Each of my kids collected more than three pounds of candy on Halloween Night. Three-plus pounds! Their efforts were not superhuman by my best late-80s-to-early-90s estimation.

We are going to have these bags until Easter.

The candy hangover was real. Both YMCA basketball games played “the day after” were utter disasters for their dad and coach.

Sugar-high crashes are real. Which is why we are talking “sleep well at night” dividends paying up to 8.6% today.

Don’t be Coach Brett the day after Halloween. If you’re worried about a Wall Street sugar withdrawal, the time to prepare ye ‘ol portfolio is right now.… Read more

If you’re retired (or planning your retirement—which, of course, we all are!), I have great news: You can probably take a lot more out of your nest egg every year than you think.

I’m talking about safely withdrawing 8% or more from your portfolio—without the prospect of living a lot longer than your money does!

We can thank an unlikely wealth generator for this turn of events: AI.

Before you ask, no, I’m not talking about putting a chatbot in charge of your finances! I’m talking about a low-key way the tech is helping retirees (and near-retirees) boost both their investment income and their net worth, leading to that huge 8%+ withdrawal rate we just talked about.… Read more

We’ve been dividend-hungry lately. Our Wednesday missives have brought 11 income ideas since Labor Day!

It’s a busy week for our brood! If you bought these payers, you have four ex-dividend dates (the dates when the stock trades at a price minus—“ex”—the dividend per share) on deck this week. Plus two pay days!

Income Calendar for This Week

This neat weekly view comes to us courtesy of Income Calendar, our homegrown dividend tracker. We developed IC for serious income investors like yourself. The tool projects every dividend payment with accuracy that is unmatched in the industry.

This calendar beats today’s best AI—it’s custom-made and precision-tuned for dividend stocks.… Read more

Some of our favorite bond funds (yielding 8%+) just took a header. And it’s setting up the best buying opportunity we’ve seen in nearly three years.

We can thank panicked mainstream investors for our shot here.

CEF Investors Are Ultra-Conservative (and Easily Spooked)

This opportunity is coming to us in closed-end funds, which we love for a lot of reasons—not the least of which is the fact that they’re a small corner of the market.

As of the end of 2024, there were just 382 CEFs out there, with $249 billion in assets among them. Compare that to roughly $11 trillion in ETFs, as of the end of June.… Read more

Treasury Secretary Scott Bessent is arguably the biggest stock-market cheerleader in American political history. And that fact is throwing a floor under stocks in a way few people realize.

It’s another reason to buy stocks now—or better still, stock-focused closed-end funds (CEFs). Because when things get rough, we can count on Scott to temper policies that might otherwise ruffle the markets.

This sounds like a minor thing, but it’s key in a market like this, which I see as still having room to run, even though, yes, valuations are getting stretched.

The Stock Market Indicator

To get at the moderating effect of Bessent’s presence, we need to start with President Trump, who has a long history of caring about the stock market, even though his career was in private real estate.… Read more

The Fed is cutting, and that’s bullish for preferred stocks and their big payouts. Let’s look at a trio yielding up to 9.8% that will benefit from every ease from Mr. “Dead Man Walking” Jay Powell.

Most vanilla investors know common shares—and stop there. They buy banks like Bank of America (BAC) or Wells Fargo (WFC) by typing “BAC” or “WFC” into their brokerage account.

Financial firms also offer preferred shares with much bigger payouts. All we need to do is keep typing.

Preferreds are part stock, part bond. These hybrids trade on regular exchanges under normal tickers. They pay dividends and represent ownership, but their income stems from “bond” DNA.… Read more

Are we in a stock market bubble or not? Let’s tackle that question head-on, because it’s all we seem to be hearing about these days.

I’ll put my cards on the table: We’re not in a bubble. I’m going to show you why I’m still bullish on stocks at these levels. Then we’re going to play overwrought bubble fears with a “cornerstone” fund that’s beaten stocks over just about every timeline but is still cheap (and yields a rich 8%, too).

When it comes to stocks, the truth is, there’s a good reason why they keep rising: We’re in a booming economy.… Read more

“I don’t have to make and update my goofy spreadsheets anymore!” my man Peter B. from New Hampshire writes.

Tell ‘em, Peter!

We are devoted to retiring on dividends here at Contrarian Outlook. But a little bit of work in retirement is OK. As income investors, we should be able to forecast our income.

Note that I said a little bit of work. Not a lot! I am not interested in fiddling with spreadsheets until the end of time, and neither is my man Peter.

If you’re with us, why not hop aboard the Income Calendar train with Peter and me?… Read more

The 10-year Treasury rate has sunk to around 4%. And we’re going to cash in.

No, we’re not purchasing Uncle Sam’s sorry paper. Instead we’re picking up a basket of ridiculously cheap bonds paying more than 2X the beaten-down payout on the 10-year.

And the lower Sam’s rate falls, the more we profit, since bond prices rise as the 10-year yield, pacesetter for rates on loans of all types, drops. Our play here is through closed-end funds (CEFs) like the two we’ll discuss below, yielding up to 10.3%.

Why Treasury Yields Are On the Mat 

There are lots of reasons floating around in the media about why Treasuries are falling, a “slowing” economy chief among them.… Read more

I hate to see investors (particularly retirees) starving for dividends, especially with inflation stuck around 3% (and you and I both know that the real number is higher—just head down to your local grocery store!).

A big myth around dividends is that you have to invest a lot upfront to get anything meaningful in return. It’s easy to see why people feel that way, with the average S&P 500 stock paying a meager 1.1% as I write this.

This is where my favorite investments, closed-end funds (CEFs), come in. Using the three we’ll delve into below, you could get a little over $1,000 a month in income, thanks to their double-digit yields.… Read more