The Edge of Chaos: Rethinking Investment Risk

I wrote the following to organize my thoughts for a presentation to financial advisors later this month.

Our business is obsessed with keeping clients from losing money when the market drops. We’re quick to show charts of past crashes, pointing to the 49 percent drop in 2000, the 56 percent plunge in 2008, and the 34 percent dive in 2020. Then we offer safe-sounding products to act like a shield. We propose CDs, T-bills, annuities, and funds designed to limit losses. It feels good. It feels safe. The client walks away thinking, This is why I hired an expert. My advisor knows what they’re doing and will make sure I don’t get hurt when things get ugly. Protecting people from short-term losses has become a cottage industry for financial planners. But protecting clients from market drops isn’t the safety net we think it is.

What if the danger we spend all our time worrying about isn’t the real problem? What if the cure is worse than the disease?

I’ll answer with five connected concepts.

Concept 1: Crashes are loud while compounding is quiet; but compounding over time is much more powerful than short-term dips.

When the market falls apart, you hear about it everywhere. Commentators look terrified. Red banners flash across the screens. Everyone panics. Bad news grabs everybody’s attention. But real growth works in total silence. It creeps ahead day after day, year after year, moving so slowly that you barely notice it happening. Yet over time, that quiet growth is much more powerful than any short-term drop.

Our brains are wired to run from scary noises. Our ancestors survived because they reacted instantly to a snapping twig or a rustle in the tall grass. If you ignored the sound of a predator, you died. You did not survive by sitting back watching an oak tree grow. Our brains still panic when something goes wrong today. But when it comes to building money, slow and steady growth is far more powerful than any sudden crash.

“Compound interest is the eighth wonder of the world. He who understands it, earns it; he who doesn’t, pays it.”

The world is filled with things that are hard to make and easy to break. Peace requires millions to cooperate, but it only takes one reckless leader to start a war. The human body requires trillions of cells to cooperate perfectly, but two milligrams of fentanyl can end it all. To build a house, it takes architects, carpenters, plumbers, and months of hard work, but knocking it down just takes a sledgehammer. Creation takes time, but destruction can happen in an instant.

The exact same thing happens with money. Building real wealth takes thirty years of steady saving, waiting for results, putting gains back to work, and sitting on your hands through gut-wrenching drops. Yet it takes only one panicked click of the “Sell All” button at the bottom of a crash to throw away a decade of progress. Destruction happens in a flash, but building takes time.

“Crashes are loud, but compounding is quiet.”

Concept 2: Return is just the market paying you to stomach risk.

Risk is simply the price of admission for making money. Return is just risk, paid out.

The market never provides a free lunch. When Peter Lynch ran the Magellan Fund from 1977 to 1990, he made an average of 29 percent a year. Over thirteen years, that kind of growth turned ordinary savings into fortunes. But that 29 percent was not handed out for free. Lynch’s fund suffered nine big drops of ten percent or more, regular falls of 20 to 30 percent, and one brutal month in October 1987 when his fund plunged more than 30 percent.

Ironically, Lynch calculated that the typical investor in his fund actually lost money over that historic run. Why? Because when the market took a loud tumble, people panicked. They sold everything at the bottom, hid in cash until they felt safe again, and only bought back after prices had already shot through the roof.

Lynch’s track record reinforced a simple truth about investing. You cannot collect a 29 percent yearly gain unless you have the stomach to watch a third of your balance disappear on paper. That sick feeling in your gut is the price of admission. If you paid the toll and stayed in your seat, you walked away wealthy. If you panicked and jumped out of the car, you wrecked yourself.

“Return is just the market paying you to stomach risk.”

Concept 3: Your clients are living much longer than traditional planning models assume.

Many retirement plans still use life expectancy charts, but looking at broad averages gives us a false picture. Those national numbers are pulled down by “deaths of despair,” people who struggle with poverty, poor healthcare, bad lifestyle choices, and chronic illness. Stanford economist Raj Chetty’s looked at how long people live based on how much money they make, the results were eye-opening. He and his team linked 1.4 billion de-identified federal tax records from 1999 to 2014 with Social Security Administration mortality data, allowing them to track actual mortality across roughly 7 million deaths. They found that the top one percent of earners live ten to fifteen years longer than the bottom one percent. Now realize, the people that hire financial advisors to manage wealth are closer to the top one percent than the bottom one percent.

Money buys extra time on earth. Deaths from heart attacks have dropped by more than 70 percent since the 1960s. Wealth-management clients do not just cross their fingers and hope for good health. They actively buy better odds. They pay for high-quality food, private doctors, full-body scans, DNA screening, private trainers, weight-loss drugs, and custom treatments.

There was a famous Framingham Heart Study that started in 1948 tracking ordinary middle-class workers in Massachusetts. It was routine for total cholesterol to be over 300 and blood pressure to be 160/100. It was considered a normal, unavoidable consequence of aging. Then a massive heart attack would strike at age fifty-eight. Their children had the exact same genes, but modern medicine changed the outcomes. Drugs to lower cholesterol and blood pressure, along with simple heart procedures, carried those kids right into their nineties. What used to be a quick ten-year retirement turned into a thirty-five-year stretch of living.

Yet our old-school playbooks still treat a sixty-five-year-old like an investor who is approaching the end. We invest their money into low-return, so-called safe investments to protect them. In reality, a healthy sixty-five-year-old today needs to plan for another twenty-five or thirty years. They are still long-term investors, and we cannot afford to park their money where it will slowly lose its buying power.

“Clients are living much longer than traditional planning models assume.”

Concept 4: The real danger isn’t the market dip; it’s the lifestyle crash.

Watching a portfolio drop during a market crash is painful, but that drop is temporary. The real disaster is waking up at eighty years old with an account that has lost its buying power, leaving too little money to cover basic bills or leave anything to future generations.

