It usually hits you on a Tuesday.

You are sandwiching a Zoom call between checking on your mom’s medical appointments and worrying about your kid’s tuition. You look at the grocery bill, then at your 401(k), and you realize the math has changed.

The “Traditional Retirement” deal we were sold—work 40 years, save 10%, get a gold watch, golf all day—is broken.

For the Sandwich Generation (that’s us, squeezed between aging parents and launching kids), the old path doesn’t offer enough margin. We don’t just need “savings” that we can’t touch until we’re 65; we need cash flow now.

But here is the trap. When you Google “how to make extra money,” the internet screams at you to:

We don’t need a second job. We are tired enough. We need a Quiet Side Hustle.

Retiring from work isn’t really the goal (let’s be honest, we’re going to be working for a while). The goal is retiring from the fragility of a single paycheck. It’s about taking the 20+ years of experience currently trapped in your head and turning it into an asset.

The vehicle for this isn’t TikTok. It’s a Newsletter Business.

While Gen Z is chasing viral trends that disappear in 24 hours, the “adults in the room” are building email lists.

The reason is simple: Email is the only algorithm you own.

You have spent decades solving hard problems. You have context, judgment, and “scar tissue” from navigating recessions and corporate pivots.

I hear this objection constantly: “This sounds like homework. I don’t want to spend my weekends writing essays.”

Good news: You don’t have to.

The “Newsletter” game has changed completely in the last 12 months. You don’t need to be Hemingway. You just need to be helpful.

Hell, these days you can just talk into your phone or computer and the AI does the writing for you.

In 2026, you are not the writer; you are the Editor-in-Chief. You use AI tools (like the ones built directly into platforms like Beehiiv) to do the heavy lifting.

Your job isn’t to stare at a blank page. Your job is to curate and correct. This turns a 4-hour writing task into a 30-minute editing task. It’s not “writing”, it’s downloading your brain.

I want to be transparent with you because the internet is full of fake “overnight success” stories.

When you start a “Quiet Side Hustle,” it doesn’t rain money immediately. It is a slow burn. But unlike a salary, which stops the moment you stop working, a newsletter builds leverage.

Here is a screenshot from the backend of my own business (using beehiiv). This isn’t to brag—in fact, it’s to show you how “boring” real growth looks.

Look closely at the numbers:

Here is the lesson: $300 a month doesn’t sound like “Retirement Money.” But that $300 pays a utility bill. Or it covers the car insurance.

And the best part? It requires zero new hours of work. That income comes from an asset I built once—referring tools I trust, writing articles that live forever—that now pays me dividends every single month.

And that is just one income stream. In addition to my Google Ads consulting, this project has lead to consulting work where I built beehiiv sites for others.

This is the goal of the Gen eXit Playbook: We aren’t trying to buy a Lamborghini. We are trying to build a floor of security under our families, $100 at a time. Stacking bricks.

You don’t need to quit your job to do this. In fact, you shouldn’t. The best time to build a lifeboat is while you are still on the ship.

But before you get lost in the tech, you just need to commit to the mindset:

“Ride Like The Wind” – Middle Aged Dad Jam Band (Cover)

I swapped out the original Christopher Cross version for this cover by the Middle Aged Dad Jam Band because I think it captures the vibe of this newsletter perfectly.

These are busy guys with careers and families, meeting up in a garage to play music just because it makes them happy (and a little jealous if I’m being honest).

That is the whole point of the Gen eXit Playbook. We aren’t building these income streams so we can buy yachts; we are doing it so we can buy time.

Plus, the lyrics hit home for anyone building a side hustle right now:

(Or in our case: To make it to financial breathing room).

It’s a long ride and it takes patience. But you gotta keep stacking bricks. And if you have the right crew, you’ll get there.