Mid-Year Tax Check-In: 5 Questions to Ask Your CPA Now

Most business owners only think about taxes in April. Or maybe December, when it's almost too late to do anything about it.

Here's the truth: The best time for tax planning is mid-year. You have six months of real data and six months to actually do something about it.

If you haven't checked in with your CPA since last tax season, here are the five questions you should be asking right now.

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1. "Am I on Track for My Estimated Payments?"

If you're self-employed or own a business, you're (hopefully) making quarterly estimated tax payments.

But are you paying the right amount?

If you're underpaying: You'll owe a big check in April, plus penalties. If you're overpaying: You're giving the IRS an interest-free loan.

Mid-year is the perfect time to recalculate. Your CPA can look at your actual income so far and adjust your Q3 and Q4 payments to avoid surprises.

The question to ask: "Based on my income through June, should I adjust my quarterly payments?"

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2. "Should I Make Any Big Purchases Before Year-End?"

If you're planning to buy equipment, vehicles, or other business assets, timing matters.

Section 179 and bonus depreciation let you deduct large purchases in the year you buy them—but only if you buy them before December 31.

Mid-year is the time to plan this out:

• What purchases are you considering?
• Do you have the cash flow?
• Will the deduction actually benefit you this year?

Real example: A Richardson contractor was planning to buy a $60,000 truck in January. We moved it to December instead—same truck, but he got the deduction a full year earlier. That's $15,000+ in tax savings, sooner.

The question to ask: "Are there any purchases I should accelerate or delay for tax purposes?"

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3. "Is My Business Structure Still Right?"

When you started your business, you probably picked the simplest structure—sole proprietor or single-member LLC.

But as your income grows, that structure might be costing you thousands in unnecessary self-employment tax.

The S-Corp question: If you're consistently earning $60,000+ in profit, S-Corp election could save you $5,000-$15,000 per year.

But here's the thing: the deadline to elect S-Corp status for the current year is March 15. If you wait until tax time to ask, you've missed it.

Mid-year is when we should be evaluating whether a change makes sense for NEXT year.

The question to ask: "Based on my projected income, would a different business structure save me money?"

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4. "Am I Maximizing Retirement Contributions?"

Here's a quick win most DFW business owners miss: retirement contributions.

With a SEP-IRA or Solo 401(k), you can contribute up to $69,000 in 2026. That's money that:

• Reduces your taxable income now
• Grows tax-free until retirement

But you can only contribute based on your income. Mid-year is the time to project:

• How much can you contribute?
• Do you have the cash flow?
• Should you set money aside monthly?

The question to ask: "What's my maximum retirement contribution this year, and how do I make sure I hit it?"

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5. "What Should I Be Tracking That I'm Not?"

Tax deductions only count if you can prove them. Mid-year is a great checkpoint to make sure you're tracking what matters:

• Mileage: Are you logging business miles?
• Home office: Do you know your square footage?
• Meals: Are you saving receipts and noting who you met with?
• Professional development: Courses, conferences, subscriptions?

If you're not tracking something now, you won't have records come tax time.

The question to ask: "What documentation should I be keeping that I might be missing?"

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Why Mid-Year (Not December)?

December planning is better than no planning. But it's reactive.

By December, you can only:

• Rush purchases before year-end
• Maybe squeeze in a retirement contribution
• Hope for the best

By mid-year, you can:

• Adjust estimated payments (4-6 months of runway)
• Plan major purchases strategically
• Restructure your business for next year
• Set up systems for better tracking
• Actually implement changes

Six months of real data + six months to act = better outcomes.

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What a Mid-Year Check-In Looks Like

At LeCPA, here's what we cover in a mid-year review:

1. Year-to-date income and expenses — Where are you vs. last year?
2. Projected annual income — What are we planning for?
3. Estimated tax status — On track, over, or under?
4. Deduction opportunities — What's coming up?
5. Entity structure review — Still optimal?
6. Action items — What do you need to do before December?

It's usually a 30-45 minute conversation that can save thousands.

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The Bottom Line

If you haven't talked to your CPA since April, now's the time.

The business owners who pay the least in taxes aren't doing anything fancy—they're just planning ahead instead of reacting.

If you're in Plano, Richardson, Frisco, or anywhere in DFW, let's do a mid-year check-in. It's the best 30 minutes you'll spend on your business this month.

Let's do a quick mid-year check. Book 30 minutes →

— Krystal Le, CPA

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LeCPA provides year-round tax planning for small business owners across Plano, Richardson, Carrollton, Frisco, and Dallas.