Enough with the "side hustle"

(This isn't the rat race. We're building long-term here...)

I hate overused buzzwords. Sure, I want you to pay down teacher debt and build your financial wellbeing.

I just hate the word “side hustle,” that’s all. It reminds me of a bunch of hamsters fighting to get on the same wheel.

“Side hustle” sounds like a hobby, a holiday bartending job or summer nannying for a friend.

Words matter, and I hate buzzwords.

I started hating buzzwords the first time I went to the Xtreme games.

I’m not going to lie—It was pretty cool watching some guy barrel into a bunch of hay bales when one wrong breeze would’ve sent him crashing through the second-story window of the First Baptist Church.

But the next day the word was everywhere—barf!

Xtreme toothpaste, Xtreme flavored Doritos, Xtreme decaf coffee…

You name it. It was XTREME.

Nowhere are there more buzzwords than in marketing—and education.

I once wrote my (oppressive evaluation) goals with a buzzword generator. 

My real from-the-heart goals got rejected. “Not enough of a stretch.”

That’s a story for another day. For now, here’s what I said:

I said, “I'm going to walk away and pretend to think deeply about this. I’ll come back in a week with new goals, which you’ll approve, but they’ll be written with a buzzword generator.” 

That’s exactly what happened.

That’s the type of thing I picture when I hear “side hustle.” Nonsense tasks, smoke and mirrors…a hamster wheel. Teachers scurrying around with second and third jobs, treading water.

That’s not the goal here—it’s two things:

  1. Recognizing and charging for your value

  2. Building on it.

I’m talking monetary “value” not fluffy-emotional value. It’s time to replace the word “side hustle” (second, third, or fourth teacher jobs) with a new thought pattern. Let’s say this: “We’re building.”

Building what?

I used to build two things as a teacher—stockpiles of “just in case” stuff, and debt.

Does that sound like you? Then definitely start with the No Spend Challenge (don’t worry…it’s pay what you want, even free, but feel free to send me a million bucks when you’ve made a few yourself…).

Stop spending in your classroom.

When you do, you’ll give yourself the biggest raise you’ve seen in a while.

Next, think… “If I could do something I love and am good at—and people would pay me for it (besides teaching) —what would that be?"

[Note: I bet you didn’t say “Hustle around on the side.”]

What’s the action verb you love best?

Do that. If you don’t know how just yet, watch people already doing “that” who make money doing those things. Who are the best of the best? What are they doing?

Study them closely. Chances are they’ve got an income stream.

Whether it’s consulting, creating content, courses, or providing services, they’re probably getting paid. You could be, too.

The first step is to see your talents for what they are and stop giving them away for free. Once you learn to say “Here are my rates,” you’ll find future opportunities.

Then, your job will be to say “yes” to the right ones.

It’s a journey. And it’s hard. And yes, everyone hustles—but we’re building intentionally for the future.

What’s the goal?

The goal isn’t to take a few crumbs from the freelancing table—it’s financial growth and career advancement. Sadly, in education “growth” is often defined as sub-par “professional development,” recertification nonsense, high-priced grad degrees, or National Certification that costs three times the price of my first car.

Don’t fall into the “spend more to ‘learn’” trap here. Learning is everywhere. You don’t have to spend a dime to grow, learn, expand, and find great ideas—especially if you don’t have one to spare.

Learning and ideas are all around you—even in your YouTube and Pinterest feeds right now.

Many of your talents and passions are paychecks and invoices waiting to happen.

  • Are you a fixer? You could be a consultant, write policy papers, work in a think tank, or join (or start) a startup.

  • Are you a storyteller? You might be an author, a course creator, a consultant, a YouTuber, a content creator, or someone who figures out how to fix the gaps, cut through the red tape, and build the next generation of learning.

  • Are you an organizer or explainer? You might discover your schools are transferable--and highly marketable--in another field. You could be a project manager or corporate trainer.

  • Are you a giver? Again, consulting, designing courses, building, ghostwriting, or advising…

There are opportunities everywhere once you learn to see them.

I recently connected with a high-end consultant. “I used to be a teacher,” she said. Now, she doesn’t get on the phone for less than what a new teacher makes in a week unless she’s intentionally donating her time—which she can afford to do because, well, you should see her rates!

You can do that—wherever you’re passionate. That’s one thing I learned after someone I knew turned a skill I taught into a high-ticket weekend course for wealthy people. He made thousands in a few hours.

“Ugg, why didn’t I do that?”

“Simple,” a friend said. “You didn’t ask.”

It’s not enough to be a “lifelong learner.”

I have to be a lifelong doer as well.

It takes a little planning, some intentional building and connecting, and the willingness to burn your “Teacher: Will Work For Coffee” sign.

Trust me, it’ll lead to some big things.

I never planned a career switch, by the way. I planned to work both jobs forever, but Job Two was fun, so I kept learning. It built into an opportunity. I said yes.

Then, it wasn’t a “side” anything anymore. It was real.

I still catch myself offering to volunteer, “help,” and sit for the “let me pick your brain,” calls. It’s what ex-teachers do. But these days, I correct course much faster and say, “Here’s how I can help you. Here are my rates.”

The hardest part is taking that first step. Once you do, you’ll find teachers everywhere are doing the same thing—building financial success by any means necessary.

It’s quite an impressive group, really.

It’s also the example I want students to see.


Please feel free to share this substack, visit some of the articles on the website, take The No Spend Challenge or even read the book. And let me know what you’re doing or building.