That quiet ruin happens because of the hidden cost of playing it safe: playing not to lose is the surest way to lose.

Putting all your money into safe investments feels great over a single year. But over thirty years, it works like a frog sitting in a pot of water on the stove. The heat turns up so slowly that the frog never realizes it is being cooked alive.

Henry Flagler co-founded Standard Oil alongside John D. Rockefeller and built the Florida East Coast Railway. When his son, Harry Harkness Flagler, passed away in 1952, substantial wealth flowed down to Harry’s three daughters: Mary Harkness Flagler Cary, Elizabeth Flagler Harris, and Jean Flagler Matthews.

History shows a clear example of this trap in the trusts set up for the three granddaughters of Henry Flagler, the co-founded with John D Rockefeller of Standard Oil. After the brutal 1929 stock market crash, the trust managers were terrified of losing money. Trying to be completely responsible under the old rules of the day, they put every single dollar into safe government bonds and cash. For forty years, the dollar balance on the statement never dropped.

Yet between 1940 and 1980, rising prices wiped out about 80 percent of what a dollar could actually buy, while the stock market grew by leaps and bounds. By the late 1970s, the grandchildren of one of the richest oil barons in history could barely afford a middle-class life on their payouts. The managers did their job of protecting the account balance on paper, but they completely ruined the family’s finances. The disaster was so bad that lawmakers rewrote trust laws across the country in the 1990s, finally admitting that avoiding the stock market in favor of so-called safe investments is an active gamble with the future.

“The real danger isn’t the market dip; it’s the lifestyle crash.”

The same thing happened to retirees in the late 1990s. Picture an engineer who retired in 1999 with a million dollars in savings. Back then, five-year bank CDs paid five to six percent interest. Tired of the wild swings in tech stocks, he walked away from the market completely. He put his entire million dollars into CDs, figuring that fifty-five to sixty thousand dollars a year in guaranteed interest was plenty to live on without taking any chances.

For the first ten years, through the dot-com crash and the 2008 financial crisis, he looked like a genius. While his friends in the stock market watched their accounts drop by 40 percent, his balance stayed rock solid. Then interest rates crashed to near zero in the 2010s. When his CDs matured, the new rates paid less than 1.5 percent. His guaranteed income dropped from fifty-five thousand dollars to barely fifteen thousand dollars, right as his groceries, taxes, and medical bills shot up.

To keep the lights on, he had to start pulling money out of his principal. He had successfully dodged every scary headline and every market plunge, only to find himself in his late seventies facing the ultimate trap: running out of cash while he was still alive.

“The real danger isn’t the market dip; it’s the lifestyle crash.”

Concept 5: The stock market is a scoreboard for human ingenuity.

Too many people treat the stock market like a giant casino, a digital game where prices just bounce around on pure luck and greed. It is not a casino. The market is where all human problem-solving is reflected. When you own an index of great companies, you own a piece of millions of hardworking, smart people. These are people who wake up every morning to cut waste, fix supply chains, cure diseases, and build tools that make life better.

Over the last hundred years, the average person’s economic output jumped eight times over. We did not get here by working workdays that were eight times longer. We got here by working smarter. Every major leap forward, like trains, electricity, computer chips, and software, became the steppingstone for other, bigger things.

The market also cleans house automatically. It weeds itself. When a big company gets lazy, sloppy, or outdated, the market punishes it. Old giants like Sears, Kodak, and Pan Am faded away, lost value, and dropped off the list. Hungry, growing companies like Apple, Amazon, and Nvidia took their places (for now). The index keeps the winners and quietly throws away the dead weight.

Crises happen, wars break out, and bad news hits the front page, but humans keep inventing new things. We do not unlearn science, engineering, or smart business practices. Knowledge only moves forward. Because people keep learning, our ability to get things done keeps climbing.

Staying in the market is just setting up a tollbooth on human effort. The scary drops that make people panic are simply the price you pay to ride along.

Consider the story of Ronald Read, who spent years workings as a gas station attendant and janitor in Vermont. Read never made more than $45,000 a year, but he died with an estate worth more than eight million dollars. Read was not a Wall Street hotshot. He wore an old jacket pinned together with safety pins, drove a beat-up car, and quietly put his small paychecks into steady companies like Procter & Gamble, Johnson & Johnson, and General Electric. He bought shares of companies he liked and reinvested the dividends.

For fifty years, through wars, wild inflation of the ‘70s, political fights, and nasty market crashes, Read held his stocks. While traders tried to time the market, thousands of unnamed chemists, engineers, and workers at those companies went to work every day to make better laundry detergent, invent new medicines, and run better businesses. Read did not have to be a genius. He just set up a tollbooth on human ambition and let their hard work build his wealth.

“The stock market is a scoreboard for human ingenuity.”

These concepts, taken together, set up a clear job for financial planners. We have to stop selling the fake promise of total safety, the empty claim that a client will never lose a single dollar on paper. Caving in to a client’s short-term fear is not good advice; it’s a failure of fiduciary leadership. Our real job is to be a steady guide. We need to give clients the perspective to see temporary market drops for what they are – temporary – so they can survive the worse threat of running out of money down the road.

I am not saying we should throw away safe investments entirely. I am saying safe investments protect from only one specific risk: a short-term drop. We cannot fool ourselves or fool our clients into thinking that cash, short-term bonds, or annuities alone will keep up with rising prices over a thirty-year retirement. We should use ultra-safe investments for near-term needs, and not a penny more. On their own, they will never be enough to protect wealth over the long haul.

The real goal isn’t just surviving the bad days; it is giving our clients the freedom to participate in the incredible, compounding growth of tomorrow.

 

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