I see ads for financial advisors saying “It’s not too late!” to catch up on your retirement savings over the next ten years.
And they often point to current the bull market as a means to make it happen.
Unfortunately, the market doesn’t share that sentiment. Not only is it a dangerous risk, it may turn out to be ineffective.
Why?
The disconnect between what investors feel and what they’re actually doing with their money presents one of the most fascinating paradoxes in today’s financial landscape.
Despite the S&P 500 hovering near record highs just days ago, sentiment gauges have taken a decidedly negative turn.
This isn’t just interesting market psychology. It’s a crucial signal for those of us planning the next decade of our financial lives.
According to Joseph Adinolfi of MarketWatch:
“A number of popular sentiment gauges have highlighted growing uncertainty about where the market might be heading next.” The latest reading from the American Association of Individual Investors saw the eight-week moving average of bullish sentiment slide to 33.9%, the lowest since November 2023.
Yet many investors continue putting money into stocks. What explains this contradiction?
The truth is that experienced market watchers understand a troubling reality: the foundations supporting this bull market are starting to show cracks, even as the headline numbers remain strong.
I’ve witnessed this pattern before, and likely so have you. Market sentiment often shifts before prices reflect the changing reality. The smart money starts positioning differently while the indexes still look healthy.
The Hidden Risks Behind Today’s Market
The bull market in stocks has delivered massive gains over the past two years. But several key factors now threaten this impressive run.
For one, stretched valuations have left equities vulnerable to disappointment.
Warren Buffett’s actions speak volumes here. Berkshire Hathaway has amassed a cash pile exceeding $300 billion. When the world’s most successful investor keeps that much powder dry, it warrants attention.
Worse, the 94-year-old investment legend has taken a break from his usual patriotic boosterism, and instead is warning about the risks to America from “fiscal folly” and from “scoundrels and promoters” who “take advantage of those who mistakenly trust them.”
Meanwhile, uncertainty surrounding Donald Trump’s policies on trade and immigration has complicated the economic outlook. As Kevin Gordon, senior investment strategist at Charles Schwab, noted:
“There has been this anxiety creeping into the market, whether it is trade-related or immigration-related. You can kind of take your pick with all that is going on in Washington.”
Rising prices have rekindled inflation concerns, while Friday’s University of Michigan consumer sentiment data reflected growing unease about the economy. The markets responded with the biggest daily drop of 2025 last Friday, with the S&P 500 alone falling 104.39 points.
These developments create a challenging environment for anyone counting on traditional investment approaches to fund their future. This matters doubly for those of us in our 50s who may be looking at traditional retirement strategies.
As I mentioned, some financial advisors nonetheless say you can still aggressively “catch up” on retirement savings through market investments. That’s incredibly risky, with threats to the economy in the form of political upheaval, the massive U.S. deficit, and job losses due to artificial intelligence looming on the horizon.
But there’s a less catastrophic but equally unsettling alternative scenario. What if the next decade simply delivers flat or negative returns?
The Intelligent Alternative to Market Dependence
Mike Wilson of Morgan Stanley predicts the S&P 500 annualized returns to be roughly flat over the next 10 years, which is an opinion that’s becoming consensus on Wall Street.
There’s a simple explanation for why: valuations, which account for much of how equities perform over a 10-year period, are historically elevated.
“My comment is not a controversial view based on valuations,” Wilson told Business Insider. “That is a very common view, that given where valuations are today, over the next 10 years, the returns from point A to point B will be basically flat-ish, and on a real basis, maybe negative.”
Unretirement planning isn’t about abandoning traditional investments entirely. Rather, it’s about creating a foundation of self-generated income that lets you participate in markets (including international markets) opportunistically, not desperately.
For those in their 50s especially, developing location-independent income streams represents a practical alternative to frantically chasing market returns to fund traditional retirement. Instead of hoping markets will deliver precisely when you need them to, you’re building systems that generate income on your terms.
The Wall Street wisdom says stocks climb a “wall of worry.” Maybe so. But I’ve found it far more reliable to build your own financial staircase. One that leads to income security regardless of what markets do next.
Creating Your Own Financial Security
In my personal experience, I’ve found that creating your own income streams offers protection that market investments simply cannot match. I’ve made way more money from my businesses than I have with stocks or even real estate.
When the S&P 500 tumbled last Friday, my business continued generating revenue exactly as it had the day before. That’s not coincidence — it’s by design.
Building a location-independent business allows you to:
- Generate income regardless of market conditions
- Scale your earnings based on your own efforts rather than market whims
- Create valuable assets you control directly
- Maintain purpose and engagement while funding your lifestyle
This approach isn’t just financially sound. It also aligns with what most of us actually want from life:
- The freedom to work from interesting locations,
- The autonomy to set your own schedule, and
- The security of knowing your income doesn’t depend on factors beyond your control.
Betting it all on the stock market is risky. Trusting an employer for your sole source of income is even riskier.
