Scaling & Mastery

How I Built Every Career I’ve Had By Teaching Myself

Photo of Andrew Henderson

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4 min read

How I Built Every Career I’ve Had By Teaching Myself

Since I started creating and posting content last year, one question keeps coming up from friends:
“How did you learn to do all this?”

It’s a fair question. I didn’t go to school for this.
I’ve just been figuring it out for almost two decades.

I studied creative writing and filmmaking at Boston College—because I loved stories. I still do.

After college, I moved to New York and worked as a production assistant on a couple of independent films.
Not long after, I landed an assistant editor job at a boutique film editorial on Madison Avenue.

We worked with major agencies like Ogilvy, McCann, BBDO, and Y&R—cutting everything from global ad campaigns to Super Bowl commercials.
I was learning fast on high-profile projects and even had the chance to contribute to music videos for artists like Jack White and Death Cab for Cutie.

It wasn’t exactly glamorous, but it was hands-on.
I learned how to work under pressure, how to tell a story in 30 seconds, and how to be useful—on set and in the edit bay.

But after a couple of years, I could feel the world shifting.
The conversations weren’t about film anymore—they were about tech.

The internet—especially social media—was starting to take over the world.

And I didn’t want to just watch that happen.
I wanted to be part of it.

So I started learning.
I bought coding books—actual paper ones—and started experimenting.

This was before course platforms.
Before YouTube tutorials made it all look easy.
There was no roadmap. Just curiosity.


The messy middle

At first, I just built websites for friends who had small businesses. I taught myself HTML and CSS.
I didn’t have a clue what I was doing at first, but I figured it out line by line.

I was drawn to web development—not because I had a grand plan, but because I liked making things from scratch and the freedom of self-publishing.

Around that time, craft beer was blowing up.
I got curious, and decided to start a blog.
Recruited writers.
We interviewed brewmasters, went to expos, built an audience.
It felt like we were part of a movement.

Eventually, I realized: beer wasn’t my passion.
But building something that mattered to people? That was.

So I kept going.

I went all-in on as a software engineer.
I taught myself full-stack development—JavaScript, Node.js, database architecture, the works.
I launched several apps—for companies—and a couple under my own name.

Some things worked. Some didn’t.
But I kept learning whatever I needed to bring my vision to life.

Then, over time, something started to bother me...


The realization

I had all these skills—coding, design, video, storytelling—but I was only using a narrow slice of them. I missed the creative side. I missed having an audience. And honestly? I missed feeling like what I was building had real impact.

Then it hit me.

So much of what I’d learned in recent years hadn’t come from college or jobs. It came from online creators.
From YouTube channels. From online courses. From people just like me, showing up, sharing what they knew, and creating something bigger than themselves.

It was empowering. I got value I didn’t even know I needed. And I realized—I wanted to do that for other people.


Finding my way to teaching

But what would I teach?

Software felt too narrow. I didn’t want to be another “learn to code” person—it’s only one part of what I care about. If I was going to help people, I wanted it to come from a place of depth.

So I made a decision:
I’d take everything I’ve learned—and my obsession with understanding how things work—and start reverse-engineering how top creators in the creator economy build their businesses.
I’d study their strategies, find the patterns they all have in common, and break it down into something others could actually use.

Because once you understand the structure behind how these creators grow, monetize, and scale—you realize it’s not luck, it’s not talent, and it’s definitely not an accident.

It’s a system.
And I’m here to teach it.


Why this matters now

I think the world is waking up to the idea that we don’t have to wait to be chosen.
We can choose ourselves. Build our own path. Teach what we’re learning. Share as we go.

The creator economy is growing fast—Goldman Sachs predicts it’ll hit half a trillion dollars by 2027—but it’s not just about the money. It’s about people finding meaning in their work again. And I want to help make that possible.

I built my course, 5-Star Creator, because I want to pass along everything I’ve learned—from content, to tech, to business, to the deeper stuff like confidence and clarity.

But more than that, I want to show people what’s possible when they stop waiting and start building—even if it’s messy at first.


If you’ve ever felt that pull—trying to figure out what’s next, learning everything you can, and wondering if you can actually turn it into something real—I just want to say: I get it.

And you're not alone.

I’ve spent years learning the hard way—through trial, error, and late-night Google searches.
From editing rooms to code editors, I’ve picked up a toolkit of creative and technical skills that, together, make this whole content creator thing actually work.

Now I’m sharing everything I’ve learned to help others build something of their own—without needing to be a filmmaker, a coder, or a startup founder first.

If you’re trying to build an online presence and earn a living doing work you actually care about, I want to help you skip the guesswork—and get there faster.

Thanks for being here. Really.

—Andrew

Tags

Personal Branding,Personal Journey,Escape the 9-to-5,Entrepreneurship,Entrepreneurial Journey,Creator Mindset,Self-Education,Lifetime Learner
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