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Mitchell Baldridge - America’s Accountant

🧮 The Known Unknowns (and Unknown Unknowns) of Filing Your Taxes

Published about 2 months ago • 2 min read

@baldridgecpa

ISSUE 28

The Most Honest Tax Letter Ever Written

Tax season has a way of making even the most confident business owners feel uncertain.

You gathered your documents. You worked with a professional (or maybe braved the forms yourself). You filed. You paid. But you still might be asking: "Did I get everything right?"

Welcome to the club.

This is the known unknown of tax season. You know you filed a return. You know the rules are mind-numbingly complex. And you know there’s a decent chance something was missed, misinterpreted, or misunderstood despite everyone’s best efforts.

The tax code is a patchwork of incentives, penalties, exceptions, and contradictions. It was designed to influence behavior (especially for business owners), not to be clear. And for that reason, every April, people hit “submit” on their returns with the quiet fear that they’ve gotten it wrong.

Even former Secretary of Defense Donald Rumsfeld (a man literally responsible for understanding “unknown unknowns”) felt this pain. Every year, he sent the IRS a letter alongside his return that read, in part:

“As in prior years, it is important for you to know that I have absolutely no idea whether our tax returns and our tax payments are accurate, which is a sad commentary on governance in our nation’s capital.”

Most business owners hate paying taxes. Not just because it’s expensive, but because the process feels like a game that can’t be won. Ten times out of ten, an entrepreneur would rather reinvest that time, money, and energy back into their business. Instead, they find themselves navigating a jungle of tax law, hoping they don’t step on a landmine.

Maybe you’re frustrated. Maybe you’re worried. Maybe you’re just exhausted.

All of that is normal.

If there’s one thing worth remembering, it’s that the uncertainty isn’t a you problem—it’s a system problem. The best you can do is stay informed, stay proactive, and surround yourself with good guidance. Rage at the system if you must, but keep building in spite of it.

My team and I are here to help you do that.

​Reach out if you're not happy with how this tax season went (or if you still haven't gotten to your 2024 taxes done). We'll get you back on track so you can confidently keep more of your hard-earned money.

Mitchell Baldridge, CPA, CFP®

Understanding your lifetime effective tax rate is one thing. Doing something about it is another.

If you want a proactive partner to help reduce taxes and maximize clarity, we built Better Bookkeeping just for you.

Ready to chat? Schedule a Tax Strategy Consultation today.
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Mitchell Baldridge - America’s Accountant

It's not what you make, it's what you get to keep

I work with hundreds of high net worth business owners and real estate investors and spend all my time thinking about how they can give less money to Uncle Sam

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