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When most people think of retirement, they picture quiet mornings, coffee on the porch, and freedom from the daily grind. That’s certainly part of it, but there’s another reality many retirees — myself included — face: living on a fixed income can be tight.
I receive about $3,000 a month from Social Security. Thanks to smart decisions like downsizing my home and paying it off, I can make that work. I live simply and spend within my means. But an extra $1,000 a month would make a real difference. It would mean more breathing room in the budget, the ability to travel, and the chance to say “yes” to opportunities I sometimes have to pass up.
That’s why I started Retired and Trying — a real-life project where I document my journey to build $1,000 a month in extra income. I’m not promising overnight success or get-rich-quick tricks. This is about real attempts, real lessons, and real progress — one step at a time.
Why I’m Doing This
Like many people, I didn’t save as much for retirement as I probably should have. I worked hard for decades, raised a family, and paid the bills — but the big retirement nest egg just never materialized. That’s okay. I can’t change the past, but I can build something new in the present.
This $1,000 goal isn’t about becoming wealthy. It’s about peace of mind, security, and a little more freedom. It’s about showing that even after retirement, it’s possible to learn, build, and grow something meaningful — even starting from almost nothing.
My $100 Head Start
The good news is I’m not starting at zero. I already have a base of about $100 a month from LegalShield, a membership-based legal services plan I promote as an affiliate. It’s a service I believe in — affordable legal help for everyday people — and it’s something retirees, families, and small business owners can truly benefit from.
Whenever someone signs up through my referral link, I earn a commission. It’s not a fortune, but that $100 proves this is possible. It’s the foundation I’ll build on. If I can grow one income stream to $100, I can grow others too. And the plan is to keep stacking those streams until they add up to $1,000 a month.
My Multi-Stream Plan to Reach $1,000
There’s no single magic solution. This isn’t about chasing one big payday — it’s about combining several small income streams that work together. Here’s how I’m doing it:
1. Growing My LegalShield Income
Since LegalShield is already producing results, it makes sense to focus on growing it further. I’m creating blog posts about legal needs in retirement, short videos explaining the service, and sharing links on social media. If I can grow that $100 to $300 or $400, I’ll already be well on my way.
2. Affiliate Marketing
Affiliate marketing is another key piece of my plan. It’s simple: I recommend products or services I trust, and when someone buys through my link, I earn a commission.
I’m already using this approach by:
- Linking to helpful books and tools I talk about in blog posts and videos.
- Recommending services that retirees might find useful.
- Including affiliate links in content that continues to earn over time.
The best part is that once the content is out there, it can keep working for me month after month.
3. Building and Flipping Websites
Another income stream I’m working on is building and selling niche websites — known as website flipping. The process is straightforward:
- Create a site focused on a specific topic (like diet plans, legal help, or retirement living).
- Write helpful content and grow its traffic.
- Sell it once it’s valuable.
If I can sell a site for $400 or $500 and repeat that a few times a year, that alone could cover a big chunk of my goal.
4. Selling T-Shirts and Mugs (Still in Progress)
I’m also exploring print-on-demand products — T-shirts and mugs with funny or relatable slogans for retirees. This type of business doesn’t require inventory or shipping. I design the product once, upload it, and the platform handles the rest.
I’ll be upfront: I haven’t made a sale yet. But that’s part of the journey. Every side hustle takes time to gain traction. I believe with more designs, consistent promotion, and better marketing, sales will come — and when they do, it’s another stream to add to the total.
5. Content Creation and YouTube
Lastly, I’m growing my Retired and Trying YouTube channel and social media presence. Right now, they’re mostly a way to document this journey, but they can eventually become income sources through affiliate links, sponsorships, or even ad revenue.
Creating content keeps me learning, keeps me connected, and helps build an audience that might benefit from what I’m building — and support it too.
Wins, Losses, and Lessons So Far
I promised to share the real story — and that includes the struggles. I’ve run promotions that didn’t convert, built websites that haven’t sold, and launched products that haven’t found buyers (yet).
But I’ve also had small wins — like that first $100 a month from LegalShield — that prove this is possible. Those small victories matter because they build momentum and confidence.
The biggest lesson? This is a marathon, not a sprint. Success doesn’t happen overnight. It’s about learning, adapting, and staying persistent.
Why I’m Sharing This Journey
There’s no shortage of “make money online” stories out there, but most skip over the hard parts. I want this to be different. Retired and Trying is about the real journey — the good, the bad, and everything in between.
I’m not a business expert. I’m just a retiree trying to build some extra income — and sharing everything I learn along the way. If my story helps someone else believe they can do it too, then it’s worth it.
Final Thoughts: It’s Never Too Late
If you’re retired and thinking, “It’s too late for me,” let me tell you — it’s not. I started with no big budget, no special skills, and no head start. Just curiosity, determination, and a willingness to try.
Whether it’s $100 or $1,000 a month, every step forward matters. And maybe one day soon, I’ll write the post announcing I’ve finally hit that $1,000 milestone. Until then, I’ll keep building, learning, and sharing it here on Retired and Trying. Because retirement isn’t the end — it’s just the start of a new chapter.
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