Helping a Dev Double Down on Creativity
I helped a creative developer explore whether contract work or launching a business is a better way to reclaim their creative freedom.
Watch or listen to this episode
YOUTUBE
SPOTIFY
APPLE
When Tech Stops Feeling Creative
If you’ve ever felt like working in tech is more about following orders than expressing your creativity, you’re not alone. It’s something I hear constantly from the clients I coach, and recently, I had a powerful session with a former client named Charlie that really brought this to life. Charlie’s story is one a lot of people can relate to—he’s deeply creative, used to run a company doing 3D animation, and now finds himself split between two worlds: one contract that’s menial and repetitive, and another that allows him to solve creative problems.
Like many people who start out in creative fields, Charlie found himself drifting into more “practical” tech work over time. That creativity didn’t disappear—it just got boxed in. And now, he’s wrestling with a problem many mid-career professionals face: “Do I try to find meaning in my career again, or do I leave that to personal projects on the side?”
Balancing Contracts, Burnout, and Creative Energy
When Charlie and I talked, he had two contracts going. One was repetitive and mechanical, and the other more freeform and creative. This duality wasn’t just logistical—it represented a deeper split in how he viewed his work and life. He wants to be a great father, have a stable income, and still feel like his work matters.
His biggest struggle wasn’t technical. It was emotional and strategic: “How do I keep my job from bleeding into the few hours I have left at night?” When we dug into it, time management came up as a lifelong challenge. Like many passionate people, Charlie struggles to put down a problem once it grabs his attention. And in tech, there’s always another problem to solve.
The biggest mistake smart, creative people make is overthinking instead of testing. Planning instead of experimenting. And chasing perfection instead of launching something imperfect but real.
So I pushed him. Not because he didn’t know what to do, but because he had already started building a narrative that this conflict was “just how it is” and would always be there. That kind of absolutist thinking can quietly kill your ambition. It sounds rational, but it’s really a cover for fear and resignation.
Is It Career Direction or Just Emotional Drag?
As we kept talking, I noticed Charlie saying things like, “I know what I want to do,” while also describing uncertainty and discomfort around self-promotion and personal branding. That contradiction told me something important: he hadn’t yet separated the kind of work he wanted to do from how he wanted to be seen doing it.
Charlie’s past business had a brand and a team—it gave him cover. But now that it’s just him, the vulnerability of “selling himself” feels awkward. That’s incredibly common. And in his case, it’s exactly where his next growth edge is.
He’s clearly not lost—he’s experimenting. But I challenged him to admit something to himself: he already ran this experiment once. He already knows what it feels like to work on both sides of the creativity spectrum. So what’s different this time?
This time, it’s personal. It’s not about hiding behind a business brand. It’s about building a future that reflects his values, creativity, and leadership—not just surviving.
The Shift: From Creative Worker to Creative Guide
Here’s where the conversation got electric. I asked Charlie: “What if the thing you did next wasn’t just doing creative work—but helping others in tech rediscover their creativity?”
I could see something shift in him.
There’s a growing number of tech workers—engineers, designers, even managers—who feel creatively stifled. They didn’t get into this field just to follow Jira tickets or optimize a CRUD app. They want to express something. But they’ve been trained to suppress it. What if Charlie could become a guide for those people?
He has the credibility. He’s done the consulting. He’s built a company. He’s worked through burnout. And he has the heart to do it. All he needs is to realize that the vulnerability he’s afraid of is actually his competitive edge.
We talked about the difference between hiding behind a business and standing in front of one. And we framed his experience not as incomplete—but as exactly the kind of story that resonates.
The message I gave him was simple: “You don’t have to be the guru. You just need to be one step ahead of the people you’re helping.”
Your Career Doesn’t Have to Be an Experiment Forever
Charlie’s been treating his contracts like an experiment. That’s fine—until you stay stuck in experiment mode. At some point, you have to decide: Is this the life I want to build on purpose?
And if not—what do I need to start building instead?
There’s a growing number of tech workers—engineers, designers, even managers—who feel creatively stifled. They didn’t get into this field just to follow JIRA tickets or optimize a CRUD app. They want to express something.
That’s the moment where coaching becomes more than support. It becomes a mirror. Because here’s the truth: Charlie already knows what matters to him. He wants to do meaningful creative work. He wants to lead. He wants to protect time for his personal life. And he wants to help others who are creatively stuck.
He just hadn’t let himself believe those desires could be the foundation of a business—not just side projects or “extra” effort at work.
I told him this: “You’ve already proven you can work two contracts and keep your life together. You’ve already run a business. You’ve already advocated for creatives. If that’s your past, imagine what you could build if you stopped waiting for a perfect plan and got started.”
From Thought to Action
By the end of the session, Charlie was buzzing with ideas. Helping creatives simplify their workflow. Supporting elderly people who are overwhelmed by tech. Both of them viable. Both aligned with who he is.
The only question left was: “Which one will you pursue now?”
Because the biggest mistake smart, creative people make is overthinking instead of testing. Planning instead of experimenting. And chasing perfection instead of launching something imperfect but real.
So I challenged him: Pick one. Run a test. Talk to five people who have the problem you want to solve. See what they actually need. And let that guide your next step.
That’s how you escape the creative cage of corporate tech—not with a perfect plan, but with a meaningful mission and some imperfect courage.
And maybe that’s where you are, too.
If you’re stuck choosing between career stability and creative fulfillment, consider this: You don’t have to pick one. You just have to own the tradeoffs and start walking.
Want to be more than just a worker in tech?
Then stop asking where you “fit” and start deciding what you stand for.
About the THRIVING TECHNOLOGIST show
On YouTube and all major podcast networks, Jayme shares teamwork and leadership strategies, guidelines for healthy company culture, and stories about real projects so you can have a sustainable career in the software industry.
Jayme Edwards
A family man and veteran of nearly 40 software projects, Jayme experienced many wins and losses over his career as an architect and consultant.
Now he's coaching software developers, managers, and business owners to overcome challenges in the IT industry - so they keep growing.