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Happy Sunday! Here’s what we’re covering in today’s Clark Smart Investing newsletter:
Are you making this common investing mistake?
Should you be nervous about all-time market highs?
What Social Security's 2027 COLA projection could mean for your check
Q&A with Wes Moss: Is it more important to have 2-3 years of dry powder or a paid down mortgage going into retirement?
💵 Are You Making This Common Investing Mistake?
There’s a simple way to make a perfectly good investment portfolio feel like a failure: Compare it to something that did better.
Maybe the S&P 500 gained 20% while your portfolio was up 13%. Or international stocks suddenly took off while most of your money was invested in the U.S. Perhaps a friend tells you how much money he made owning a handful of technology stocks. Suddenly, earning 13% doesn’t feel so great.
This is benchmarking, and Wes Moss, a fiduciary financial advisor and host of Ask an Advisor on the Clark Howard Podcast, says it can be an especially dangerous mistake for retirement investors.
“Benchmarking is a dangerous retirement mistake because it feeds the phenomenon of always seeing something greener on the other side of the investment fence,” Wes says.
The problem isn’t looking at a benchmark. Benchmarks can be useful tools. The problem starts when you use someone else’s performance, or the performance of an index that doesn’t resemble your portfolio, to decide whether you’re succeeding.
Are you making this mistake? Here's why your personal "benchmark" should have nothing to do with the stock market.
📚 Recommended Reading
The stock market just hit another all-time high—so is a crash right around the corner? When the market hits record territory, it's natural to feel nervous and wonder if it's time to wait on the sidelines. But history tells a very different story. Here is what the data reveals about record highs, market momentum, and why sitting in cash might cost you long-term growth. Read more.
While a 3.6% boost would mark the highest adjustment since 2023, a higher COLA doesn't necessarily mean more spending money. Here is what you need to know about the new projection, key dates to watch, and how to prepare. Read more.
Sponsored by Retire Sooner Method
Does more money actually make you happier in retirement? The data in this chart from Wes Moss' new book, The Retire Sooner Method, shows a direct link between your savings and your overall well-being, broken down into three distinct zones: The Red Zone, Yellow Zone and Green Zone.
But your investment assets are just one of the many Retire Sooner Method “Green Zones” Wes explores in the book.

Source: The 2025 Money & Happiness in American survey from Wes Moss’s new book, The Retire Sooner Method
💬 Ask an Advisor
✅ Poll: What’s Your Take?
Every week, we'll ask a new question to get your take on the latest financial trends and topics.
Last Week’s Poll Results
We asked: “Have you regretted any of the "hard to undo" retirement decisions?” Here’s how you answered:
More than one. - (8%)
One. - (15%)
None. - (51%)
Still working / Not retired yet. - (26%)
💸 Money Tip of the Week
Check your files for three essential documents: Taking just a few minutes this afternoon to ensure you have a will, an advance health care directive, and a durable power of attorney ready can save your loved ones from severe legal headaches later. Check out this quick guide to see if you have these three essential documents in place and how easy they are to set up today!
☎ Need Money Help?
The Team Clark Consumer Action Center is a free helpline that can help you navigate your money questions. Call 636-492-5275. Visit clark.com/cac for more information.
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This information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations. Investing involves risk, including the possible loss of principal. There is no guarantee offered that investment return, yield, or performance will be achieved. This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. Any company names shown are for illustrative purposes only and are not a recommendation, offer to sell, or a solicitation of an offer to buy any security. The views and opinions expressed are for educational purposes only as of the date of production/writing and may change without notice at any time based on numerous factors, such as market or other conditions. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.






