Last week, we talked about building an entrepreneurial mindset.
This week? We’re going to put it into practice.
The two moves you need in your toolkit right now:
Be proactive in finding and testing solutions (instead of waiting for step-by-step instructions).
Adapt fast when things change (because they will).
Let’s get into both and become more AI resistant in the process…
Who’s In Your Corner?
As much as preach the solopreneur life, I still need other people.
The world is changing fast and if you don’t have someone to learn from, bounce ideas off of, or challenge your assumptions… you’ll stall out. Or worse, drift into irrelevant territory without realizing it.
Mentorship is underrated. Big time.
I’ve been following Perry Marshall for almost 20 years. If you’ve never heard of him, think of the kind of person who was calling shots on Google Ads in 2005 before most people even knew what it was.
He’s always a few steps ahead. I’ve taken his courses, traveled hundreds of miles for his events, and sponged up as much as I could.
A big chunk of the reason I’ve been able to stay self-employed for 11 years is because of what I learned from Perry.
Now he’s deep into AI and his most recent printed (yes, printed… on paper) newsletter was a good one. It was about finding your AI-resistant territory.
Here's the 5-step framework he laid out:
Identify areas of disagreement in your field. Where do experts have fundamentally different approaches? What are the schools of thought? These are fertile grounds for staking your claim.
Articulate your unique perspective. What approach do you take that differs from the mainstream? How can you sharpen contrast?
Formulate better questions. The quality of answers you get from AI depends entirely on the quality of questions you ask. Develop expertise in question crafting. This is not a class you take. It’s a daily skill.
Create specialized tools. Build AI systems that embody your unique approach and perspective. For many of our members, this is an unexplored cosmos.
Package human + AI offerings. Combine the strengths of both to create something neither could achieve alone. (side note: this is verbatim from the newsletter. If you end up reading this Perry sorry if I over stepped but I just had to share. Too good not to.)
(Side note: this is verbatim from the newsletter. If you end up reading this Perry sorry if I over stepped but I just had to share. Too good not to.)
Here’s where we get proactive…
Turning the Lens Inward
That newsletter made me stop and look at what I’m actually building here with Redefining Retirement. I wondered, how AI resistant my content.
So, I fed some of my best articles, blog drafts, and my Gen eXit Playbook into ChatGPT and asked it to analyze my stuff using Perry’s framework.
Here’s a slightly abbreviated version of what it spit out:
Redefining Retirement: Finding AI-Resistant Territory
1.Identify Areas of Disagreement in Your Field
Mainstream says:
Retire early
Build fast on social
AI is taking your job
I say:
Evolve your work
Own your audience through a newsletter
AI + Experience > AI alone
2. Articulate Your Unique Perspective
You’re not just teaching newsletter strategy. You’re saying:
“A personal-branded newsletter is the Gen Xer's insurance policy in the AI era. It turns your experience into equity and gives you a platform nobody can take away.”
You’re also selling a mindset shift
From employee to entrepreneur.
From fragile income to offensive income.
From working to retire… to working on what you love.
That combo—real-world experience + newsletter + AI—is your wedge.
3. Formulate Better Questions
The most valuable people in the AI era aren’t the best prompt engineers. They’re the ones who ask sharper, more human questions that AI alone can’t answer.
You’re helping Gen Xers ask:
“What do I really want to spend my time doing?”
“What do I know that others don’t—and how can I package that?”
“What will keep me relevant and independent when the world changes again?”
This builds long-term defensibility because you’re training a thinking muscle, not just handing off tactics.
4. Create Specialized Tools
Templates, content systems, and prompt stacks.
Everything I build in RR Pro and The WorXshop is based on how I think, not just what I know.
5. Package Human + AI Offerings
Real-world taste and storytelling + AI speed and structure. That’s the lane I’m building in. And it’s working.
I used the feedback to adapt it to my approach here on Redefining Retirement. I summarized everything into a more refined messaging plan for the future.
I created a manifesto, and I shared a short preview of it on LinkedIn last week. Tap here to check it out (and say hi).
AI-Resistance Prompt of the Week
Let’s see how AI resistant you are. Here’s a prompt i created to use it on your current business or profession.
You’ve got experience. Let’s make it defensible.
