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- Building a Business at 50+ Without Quitting My Day Job: Week 5 Results
Building a Business at 50+ Without Quitting My Day Job: Week 5 Results
Week 5 is in the books. Check out the lessons on building a side hustle at 52.

BAM BABY!
Ever have one of those weeks where everything you've been working towards finally starts clicking?
The kind where you go from wondering "Is this actually going to work?" to "Holy crap, this is really happening!"?
Well, that was my week.
After what felt like an eternity (but was really just a few weeks), I landed my first real newsletter client. And while the $629.10 (after Upwork fees) might not sound like much to some, it's not about the money.
It's about validation.
Proof that this crazy idea of building a business at 50+ isn't just a mid-life crisis in disguise.
Quick side note: If you're just joining this journey, I'm documenting my attempt to build a newsletter/AI marketing business while keeping my day job. No fancy venture capital, no trust fund – just leveraging decades of experience and a willingness to learn new tricks. (You can catch up on previous weeks here.)
Let's dive into what happened this week...
Income: $629.10 (after Upwork fees)
Leads: 2 new conversations to be had
Meeting: 5 meetings (4 pending decisions)
Newsletter Clients: 1 newsletter client

The income is from the newsletter business specifically. But leads and meetings are a mix of Google Ads, Newsletter biz leads plus, new entry into the income portfolio, 1 potential AI marketing client (more on that below).
I’ve been finding way to interweave all those skills (Google Ads, newsletters and AI) into the conversations and its been super effective.
Weekly Wins
We're officially in business!
After what felt like forever (okay, just a week longer than planned), landed my first newsletter client. Quick side note: even after Upwork's cut, we're looking at $629.10. Not exactly retirement money, but definitely "yeah baby, this actually works" money.
But here's where it gets interesting...
Reaching out to my network (something I probably should've done years ago) landed a potential AI marketing gig. This prospect has a goldmine - huge email list, tons of content assets, big ideas - but zero time. Perfect opportunity to show how AI can turn an email list into a profit center.
I reached an agreement with another Google Ads client this week too (when you add in last weeks that’s two in two weeks).
Oh, and remember that newsletter I helped build? It's alive! Just launched. (If you're looking for help with LinkedIn marketing, check out “Social Media Bites” - Dustin knows his stuff.)
What I Worked On This Week
Kept the LinkedIn momentum going (more on why this matters below)
Reached out to some old connections (including a music industry buddy from England I met online in 2013ish but I've never met in person. He helped me clarify some things about my business ideas and is another site of eyes watching out for opportunity)
Had some killer conversations with newsletter industry folks (not clients yet, but man, the insights...)
Sent out 4 more proposals on Upwork.
Created a blog post on how to use ChatGPT to create a Mock Newsletter Case Study (more on that below)
Still keeping an iron in the music fire (completed a demo and copyrighted a song I co-wrote with singer-songwriter Amanda Grace)
What I Learned
The power of just showing up and helping people is real. Case in point: had a Zoom call with a gal named Elizabeth (hi if you're reading this!) who works in PR and podcasting. Within a week, she's introduced me to potential clients, shared content ideas, and we're helping boost each other's LinkedIn presence.
Quick side note on networking: You never know which connection will lead to your next big break. Stop trying to predict it and just be helpful.
Next Week's Focus
Keep the LinkedIn train rolling - even when it feels like a chore somedays.
Be more selective with network outreach - now that we have some lead flow.
Focus on quick wins for new clients - super important to make a great first impression.
Making these updates shorter - My wife kindly pointed that these emails have been getting WAY to long. She's right... (but don't tell her I said that.) I don’t want you feeling like you have to read a 1000 page Stephen King novel every week. I’m going to break out some of the deeper dive stuff into its own post like I’m doing with this weeks AI Tip Of The Week.
Opportunity of the Week
Newsletters. Newsletters. Newsletters.
(Yeah, I know I sound like a broken record, but hear me out...)
The more conversations I have, the more I realize how many businesses need help with email marketing. I actually have this idea how I could REALLY ramp up my, but I'm almost scared to pursue it because it might work too well and I’ll be too busy. (Anyone want to partner up? Reply to this email and let's talk.)
AI Tip of the Week
Check out my detailed post on using ChatGPT to build custom newsletter business case studies. The results might surprise you...
(warning, it’s kind of long BUT its a fun exercise)
Music Memory Lane
Remember USA for Africa? Well, the metalheads had their version too - Hear 'n Aid.
I shared an image of the cassette tape from my collection last week on Reddit and it blew up (a little 150 upvotes, 33 comments).
Check out their song "Stars" if you want to hear (or relive) what happens when metal meets charity.
The song still kicks ass in my humble opinion.
What you think? Let me know if you remember Hear 'n Aid.
Have a good one,
Corey
What'd you think of today's email? |
No rush, but when you're ready to start your side hustle, here are a couple ways I can help you…
1. Start Your Future-Proof Blogletter: Discover how a "blogletter" lets you turn decades of experience into income streams. Perfect for Gen Xers who want to create their own job security. Check out my complete guide on building a long-term asset that pays you while working on your own terms.
2. Grab Your Gen eXit Playbook: Discover my offensive approach to retirement—no more waiting until 65 to do what you love. You'll learn how I went from a $40K/year cubicle guy to a six-figure solopreneur and how to stay relevant doing work you actually enjoy.
3. Join The Newsletter: If you liked this post, introduce yourself and join our community of Gen Xers going from employment to self-deployment. Get weekly insights on staying relevant, building multiple income streams, and creating lifestyle-focused work. It's free, and you'll get The Gen eXit Playbook.
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