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- Building Your Way Out: A Gen Xer’s Newsletter Strategy to Escape the Retirement Trap
Building Your Way Out: A Gen Xer’s Newsletter Strategy to Escape the Retirement Trap
Turn your expertise into income by sharing your work and building an audience.
Last week, we talked about future-proofing yourself by skipping the gatekeepers and going straight to the audience.
This week, I am going to share a newsletter business model you could use to attract and build an audience.
It’s a marketing strategy where you're sharing what you're working on.
It’s a solid strategy if you are looking for ways to start a newsletter business (and any online business, for that matter). Or if you want a different way to stand out in the job market and attract potential employers.
It's a strategy that, in hindsight, I used to build my music marketing blog back in the late 2000’s.
I’ll explain more, but first, let me tell you what inspired this all this…
Build In Public
A couple of years ago, I was dabbling in the Software as a Service (SaaS) start-up world when I came across a term called building in public (BIP).
Here’s the definition:
Building in public (BIP) refers to the practice of transparently sharing the process of creating a product, company, or project with an audience. This approach involves openly documenting and communicating the journey, including successes, challenges, learnings, and even business metrics, often via social media or other public platforms.perplexity.ai - “What is Build In Public”
A whole BIP community on x.com shares their successes and failures with the audience.
Here a few quick examples:
Sahil Lavingia, Gumroad's founder, who raised $5 million through crowdfunding by while sharing all the gory details about his journey.
Arvid Kahl, who, with his partner, built and sold FeedbackPanda in just TWO years, reached $55,000 in monthly recurring revenue with only TWO employees. Now, he has a huge audience he teaches BIP to.
At the time, I realized this wasn’t the first time I saw building in public as a marketing strategy…
Smart Passive Income
Pat Flynn was one of the first people I can remember who documented everything.
Way back in 2008, after being laid off from architecture, he parlayed a successful LEED exam website into SmartPassiveIncome.com, where he publicly shared everything – revenue, expenses, processes. Today, his net worth sits at $3-3.5 million. (Here’s one of his early reports).
It wasn’t called a building in public at the time; it was called blogging.
And in 2014, we had another take on this strategy…
Show Your Work
Earlier this year, I read the book “Show Your Work” by Austin Kleon.
He reinforces this idea for creative professionals - artists, writers, musicians, designers, etc.
The stories you tell about the work you do have a huge effect on how people feel and what they understand about your work, (...) affects how they value it.
So, you add it all up, and you get a…
Light Bulb Moment
But, what does this have to do with Gen X and newsletters?
Here’s what I’m thinking, if…
It works in the software start-up world.
It works in the blogging world.
It works in the creative world.
It only makes sense that it should work with a newsletter business too, right?
By sharing your work, you’re building a personal brand, a portfolio, and a pipeline of opportunities—all at the same time.
And this is why I think it works across the board…
Why Building In Public, Sharing Your Work, Etc Work
People don't pay for experience; they pay for transformations and results.
Your expertise matters when it delivers outcomes. As business growth consultant Jaime Ellithorpe told me in a Zoom meeting recently…
"People want to play with winners... It's about your personal brand, who you are, what you know and displaying that in a public way."
SHOW, don’t tell.
Content like a frequently updated blog or newsletter shows
a resume only tells.
Then, as you acquire new skills, put them on display.
This approach:
Creates rapid feedback loops for improvement
Builds trust through transparency
Generates buzz with a "what happens next" effect (Who Shot JR?)
Develops a network of potential collaborators
Fosters loyalty through audience connection
Can you see how powerful this is?
And, this strategy will work whether you want to go on your own or continue in a traditional job role.
Think of it as a live resume. While traditional resumes are static, sharing your work shows real-time growth and results.
Potential customers or employers don’t have to look at your resume; they can look at your newsletter and see you gain skills and get results in real-time.
How To Get Started
A newsletter is a perfect way to build in a public. You don’t need audio or camera equipment. You don’t have to be on a camera; you just need a computer (or even a smartphone - which is where I keep notes and photos).
Here’s how to get started.
Pick three topics:
One skill or area of expertise that has the potential to make you money
One topic that excites you when it is brought up in conversation
One topic or skill that compliments your other interests OR you are curious about
This strategy is also really cool because the intersection of those will make your content unique and original.
You can use ChatGPT to walk you through these step by step and give you some ideas on your newsletter. Just enter this prompt…
You are an expert and coach in building successful newsletter businesses in public. I want to find a niche for a blog and newsletter business that aligns with my skills, passions, and curiosity while being financially sustainable. Help me explore these questions step by step, one step at a time:
1. Earning Potential: What skills or expertise do I have from my current or past jobs that people are willing to pay for?
2. Passion and Energy: What topics excite me when they come up in conversation?
3. Curiousities: What topics am I curious about learning more about?
4. Unique Perspectives: How can I combine my skills, interests and curiosities to create a fresh, unique angle?
5. Monetization Potential: What are some ways I could make money in this niche (e.g., ads, affiliate marketing, subscriptions)?
6. AI Integration: How can AI tools like ChatGPT help me save time or enhance my work in this niche?
7. Future Trends: Are there emerging trends in this niche that could keep it relevant in the next 5–10 years?"
Start Working On Your Newsletter:
Launch your newsletter (I use beehiiv)
Share your journey – mix existing skills with new ones
Put your content where your ideal audience hangs out
Need a little more info? No worries.
Just read my Blogletter post for more on that.
Let’s do it,
Corey
No rush, but when you're ready to get start building, 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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