The Tom Dupree Show

Market Highs and Retirement Planning: Essential Investment Strategies for Pre-Retirees in Lexington, KY
Are you a pre-retiree in Lexington, KY, approaching retirement while markets sit at historic highs? In this episode of The Financial Hour, Lexington-based financial advisors Tom Dupree and Mike Johnson break down critical retirement planning strategies for pre-retirees navigating today’s investment landscape. Learn why simple “set it and forget it” approaches may not be enough and discover personalized investment management insights for protecting and growing your retirement wealth.
Current Market Conditions and Pre-Retirement PlanningWith markets reaching unprecedented levels in July 2025, many pre-retirees are questioning their investment strategies. As Tom Dupree explains in the episode:
“The market is effectively as high as it’s ever been… we’re sitting here in the middle of July when it used to be most of the market participants were gone on summer vacation.”
Why Market Timing Matters Less Than StrategyThe traditional “sell in May and go away” market strategy no longer applies in today’s 24/7 trading environment. For pre-retirees, this means:
- Constant market vigilance is necessary
- Diversification beyond tech stocks is crucial
- Active portfolio management outperforms passive strategies
Many pre-retirees rely heavily on S&P 500 funds in their 401(k) plans without understanding the underlying components. The episode reveals a critical shift happening in 2025:
The Magnificent Seven Reality Check“When you look at the magnificent seven stocks, specifically from their all time high to where they are now, when you look at ’em as a group, it’s basically been a nothing burger.”
Key Portfolio Insights for Pre-Retirees:
- Technology sector concentration risks
- Industrial and financial sector opportunities
- The importance of sector rotation strategies
- Why broad market indexes may underperform
One of the most important decisions pre-retirees face is how to handle pension distributions. The show provides essential guidance:
“Always do the analysis… If you have a fully funded pension that has the right to do a lump sum rollover. Always do the analysis before anybody talks you into annuitizing it.”
Pension Decision Factors to Consider:- Life expectancy calculations
- Beneficiary considerations
- Investment growth potential
- Inflation protection
- Control and flexibility
Warning Signs to Watch:
- Single life annuity limitations
- Insurance company profit motives
- Irreversible nature of annuitization
Unlike large investment firms that use one-size-fits-all approaches, the episode emphasizes the importance of personalized financial planning for pre-retirees in Kentucky. This addresses a critical gap in the market where many investors receive generic advice that doesn’t account for their unique circumstances.
The Danger of Mass-Market Investment Strategies“Anybody that gives you cookie cutter investment, retirement investment advice, they’re not getting to know your situation.”
Key Differences in Personalized Wealth Management:
- Comprehensive financial situation assessment
- Customized portfolio design based on individual goals
- Regular strategy adjustments for changing life circumstances
- Local understanding of Kentucky tax implications
- Direct access to decision-makers vs. assigned counselors
For Lexington area pre-retirees, understanding your investment strategy reduces anxiety and improves decision-making:
“People get the most afraid about stuff they don’t understand. They’re scared of what, of things they can’t see and cannot understand.”
Benefits of Working with Financial Professionals:
- Lower stress during market downturns
- Better understanding of investment choices
- Proactive strategy adjustments
- Peace of mind approaching retirement
The discussion of historical technology adoption provides valuable context for pre-retirees:
Learning from Technology Investment HistoryAutomobile Industry Parallels (1900-1940):
- From 8,000 to 23 million registered vehicles
- 2% to 90% household adoption rate
- Massive wealth creation opportunities
Modern Technology Examples:
- Apple’s growth from iPod ($15B) to current valuation
- NVIDIA’s transformation from gaming chips to AI leadership
- The unpredictable nature of technological advancement
- Maintain exposure to innovation
- Don’t miss transformational opportunities
- Balance growth with capital preservation
- Stay informed about emerging sectors
- Diversify beyond S&P 500 index funds – understand what you actually own
- Always analyze pension lump sum options before making irreversible decisions
- Work with professionals who provide education and personalized strategies
- Maintain some growth exposure while protecting capital
- Stay flexible – economic conditions change rapidly
- Avoid cookie-cutter investment solutions that don’t fit your specific situation
- Develop healthy skepticism about investment promises and political influences
As you approach retirement, remember that successful wealth management requires more than hoping market trends continue. The episode reinforces a crucial point:
“A dollar amount in and of itself isn’t the end game. It’s the use of the dollars… what it can produce in terms of income, because you got bills to pay every month.”
Your retirement planning should focus on:
- Income generation rather than just accumulation
- Risk management that is appropriate for your timeline
- Flexibility to adapt to changing conditions
- Professional guidance for complex decisions
Don’t let market uncertainty derail your retirement plans. Whether you’ve been listening for years or this is your first episode, now is the time to take action with local financial advisors who understand your unique needs.
Schedule your complimentary portfolio review today:
- Call: 859-233-0400
- Online: Visit dupreefinancial.com to schedule directly
- Discover: Get a personalized analysis of your current investments and retirement readiness
Unlike mass-market investment firms, Dupree Financial Group provides personalized investment management with direct access to decision-makers. Learn exactly what you own in your portfolio and how it aligns with your retirement timeline.
“If you don’t know what you own, you need to and we can help.”
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