Dealing with tax collectors, like the IRS, can feel like an uphill battle. It’s frustrating when, despite your best efforts to file correctly, you find out years later you owe more money, plus fines. With a tax code that’s a whopping 70,000 pages long, it’s no wonder many feel overwhelmed and beaten by the system.

Even though every IRS agent I’ve talked to seems nice, it’s still stressful every time their correspondence arrives. It feels like David vs. Goliath—just me against a massive government machine. The complexity of tax laws doesn’t help, and it often feels like the IRS agents themselves struggle to keep up.

Here’s some insider insight from a friend who worked at the IRS. He confirmed that the job is tough and often thankless, made harder by the convoluted tax system designed to benefit tax preparation businesses more than taxpayers. Despite this, he reassured me that most IRS workers are on our side, trying to help rather than hunt us down for every penny.

However, my personal experiences have shown how this system can be merciless. For example, I once received a confusing tax bill from New York State, demanding income tax for a year I barely worked there. Despite proving I shouldn’t owe anything, I learned about the three-year limit for filing an appeal or amendment. So when they contacted me five years later, I had no recourse to reclaim any overpaid taxes.

This experience highlights the IRS’s frustrating “heads I win, tails you lose” approach. They benefit from obscure rules and lengthy documentation, which can trap unsuspecting individuals into paying more than they should.

The system feels particularly predatory when you consider how it uses its power to enforce compliance. The government’s leverage over us is disproportionate, wielding tax policy as a tool to control behavior and keep taxpayers in line.

So, what can you do? Starting a business might be a way to protect more of your income from taxes. Business expenses are deductible, and structuring your finances through a business can significantly lower your taxable income.

Ultimately, the tax system’s complexity and the IRS’s daunting power remind us of the importance of staying informed and prepared. It’s a challenging battle, but knowledge and proactive financial planning can help safeguard your hard-earned money against an often unforgiving tax system.