Back in my cubicle days, raises were a crapshoot.
I asked for a raise—but I didn’t just ask. I made a case. I actually went over my boss’s head and walked into the owner’s office with a list of things I had done to improve processes, cut costs, and increase output.
And guess what? My boss wasn’t thrilled about me going over his head—but it worked.
That raise wasn’t handed to me. It was earned because I framed it in terms of value, not just time served. And I asked the person signing the checks.
Where did I get the idea?
It came on a plane to Dallas, from a guy named Dave.
How to Ask for a Raise: What Are You Gonna Do For It?
Dave was the guy who recruited me into one of those multi-level marketing (MLM) businesses back in my "I'm gonna get rich quick" phase. He wasn’t just an MLM guy; he also owned a gym. Ran a few businesses. And had a much bigger bank account that anyone I knew at the time.
We were on our way to a big MLM team conference in Dallas, and he told me a story about an employee who asked him for a raise.
Dave didn’t say no.
He just asked, "What are you gonna do for it?"
Not in a jerky way. Just matter-of-fact.
"If you're doing the same job, why would I pay you more? I can hire someone else to do that. But if you’re gonna bring in more value—I’m listening."
That really hit me.
Until then, I saw raises as something you got for time served.
Dave saw it as something you earned with leverage.
It was the first time I really saw the world through a millionaire business owner's eyes. And I couldn’t unsee it.
From "Permission" to "Possibility"—How Gen X Can Give Themselves a Raise
Now fast forward.
I don’t have a boss to ask anymore. I work for myself.
But I still have to earn raises.
The difference? I don’t need permission. I just need a reason.
That reason might be:
Launching a new offer
Adding more value for clients
Creating a new income stream
But I’m not off the hook.
The market is my new boss. But I’m closer to the one signing the checks, and it’s way more honest.
People either buy or they don’t. If they don’t, I tweak it. I improve it. I try something else. I keep showing up until it clicks.
That’s how I gave myself a raise this month.
And the good news?
You can do the same.
Here’s What Giving Myself a Raise Looks Like at 52
I’ve actually given myself multiple raises recently.
First, I started leveraging all the AI learning I’ve been doing and added AI marketing consulting and implementation services. I’m currently working with two clients. And that gives me a raise in two ways:
I added a new income stream
It’s an income stream that pays better than most of my others—because it delivers higher value.
Second, I launched a premium tier of this newsletter—Redefining Retirement Pro.
That means every free post will stand on its own. You’ll learn something useful. You’ll be able to take action.
But if you want to go deeper? There’s an upgrade that gives you the system, template, or tool to make that lesson 3x to 10x more valuable.
Think of it like the difference between reading about how to change your oil vs. getting the wrench and jack delivered to your door.
That’s the raise. The pro tier is the offer. The market will decide if I deserve it.
How You Can Give Yourself a Raise Too
You don’t have to build your empire overnight or quit your day gig to do it. You just need a first step. Here are a few ideas:
1. Learn a New Skill
Learn Vibe Coding (watch this, pretty cool and crazy)
Get fluent in ChatGPT, Notion, or Beehiiv
Study newsletter writing, SEO, or basic funnel building
These aren't just skills. They're leverage. Learn one, use it to create something once, and benefit from it over and over.
2. Start a Side Income Stream
Launch a Blogletter (write once, publish twice)
Recommend tools you use with affiliate links
Sell a premium tier like I just did
Package a skill into a freelance service
3. Productize Something You Already Know
Create a digital product or micro-course
Offer a 1-hour paid consult, then turn that recording into a passive product.
Build a Notion or Canva template that saves people time
4. Let AI Do the Heavy Lifting
Use ChatGPT to write your first lead magnet
Build a GPT trained on your content (yes, this is a thing)
Automate your welcome emails, blog writing, or customer research
If you’re in RR Pro, you’ve already got access to step-by-step systems for some of these.
If not? Start with this...
AI Prompt of the Week
Let AI help you find some ideas on how to give yourself a raise.
Use my Pathfinder prompt. It’s perfect if you're ready to earn more without begging for it:
"I am a [YOUR AGE] individual with [YOUR EXPERIENCE, SKILLS, KNOWLEDGE ARE and/or PASSION FOR X HOBBY]. I want to start a blog and newsletter business that aligns with my life experiences, passions, and what the world needs while being financially sustainable. Please suggest 5 in-demand topics that:
1. Leverage my unique skills, knowledge, or life experiences.
2. Address intrinsic, extrinsic, and systemic values to ensure relevance, fulfillment, and impact.
3. Fall into the monetizable categories of health, wealth, relationships, or hobbies.
4. Meet the principles of Ikigai, ensuring they align with what I love, what I’m good at, what the world needs, and what I can be paid for.
5. Appeal to a defined target audience that I can connect with easily, fostering community and engagement.
6. Allow for scalability into additional revenue streams like courses, books, or consulting.
7. Include a unique angle or differentiation to stand out in the market.
8. Suggest ways to use AI tools for content creation, audience analysis, or automation.
9. Are practical to implement considering my level of technical expertise, time, and budget.
10. Address emerging trends to ensure the topics remain relevant in the next 5–10 years.
11. Have potential for cross-platform expansion into podcasts, video content, or social media."
Additionally, for each topic, include specific monetization strategies and examples of successful blogs or newsletters in that area as inspiration.Drop that into ChatGPT, then sit with the answers.
Pick one. Build the first version. Try it out.
You don’t need to get it perfect. You just need to get it moving.
Music of the Week
This song was everywhere in the late ’90s. Catchy as hell. But if you really listen to the lyrics… it’s wild it ever got radio play.
I always wondered how many people were cruising down the highway, singing along to a song about doing meth—without even realizing it.
Anyway, in a roundabout way it fits the theme of today’s post perfectly.
The song’s about knowing it’s time for a change. For the singer, that meant ditching meth and the spiral that came with it.
For me? It was ditching the dependence on a weekly paycheck. Letting go of the idea that I had to wait 50 years to “retire.”
That shift—just like the song—was loud and addictive in its own way. But it was a turning point.
Final Thought
You don’t need permission to make more money. You need a reason and a system.
The beauty of working for yourself is that you get to decide when it’s time for a raise.
But the hard truth?
You also have to earn it.
No more hoping. No more waiting.
Just building.
And that’s what Redefining Retirement is all about.
Have a good one,
Corey
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