A few months ago, I was talking with a gal named Carolyn - a super smart fractional CMO.
We were chatting about the mission here on Redefining Retirement and she said (I’m paraphrasing):
“Why don’t you include us millennials too. I think we’d love your message.”
So I asked her:
“Who is Mr. T?”
She said:
“Who?”
And I I said,
“That’s why.”
If you don’t get it, then I’d have to water down the message.
I don’t want to do that. I’m building a community of people who share the same cultural moments. Who get the references. Who share the same perspective nobody else has.
And here’s the kicker: the better I understand my people, the better I can serve them.
Why am I telling you this? Glad you asked…
What Dale Carnegie Knew Before TikTok
One of the first lessons I picked up as I moved from employee mindset to thinking like an entrepreneur came from How to Win Friends and Influence People:
“People are not interested in you. They are not interested in me. They are interested in themselves – morning, noon, and after dinner.”
Translation: if you want to grab attention — boss, customer, client, future employer — you’ve got to understand them first.
That’s what this week is about: pain points.
The Exercise
I just did an exercise inside Dustin Reichman’s 7-Figure Leap cohort.
It helped be really drill down on what the audience I’m trying to reach with my new venture need help with.
My target audience: 40 to 60 year old Gen X YouTubers with 500k subscribers
Here’s the quick version of how I did it (and how you can too):
Collect the Complaints
I ran a ChatGPT prompt that scraped pain points from Reddit threads, YouTube comments, and forums. No “marketing speak” — just raw, real-world rants.Like: “the YouTube algorithm has essentially thrown [my work] in the garbage… something’s wrong” or “ZERO idea how to get brand deals… probably lost out on $100,000s of income… am I just being stupid?”
Sort the Big Stuff
Dumped it all into a doc, had ChatGPT help me ranked them most painful to least based on the data it found. For my crowd, the top three were:Unstable revenue
Algorithm dependence
No direct contact with their audience
Write the Before/After
This is where it clicked. I wrote out what people have, feel, and do now… then flipped it to what they want life to look like after.(Side note: to keep this post shorter the following example has abbreviated versions of the actual info it spit out).
Category | Before (Life Sucks) | After (Life Kicks Ass) |
|---|---|---|
Have | A couple AdSense checks, maybe a sponsor, zero email list | A direct audience they own + multiple ways to get paid |
Feel | Stressed, frustrated, checking analytics every hour | Confident, in control, actually excited to create again |
Average Day | Chasing trends, praying for views, glued to YouTube Studio | Creating cool stuff, talking to their audience, building assets that grow |
Status | “At the mercy of the algorithm” | “Running a real business” |
Boil It Down
My “working” transformation statement became:“Unstable YouTube Income → Profitable Creator Brand You Own”
And this isn’t just for entrepreneurs…
Why It Matters For All Gen Xers
This little framework doesn’t just work if you’re selling something.
If you run a business, it helps you design offers people actually want to buy.
If you’re job-hunting, it helps you rewrite your resume so the hiring manager thinks, we need this person.
If you’re posting on social, it helps you write stuff that makes people stop scrolling because they feel seen.
Prompt of the Week
Here’s the exact ChatGPT research prompt I used to dig up real pain points from Reddit, YouTube, and forums.
Important: Be sure to select “Deep research” mode to get more thorough information.
Help me research [insert your target audience here]. I want to understand, at a deep level, what transformation I can provide to them.
Criteria (customize):
[Insert age, role, or niche requirements]
[Insert platform, reach, or income level if relevant]
[Insert struggles or situations you want to focus on]
Research sources:
Real posts, forum threads, YouTube comments, Reddit discussions, product reviews, or community conversations
Instructions:
- Highlight the exact language they use (not marketing jargon)
- Rank pain points by frequency and emotional intensity
- Organize findings into a Before/After Matrix with these categories:
1. Have – What they currently have (income streams, assets, struggles)
2. Feel – Emotional language they use (frustrations, fears, desires)
3. Average Day – What their average day looks like right now
4. Status – How they describe themselves in their own words
5. After State – What they want instead (transformation outcome in their own words)
Output Format:
Provide results in a table with “Before (Life Sucks)” on one side and “After (Life Kicks Ass)” on the other, so I can clearly see the transformation.Try it yourself and see what your people are really saying out there.
Extra credit: Try this on same prompt with perplexity Deep Research and compare results.
Music Of The Week
Speaking of Mr. T, Remember when he played Clubber Lang on Rocky III?
Remember the big song from that movie?
Yep!
“Eye Or The Tiger” by Survivor
Perfect soundtrack while you’re mapping out your own before-and-after.
Takeaways
Here’s the short version, Gen Xer-to-Gen Xer:
If they don’t get your references, they’re probably not your people.
The more you listen, the easier it is to actually help.
A simple before/after flip can turn a confusing message into one clear line that sticks (in a newsletter, social post, resume, email to your boss, etc).
Have a good one,
Corey
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