I’m a Boomer: The Best $500 I Spent To Boost My Retirement Savings

A jar of $100 dollar bills next to a jar of coins labeled "Retirement."
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While $500 doesn’t seem like much money in the context of a 30-year retirement, a small amount of money can open up massive tax savings. 

These baby boomers and investing experts found the following $500 investments to pay massive dividends in the years that followed. 

Tax Planning Software

Julia Rueschemeyer, divorce attorney, said the best $500 she ever spent to boost her retirement savings went toward tax planning software. 

“I spent $149 on the Maxifi financial planning software which does complicated calculations about federal, state and IRMAA taxes along with RMD’s,” Rueschemeyer explained. “Counterintuitively, it shows you how massive (e.g., $1,000,000) Roth conversions can save you hundreds of thousands of dollars over thirty years, even if it temporarily puts you in nosebleed tax brackets today.”

She went on to explain that while you can’t control your investment returns, you have more control over your taxes. By losing less money to taxes in retirement, you don’t need to save as much for a nest egg.

“The tax strategies I’m using are saving me a couple hundred thousand dollars over the course of my lifetime,” Rueschemeyer added.

Tax Strategy Session

Not everyone wants to DIY their tax planning. For them, that $500 can go toward sitting down with a certified public accountant (CPA) or a certified financial planner (CFP) for a few hours. 

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Financial planner Jay Zigmont of Childfree Trust pointed out that most workers and retirees don’t know which accounts they should withdraw from in which order in retirement. “You need to know what money to use and when to lower your total tax bill. Your tax plan will also outline when you should do a Roth conversion and how to avoid IRMAA surcharges.”

Health Savings Account

Many Americans don’t realize that health savings accounts (HSAs) offer the best tax benefits of any account. They combine the immediate tax deduction of a traditional IRA with the tax-free withdrawals of a Roth account. 

“This oft-overlooked account is one of the best ways to save for healthcare costs during retirement,” said Whitney Stidom of eHealth. She urged investors to think of their HSA not just as health savings, but as a secondary retirement account. In 2026, the individual contribution limit rises to $4,400 and the family limit rises to $8,750. 

These accounts do require a high-deductible health plan — which could either save you money or cost you money, depending on your health-related spending in any given year. 

Precious Metals

Beyond investment returns, you also don’t have any control over inflation, government debt or loss of purchasing power. 

Joshua Glawson of MoneyMetals.com noted that $500 in cash today doesn’t go very far. But for people like him who invested $500 in gold years ago, today it’s worth many times more and keeps growing. 

“The federal government is not expected to stop with easy money printing. As the dollar falls, we will continue to see a rise in the purchasing cost of gold, silver and other precious metals,” Glawson said.

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Beyond a hedge against a weakening dollar, it also hedges against stock market bubbles and geopolitical risk. You can’t control macroeconomic trends. But you can control your own tax and investment strategies and protect against risks like future tax hikes. 

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