When Investing for Retirement, Be Like Rip Van Winkle
Spend 20 years in a stupor, rather than getting anxious about daily stock market fluctuations, and reap the rewards of retirement investment returns adding up.


I love a good children’s fairy tale. Those stories have a way of teaching us a message without us feeling like it is learning. We simply get lost in the story, and the next thing we know, boom, message learned. I thought I would take a shot at making a parallel to one of my favorite children’s books with Rip Van Winkle.
Now, I know what you are thinking, and no, I don’t love this story because it is about a drunkard who goes hunting to avoid his wife’s nagging only to meet a friendly Dutchman who offers him booze, causing him to pass out for 20 years. Funny, as I recap the story, it seems odd that this is a children’s book, no?
The investing analogy
Rather, I tell clients this story quite often as an analogy to investing. You see, much like Rip Van Winkle, the world goes on with or without us. Things evolve, economies mature, and markets grow. More pertinent, the markets continue to ebb and flow in an upward trajectory.
From just $107.88 $24.99 for Kiplinger Personal Finance
Be a smarter, better informed investor.

Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
I’ll often tell people that if they look at the stock market every day and dwell over its gyrations, they will go insane, and trust me, I’ve tried — why else do you think I’m writing an article about Rip Van Winkle? The only thing accomplished by looking at and putting so much emotion into the daily swings of the markets is increased anxiety. What happens when you have increased anxiety, one may ask? Simple, we tend to do something ill-advised or emotionally charged, when the markets just don’t care.
While Rip Van Winkle was away, his village grew, his kids had children, and his wife passed away. These things happened irrespective of the fact that Rip was in a drunken stupor for 20 years. Much the same happens whether you freak out over the stock markets, pay no attention at all or get your CFA designation — the markets simply don’t care. They will continue to ebb and flow with or without your investment. That is why I often give this advice: Be Rip Van Winkle — you’ll be happier, less stressed and, magically enough, get 100% of the market growth that you very much deserve.
Let’s go back in time
Let me take a moment to drive my point home. If we looked back 20 years — yes, to a time before iPhones when BlackBerrys ruled — and studied the markets, we would learn some very important data. The Dow Jones was at about 10,315, while the S&P 500 was at about 1,100. Over those 20 years, we have witnessed an insane number of happenings in the world around us and, subsequently, the stock markets. We saw the Great Recession, the global pandemic, multiple wars, Brexit, hyperinflation and like 50 rounds of quantitative easing, just to name a few.
Think back on your own life of what happened during those 20 years — it is quite humbling. Now, if we fast-forward to the present, we have a Dow Jones close to 40,000 and an S&P at about 5,300 — about four to five times their values 20 years ago. Astonishing, right? It was far from a straight line, of course. Heck, in 2008, these indexes were both below their 2004 values, again causing mass panic to those who were tuned in. As a matter of fact, I still have new clients come in who are feeling the aftermath of those years, refusing to believe in the markets ever again. Which, as you can see, is a real shame since if they’d listened to Mr. Van Winkle, they would have multiples of their assets by simply doing nothing.
You see what I just did there, folks? You were reading a nice little story about a children’s book, and boom, you learned a hugely important investing lesson without you even noticing. I can’t stress enough that trust, faith and 20 years in a stupor will do wonders for your investment portfolio!
In the words of Rip Van Winkle, stay wealthy, healthy and happy, everyone.
Diversified is a registered investment adviser, and the registration of an investment adviser does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the SEC.
A copy of Diversified’s current written disclosure brochure which discusses, among other things, the firm’s business practices, services and fees, is available through the SEC’s website at: www.adviserinfo.sec.gov.
Diversified, LLC does not provide tax advice and should not be relied upon for purposes of filing taxes, estimating tax liabilities or avoiding any tax or penalty imposed by law. The information provided by Diversified, LLC should not be a substitute for consulting a qualified tax advisor, accountant, or other professional concerning the application of tax law or an individual tax situation.
Nothing provided on this site constitutes tax advice. Individuals should seek the advice of their own tax advisor for specific information regarding tax consequences of investments. Investments in securities entail risk and are not suitable for all investors. This site is not a recommendation nor an offer to sell (or solicitation of an offer to buy) securities in the United States or in any other jurisdiction.
Related Content
- Four Things That Impact the Financial Plans of Every One of Us
- Nine of the Biggest Regrets I See as a Financial Planner
- How Average Is Your Net Worth?
- Being Rich vs. Being Wealthy: What’s the Difference?
- The Theory of (Financial) Relativity
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

In March 2010, Andrew Rosen joined Diversified, bringing with him nine years of financial industry experience. As a financial planner, Andrew forges lifelong relationships with clients, coaching them through all stages of life. He has obtained his Series 6, 7 and 63, along with property/casualty and health/life insurance licenses. Andrew consistently delivers high-level, concierge service to all clients.
-
The Most Tax-Friendly States for Investing in 2025 (Hint: There Are Two)
State Taxes Living in one of these places could lower your 2025 investment taxes — especially if you invest in real estate.
-
Want To Retire at 55? See If You Can Answer These Five Questions
Who said you can’t retire at 55? If you say yes to these questions, you may be on your way to an early retirement.
-
Potential Trouble for Retirees: A Wealth Adviser's Guide to the OBBB's Impact on Retirement
While some provisions might help, others could push you into a higher tax bracket and raise your costs. Be strategic about Roth conversions, charitable donations, estate tax plans and health care expenditures.
-
One Small Step for Your Money, One Giant Leap for Retirement
Saving enough for retirement can sound as daunting as walking on the moon. But what would your future look like if you took one small step toward it this year?
-
This Is What You Really Need to Know About Medicare, From a Financial Expert
Health care costs are a significant retirement expense, and Medicare offers essential but complex coverage that requires careful planning. Here's how to navigate Medicare's various parts, enrollment periods and income-based costs.
-
I'm a Financial Planner: Could Partial Retirement Be the Right Move for You?
Many Americans close to retirement are questioning whether they should take the full leap into retirement or continue to work part-time.
-
From Mortgages to Taxes to Estates: How to Prepare for Falling Interest Rates
As speculation grows that the Federal Reserve will soon start lowering interest rates, now is a good time to review your financial plans for housing, estate, taxes, investing and retirement to make the most of potential changes.
-
This Is How Lottery Winners Build Lasting Legacies, From a Financial Professional
Winning a massive lottery jackpot, like the recent $1.4 billion Powerball, requires seeking immediate legal and financial counsel, protecting your identity and winnings and planning your legacy.
-
I'm an Investment Strategist: This Is How the Fed's Next Rate Move Could Impact Your Wallet
Interest rate cuts might be coming, which could affect everything from your credit card debt to your mortgage. It's smart to prepare now — here's how.
-
I'm a Retirement Planner: These Are Three Common Tax Mistakes You Could Be Making With Your Investments
Don't pay more tax on your investments than you need to. You can keep more money in your pocket (or for retirement) by avoiding these three common mistakes.