How to Ask for a Raise and Get It (What's Working for Me at 52)

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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.

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:

1. I added a new income stream

2. 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: