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When I set out on this $1,000-a-month journey, I thought I knew what I was getting into. I’ve built websites, sold T-shirts, written books, and tried just about every side hustle you can name. I’ve had small wins and a lot of failures. But I always believed that if I just stayed at it, one day the pieces would fall into place.
This time around, I thought things would be different. And in some ways, they are — but not for the reasons I expected.
The Hard Truth About Chasing Passive Income
Let’s be honest — the idea of earning $1,000 a month in passive income sounds simple enough. You start a few projects, stay consistent, and the money will start rolling in… right?
That’s what I used to think. But the truth is, this journey has tested my patience and persistence more than almost anything I’ve done before.
I figured using ChatGPT as my coach and business assistant would make everything easier — and it does make a big difference. I’m more organized, my content looks better, and I’m learning faster than ever.
But what I didn’t expect was how long it would take to actually see results.
Even with all the tools and experience I’ve got, there are still days when I look at the numbers and think, “Why isn’t this working yet?”
The Illusion of Easy Success
If you scroll through YouTube, TikTok, or social media, it feels like everyone is making money online in their sleep. Courses, ads, affiliate links — it all looks effortless. But behind those quick success stories are months, sometimes years, of work most people never see.
And that’s what I wish I had reminded myself before I started.
Even though I’ve done this before — even though I’ve failed before — I still thought this time would be different. I thought having more tools, better knowledge, and smarter strategies would make it easier.
The truth is, the work is still the work.
It takes time to build traffic. It takes time for search engines to trust a website. It takes time to earn a following.
And that “time” part is where most people give up — right before the gold.
“Three Feet from Gold”
There’s an old story I love called Three Feet from Gold. It comes from Napoleon Hill’s classic, Think and Grow Rich.
It’s about a man who started digging for gold, found a little success, and then hit a dry patch. After months of no luck, he gave up and sold his equipment. The next person who took over dug just three feet further — and struck one of the richest gold veins ever found.
That story sticks with me. Because that’s how this journey feels some days.
I know I’m doing the right things — posting consistently, improving my websites, creating products, writing blog posts, and trying new ideas. The foundation is being built, even when it doesn’t look like it from the outside.
And I remind myself every day: Don, you might just be three feet from gold.
What’s Different This Time
Even though I haven’t hit that $1,000 a month mark yet, something has changed — my mindset.
Before, I chased quick results. Now, I focus on progress.
I treat every small step as part of the larger goal. Whether that’s getting a new visitor to a blog post, a like on a YouTube video, or someone grabbing one of my books — it all matters.
I’m no longer doing this to “get rich.” I’m doing it to prove that persistence pays off, even in retirement. I’m doing it because creating things — shirts, websites, books, videos — gives me purpose.
And I’m doing it because someone out there needs to see that it’s still possible to build something meaningful after 60.
The Lesson I Want to Share
If you’re on your own side hustle journey — whether you’re retired or still working — here’s my best advice:
Don’t quit when it gets quiet.
That’s when the real work happens. That’s when you’re building the habits and systems that will eventually pay off.
It’s easy to compare yourself to others who look like they’re “winning,” but your timeline is your own. Most of the time, success shows up right after you almost give up.
So keep digging. Keep learning. Keep showing up.
You might just be three feet from gold.
Final Thoughts
This $1,000 per month journey has been harder than I expected. But it’s also been more rewarding than I imagined — not financially (yet), but personally.
Every video, every blog post, every design — it all adds up. I believe the results will come, and when they do, it’ll be because I didn’t stop.
If you’ve ever felt stuck or discouraged, I get it. I’ve been there. But remember — it’s not over until you stop digging.
📘 From the Floor to Six Figures
If you haven’t yet, grab my book From the Floor to Six Figures on Amazon. It’s my story of going from the factory floor to leadership — filled with lessons about work, persistence, and finding purpose.