Tax Planning Is a What-Have-You-Done-for-Me-Lately Game.

And that's exactly the problem

Author

Vince Porter
March 30, 2026

Table of Contents

Tax Planning Is a What-Have-You-Done-for-Me-Lately Game.

And that's exactly the problem.

The coach who wins the national championship in Year 1 is expected to repeat it in Year 2. When he doesn't, the fans get restless. Tax planning works the same way. We can save a client $200K last year. This year, if we're not replicating that result, they start to lose sight of the value. That's why the multi-year picture matters more than any single number.

The Real Playbook

This year we're working with a client who has a long-term capital gain pushing their effective rate to around 15%. On the surface, that looks like a perfect year to act. Pull deductions forward. Knock down that tax bill. Get the win.

But here's the question we had to ask: what does next year look like?

Is a $15K tax savings today better than a $40K savings 18 months from now?

Income is expected to grow. Their rate could reach 30 to 40% within the next year or two. A $100,000 deduction at 15% saves $15,000. That same deduction at 40% saves $40,000. That's not a rounding error. That's a $25,000 difference on a single decision.

That's the conversation we're having. And that's the conversation every high-income investor deserves.

The Math Behind the Decision

$100,000 deduction at different tax rates:

Deduction today at 15% effective rate → $15,000 saved
Same deduction at 40% rate next year → $40,000 saved
Difference from waiting 18 months → +$25,000

The right answer depends on cash flow, liquidity, and how much certainty you have about future income. That's where time value of money comes in. A dollar saved today is worth more than a dollar saved tomorrow. But when the rate differential is this large, the math can flip.

We're not here to make that decision for you. We're here to make sure you have the information to make it yourself.

What This Means for You

Tax planning done in a vacuum for one year is not tax planning. It's tax compliance. Real planning means looking at the full arc: where you are now, where income is heading, and which years are the right years to act.

Fluctuations happen. Rates matter. And the difference between reacting to one tax year versus planning across 2 to 3 years can be six figures.

Want to map out your multi-year tax picture?

If your income is growing, or you had an unusual year, this is exactly the right time to look ahead. Let's put the numbers in front of you so you can decide.

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