The Hardest Part of the Dividend Investing Journey
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In one of my recent Dividend Happy Hours, I got a very thought-provoking question from my friend Salvatore.
Normally, I’d save something like this for the “Since You Asked” section of the newsletter, but this one felt main article worthy. Salvatore asked:
"Do you ever get the feeling that dividend investing will never snowball and get you to your ultimate goal?"
Absolutely! The truth is, we all have those moments of doubt. I don’t think any of us are completely immune to feeling that way from time to time.
As you know, the journey toward financial freedom is not a fast and easy one. You go into it knowing that it will take years (decades, really) before you get to the point where you can finally live off your dividends.
And because it takes so long, there are naturally going to be times when you question whether it’s actually working—especially when the world around you feels like it’s moving so much faster.
You see people on YouTube or Blossom making crazy money on crypto, or bringing in $10,000 a month from something like MSTY or ULTY (don’t even get me started). And then there you are—dollar-cost averaging into SCHD, collecting what feels like spare change in comparison.
It’s hard not to feel like you’re missing out. But then again, nothing about reaching financial freedom is easy, and it’s not supposed to be.
During those moments of self-doubt, I find it incredibly helpful to just zoom out. When you step back and look at your progress over time, you start to realize a couple of important things.
First, you are making progress. You just don’t always see it when you’re glued to your portfolio every day. And second, it doesn’t really matter what anyone else is doing.
They’re not your competition, so don’t try and chase them. Investing is a personal game—you’re only playing against yourself.
The goal is to be further along today than you were yesterday. While it might not always be obvious, it is happening.
Just a few years ago, my dividend income was barely touching $25 a month. A year later, it jumped to $100. Then over $200. And now, I’m averaging close to $300 a month.
It’s not life-changing (yet), but the passive income is definitely growing. And that’s the great thing about dividend investing: it just gets better the longer you do it.
The bigger your portfolio gets, the more passive income it pays you. And the more income you have to reinvest, the faster your dividend snowball will grow.
Since it’s a matter of building momentum, the beginning of the journey is undoubtedly the most grueling. That’s where progress feels the slowest, and pushing through it is a rite of passage for investors. You just have to get through it.
Besides…what’s the alternative? Give up?
The hardest part—which is starting—is already behind you. You just have to keep doing what you’re doing, and time will take care of the rest.
With that said, I’d love to hear from you: What’s been the hardest part of the investing journey for you so far? Write to me here and let me know.
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ICYMI 🎥
Know This Before Dividend Investing | Ep. 27
In this episode of The Deep End, we're breaking down the real difference between dividend investing and income investing—and why chasing high yields can often lead to disappointment.
CAREFULLY CURATED 🔍
📺 Russ's Big Sell - In a surprising twist, Russ’s recent reflections on what had been his top dividend stock led him to reconsider the investment and ultimately remove it from his portfolio.
🎧 Richer, Wiser, Happier - In this episode of the We Study Billionaires podcast, Stig Brodersen and William Green reunite for their quarterly conversation about the things that have made them richer, wiser, or happier over the past few months.
📚 A Finance Fairytale? - Daniel Peris—author of The Ownership Dividend (one of my favorite investing books and a must-read for any dividend investor)—dives into the topic of share buybacks and questions whether they truly live up to the hype.
LAST WORD 👋
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