Perhaps the article that has influenced my personal finance journey the most is a piece called "What if You Only Invested at Market Peaks? by Ben Carlson. Like many investors, I was plagued by the common fear: what if I invest at the worst possible time? The nagging worry that putting money into the stock market when it’s doing well means buying at the peak, only to watch your hard-earned savings evaporate in a market crash.
Ben Carlson masterfully addressed these concerns through the story of Bob, the world’s worst market timer. Today, I’d like to introduce you to Jane, Bob’s spiritual successor, who followed in his unfortunate footsteps a decade later, demonstrating the power of persistence in long-term investing.
Meet Jane: A Case Study in Poor Market Timing
Jane, like Bob, was a diligent saver but a terribly anxious investor. She followed the same rigid investment strategy:
- Saved $2,000 each year, increasing by $2,000 every decade starting from 1980
- Only invested in the stock market when it was at its peak (right before a crash)
- Never found the courage to invest unless stocks were at all-time highs
- Once invested, she held firm and never withdrew her money until retirement
Jane was a kindergarten teacher who lived well below her means. Despite her modest salary, she faithfully tucked away her savings each year. However, her fear of market downturns led her to keep her money in a savings account until she could no longer resist the temptation of seemingly endless market rises. Invariably, this meant she invested at the worst possible moments in the stock market.
Jane’s Investment Timeline: A Series of Unfortunate Market Entries
Let’s follow Jane’s nerve-wracking journey through five major stock market crashes:
Black Monday (August 1987)
- Investment: $16,000
- Market Drop: 34%
- Jane’s thoughts: “I finally invested, and the market immediately had its worst single-day crash in history!”
- The S&P500 crashed 20.4% in a single day, triggered by program trading and market psychology
Dot Com Bubble (December 1999)
- Investment: $44,000
- Market Drop: 49%
- Jane watched in horror as her tech-heavy S&P 500 investment nearly halved in value
- Internet-based companies crashed after years of speculation, wiping out $5 trillion in market value
Financial Crisis (October 2007)
- Investment: $48,000
- Market Drop: 52%
- The worst crash since the Great Depression tested Jane’s resolve in long-term investing
- The collapse of the housing market and subprime mortgages triggered a global financial crisis
COVID-19 Pandemic (December 2019)
- Investment: $96,000
- Market Drop: 20%
- A global pandemic wasn’t on Jane’s radar when she made her largest stock market investment
- Global lockdowns and economic uncertainty caused the fastest bear market in history
Omicron Variant (December 2021)
- Investment: $20,000
- Market Drop: 25%
- Jane’s final ill-timed investment before retirement
- Markets tumbled as a new COVID variant emerged alongside rising inflation concerns
The Results: The Triumph of Persistence in Long-Term Investing
Despite her consistently poor market timing, Jane ended her career in September 2024 with a net worth of approximately $840,000. While she didn’t match Bob’s $1.1 million, she still achieved impressive results considering her investing strategy was impressively bad. It’s worth noting that Jane invested a total of $224,000 of her saved money over the years, making her final net worth even more remarkable given her poor timing.
The Power of Simply Staying Invested
Jane’s story teaches us several valuable lessons about long-term investing and market timing:
- Time in the market beats timing the market: Despite investing at the worst possible moments, Jane’s long-term returns were substantial
- Consistency matters more than timing: Even the world’s worst market timer can succeed through persistent saving and investing
- The power of holding steady: Jane’s success came from her ability to stay invested during market downturns
- Long-term perspective is crucial: Short-term market volatility matters less when you have a long investment horizon
However, there’s an important caveat: Had Jane invested monthly instead of waiting for market peaks (a strategy called Dollar Cost Averaging ), her retirement portfolio would have grown to approximately $3.15 million. This stark difference highlights that while you can succeed even with poor timing, a systematic investment approach typically yields far better results in the stock market.
Alternatively, if Jane had chosen to put her money into a high yield savings account every year at 2% interest, she would have ended up with approximately $353,000. This comparison further emphasizes the potential benefits of investing in the stock market over simply saving.
The Bottom Line: Persistence Trumps Perfect Timing
Jane’s journey, like Bob’s before her, proves that the most important investment decisions are not about timing but about commitment. Starting early, saving consistently, and staying invested through market turbulence are the real keys to long-term investment success. Even if you’re convinced you have the worst timing in the world, remember Jane – and invest anyway.
Frequently Asked Questions About Market Timing and Long-Term Investing
Q: Is it possible to consistently time the market?
A: While some investors may have short-term success, consistently timing the market over the long term is extremely difficult, if not impossible. Even professional investors struggle to outperform the market consistently through timing strategies.
Q: How does dollar-cost averaging compare to lump-sum investing?
A: Dollar-cost averaging (investing a fixed amount regularly) can help reduce the impact of market volatility and poor timing. However, studies have shown that lump-sum investing often outperforms in the long run, assuming you have the capital available upfront.
Q: What’s the minimum time horizon for stock market investing?
A: Generally, a minimum of 5-7 years is recommended for stock market investing to ride out short-term volatility. However, longer time horizons (10+ years) provide even better opportunities for compound growth and recovery from market downturns.
Q: How can I overcome the fear of investing at market highs?
A: Education about market history, understanding your risk tolerance, and having a well-diversified portfolio can help. Remember Jane’s story – even investing at peaks can lead to significant long-term gains if you stay invested.
Q: What’s the best way to start investing for long-term growth?
A: Start by educating yourself about investment options, determine your risk tolerance, and consider low-cost index funds or ETFs that provide broad market exposure. Consistent contributions and a long-term perspective are key to building wealth through investing.
Disclaimer: This analysis is purely hypothetical and designed to illustrate the power of long-term investing and compounding – it is not financial advice. The calculations assume a 100% S&P 500 allocation with reinvested dividends, but do not account for expense ratios, taxes, or other fees that would reduce actual returns. While the scenario demonstrates that even poor market timing can result in significant returns over decades, maintaining a 100% stock portfolio through market downturns requires exceptional emotional discipline that few investors possess. A more diversified portfolio aligned with your personal risk tolerance, managed with professional guidance, is typically more appropriate for most investors. Past performance does not guarantee future results.