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,

I have an exasperating and ever-increasing case of double FOMOitis. Today’s stretched stock market valuations have given me a case of fear of missing out (FOMO) for not selling and locking in assured gains – sensible rebalancing theory suggests that we should all be selling on the way up. On the other hand, I have FOMO even considering selling because of the potential opportunity cost of not capturing further gains in a market with clear upward momentum – sensible investing theory (and Jonathan recently) suggests that we should ride the winners while they are hot.

WHERE YOU PUT your investments can make a huge difference for your after-tax wealth. 
As you know, we have 3 main investment accounts:

Taxable account. A traditional brokerage account where you are taxed every time you dividends or sell investments at a gain.
Tax deferred account. Traditional 401(k), 403(b), and traditional IRAs allow taxes to be deferred to the future. You pay taxes when your investments are withdrawn, and generally come with an immediate tax deduction.

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.

STOCK MARKET INVESTORS are enjoying yet another strong year. The S&P 500 has gained about 14% so far, shrugging off, for the most part, uncertainty over tariffs, interest rates and the latest government shutdown.
Should this worry us?
Since ancient times, soothsayers have been attempting—without luck—to forecast the future. As it relates to investment markets, the frustrating reality is that no one knows what the future will bring. But that doesn’t mean there’s nothing we can do.

The secret is revealed at the end.

TIME VALUE OF MONEY, asset class, diversification, dollar-cost averaging: This is the language of investment professionals. But it isn’t the language of everyday Americans, including those saving for retirement in their employer’s 401(k) plan.
Trust me, I know. During my nearly 30 years overseeing 401(k) plans, including providing financial education to participants, it became clear to me that using such plans as intended wasn’t easy for most people.