Tax season is officially underway. Whether you’re an individual taxpayer or a business owner, this is the best time of year to get proactive — not just to survive April 15, but to pay less in taxes next year.
Here are practical, legal moves you can make right now to reduce stress, avoid surprises, and keep more of your money in 2026.
1. Get Organized Early (This Alone Saves Money)
The biggest tax bills usually come from disorganization.
Do this now:
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Gather W-2s, 1099s, mortgage interest statements, and investment summaries
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Reconcile your bank accounts
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Make sure your income records match what was reported to the IRS
For businesses:
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Clean up QuickBooks (or your bookkeeping system)
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Verify contractor payments and W-9s
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Separate business and personal expenses
Clean records reduce errors, missed deductions, and costly last-minute fixes.
2. Review Last Year’s Return for Clues
Your most recent tax return is a roadmap.
Look for:
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High tax owed or low refund
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Missed deductions or credits
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Self-employment tax surprises
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Underpayment penalties
If something hurt last year, it’s a signal that planning - not just preparation - is needed.
3. Adjust Withholding or Estimated Payments Now
If you owed money last year, waiting until December to fix it is too late.
Individuals:
Business owners:
Small adjustments now can prevent a painful April bill later.
4. Track Deductions Monthly (Not Annually)
Most missed deductions are forgotten deductions.
Commonly overlooked items:
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Home office expenses
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Mileage and vehicle use
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Phone and internet (business portion)
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Software, subscriptions, and education
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Health insurance for the self-employed
Create a habit of reviewing expenses monthly instead of scrambling once a year.
5. Make Smart Retirement Moves
Retirement contributions lower today’s tax bill and build future security.
Depending on your situation:
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Traditional IRA or Roth IRA
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SEP IRA or Solo 401(k) for business owners
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Employer retirement plans
Contribution timing and account type matter - this is an area where advice pays for itself.
6. Business Owners: Think Beyond Write-Offs
Write-offs are good. Strategy is better.
Examples of forward-looking tax planning:
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Choosing the right entity structure
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Timing income and expenses
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Depreciation strategies
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Retirement and health-related deductions
If your tax strategy is limited to “save receipts,” you’re likely overpaying.
7. Don’t Wait Until April 15
April 15 is a deadline, not a strategy.
The best tax moves:
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Happen before income is earned
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Are planned months in advance
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Reduce taxes legally and predictably
If you’re reacting in April, you’re already too late for that year.
Final Thought
Tax season isn’t just about filing - it’s about positioning.
The steps you take now can:
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Lower your 2026 tax bill
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Reduce stress
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Improve cash flow
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Eliminate surprises
Whether you’re an employee, a contractor, or a business owner, proactive planning beats last-minute panic every time.
If you want help identifying which strategies actually apply to your situation - and which ones don’t - that’s where a focused tax review can make all the difference.
by Roy Shipley
Shipley Bookkeeping Solutions
