Solving the Income Investor Dilemma

My friends like to make fun of me by taunting that I don’t like to commit to things. I’m constantly trying new hobbies. I don’t like to make plans too far in advance because something more exciting might pop up. I don’t even like to renew my car tags for more than one year.

I have the opposite problem with my investments. When it comes to those, I’m a bit of a hoarder.

My two-pronged strategy is based on long-term holding. Building wealth through compounding means holding Bedrock Income stocks for years or even decades. It usually takes at least seven years to really see compounding take off. Even my “short term” Current Yield picks are meant to generate income through dividends for “as long as it makes sense.” This could be years as well.

When I find dividend stocks I love, I want to hold them forever and just keep collecting my income. This creates a few issues.

Our money can only be invested in so many places at once. And we want them to be the best investments at the right time. Unless we bring new money to the table, it means selling less optimal positions for new ones. There’s always an opportunity cost.

Income is our main goal, whether we pocket the money or reinvest it. It’s easy to sell a position if it has cut the dividend or a cut looks likely. And it’s easy to cut a position if you’re sitting on a gain and the industry looks like it’s headed for a downturn.

But what about a stock where you’ve locked in a great dividend that keeps rising and the shares keep going up and up? When, if ever, should we shift focus to capital gains instead of our income goals? Is it worth waiting if a potential correction is around the corner?

The Steady Income or Big Payday Question

We have two stocks in the Yield Shark portfolio in this position—Philip Morris International (PM) and AT&T (T). I’ve mentioned both of them in past Dividend Digest issues, so you might own them. Let’s take a look.

My readers’ original PM entry date was October 2021 at $94.87. Shares were up another 5% last week hitting $150.46. They’re now up 58.5%.

Philip Morris