Why Obsessing Over Market Entry Points Could Be Your Biggest Investment Mistake

In a recent discussion, prominent analyst Keith Fitz-Gerald and celebrated financial strategist Suze Orman tackled one of the most persistent myths among investors: the belief that picking the perfect moment to buy stocks is the secret to building wealth. Their conclusion challenges conventional wisdom and offers a refreshingly simple alternative.

The Consistency Principle Beats Perfect Timing Every Time

When asked whether investment success depends on the specific date or market conditions at the time of purchase, Fitz-Gerald delivered a direct answer: it doesn’t. The real differentiator between successful and struggling investors isn’t luck or impeccable timing—it’s discipline and regularity.

According to Fitz-Gerald, the solution is straightforward: commit to a consistent investment schedule. “Once you establish a regular cadence, you automatically hedge against market timing risks,” he explained. “You’re converting volatility from a threat into an opportunity that intimidates other investors. Whether you invest monthly, weekly, or even on a fixed day like the first Monday of each month, the mechanism works as long as you maintain it.”

This approach is grounded in decades of investment research showing that steady contributions compound more effectively than sporadic attempts to catch market bottoms.

Why Micromanaging Investment Decisions Backfires

Beyond obsessing over the perfect entry date, many investors fall into the trap of overthinking granular decisions: Should I invest on Mondays or Fridays? Morning or afternoon? Weekly or biweekly? This level of scrutiny can paralyze decision-making and erode returns.

Early in his career, Fitz-Gerald admitted there was theoretical merit to timing intraday trades around market inefficiencies. However, the landscape has transformed dramatically. The rise of algorithmic trading and 24/7 digital markets has eliminated the lulls that traders once exploited. “The technology revolution has neutralized timing advantages,” he noted. “What once seemed like precision trading is now just noise.”

In today’s environment, the notion of a ‘best time to buy’ is largely obsolete. Markets operate continuously across global exchanges, and human psychology—not clock positions—drives actual pricing.

Stepping Back Creates Better Outcomes

Fitz-Gerald emphasizes an often-overlooked truth: investing becomes more successful when you stop treating it like a high-precision game. The more you fixate on microscopic details and market fluctuations, the more vulnerable you become to emotional decisions and psychological biases.

“When you’re constantly second-guessing yourself and caught up in minutiae, you expose yourself to costly mistakes,” he said. “The smarter approach is to adopt perspective, acknowledge that investing is fundamentally about being reasonably positioned, not perfectly timed, and let your plan work.”

This mindset shift—from obsessing over perfection to embracing a solid, consistent strategy—may be the most valuable lesson both experts offer. Building substantial wealth doesn’t require superhuman timing or constant monitoring. It requires patience, regularity, and the wisdom to know when to stop overthinking.