One planning insight. Two charts that caught our eye. Helping you stay the course in under three minutes.

Planning Insight | September 2026

The Swoosh Went Back to 2014

On September 1, Nike closed at $38.12. The stock hasn't finished a day that low since 2014. Its all-time high was $161.91 in November 2021, which means the shares are down roughly 76% from the peak and have surrendered twelve years of progress along the way.

Take a second with that. A company whose logo is on the shoes of nearly everyone you know, with a brand as recognizable as any on earth, has produced nothing for a shareholder who bought in 2014.

Someone who put $100,000 into Nike twelve years ago and reinvested every dividend has roughly $120,000 today. The same $100,000 in a plain S&P 500 index fund is worth somewhere near $460,000. Same twelve years. Same economy. Same everything, except one bet was on a company and the other was on the market.

And it isn't just Nike.

Volkswagen, an 89-year-old company and Europe's largest automaker, announced in September it's cutting another 50,000 jobs in what it called the most profound transformation in its history. Wynn Resorts, Las Vegas Sands, Carnival, and VICI Properties all touched 52-week lows the same week.

Meanwhile, Marathon Petroleum hit a price it hadn't seen since June 2011, and the energy sector is up 32% on the year. That's the sector most investors spent the last decade explaining why they'd excluded.

The uncomfortable lesson: familiarity is not analysis.

We're wired to believe we understand the companies whose products we use. You've bought the shoes. You've seen the ads. It feels like knowledge.

But knowing the product tells you almost nothing about whether the stock is priced attractively, and price is the only variable that determines your return. Nike's problems in 2026 are real, with revenue down 2% and Greater China guided to fall roughly 20%. None of that is visible from the shoe aisle.

A great company and a great stock are different things. What separates them is the price you pay. Nike, in November 2021, was an excellent company priced as though nothing would ever go wrong. Shareholders have been paying for that assumption ever since.

The math is worse than most people realize.

Research by Hendrik Bessembinder examined every U.S. stock from 1926 through 2016 and found that just 4% of listed companies accounted for the entire net gain of the stock market above Treasury bills. The majority of individual stocks underperformed a one-month T-bill over their lifetimes.

Most stocks lose to cash. The market's returns come from a small handful of enormous winners, and the entire job of a diversified portfolio is making sure you own them without having to identify them in advance.

Picking individual stocks isn't a coin flip with even odds. It's a lottery where the average ticket loses and a few pay for everything.

Why your index fund didn't flinch.

Nike's collapse shows up in your S&P 500 fund as a rounding error, because as the price fell, its weight in the index fell with it. Nobody had to make a call. Nobody had to be right about sneakers or China.

That same index quietly held the energy names everyone had written off and collected the 32% when the Iran conflict rewrote the story. Not because it was clever. Because it wasn't trying to be.

We used the S&P 500 here because everyone recognizes it, but a properly diversified portfolio doesn't stop at large U.S. companies. It reaches across small and mid-size businesses, developed markets abroad, and emerging economies, which adds up to several thousand companies in dozens of countries. You aren't betting on Nike. You aren't even betting on America. You're betting that businesses around the world will keep earning money, which is a bet that has paid off through every decade that anyone alive has lived through.

If you're holding a concentrated position, this is the conversation.

Whether it's inherited stock, accumulated RSUs, or a position you've held so long the cost basis is a rounding error, single-company risk is the one risk in a portfolio that pays you nothing for taking it. The market compensates you for market risk. It does not compensate you for owning one company instead of thousands.

There are ways to unwind without detonating your tax bill. What's usually missing is the decision, and the decision usually gets made for you by a chart like the one above. Loving a company isn't a plan, and loving it more doesn't make it one.

Nike may well be fine from here. That was also true at $161.

What Caught Our Eye

A couple of charts and graphics we found insightful this month.

What Worked Best Depends Entirely on When You Looked.

Three windows, three different winners. Over the full stretch since 1990, private markets led on return and also on volatility. From 2010 to 2025, global equities annualized 10.5% while sovereign bonds delivered under 1%. Since 2020, gold has been the top performer at 18.4% annualized while bonds went negative in both nominal and real terms. Nobody sitting in 1990 could have called that sequence, and nobody today can call the next one. Owning a bit of everything isn't a hedge against being wrong. It's an admission that being right consistently isn't available.

A Frozen PB&J Is Now a Billion-Dollar Business.

Uncrustables took eleven years to reach $116 million in annual sales. It took twelve more to add another $884 million. That shape, flat for a long time and then suddenly not, is what compounding actually looks like from the inside. The frustrating part is that you cannot tell the difference between the flat part of this curve and a product that simply is not working. The same is true of a savings plan in year four.

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