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_{Exploring tax folly, not knowing, and alignment}

Happy Sunday! Thanks for reading Intentional Dollar — where we look at old money ideas through a new perspective.

What’s inside?

• One idea to experiment with

• Two quotes from others

• Three questions to dig deeper

• Four lines of poetry for the point

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

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_{One idea to experiment with:}

Tax Folly

It’s that time again. CPAs are emailing their checklists. W-2s, 1099s, K-1s, and the like are rolling in. If you didn’t do much planning in 2025, now might be the moment you start to sweat.

What bracket will I fall into?
Will I owe this year?
How much?
What can I still do?

The fear of owing at tax time causes a lot of folly. We get so focused on the short-term tax bill that we end up making decisions with long-term consequences.

Let’s say you run your projections and discover you owe the IRS $1,000. That prospect sends you spinning. You scan your accounts and realize you can still make prior-year contributions to a spousal IRA or an HSA. You’ve got $5,000 of available capacity, just enough to eliminate the tax bill entirely. You move the money, erase the liability, and feel a deep sense of satisfaction that you stuck it to Uncle Sam.

But a few things are worth noting.

From a cash perspective, you’re now down $5,000 instead of the $1,000 you would have been by simply paying the tax. You’ve traded a manageable expense for a $4,000 reduction in liquidity.

You’ve also made a long-term decision with money you hadn’t planned to commit throughout the year. How long will it be before you can access those funds again? What trade-offs did you just lock in?

And what if you had already saved enough in retirement accounts or your HSA? Yes, eliminating the tax bill “saves” money. Your net worth will be higher than if you had paid the tax outright. But net worth alone doesn’t tell you much about financial robustness, about how resilient your overall structure really is.

There are times when playing the tax game makes sense. Intentional, well-planned contributions aligned with broader goals can be incredibly powerful.

But more often than not, these moves happen in a moment of panic. Once the potential liability shows up on the screen, our brains flip into solver mode, frantically racing through the maze toward one outcome: make the tax bill go away.

Be strong this tax season. Remember that refunds aren’t windfalls, but interest-free loans to the government. And avoiding tax at all costs can be far more expensive than simply writing the check

_{Two quotes on not knowing}

The base to acquire a little more knowledge than you presently own is to debase the knowledge you think you have. Question the assumptions and rebuild from the ground up.

_{Three questions on alignment:}

1. Are my actions aligned with my priorities?

2. Is my spending aligned with my values?

3. Are my goals aligned with my internal metrics, or an external scorecard?

Which question stuck with you? Questions like these are spotlights for the mind. Reply to this email and let me know which one shined light on a previously dark cave.

_{Four lines of poetry for the point:}

Contact Me:

Content ideas, questions? Reply to this email or reach out to me at [email protected]

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

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