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This week? We’re going to put it into practice.
The two moves you need in your toolkit right now:
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:
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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.
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Articulate your unique perspective. What approach do you take that differs from the mainstream? How can you sharpen contrast?
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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.
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Create specialized tools. Build AI systems that embody your unique approach and perspective. For many of our members, this is an unexplored cosmos.
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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
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Retire early
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Build fast on social
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AI is taking your job
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
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From employee to entrepreneur.
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From fragile income to offensive income.
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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 my LetterWingman Pickaxe 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 adapted it it to my approach here on Redefining Retirement. I summarized everything into a more refined messaging plan for the future.
AI-Resistance Prompt of the Week
Lets 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:
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Resume or LinkedIn profile
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Client emails, proposals, or strategy docs
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Blog posts, presentations, social posts
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Audio or video transcripts of you explaining something
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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: