Look Poor. Retire Rich. The Retirement Tax Hack Nobody Talks About.
Jun 03, 2025When most people think of retirement, they imagine beach vacations, spoiling the grandkids, and finally having time to enjoy life. But what if the secret to achieving that dream lies in looking poor on paper?
That’s right. According to retirement planning expert Leibel Sternbach, appearing broke—at least to the IRS—could be your smartest financial move in retirement.
Why Looking Poor Makes You Richer
It sounds counterintuitive, but here's the logic: The U.S. tax system rewards people with lower incomes. That means if you can legally reduce your taxable income in retirement, you gain access to more benefits, pay fewer taxes, and avoid common financial traps that trip up many retirees.
As Leibel explains, it’s not about wearing tattered clothes or living without luxuries—it’s about controlling how much of your income shows up on your tax return. The less you report, the less you owe.
The Tax Traps You Need to Avoid
There are several hidden "gotchas" that can eat away at your retirement savings:
-
Required Minimum Distributions (RMDs): These IRS-mandated withdrawals from your retirement accounts can push you into a higher tax bracket.
-
Social Security Taxes: Depending on your income, up to 85% of your Social Security benefits can be taxed.
-
Medicare Premiums (IRMAA): If your income crosses certain thresholds, your Medicare premiums increase significantly—up to $10,000 a year in some cases.
-
Capital Gains Tax: Higher taxable income also means higher rates on your investment gains.
How to Beat the System (Legally)
So how do you play smart? Leibel recommends a few powerful strategies:
-
Roth Conversions
By converting traditional IRA or 401(k) funds into a Roth IRA, you pay taxes now at a potentially lower rate and let that money grow tax-free for life. This reduces your future RMDs and protects your Social Security from taxation. -
Withdraw Strategically
Take distributions from your retirement accounts before touching taxable brokerage accounts. This helps manage your tax bracket more effectively. -
Leverage Real Estate and Business Ownership
Owning assets like rental property can provide depreciation benefits that reduce your taxable income. Business income can also be structured to take advantage of deductions. -
Avoid High-Yield Tax Traps
That high-interest savings account might be hurting you. The interest it earns shows up as income and could push you into a higher tax bracket.
Real-World Example: Peter Thiel
Even billionaires use these strategies. Peter Thiel, co-founder of PayPal, famously used a Roth IRA to hold his PayPal stock, eventually growing his account to over $5 billion—tax-free.
It’s Not About Being Cheap—It’s About Being Smart
Looking poor on paper isn’t about deprivation—it’s about being strategic. With the right moves, you can pay less in taxes and keep more of your hard-earned savings.
Want to find out how these strategies could work for your retirement?
Book your free retirement tax consultation now: https://www.yields4u.com/pages/book
You’ve paid into the system your whole life. Now it’s time to make the system work for you.
Have Questions? Get the answers you need.