Markets are at record highs again. If you’ve been diligently dollar-cost averaging into your 401(k) for years, watching your portfolio grow, you might be feeling pretty good right now. But here’s a critical question: Have you adjusted your risk management to match where you are in life today?
At Dupree Financial Group, we recently revisited some key concepts from Morgan Housel’s excellent book, The Psychology of Money. These principles are especially relevant in today’s market environment, and they might change how you think about your investment strategy.
Housel makes a fascinating observation: “Getting money requires taking risks, being optimistic, and putting yourself out there. But keeping money requires the opposite of taking risk. It requires humility and fear that what you’ve made can be taken away from you just as fast.”
For years, you’ve been an optimist—investing in your 401(k), believing in human ingenuity and the ability of companies to create value. That optimism has likely served you well. But as your portfolio has grown and you’ve moved closer to retirement, have you adjusted your approach?
The risk you were taking at 35 shouldn’t be the same risk you’re taking at 60. Yet many investors continue with the same aggressive allocations simply because “it’s been working.” That’s not a strategy—that’s momentum, and momentum eventually stops.
One of the most powerful concepts in Housel’s book is the idea of “enough.” This isn’t about being conservative or afraid to grow your wealth. It’s about clearly understanding what happens if things go wrong.
If you make this investment and it doesn’t work out, will it derail your retirement goals? That’s the question that matters.
Having “enough” means you can identify a baseline—a number that allows you to accomplish your goals. Once you have that baseline, you can make informed decisions about risk. You can look at your portfolio and ask: “Do these numbers work for me now, where they are today?”
With markets at current valuations and some investors heavily concentrated in high-flying tech stocks, this question has never been more important. Yes, you might have been rewarded for that concentration. But is the additional risk still worth it if you already have enough to meet your goals?
According to Housel, there are some things that should never be risked, no matter the potential gain:
Reputation – In our business, reputation is everything. It’s all we have, and it’s all we’ll ever have. We learned this lesson early when an energy partnership we recommended didn’t work out as planned. Even though legally we weren’t obligated to make clients whole, we did—because our reputation was worth more than the potential loss.
Happiness and Peace of Mind – True wealth isn’t just about a number on a statement. It’s about having the freedom to make choices, to sleep well at night, and to do what’s right when the opportunity presents itself. We’ve seen clients with substantial portfolios who aren’t happy because they’re constantly worried about market volatility. And we’ve seen clients with more modest portfolios who sleep soundly because their investments align with their goals and values.
Freedom and Independence – The real value of wealth isn’t in consumption—it’s in the flexibility it provides. The ability to choose what you do with your time, to help family members in need, to support causes you care about—that’s what financial independence really means.
Here’s something most financial advisors won’t tell you: life isn’t a spreadsheet.
From a purely mathematical standpoint, it might not make sense to pay off a 3.5% mortgage when you could potentially earn more in the market. But if paying off that mortgage helps you sleep better at night and aligns with your values, then it’s the right decision for you.
We call this being “reasonable” rather than purely “rational.” Reasonable takes into account your feelings, your values, and what makes sense for your life—not just what looks best on paper.
This principle applies to investment strategy too. Right now, many investors are actively trading stocks, caught up in the AI and tech frenzy. They’re buying this stock, selling that one, assuming they
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