You’re going to use your own material—emails, posts, bios, client work, whatever—to see if you're operating in an AI-resistant way… or if you’re drifting toward automation roadkill.
STEP 1: Gather the Goods
Before you start, collect anything that shows how you think, solve problems, and explain stuff:
Resume or LinkedIn profile
Client emails, proposals, or strategy docs
Blog posts, presentations, social posts
Audio or video transcripts of you explaining something
About pages, bios, or internal training material
You're looking for your voice, process, and point of view. Not just your job titles.
And if you have been using ChatGPT or any other LLM for awhile, it might already have some of this stuff in it memory.
STEP 2: COPY + PASTE THIS INTO CHATGPT:
Drop it all into ChatGPT with this prompt:
You're my no-BS strategist.
I'm uploading material from my [business and/or professional life]- resumes, bios, social posts, emails, blog posts, website, transripts, etc.
I want you to analyze it through the lens of AI-resistance.
Don’t flatter me. Help me find my edge—or admit where I’m vulnerable. Use the 5 steps below:
---
1. Identify Areas of Disagreement in My Field
- What debates or opposing views exist in my industry?
- Where (if anywhere) do I take a stand or challenge conventional thinking?
- Quote back moments where I show backbone—and call out where I play it safe.
- What obvious industry BS am I ignoring that I should be calling out?
---
2. Articulate My Unique Perspective
- Based on my words, what is my specific take or method that sets me apart?
- What would I say differently than the average person in my role?
- Write 3 bold positioning statements that sound like me—but sharper.
- Push me to be more specific, not more clever.
---
3. Formulate Better Questions
- What kinds of questions do I ask or imply in my material?
- Are they generic, or do they reflect hard-won experience?
- List 5 of my weaker questions—and rewrite them to show more depth or insight.
- Bonus: Suggest 2 new questions I should be asking that reflect my lived experience.
---
4. Create Specialized Tools
- Where in my process or thinking could I create a repeatable system, template, or diagnostic?
- What am I doing manually that could become a lightweight AI tool or framework?
- Suggest 3 simple tools I could build or co-create with AI that reflect my unique method or POV.
- Be specific—give names, formats, and outcomes if possible.
---
5. Package Human + AI Offerings
- Where could my judgment + AI capabilities create a hybrid offer that’s tough to copy?
- What could I sell, teach, or deliver that depends on both my expertise and the power of automation?
- Propose 3 offers I could launch—each combining AI utility with my lived insight.
- Think services, digital products, content formats, or even newsletter angles.
---
Then give me the final verdict:
AI-Resistance Score: Low / Medium / High
Biggest Risk: Where am I most easily replaced?
Biggest Advantage: What part of my work would be hard for AI to clone?
Next 90 Days: What’s my smartest move to boost resistance and grow income?
Don’t sugarcoat it. Gen X doesn’t need coddling.
Pro Tip: If you haven't done so yet, create a folder on your computer or in Google Drive to store all your AI-related files. I have a folder for AI assets that I can easily access when I'm working on something. This will be very useful as you work with AI.
Now, if you haven’t you can take all that experience and start a business just by telling your story. Click here to see how to do that.
Music of the Week:
John Waite + Alison Krauss – “Missing You”
No big connection with the theme of the newsletter and the music this week. Just sharing a cool song that popped into my YouTube feed last week.
Haven’t heard it in awhile and it stands up. Honestly, they should’ve harmonized more but whatever, it works.
Check it out.
Big Takeaway
Being entrepreneurial doesn’t mean launching a startup or quitting your job tomorrow. It means thinking for yourself, moving quicker when things shift, and building a work life that doesn’t need outside permission.
Having mentors helps. Having a system helps more. But it really starts with owning what’s already yours—your story, your skills, your experience.
And if you’re not sure where to begin? Start by telling your story. That’s how I built this site.
Have a good one,
Corey
P.S. If you’ve been thinking about starting a newsletter or building a home base you actually own, Beehiiv just launched their new website builder. Now so your newsletter and a more complete version of your website can live under one roof.
They’re offering 20% off your first 3 months to my readers (that’s you) when you use the promo code: REDEFINE.
P.S.S. Get more AI goodness delivered to your inbox…
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