Chewy Careers and the Hidden Advantage of Experience in the Age of AI

“Many Chewy employees approaching retirement have lived through multiple market cycles, and those experiences can provide valuable perspective when evaluating future financial decisions and retirement goals,” — Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

“Chewy employees who have experienced events like Black Monday, the dot-com bubble, and the global financial crisis often bring valuable perspective to retirement conversations, using those experiences to think more thoughtfully about long-term financial decisions and life after their careers,” — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. How major market events such as Black Monday, the dot-com bubble, and the global financial crisis shaped the financial experiences of professionals now approaching retirement.

2. Why decades of living through economic cycles can influence how Chewy professionals think about financial decisions and long-term planning.

3. How reflecting on past market experiences may help frame retirement planning conversations and future financial choices.

By Kevin Won, CFP® | Wealth Enhancement

“In the business world, unfortunately, the rear-view mirror is always clearer than the windshield.” — Warren Buffett ¹

Many professionals preparing for retirement have spent decades building careers, raising families, and accumulating wealth. For many long-tenured professionals working at Chewy, those decades also include witnessing major economic shifts that influenced their financial decisions.

People over 50 have gone through multiple periods of economic instability and market volatility. Among these events is 'Black Monday' (October 19, 1987), when the Dow Jones Industrial Average declined 22.6% in a single trading day, the largest one-day percentage drop in the index’s history. ²

Many professionals also lived through the dot-com bubble of the late 1990s and early 2000s, when technology stock valuations surged and later declined dramatically. Between March 2000 and October 2002, the Nasdaq Composite Index fell nearly 78% from its peak, ³  illustrating the volatility that can occur during periods of rapid technological change.

Another defining event was the global financial crisis, which followed the collapse of the U.S. housing market and created financial instability worldwide. During this period, the S&P 500 declined approximately 57% from October 2007 to March 2009, ⁴  one of the most significant market declines since the Great Depression.

Investors more recently experienced pandemic-era market volatility beginning in 2020, when the spread of COVID-19 triggered sharp swings across financial markets. In March 2020, the S&P 500 entered a bear market after falling more than 30% from its February peak during the early stages of the pandemic. ⁵

For many Chewy professionals, experiencing several major market cycles over the course of a long career can contribute to a broader understanding of how markets evolve and how economic conditions change over time. Living through multiple disruptions often leads individuals to develop a longer-term perspective when making financial decisions.

As retirement approaches, many Chewy professionals begin reviewing the financial choices they made throughout their careers. Looking back at how previous economic events influenced investment decisions, career moves, and savings strategies can become part of broader conversations about lifestyle goals and retirement timing.

For those nearing retirement from Chewy, understanding how previous economic cycles unfolded may provide context when evaluating future financial decisions. Reflecting on past experiences can be one way individuals frame their thinking about the years ahead.

If you have questions about retirement preparation or would like to discuss your retirement planning approach,  The Retirement Group  may be able to help. Professionals working at Chewy companies can learn more by attending one of our upcoming webinars or seminars or by contacting a representative at  (800) 900-5867 .

At  Wealth Enhancement , retirement planning discussions often include reviewing prior financial experiences while considering the tools and strategies currently available.

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  Sources:

1. Warren Buffett, Berkshire Hathaway:  Letter to Shareholders (1991) . Feb. 28, 1992.

2. Bernhardt, Donald, and Marshall Eckblad. “Stock Market Crash of 1987.”  Federal Reserve History , Federal Reserve Bank of St. Louis, Oct. 1987,  https://www.federalreservehistory.org/essays/stock-market-crash-of-1987 .

3. Hayes, Adam. “Dot-Com Bubble.”  Investopedia , Dotdash Meredith, 10 Aug. 2025,  https://www.investopedia.com/terms/d/dotcom-bubble.asp . 

4. Duignan, Brian. “Great Recession.”  Britannica Money , Encyclopaedia Britannica,  https://www.britannica.com/money/great-recession .

5. Mikolajczak, Chuck, and Noel Randewich. “U.S. Stocks in 2020: A Year for the History Books.”  Reuters , 31 Dec. 2020,  https://www.reuters.com/business/graphic-us-stocks-2020-year-history-books-charts-2020-12-31/ .