Where to Wiggle

When you're staring down a big messy problem, the question is always the same: Where do you start?

For me, the metaphor that’s always stuck is this: most problems are like trees. What you see above ground — the gnarly bark, the branches sticking out, the bit you keep tripping over — that’s the part driving you nuts. That’s what’s hurting people. But here’s the thing: that visible part is held in place by a whole tangle of roots underground. And if you focus only on what’s above the surface — reacting to the symptom — you’ll just keep stubbing your toe.

You can hack away at that visible bit all you like, but unless you understand the root system holding it in place, nothing’s going to change. You’ll hurt yourself, burn out, and the tree will just keep growing back.

So the real trick is to go underground. Get curious about the root structure. Figure out which parts of it you might actually be able to shift. Not every root is equal — some are buried deep and rock-solid, but some… some have a bit of give.

Over the years, I’ve developed a simple mental model for figuring out which roots are worth pulling on. I look for three things: wiggliness, resources, and impact (this likely came from somewhere but I can't place it).

1. WIGGLINESS — Is this part of the system ready to move?

Sometimes, a part of the system is already under pressure to change. There’s momentum. Openness. Even just a little looseness in the soil. That’s what I call wiggliness — or, more formally, business readiness.

You want to find the part of the system where there’s already some movement. It might be a unit that knows it needs to change. A process under review. A team with a new mandate. If there’s no give — if it’s all locked in — you’ll exhaust yourself trying to force it. Start where the wiggle is.

2. RESOURCES — Are there people and tools to actually do the work?

You can find the wiggliest root in the world, but if there’s no one around to help pull on it — no budget, no team, no skills, no political cover — it’s a dead end.

Intervention without capacity is a fast track to frustration. So when you spot something that’s ready to move, ask: do we have the means to move it?

3. IMPACT — Will shifting this root shake others loose?

Finally, some roots are more connected than others. Move one, and a few more shift with it. That’s the kind of leverage you’re after — a small move with big ripple effects.

When you’re assessing where to focus, ask: if we change this, what else might it unlock? What system-wide consequences might follow?

When I applied this lens to government, all signs pointed to one place: digital transformation.

Back when I was looking around trying to figure out where to work, digital ticked all the boxes. Wiggliness? Check — every government was grappling with what “digital” even meant. Resources? Yep — lots of attention, money, and talent were pouring in. Impact? Absolutely — digital cut across every sector and service. It was connected to everything.

But if I’m honest, there’s a shortcut here too. You can spend weeks mapping the system and diagramming leverage points. That’s useful, for sure.

But in the end, the simplest — and maybe most effective — move is just to follow the people who inspire you.

For me, the folks I looked up to were already deep in the digital transformation space. They were curious, humble, hopeful, and pragmatic. So I went where they were. Sometimes that’s the best root to grab: the one being pulled by people you trust.

What roots are you trying to shift right now? And who’s tugging on them with you?