Zipline or Stepping Stones?


You’re standing at the edge of a stream. You need to get to the other side, and getting wet isn’t an option. You scan the area and see two possible ways across. There’s a zipline stretched overhead its fast, direct, clearly built for this specific crossing. Or there’s a line of stepping stones that would require a series of careful hops. Both paths could work.

Most of us instinctively lean toward the stepping stones. Small steps feel safer. You stay close to the water. You control each move. But every hop still carries risk. The rocks could be slick. You could lose your balance halfway across.

The zipline feels bolder. It’s higher. It’s faster. If something fails, it fails quickly. But it was engineered for one job: getting you across the stream.

IT operations teams face this exact decision every time they plan a major change. Do we take one big swing, or do we break it into a series of smaller ones?

The Risk We Don’t Talk About Enough

When I think about this scenario, I keep coming back to one word: exposure.

Not impact. Not optics. Exposure.

Incremental changes feel safer at first. But over time, they often leave us living in an in-between architecture. Temporary routing logic, temporary firewall rules, temporary exceptions — these transitional states introduce complexity. And complexity is where risk tends to hide.

The longer we remain in that hybrid state, the more fragile things can become. Temporary has a way of sticking around. That’s not just operational overhead — it’s technical debt in disguise.

It’s Not Just Technical Risk

There’s also a human side that rarely makes it into risk registers.

Change fatigue is real. Stakeholders get tired of repeated disruption. Engineers context-switch between projects. Subject matter experts aren’t always available during every incremental window. Over time, momentum fades and attention drops.

Ten small changes may feel manageable on their own. But ten change windows mean ten coordination cycles, ten communication efforts, and ten opportunities for something small to go wrong.

Each additional hop across the stones is another roll of the dice.

Big Doesn’t Mean Reckless

I’ve always liked this quote:

“A goal without a plan is just a wish.” — Antoine de Saint-Exupéry

A large change without planning is reckless. But a large change backed by disciplined engineering, structured testing, clear rollback paths, and coordinated communication is something very different. It’s intentional.

Strong teams don’t rely on hope when executing major changes. They design their deployments carefully. They validate assumptions. They prepare recovery plans. They align stakeholders ahead of time.

A zipline isn’t risky simply because it’s fast. It’s risky if it’s poorly built.

The Real Question

The decision isn’t really about whether the change is big or small. It’s about whether the intermediate state introduces more risk than the final state. It’s about whether stretching a transition over time increases total exposure. It’s about how long you’re willing to live halfway across the stream.

Sometimes incremental change is the right move. But sometimes the safest approach is to engineer the zipline properly, swing across with focus, and get out of the water.

The true risk isn’t the size of the change. It’s how long you choose to remain exposed.