It is mid-July 2026. For most business owners, “tax season” feels like a distant memory: or a looming shadow they won’t have to face until next spring.
But here is the truth that the most successful entrepreneurs know: Tax season is a myth. If you are only thinking about taxes in March or April, you aren’t planning; you’re just performing an autopsy on your bank account.
At Haller Group, we don’t just “do taxes.” We are tax strategists who believe in a Year-Round advisory relationship. By the time December 31st rolls around, most of your opportunities to save money have already expired. The real magic happens right now, in the heat of the summer, when there is still enough runway to pivot, invest, and restructure.
Here are the 7 critical moves every business owner should make before the sun sets on the third quarter.
1. Audit Your Multi-Entity Structure
Most businesses start as a simple LLC or a sole proprietorship. As you grow, that structure often becomes an anchor rather than a sail. One of the most powerful moves we make for our clients involves multi-entity level strategies.
Are you still operating entirely under one roof? You might be missing out on significant tax arbitrage. For example, holding your business real estate in a separate entity from your operations can provide both asset protection and unique tax advantages through rental income and Section 199A (QBI) deductions.
Mid-year is the perfect time to evaluate if an S-Corp election (using Form 2553) is appropriate or if a management company structure could help shift income into lower tax brackets or more favorable entity types.
2. Maximize Section 179 and Bonus Depreciation
If you’ve been eyeing new equipment, vehicles, or technology, don’t wait until the week before Christmas to pull the trigger. Supply chains in 2026 can still be unpredictable, and the IRS requires assets to be placed in service: not just purchased: by December 31.
Under IRC Section 179, you can often deduct the full purchase price of qualifying equipment in the year you buy it. Furthermore, while bonus depreciation has seen various phase-outs, it remains a potent tool for 2026.
Pro Tip: Your tax strategist should model whether it’s better to take the full deduction now or save some for 2027 if you anticipate being in a higher tax bracket next year.
3. Implement or Refresh Your “Accountable Plan”
Are you paying for business expenses out of your personal pocket? Or perhaps you’re “reimbursing” yourself without the proper paperwork? Without a formal Accountable Plan, the IRS may view those reimbursements as taxable income.
A mid-year checkup ensures your plan is up to date, allowing you to deduct:
- Home office expenses (under IRC § 280A).
- Travel and mileage (ensure your 2026 logs are current!).
- Internet and cell phone usage.
This is also a smart time to coordinate your Accountable Plan with two other high-impact strategies:
- The Augusta Rule. Under IRC § 280A(g), you may be able to rent your home to your business for up to 14 days per year without recognizing that rental income on your personal return, as long as the arrangement is properly documented and the rate is reasonable. For many owners, that can create a clean deduction at the business level and tax-free income personally.
- HRA plans. A properly designed Health Reimbursement Arrangement can allow the business to reimburse qualifying medical expenses on a tax-advantaged basis, depending on the structure and eligibility rules. The IRS provides core guidance in Publication 969 and Publication 502.
The key is planning at the entity level, not just the transaction level. In many cases, multi-entity level strategies can help business owners stack reimbursements, home-use strategies, and health plan design in a way that supports both tax savings and long-term wealth creation.
Getting this right now means clean books in January and more money in your pocket today.
4. Supercharge Your Retirement Strategy
Are you still just “maxing out” a traditional IRA? For high-earning business owners, that’s barely scratching the surface.
July is the time to look at Cash Balance Plans or Defined Benefit Plans. These allow for much higher contribution limits than a standard 401(k): sometimes exceeding $200,000 in tax-deductible contributions depending on your age and income. These plans require specialized setup and actuary calculations, which is why you cannot wait until December.
Check our 2026 Important Tax Dates to ensure you don’t miss the setup deadlines for these powerful wealth-building tools.
5. The 5 Tax-Free Accounts Every Client Should Know
A strong retirement plan matters, but it should not be your only bucket. The most resilient tax strategy usually includes multiple pools of money that can grow, compound, and in many cases come out tax-free when structured correctly.
Here are five tax-free or tax-advantaged accounts we regularly review with clients:
- Roth IRA. Qualified distributions from a Roth IRA can be tax-free if you meet the holding period and age requirements. See IRS Publication 590-B.
- Roth 401(k). This can be a powerful option for business owners and key employees who want tax-free qualified withdrawals in retirement, subject to plan rules. See the IRS overview of retirement plans.
- Health Savings Account (HSA). For eligible individuals, an HSA offers a rare triple tax benefit: deductible contributions, tax-free growth, and tax-free distributions for qualified medical expenses. See IRS Publication 969.
- 529 Plan. While contributions are generally not deductible for federal purposes, growth and qualified education distributions are tax-free under IRC § 529.
- Cash Value Life Insurance. When properly designed, life insurance can provide tax-advantaged access to policy values and tax-free death benefits under IRC § 101(a). This is not a one-size-fits-all solution, but for the right client it can play an important role in legacy planning and liquidity.
The real opportunity is not just opening accounts. It is coordinating contribution limits, cash flow, entity structure, compensation design, and family goals so each account works as part of a bigger tax and wealth strategy. That is where Year-Round planning creates outsized value.
6. Optimize the QBI (Qualified Business Income) Deduction
The Section 199A deduction allows many business owners to deduct up to 20% of their qualified business income. However, this deduction is subject to complex “phase-outs” based on your total taxable income and the type of business you run (SSTBs).
If your income is hovering near the threshold, a tax strategist can help you make moves right now to lower your taxable income: perhaps through a large equipment purchase or an increased retirement contribution: to “rescue” your QBI deduction. Waiting until year-end often makes these thresholds impossible to beat.
7. Strategic Hiring of Family Members
If you have children or family members who can perform legitimate work for your business, hiring them can be a brilliant income-shifting strategy.
By paying a reasonable wage for actual services (like social media management, cleaning the office, or data entry), you shift income from your high tax bracket to their lower (often 0%) bracket. Plus, they can use that earned income to start a Roth IRA, building multi-generational wealth. Just ensure you are following all IRS payroll guidelines and documenting their work.
Why a “Tax Strategist” Beats a “Tax Preparer”
Most people hire someone to look in the rearview mirror. They gather their receipts, hand them over in February, and hope for the best.
At Haller Group, we look through the windshield. We prioritize an ongoing advisory relationship because we know that your business is dynamic. Your goals change, the laws change, and your strategy should change with them.
Our proactive approach focuses on:
- Holistic Optimization: Looking at both your business and personal finances as one ecosystem.
- Wealth Creation: Using tax savings to fuel investments that build your long-term net worth.
- Personalized Strategy: No “cookie-cutter” templates. Your entity structure and plan are tailored to your specific life goals.
Don’t wait for the year-end crunch. Let’s make sure you’re paying the absolute minimum required by law while maximizing every dollar you earn.
Contact Haller Group today to schedule your mid-year tax strategy session.
