It was not a wise thing to do—and it’s not an example I’d want my kids or grandkids to follow. But I’ll tell you a tale anyway. It’s a story of loss and comeback, of fear… and, truthfully, more fear. I guess confession is good for the soul.
Quite a few years ago, I noticed something simple: the price of gasoline was falling. From that observation, I made a leap. I began buying oil companies and energy ETFs.

Prices are not coming down, inflation is rising, mortgage rates are rising, the stock market is near bear territory.
Given all the planning and various strategies that have been discussed on HD, do those retired have any concerns about weathering this storm?
How about those within a few years of retirement? Anything happening that may change your plans.

HAVE YOU GIVEN any thought to what’s about to happen to your S&P 500 tracker?
Three enormous IPOs are expected later this year: SpaceX, OpenAI, and Anthropic. Based on their most recent private transactions, SpaceX appears to be valued at around $1.25 trillion, OpenAI at roughly $800 billion, and Anthropic at approximately $380 billion. Combined, we could be looking at close to $3 trillion in private market value that wants to go public. To put that in perspective,

IN AN INTERVIEW a little while back, the technology investor Peter Thiel drew an uncomfortable comparison. Today’s frenzy around artificial intelligence, he said, parallels the tech stock bubble of the 1990s. To illustrate his point, Thiel pointed to Amazon.
By any measure, it’s been an extraordinary success. But, Thiel points out, it hasn’t been a straight line. At one point early on, Amazon shares lost more than 90% of their value.
“My suspicion is that that’s roughly where we are in AI.

The first line of defence against a portfolio in freefall is, of course, the chill pill (pioneered by Dan Smith). Unfortunately, clinical trials have shown that effectiveness drops by approximately 80% during periods of elevated market volatility, rising to 100% during a full correction. Researchers described it as “a notable flaw in the product.”
With pharmaceuticals neutralised, you will need to work through the following antidotes in order of increasing strength.
Antidote One: The Micro-Shrug (Usage Case: early denial,

LAST WEEK THE government released its monthly employment figures for February. The results weren’t great. Payrolls declined, and unemployment ticked up. These numbers square with other downbeat data, including a recent uptick in bankruptcy filings.
Another worry: Oil prices have been rising, a result of the conflict in the Middle East. That’s a concern because it could lead to a reacceleration of inflation. It could also dampen consumer spending because higher gas prices act like a tax on consumers,

I drink the odd can of Coke Zero — sugar free, caffeine free. Unfortunately the caffeine free version is rarely on offer, but on those odd occasions when I discover it at a good discount I buy multiple cases. I enjoy a good bargain.
My instinct for a bargain extends to my retirement portfolio. I scratch that itch by having a policy statement around rebalancing during market volatility. Normally I only rebalance once a year, but my policy statement has a clause to enact a threshold rebalance if the equity portion of my portfolio drops more than 15% — a once and done strategy.

“What, me worry?” — Alfred E. Neuman
What should worry me more—inflation or market declines? Both reduce the value of our savings, but they behave very differently. Inflation tends to work slowly and quietly. Market declines, by contrast, often happen quickly and visibly.
Consider several bear markets—defined as declines of 20% or more in the S&P 500.

Bear Market
Market Decline
Time to Bottom
Time to Recover

1973–74 Oil Crisis
-48%
21 months
~7 years

1987 Crash
-34%
3 months
~2 years

2000–02 Dot-com Bust
-49%
30 months
~7 years

2008 Financial Crisis
-57%
17 months
~4 years

2020 COVID Crash
-34%
1 month
~5 months

2022 Inflation Bear Market
-25%
9 months
~2 years

Market declines are dramatic.

One of the stranger paradoxes in finance is volatility — the degree to which an asset’s price swings up or down over time. Most investors hear the word and flinch. But once you understand what volatility actually is, and what it makes possible, you might start to see it very differently.
Think about it this way. A savings account is about as predictable as it gets, your money sits there, safe and stable, and grows at a modest rate.

HEALTH SAVINGS ACCOUNT (HSA) is the most efficient tax-advantaged investment account because it offers a triple tax advantage:

Contributions are tax-deductible
Earnings grow tax-free
Withdrawals are tax-free if used for medical expenses

One of the best uses of an HSA is to actually invest the balance.
For example, I keep $500 (the minimum required balance) in cash. The rest, I invest in low-cost index funds. This allows me to maximize compounding inside the HSA account.

BEFORE ITS FAILURE in 2008, Lehman Brothers had been one of the most prominent investment firms in the United States. After 158 years in business, what caused it to collapse so suddenly? In a word: complexity.
Lehman had been involved in the securitization of mortgages, a process that resulted in taking something relatively simple—a home mortgage—and turning it into something much more complicated, thus obscuring its true risk level. That was the proximate cause for the firm’s failure.

This futuristic Research Report from June 2028 got Wall Street scared a few days ago. It predicts that AI will cause massive disruption and displacement in the economy which will lead to a terrible market decline.
It’s very scary reading not for the faint of heart.
Personally, with national debt at $38 trillion, I worry more about a looming debt crisis than AI.
What is your take on either of these topics? What are you worried about?

TRUMP ACCOUNT WAS created as part of the OBBBA signed on July 4, 2025. I’ve been getting a lot of messages about it, because there is a lot of conflicting information. The IRS has also posted some instructions for the account.
My goal with this post is to walk through the rules and give my take on when (if ever), this account makes sense.
Timing & Creation
First and foremost, no contributions are allowed in this savings account for children until 12 months after the law’s enactment,

LAST YEAR, an unusual story made the news: The University of Chicago was reportedly looking to sell an entity known as the Center for Research in Security Prices (CRSP). The story came and went quietly, but it’s worth pausing to understand it.
CRSP’s origins date back to the 1960s. Its initial goal was to build a database of historical stock prices. This is harder than it might seem. Before trading was computerized, stock prices were maintained on paper.

No one wants to see a rollback. But we all know it occasionally happens.
As of February 20, 2026, the all-time high for the Vanguard S&P 500 ETF (VOO) is about $642.
If we experienced a decline from that level:

A 20% drop would take VOO to roughly $513 — about where it traded in September 2024.
A 30% drop would land near $449 — roughly January 2024 levels.
A 40% drop would bring it to about $385 — prices last seen around May 2023.