#10 Why $60K to $220K Isn’t About Hard Work—It’s About Smart Work

Let’s rewind to when I was 15. Teenage Dan—awkward, unsure, and figuring out life one mistake at a time.

It’s November. Report card season. My grades for the year are in, and they’re… less than stellar. Especially in maths. But I had a brilliant idea (or so I thought): I grabbed a red pen, scratched out my grade, and wrote in a higher one.

“Maybe this’ll fool my parents,” I thought.

Spoiler: it didn’t.

Fast forward 24 years, and I’m at an end-of-year Adobe social event. Someone asks me, “So, what do you do?”

It’s an innocent question. But it’s one I’ve never had a clear answer to.

I glance around the room and see colleagues thriving in their niches—JavaScript experts, content specialists, technical SEO wizards. And here I am, still wondering: what bucket do I fit into?

Before I can respond, someone introduces me: “Oh, this is Dan. He’s our SEO.”

Simple enough. But …

The Jack-of-All-Trades Dilemma

Early in my career, I leaned toward content. Technical SEO? Avoided it like the plague. But as time went on, technical SEO became part of my skill set. Then I picked up link building. And digital PR. And client management.

I didn’t just dabble in these areas—I dove deep enough to understand how they connected.

Now, what do I call myself? A specialist? A generalist?

Here’s what I know: I’m insatiably curious. Whether it’s a podcast, a Twitter thread, or a YouTube tutorial, I’m always learning. And not just at a surface level—I need to understand something well enough to explain it to someone else.

The more I learn, the more I realise how much I don’t know.

That’s why I’m coining a new term: generalist specialist.

What is a Generalist Specialist?

A generalist specialist is someone who knows enough about everything to get the job done—and goes deep enough into specific areas to truly excel.

I’ve built my career by being adaptable, by knowing how to connect the dots across disciplines. This isn’t about being mediocre at many things. It’s about being great at integrating knowledge.

And this mindset has changed everything for me.

From $60K to $220K: The Generalist Specialist Path

Five years ago, I was earning $60K.

I didn’t think it was possible to break out of that ceiling. But by leaning into the generalist specialist mindset—connecting skills, learning relentlessly, and applying them across disciplines—I’ve grown that number to $220K.

If you think being a generalist is a disadvantage, think again.

The Power of Learning by Doing

Let me be real: I’ve never been “book smart.” My school grades? Average at best. University? Took me six years to finish a four-year degree. Even attempted two master’s degrees (speech pathology and an MBA)—both unfinished.

But when I started my first business as a wedding photographer, something clicked. I wasn’t just consuming information—I was applying it.

Photography taught me how I learn best: through hands-on, practical experience. Experimenting with light, solving problems under pressure, editing RAW files in Adobe Lightroom—that’s where I thrived.

Marketing has been the same. Theoretical concepts felt abstract. But when I applied them—optimising campaigns, analysing data, managing stakeholders—it all started to make sense.

Why Being a Generalist Specialist Works

I’m not the smartest person in the room. Never have been. But I’ve built my career on a relentless drive to learn and apply.

That’s why this mindset—this blend of generalist curiosity and specialist depth—has worked for me. It’s why I’ve been able to progress faster than I ever thought possible.

And I know the next evolution is coming. Machine learning, AI, data science—there’s always more to learn.

The question is: are you ready to become a generalist specialist, too?