553: How To Think about Taxes

If you’re paying a ton in taxes right now… it’s because you’re playing the wrong game.

Most people think taxes are about income. They’re not. They’re about behavior—more specifically, incentivizing behavior. The government is constantly telling you what it wants through the tax code, and once you stop looking at it emotionally, it’s actually pretty obvious.

It wants businesses. It wants jobs. It wants housing. It wants capital deployed in specific areas like energy and infrastructure. And when you do those things, it rewards you with lower taxes.

Now contrast that with the high-income W2 professional. You did everything right. You trained forever, built a career, and you’re producing at a high level—often doing a lot of good in the world. But the government doesn’t see working for someone else as something it needs to incentivize. In fact, as a high-earning professional, you often end up paying a higher effective tax rate than almost anyone else.

Not because you’re doing something wrong, but because you’re not doing what the system is designed to reward.

I know that doesn’t feel fair. But fairness isn’t really the point.

The people who seem like they’ve “figured out taxes” aren’t gaming the system. They’ve simply figured out what the government wants and aligned themselves with it.

If all your income is W2, you’re largely boxed in. But when you start owning assets—businesses, real estate—you step into a completely different framework. Now you’re not just earning income, you’re creating it. You have expenses, deductions, and depreciation that fundamentally change how that income is recognized. Same economic reality, very different tax outcome.

This is one of the biggest advantages of real assets over simply owning stocks and bonds. It’s not just about return—it’s about control over how you’re taxed.

And if you really think about it, you should be looking at your financial life like a business. You already have revenue in the form of your paycheck, and you have expenses. But your biggest expense, by far, is your tax bill. If you want to maximize your “profit,” you have to figure out how to reduce that expense. And the only real way to do that is to change your facts—change how you earn, what you own, and how your income shows up.

That shift—from focusing on how much you make to focusing on what you keep—is really what this whole conversation is about.

It’s also exactly where this week’s podcast goes. I had a conversation with Steven M. Sheffrin that digs into how tax systems actually work in the real world. Not in theory, but in terms of how people respond to them—psychologically and behaviorally—and why so many well-intended policies fail because they ignore that.

If you want a better mental model for thinking about taxes—and how to position yourself within the system—it’s worth a listen.