Raise your hand if you want to actively work for income in 2024.

(Please note your dividend strategist already has his pointer finger in the tip of his nose. Not it!)

Here at Contrarian Outlook, we prefer passive dividend income to active income, thank you very much. Because trading hours for dollars is, let’s just say it, such a drag.

A job? Tired. Dividends, meanwhile, are wired. Since ‘tis the season for resolutions, let’s discuss my top four to retire on dividends in 2024.

Dividend Resolution #1: Project Our Income

If you’re a serious dividend investor, I hope you took my advice last week and grabbed your risk-free trial to Income Calendar.… Read more

If there’s one thing we need to remember when we buy high-yield closed-end funds (CEFs), it’s this: always demand a discount.

Well, make that two: always demand a high dividend, too! Because CEFs are renowned for their high—and often monthly—payouts, with the average CEF yielding around 8% today.

But back to discounts. Luckily for us, they’re common with CEFs: of the 422 CEFs tracked by the CEF Connect screener, 384 trade at discounts to net asset value (NAV).

That’s a great place to start our search for top-notch CEFs, because these discounts are basically free money: they let us pick up, say, Mastercard (MA) for 85 cents on the dollar through a CEF like the Gabelli Dividend & Income Trust (GDV).… Read more

Let’s go ahead and use the quickest, most reliable strategy I know of to kickstart a reliable 7% income stream that rolls our way every month.

My specialty is writing about stocks, bonds and closed-end funds (CEFs), but all of these are really a means to the end of achieving financial independence. What really matters is how much income you can pull out of these investments to fund your lifestyle.

The answer is a lot more than you might imagine. I’m going to show you how to pull 7% out of three funds that pay monthly and offer diversified income streams based on bonds issued by large, well-established companies (think of this portfolio as being like a big commercial bank, but one diversified across the world).… Read more

Select real estate may be the income investing play for 2024. As I write, seven real estate investment trusts (REITs) are dishing dividends from 8.7% all the way up to 15.4%.

These REITs—and their ilk—are literally designed to deliver dividends. That’s how Congress wrote the rules when they legislated these real estate investments into existence back in 1960.

REITs avoid taxes at the corporate level. But in exchange, they need to pony up at least 90% of their taxable income and redistribute it to investors as dividends.

As a result, our average REIT yields somewhere around 2x to 3x the market.… Read more

The stock market’s 2023 recovery begs the question: are we in for a reversal next year? And if so, what does that mean for our closed-end funds (CEFs)?

It’s a natural concern, but it’s important to remember that bull markets don’t die of old age. Plus, we aren’t in a bull market—the S&P 500 still hasn’t fully recovered from its drop over the last two years, let alone priced in the economic growth over that time.

Whether stocks will or won’t price in that growth in 2024 depends on three things we’re likely to hear a lot about next year. The first will be something that’s seemingly been everywhere for the last two years.… Read more

If you are a serious dividend investor, then you know the answer to this question:

How much dividend income are you going to make in 2024?

In other words, what are your projected dividends next year?

If you don’t know, then you’re not as dedicated to dividends as you thought. Disappointing, but fixable with Income Calendar.

And please, don’t tell me I’m being hard on you. If that’s the way you feel, then this is the tough love that you need. Your wakeup call for 2024.

It’s time to treat your dividend investing like a business. Because it is.… Read more

I hear that robots are standing by to run the world.

Fine—just have them send us a nice, neat report on our dividends. Preferably daily. Thanks.

Seriously, my fellow contrarian, enough with the hype. I tried, albeit briefly, to use ChatGPT as a research assistant for this column. Really it was a softball that I knew the answer to:

Hello ChatGPT, how much did iShares 20+ Treasury Bond ETF (TLT) drop in 2022?

The answer, of course, was 31%, but the robot hadn’t been fed the info so didn’t know. I lost interest and carried on as usual, “manually” verifying my numbers.… Read more

Today we’re going to use a simple strategy to (legally!) beat the tax man. The key is a (too) often-ignored group of funds whose dividends are beyond the reach of the IRS.

The low-risk assets behind this income stream really should be part of any income investor’s portfolio. And the three tickers we’ll discuss below, which yield up to 7.9%, are a great place to start. Thanks to their tax-free status, their “real” yields will likely be considerably more for us.

Enter “Boring But Beautiful” Municipal Bond Funds

Here’s the truth on taxes: If you’re an American and you receive any kind of income, you’re going to get taxed.… Read more

Buying a business development company (BDCs) is kinda, sorta like investing like a venture capitalist (VC).

Minus the arrogance. And the lack of yields!

I was 26 when I realized that VCs were just regular guys and gals. Well, let’s be honest—mostly guys. They didn’t necessarily know anything special. But VCs play the part, sitting in their Steelcase chairs and short sleeved polo shirts while it’s 60 degrees out here in Northern California.

BDCs, on the other hand, are investments for the people. Plus, they pay—up to 15% in dividends!

Here’s a quick primer. BDCs lend to small and midsized businesses that the big banks either won’t touch.… Read more

It’s mid-December, and everyone wants to know if stocks—and by extension high-yield closed-end funds (CEFs)—are poised to roar into ’24 in a so-called “Santa Claus rally.”

I’ll venture a prediction, but before I do, I should tell you that I come at the whole idea of a Santa Claus rally from a bit of a different angle than most folks in the business media or on Wall Street.

I actually dislike Christmas cheer in the markets. Not because I’m a Grinch. Rather, it’s because I think Santa rallies are not a good sign for stocks going forward.

Take 2021, a year in which market sentiment whipsawed.… Read more