The Digital Strategist’s Dilemma

Tech moves faster than meaning.

In major transformation projects, you can find yourself knee-deep in legacy systems, fighting through constraints. You haven’t even gone live with v1.0 and you’re already carrying tech debt.

Multi-year timelines make it worse. Whole technologies rise and fall in the time it takes to deliver a single program. It’s easy to start wondering: Is any of this still meaningful?

That’s when I have to pull back and re-anchor in my why.
I’m a builder. That’s the core of it. I love solving problems with tech. I love the moment of launch, seeing the numbers tick up, reading the feedback that says, “This made my experience better.”

For me, strategy isn’t just about what comes next. It’s about asking why this is still worth building. With limited time and infinite problems, that’s the only way to make the work matter.

Strategy is asking not just what next, but why still.