How To Find "Work" That Feels Like "Play"

"How did you stumble upon writing?"

I got this question from a friend a few weeks ago, and I decided to take my time crafting a more engaging and informative response.

Coz, well, why not?

Buckle up; it's quite a story...

After I left university, I started journaling to document my self-development journey. I even launched a Substack newsletter that my mom religiously read. But I quickly realized I needed to generate some income, because it was only a matter of time before she discovered I had quit university—definitely a conversation I wanted to avoid.

(Side note: I never told her I dropped out. She found out on her own, and let’s just say, she was not pleased.)

Over the past two years, I dabbled in various pursuits—forex trading, fruit vending, home tutoring, and even Twitter growth coaching. None of them worked out, but one habit stuck around.

You guessed it...

Journaling!

By that time, journaling had evolved into an essential part of my daily routine and transformed into a passion. I wrote about everything: beautiful sunsets, meaningful conversations, my insecurities, my aspirations—you name it. I was always jotting down ideas, whether I was walking, eating, or even in the shower (which I still enjoy immensely).

It became glaringly obvious that I loved writing.

Upon reflecting on my childhood...

I recognized that when I daydreamed about the future, it was always through the lens of writing.

That connection was no coincidence.

Back in high school, I even wrote a fictional book titled *The Martian Diaries*, about an astronaut colonizing Mars—think of it as my own version of "The Martian" with Matt Damon.

But... I never published it.

Through daily journaling, I discovered my passion for writing.

That alone answers my friend's question, but because you’re still reading, I wanted to make this more valuable by addressing a crucial and sister question to the one above regarding work and career.

"Is it possible to find work that you are truly passionate about and turn it into a lifelong career?"

So you never have to “work” a day in your life again?

Back to my story...

Once I noticed the pattern, I began to explore how writing could be a viable career. I believed that if I could hone my writing skills, I could monetize my Substack newsletter. But to be honest, my writing was subpar at that time, and I eventually decided to “kill” the newsletter.

I also tried to grow an audience on Twitter (now X) but ended up abandoning my first account with over 850 followers when I realized it didn’t truly represent me. However, something amazing happened around that time: I wrote another personal development book and published it on Gumroad, giving it away for free to friends who couldn’t afford it (I laughed about it later).

Ultimately, I made zero dollars off that e-book.

But remember, I needed money fast—before my mom pieced together the puzzle.

So, I quickly recognized that I needed a hard skill I could learn and monetize.

I dove head-first into copywriting.

I won’t lie—this was not something I initially set out to do. I stumbled upon it by accident.

Looking back, I’ve always had a knack for selling ideas, but I wasn't great at articulating them verbally. Writing, however, came naturally to me. Now, I’m actively building a career around this craft by mastering persuasive writing. Sure, I’ve encountered my share of setbacks in this journey, but I’ve never wavered in my commitment to the craft.

When I talk about work that feels like play, I’m referring to writing. Nothing brings me more joy than weaving words into cohesive, impactful sentences that can resonate with and shift people's emotions.

That’s why I’m grateful for my failures.

Each setback reinforced that writing is the one thing I can’t walk away from.

And to answer the second question...

Absolutely, it's possible. I’m on that very trajectory myself -- Monetize my craft of writing, and live life of freedom thereafter.

In today’s digital age, anything is possible.

Bottom line:

I genuinely believe everyone has that ONE thing they can’t resist. If you don’t know what yours is yet, it’s time to get to work.

The purpose of life is to find that thing.

It doesn’t matter how long it takes—what matters is that you find it. Coz how else will you truly live with yourself?

Some are fortunate enough to discover their passion in their 20s.

I know I am.

But for others, it might take a bit longer, and that’s perfectly okay—as long as you keep experimenting, seeking feedback, and iterating until you stumble upon what sets your soul on fire.

And I promise, once you stumble on it, you'll know.

It's an Eureka moment in time.

It may not be a specific day in time, but you feel that transition gradually, and finally, you can't pull yourself away from the thing.

The blueprint?

Quite simple...

▪︎ Be curious enough to try new things.

▪︎ Be brutally honest with yourself.

▪︎ Be courageous to quit things.

Find that thing, find a way to make it a career and you'll never have to "work" in your life. Yeah, at least that's the goal.

Not eliminating work but doing work that feels like play every single day.

Might take you months, years or even a decade but again, if that means you'll get to do what you love for a living, I'd say it's worth a shot.

Get to work!

Talk soon,

Dennis