Turning Pro: Showing Up for the Work You Love

There was a moment when I decided to take writing more seriously.

I always wanted to be a writer — a blogger, a podcaster. I even had a fairly successful blog and podcast years ago, back when podcasting was just getting started. But it was nothing like this. It wasn’t the work I feel called to do now.

As I got busier at work and my career elevated, everything else had to take a back seat. I was learning, growing, and changing. The person I was 20 years ago isn’t who I am today.

I started Happy Heading Nowhere a couple of years ago, but I just couldn’t make the time. I told myself, maybe someday, maybe later.

Then two years ago, I started thinking more seriously about the end of my IT career. What would come next? Not just after retirement, but as a next chapter. And the opportunity eventually came, and the timing lined up. I left the company I was with and began to imagine what it might look like to take this writing thing seriously.

That’s when the shift happened.
It wasn’t about going viral or making money.
It wasn’t about a career pivot.
It was simply this: I could do this now.

And that realization — that I didn’t have to wait — was the moment I decided to turn pro.

What It Means to Turn Pro

Turning pro isn’t about money.

It’s not about chasing sponsors or building a massive audience (though that’s fine too).

It’s an internal shift. A quiet decision. A personal line in the sand.

For me, this meant treating this writing—this blog, this creative work—with intention, structure, and respect.

So I made it public. I posted regular content. I committed to themes. I built a cadence, a schedule. Tuesdays became blog day. I carved out space and time. I treated the work like a job.

And that structure helped. It kept me honest.

But then, life ramped up again. Consulting picked up. Schedules got tight. Writing became irregular. The structure wobbled. And I missed a whole month of May entirely.

Balancing Art, Work, and the Long Game

One thing I’ve seen over and over in creative spaces: when people turn their art into their income, it often changes the relationship.

There’s an old saying:

“Even the candy-maker loses his taste for candy after a while.”

When your creative outlet becomes your paycheck, joy can take a back seat to pressure.

Thankfully, I don’t need writing to pay the bills. My consulting work is for that. It gives me the freedom to approach this space—this blog, this voice—as art.

But even with that freedom, time is still finite. Sometimes the “money work” bleeds into the day, and creative work gets crowded out. That tension? It’s real. And it’s frustrating.

When I missed May, I was trying to do too much: write, post, market, stay visible. It was a lot.

And that’s where this idea of discipline and grace came into focus.

Discipline, Grace, and the Real Win

Discipline says, show up anyway.

Grace says, you’re still a writer, even if you missed a week.

The trick is knowing when it’s one… and when it’s the other.

Sometimes I confuse grace with excuses.
Grace isn’t “I’ll get to it eventually.”
Grace is “I missed a step, but I’m still on the path.”

Steven Pressfield says:

“Put your ass where your heart wants to be.”

That’s the work.
Sit down.
Begin.

The result is the bonus. But the showing up — that’s the win.

What keeps me coming back is the challenge of finishing what I start. Of keeping promises to myself. Of writing and podcasting because I believe I have something to say. Something that might matter.

Even if it’s imperfect.
Even if it’s late.
Even if no one sees it.

The work is still here.

And so am I.