Your dividend investing journey unfolds in stages, with each one marking a milestone in the pursuit of financial freedom. In my own brief investing experience, I've found that there are five levels of dividend investing.

One of the things I like most about dividend investing is that it’s typically pretty boring. It’s usually a pretty low-stress way to invest, but this week in the world of dividend investing was most definitely a departure from the norm, and has been more high-octane that most with nothing but bad news.

In my portfolio, there are quite a few dividend stock discounts to take advantage of right now. Out of the bunch, two stocks, in particular, have caught my eye during this downturn.

My biggest struggle as an investor came from not having a concrete process for researching stocks. Because of that, I wasn’t able to think for myself, and I didn’t have the tools I needed to think for myself.

Even during tough economic periods, family-controlled businesses tend to be incredibly dependable when it comes to paying dividends. Fortunately, for us investors, there's no shortage of dividend paying companies that contain a strong family presence at their core.

In the few short years that I’ve been investing, none of my dividend stocks have moved with the ferocity that Williams-Sonoma (WSM) has. But what exactly is driving this success story? This newsletter delves into the company a bit more.

When share prices seem to be doing nothing but going up, it's understandable if you’re starting to feel the fear of missing out. During these times, it helps to listen to the advice of John Bogle, the founder of Vanguard, who said that “dividends are an investor’s best friend.”

Dividend investing consists of a series of small victories, two of which I recently experienced in my portfolio.

While it’s true that dividend cuts do sometimes come out of nowhere, there are a few key signs to watch for that can suggest a higher degree of dividend safety.

By understanding what never changes about human behavior (things like fear, greed, etc.), you can build a more durable dividend portfolio. Risk, recessions, and stock market crashes can never be fully controlled or eliminated, but they can be anticipated.

You know how it goes: You start something new, and at first, it's super exciting—maybe even a bit obsessive. But after a while, whatever that thing is starts to lose its luster, and you find yourself in this "boring middle" where things begin to feel more routine, and possibly a bit monotonous. I think every investor reaches this “boring middle” in their dividend investing journey (probably more than once) and this is how it happens.

Charlie Munger was a voracious reader, and used to say that investing is a subset of "worldly wisdom." He also said that, "If it’s wisdom you are after, you are going to spend a lot of time sitting on your a** and reading.” So, connecting the dots here, becoming a wise and experienced investor is going to require an immense amount of reading, which makes sense, and is an idea that all investors should pay attention to.

I recently got an email from a member of our community here. He’s 40 years old, so 10 years older than me, and instead of getting excited about what lies ahead, he's worried about the future of his dividend stock portfolio.