According to Forbes, financial coach and author Chris Sain argues that investors should ignore market timing fears and focus on consistent investing strategies, even during record highs. Sain revealed that markets saw 57 new highs in 2024 and have already achieved 16 new highs in 2025, demonstrating that momentum often continues upward. His approach emphasizes dollar-cost averaging during pullbacks, using previous highs as entry points rather than waiting for perfect timing. Sain also highlighted his ongoing $1 million ‘100 Days of Giving’ Tour, where he’s distributing $25,000 checks to families and small businesses nationwide. This perspective challenges conventional wisdom about market timing and emotional investing.
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The Psychological Traps of Market Timing
What makes market timing so seductive yet ultimately destructive is how it plays into fundamental human psychology. The fear of missing out isn’t just a modern social media phenomenon—it’s deeply rooted in our evolutionary psychology as social creatures who historically depended on group consensus for survival. When we see others profiting from market movements, our brains interpret this as social proof that we’re missing something crucial. This explains why so many investors chase momentum at precisely the wrong moments, buying high out of anxiety and selling low out of panic. The emotional rollercoaster of trying to predict market turns creates decision fatigue that often leads to poorer outcomes than simple, automated strategies.
The Mathematical Advantage of Dollar-Cost Averaging
While Sain mentions dollar-cost averaging as a solution, the mathematical foundation behind why it works deserves deeper exploration. This strategy leverages what statisticians call “variance reduction”—by investing fixed amounts at regular intervals, you naturally buy more shares when prices are low and fewer when prices are high. Over time, this creates a lower average cost per share than trying to time lump-sum investments. The strategy particularly shines in volatile markets where prices fluctuate significantly. What most investors don’t realize is that dollar-cost averaging also provides psychological benefits by creating a disciplined framework that removes the stress of deciding “when” to invest, turning emotional decisions into systematic processes.
The Hidden Risks in Sector Concentration
While Sain mentions momentum investing in emerging technologies like AI, this approach carries significant risks that require careful management. Sector-specific investing can create dangerous concentration in portfolios, particularly when chasing hot trends. The technology sector’s historical volatility shows that what goes up dramatically can also correct sharply—remember the dot-com bubble or more recent crypto winters. Successful sector investing requires not just identifying growth areas but understanding their valuation metrics, competitive landscapes, and regulatory environments. Many individual investors lack the research capacity to properly assess these factors, making broad diversification through index funds often a safer approach for long-term wealth building.
How Automation Defeats Behavioral Biases
The power of automated investing extends far beyond convenience—it directly counters well-documented behavioral economic biases that sabotage investment returns. Research in behavioral finance consistently shows that investors suffer from overconfidence bias (believing they can time the market), recency bias (overweighting recent events), and loss aversion (feeling losses more acutely than gains). Automated systems create what psychologists call “commitment devices” that lock in beneficial behaviors before emotions can interfere. This approach aligns with how professional wealth managers structure client relationships—by establishing clear investment policies upfront that prevent emotional decisions during market turbulence. The real value isn’t just in the mechanical execution but in creating a system that protects investors from themselves.
Building Sustainable Wealth Beyond Market Cycles
The most overlooked aspect of Sain’s advice is how consistent investing builds not just financial wealth but financial resilience. Investors who automate their contributions develop what I call “financial muscle memory”—the habitual behavior of treating investing as a non-negotiable expense rather than an optional activity. This mindset shift is crucial for weathering the inevitable market corrections that test every investor’s resolve. Historical data shows that missing just a handful of the market’s best days can dramatically reduce long-term returns, which is why staying consistently invested typically outperforms attempts to time entries and exits. The true secret isn’t finding the perfect strategy but sticking with a good strategy perfectly through market cycles.
