Future of Work for Gen X, Entrepreneurial Survival and AI Prompting Techniques

Before we get into the tools and takeaways this week, I wanted to come clean.

I’ve been self-employed for 11 years. Other than 9 month stint as a RV salesman, I haven’t had a full-time job since 2013. But I still feeling the pressure.

Still in bed sometimes, starring at the ceiling wondering: “WTF! What if all this all goes away?”

Because here’s the truth…

AI isn’t just disrupting white-collar jobs. It’s coming for entrepreneurs too. Freelancers. Solopreneurs. People like me. People like you.

The industry I’ve built my entire business on for the past 10+ years, search engine marketing, is changing fast. Like, way faster than I thought.

Search isn’t what it used to be. People don’t “Google” the way they did even 12 months ago. Answers are getting summarized. Clicks are disappearing. And the thing that made Google billions, selling those top spots, is breaking too.

So yeah… I’m being disrupted. And I’m not gonna pretend I’ve got it all figured out. But I’m testing, learning, and sharing everything I find that might help us stay ahead.

If you’ve ever laid awake wondering “WTF do I do next?”, know that I’m right there with you.

Why I’m Still Optimistic

Because even though the ground is shifting, I’ve got something many people don’t:

Practice.

I’ve spent the last 10–15 years learning how to survive outside the system.

Not relying on one income stream.

Not hoping one boss or one company would have my back.

Learning how to build skills that travel with me.

A slightly higher tolerance for risk.

That’s the whole reason I write this newsletter, to share what I’ve learned, what I’m learning now and meet people in the same boat so we can compare notes and figure this shit out together.

At the end of the day, if it helps even one of you stay relevant, stay funded, and stay in the game (whatever that game even is any more), I’ll keep posting.

Ok, stepping off the soapbox now.

Let’s learn something…

Your New Job Title is: Entrepreneur

I heard a quote this week on the Moonshots Podcast that stuck with me:

Sounds cool. But let’s be honest, it’s not something you just flip a switch and become overnight.

If you’ve been in a job for 10, 15, or 25 years, chances are nobody ever taught you how to think like an entrepreneur. I know I wasn’t.

You and I were trained to be reliable, not resourceful. To follow processes, not break them. I had to learn a lot of that on my own.

But I believe this shift is baked into our DNA. Our great, great, great grandparents were entrepreneurs - farmers, builders, side hustlers. It’s only in the last 100 years-ish that we were trained to be employees.

That’s changing again.

So to help you make the leap (mentally, not necessarily financially just yet), I prompted a Perplexity thread that you can skim to get the gist of what entrepreneurial thinking looks like.

👉 Entrepreneurship 101 — Perplexity AI thread

Then, check out the podcast I heard this on. The first part of the discussion is well worth the listen.

PRO TIP: Start using LLMs to learn and teach others. I used perplexity for today’s post but you can also use ChatGPT, Claude, or any other LLM. I just chose perplexity for this post because it's easier to share the thread.

AI Tool of the Week: Pickaxe

I built a custom GPT using Pickaxe.co ($) that helps newsletter creators estimate their monetization potential. I call it LetterWingman.

I used a prompt from my Audience to Income guide, turned it into an interactive tool, and now it sits on a landing page—working 24/7 while I sleep.

Here’s the good:

• Great for lead magnets for list-building

• Easy way to monetize your knowledge with affiliate links

• Can help productize your expertise

Here’s the not-so-good:

• No native email automation

• Some learning curve if you’re new to prompt-building

• Help documentation could be better (kind of scattered)

You can turn one good GPT into tool or income stream:

• Lead Magnet Tool – Embed GPTs on your site

• Client Work – Build tools/GPTs for businesses, solopreneurs or consultants and charge for setup + strategy

• Affiliate Link Pathway – Use the GPT to recommend tools like Beehiiv, Kit or any affiliate program you’re promoting.

• Digital Product Add-On – Bundle a GPT with a paid course, Notion system, or ebook.

• Done-For-You GPT Setup Service – Upsell for people who want you to build these for them.

• SaaS-style Subscriptions – Charge for access to premium tools.

Still early days for Pickaxe, but if you’re looking to turn your skills or frameworks into tools people can use, and pay for this is worth playing with.

🎯 Try the GPT I built (LetterWingman) Get 20% Off Pickaxe for trying

AI Prompting Isn’t a Shortcut—It’s a Skill

When I was designing my pickaxe I wanted to sharpen up my prompting skills so I could produce more consistent results for the users.

I found a video on creating prompts that hooked me with two great quotes…

and…

Then the gal in the video went on to explain prompting techniques;

• First principles - Learn more

• Chain of thought prompting - Learn more

• Meta prompting - Learn more

Simple concepts that help you get much better results.

Watch this video to see how better prompting can help you build better tools, write better content, and make faster decisions.

Oh and it’s also worth checking out: Semantic Prompt Design by Pickaxe

Music of the Week

Man in the Box – Alice in Chains

That opening riff feels like a warning siren for anyone still sticking to the old rules.

That chorus feels like Gen X finally tearing the duct tape off and saying, “Enough.”

And man did Layne have a great voice or what? One of the best all time IMHO.

Big Takeaway This Week

You’re not behind.

You’re just in the middle of a shift that most people don’t even realize is happening.

The good news?

You are aware of the shift.
You’ve got experience.
You’ve got tools.
You’ve got stories worth sharing.

And now with a little help from AI you’ve got leverage.

Let’s build.

Have a good one,

Corey

P.S. A new sponsor this week is a tool I’ve recommended to some local business owners to help them document their processes…