement strategies like hiring your kids, using the Augusta Rule, setting up an accountable plan, reviewing health insurance deductions, and timing income and expenses.

13:20 Review Core and Advanced Tax Strategies
Business owners who already use tax strategies should review whether they’re getting the full benefit. Higher-income business owners may need to look at more advanced planning opportunities.

16:00 Tax Planning Is Not a December Activity
The best tax-saving opportunities happen when business owners still have time to make decisions, fix mistakes, and plan strategically before year-end.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.