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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.”
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):
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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?”
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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: -
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.
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If you run a business, it helps you design offers people actually want to buy.
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If you’re job-hunting, it helps you rewrite your resume so the hiring manager thinks, we need this person.
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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.