How High Earners Can Avoid Unexpected Tax Bills
The phone call always starts the same way:
“How do I owe over $10,000 in taxes?!”
As an Enrolled Agent, I hear this more often than you’d think. Let me share a recent story that might sound familiar…
A military power couple — both high-ranking officers — came to me for tax preparation. Their income sources seemed straightforward:
• Two military W-2s
• Some “casual” day trading on Robinhood
Simple enough, right?
Wrong.
When I finished their return, they were shocked by a five-figure tax bill. “But they take taxes from us all year long!” they protested.
Here’s what happened — and why it matters to you.
The Three Tax Traps for High Earners
If you’re facing an unexpected tax bill, it usually comes down to these three culprits:
- Insufficient Withholding
• Your W-4 isn’t optimized for your total income
• Multiple income sources complicate your tax situation
• Deductions changed from previous years - Self-Employment Income Without Estimated Taxes
• Side businesses
• Consulting work
• 1099 income - Capital Gains
• Stock market trades
• Cryptocurrency transactions
• Real estate sales
• Investment property income
In my military couple’s case, their successful day trading created significant capital gains — but their withholding was only set up for their military pay and guess what? They werent witholding enough.
The $10,000+ Problem… And Its Solution
Here’s what most people do:
• File taxes
• Get shocked by the bill
• Pay it
• Repeat the cycle next year
Here’s what smart taxpayers do:
• Work with a tax advisor
• Plan throughout the year
• Adjust withholdings proactively
• Maximize available deductions
• Structure investments tax-efficiently
The Missing Piece: Tax Planning
Think of it this way:
• Tax preparation is looking in the rearview mirror
• Tax planning is looking through the windshield
For high earners and business owners, tax planning isn’t optional — it’s essential.
What Professional Tax Planning Includes:
• Quarterly review of income and projections
• Strategic timing of income and deductions
• Investment tax efficiency analysis
• Business structure optimization
• Retirement account strategies
• Real estate tax planning
Your Next Steps
If you’re:
• Earning over $100,000 annually
• Running a successful business
• Actively investing
• Or combining multiple income streams
You need more than just tax preparation. You need a tax strategy.
Here’s What To Do:
- Schedule a Tax Strategy Session
We’ll review:
• Your current tax situation
• Potential savings opportunities
• Customized tax planning strategies
• Implementation timeline - Get a Clear Action Plan
• Specific steps to optimize your tax position
• Quarterly checkpoints
• Year-end strategies - Start Saving Money
• Implement recommendations
• Track progress
• Adjust as needed
Don’t wait for another $10,000 surprise.
Click here to schedule your Tax Strategy Session.
Special Offer: First-time clients receive a complimentary tax projection ($500 value) during their strategy session.
Until Next time,
Andrew “ The Planner” Samaniego, EA
Andrew Samaniego Tax Planning & Resolution
(619) 268–1084 | AndrewSamaniego.com
Remember: The best time to plan your taxes was last December. The second best time is today.
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