Is Dow 100,000 Closer Than You Think?
Longtime Keen on Retirement listeners and friends of the firm are probably familiar with The Big Hat.
Matt Wilson, our Chief Investment Officer and President, is the proud owner of an oversized Dow 100,000 cap that he wears on our show from time to time. And when folks visit our offices, such as during our annual Holiday Breakfast, they often spot Matt's hat in his office and have a bit of a chuckle about its pie-in-the-sky prediction. More than once, I've heard someone tell Matt, "Gosh, I'll never see that in my lifetime."
But ... is the Dow hitting 100,000 really all that far-fetched?
On our final show of 2025, we look to market history and current trends to give you a head start in your financial planning for 2026.
I also share some stories from my big Hollywood red carpet debut as part of the Keen Wealth Foundation’s charitable mission.
The Psychology of Big Numbers
As I write this, in late December of 2025, the Dow Jones Industrial Average is hovering right below the 50,000 mark. How did we get here?
Take a look at some other recent Dow milestones:
1972: The Dow hits 1,000.
1995: The Dow hits 5,000.
2018: The Dow hit 25,000.
Crunch the numbers between those points and you'll find an interesting trend: around a 5x return over 23 years. If that trend holds – and, as always, past returns are no guarantee of future performance – the Dow would break 100,000 in 2041.
"Not in my lifetime?" I certainly plan on being around!
So why does 100,000 sound impossible? Why does any big market number feel unsustainable?
Because of the biases many of us have around money and investing.
Every day, investors tend to anchor their expectations to lower historical numbers. They might remember when the Dow first passed 5,000 in 1995. And there's some part of their brain that just expects those numbers to return to that baseline. 100,000 is just so much bigger than 5,000 that it feels impossibly far off.
But, mathematically, moving from 50,000 to 100,000 is no different than moving from 5,000 to 10,000 or from 10,000 to 20,000!
Also, market prices don’t just grow in a vacuum. They’re driven, by and large, by corporate earnings. As the companies on the major indexes have grown over the decades, their economic output has grown, and so has their value. There will always be instances of companies being overvalued, leading to corrections. But companies like Apple and Microsoft are also much bigger and more valuable today than they were in the 1980s, and their stock prices reflect that.
Finally, note that between 2018 and 2025, the Dow has seen a compound annual return of roughly 10% if you factor in reinvested dividends. Project that forward, using a more conservative 8% rate of return, and the Dow would hit 100,000 in just over nine years. At a 10% rate of return, we could see 100,000 in just over seven years.
Paying the Price of Admission
In other words, Dow 100,000 is not a question of if, but when.
The bigger question for investors is: What's your plan?
While the long-term trend is upward, the journey is never a straight line. And you don't have to look back very far to see examples of that.
In April, uncertainty around President Trump's tariffs caused significant intraday volatility on the S&P 500, which dropped almost 20% at one point. Cable news and social media were predicting market collapses and recessions.
And yet, here we are, six months later, and the S&P 500 hasn't just recovered, it's up about 16% for the year – a 35% swing.
You can go back and study market data around COVID, the Great Recession, 9/11, the Dotcom Bubble, and so on, and the story will be the same.
And so will the main lesson for investors: panic is expensive.
Anyone who bailed on the markets during those low points – who decided to "get out" while things were bad so they could "get back in" when things were good again – missed out on compounding returns once the markets recovered. They locked in losses and locked out gains they'll never recover.
I understand that looking at historical market data just isn't all that comforting during moments of economic uncertainty, especially if you're retired or getting ready to retire. But volatility is just the price that investors have to pay from time to time in order to harness the wealth-building power of the markets.
The Outlook for 2026
As Matt Wilson discussed in his most recent Market Outlook webinar, the team at Keen Wealth is very optimistic about the year ahead. There will be more uncertainty as the global economy continues to go through some major changes. And that uncertainty will probably create some ups and downs in the markets.
But if you're following a comprehensive financial plan, with the guidance of a fiduciary advisor, you'll usually have options for coping with volatility and for taking advantage of opportunities.
And if you need help revamping that plan, put an appointment with Keen Wealth at the top of your January to-do list.
Happy New Year, and here’s to making 2026 your best year yet.
Bonus: Bill and Carissa on the Red Carpet
Thanks to our support of Big Slick KC and Children’s Mercy Hospital, Carissa and I had an opportunity to join Paul Rudd and Jack Black on the red carpet for the Hollywood premiere of “Anaconda.” Paul and Jack were incredibly gracious hosts and shared their appreciation for the impact that the Keen Wealth Foundation is having in our community.
About Bill
Bill Keen is a financial advisor with over 30 years of industry experience. As the founder and CEO of Keen Wealth Advisors, a registered investment advisory firm, he focuses on providing personalized retirement planning designed to help people thrive before and during their retirement years. With a passion for educating others, Bill regularly blogs about retirement planning, hosts the podcast Keen on Retirement, and has contributed to Forbes, U.S. News and World Report, Reuters, Wall Street Journal’s Market Watch, Yahoo Finance, and other publications. Based in Overland Park, Kansas, Bill and his team work with clients throughout the greater Kansas City area and across the nation. To learn more, connect with him on LinkedIn or visit www.keenwealthadvisors.com.
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