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Kelly Evans: How I Learned to Stop Worrying and Love the Stock Market



Navigating the world of investing can feel like a journey of contradictions, fear, and personal growth. For Kelly Evans, her relationship with the stock market mirrors her life’s evolution—marked by caution, missteps, and, eventually, acceptance of long-term strategies.

The Early Years: Fear and the Apocalypse

Evans’s market skepticism took root early, shaped by history, horror movies, and a healthy dose of financial anxiety. Her introduction to financial journalism in 2007 coincided with the housing market collapse and the ensuing Great Recession. Witnessing the economy’s vulnerability firsthand confirmed her belief in looming economic catastrophes.

“I saw nine of the next four recessions coming,” Evans quips, reflecting on her tendency to overpredict doom. As a young journalist without significant financial stakes, her pessimism was theoretical, not personal—until she began investing herself.

A Lesson in Timing

In 2009, Evans began contributing to her 401(k), seizing the opportunity presented by the market's lows. But her cautious nature led her astray in 2012 when she moved to cash, fearing a double-dip recession amid sluggish growth and fiscal uncertainty. She later regretted trying to time the market, as she re-entered at higher levels.

This cycle repeated last year when a real estate sale left her with cash to invest. With Treasury bonds yielding 5%, Evans opted to wait for a market downturn that never materialized. Once again, she bought back in at higher levels, reinforcing a hard-learned lesson: timing the market is a losing game.

From Conservative to Cautiously Bullish

Now nearing 40, Evans is finally embracing a long-term, disciplined approach to investing. Contributions to her children’s 529 plans and consistent stock market investments have brought her closer to a mindset of growth over fear.

She acknowledges that millennials like herself often err on the side of financial conservatism. Financial advisors, like Doug Boneparth, have echoed this sentiment, urging younger investors to be less risk-averse. For Evans, the realization has been liberating, if unsettling.

The Bullish Paradox

Despite her growing confidence, Evans admits it feels unnatural to embrace a bullish outlook. Her internal dialogue is still crowded with reasons to doubt the market: demographic challenges, inflation, stifling regulations, fears of stagnation, and concerns over speculative bubbles like AI. Yet, she’s learning to prioritize participation over perfection.

The cost of staying out of the market, she concludes, outweighs the potential risks. “I’m no longer behaving that way,” she says, emphasizing the importance of being invested in assets like stocks, gold, Bitcoin, or real estate.

A Family Debate

Evans’s evolution isn’t without humor. When she told her husband about her plans to write this piece, he joked, “Now that’s really the sign of a top!” The comment underscores a perennial investor fear: What if now is the worst time to invest?

Conclusion: Embracing Growth Over Fear

Kelly Evans’s journey from financial caution to measured optimism offers a relatable blueprint for investors navigating their own uncertainties. Her story reminds us that perfection isn’t the goal—consistent participation is. The stock market, for all its risks, remains a powerful tool for long-term wealth creation.

Her ultimate lesson? Stop worrying so much about timing the market and start appreciating its potential. While fears will always linger, the key is to invest with discipline, trust the process, and, most importantly, keep moving forward.


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