Stop Chasing Long-Term Goals. Start Zigzagging.

There. I said it.

As an IT Leader, I’ve stopped pretending that a perfectly aligned, 5-year strategic plan is the holy grail. Especially not when the business throws everything—including the proverbial kitchen sink—at teams already drowning in technical debt, underfunded initiatives, and overloaded calendars.

Sound familiar?

It should. Because this is the reality in a lot of modern organizations: too much to do, not enough people or money to do it, and wildly optimistic deadlines. Everything is priority #1. So what do people do? They zigzag. Often in chaos, without direction, making the best guess they can in the moment.

And here’s the twist: maybe that’s not a bug. Maybe that’s the feature.

Zigzagging: The New Productivity Framework

Harvard’s Dark Horse Project studied high achievers across business, science, and the arts. They didn’t find rigid 10-year plans. They found people who made short-term, purpose-driven decisions based on what excited them right now. These weren’t random moves. They were small bets—experiments—that added up to serious progress over time.

I’m leaning into that. Hard.

My Reality Check: The Technical Debt Avalanche

In many of the companies I’ve stepped into, the situation is the same: a massive backlog of unfinished tech, duct-taped systems, and unrealistic roadmaps that ignore this inconvenient truth. Then someone says, “Let’s also roll out these five new projects.”

It’s like trying to renovate a house while simultaneously building a second one… on top of it… during a thunderstorm.

So here’s what I’ve learned: Instead of being paralyzed by the sheer weight of everything, pick the next best thing. Try it. Learn. Move on. Zig. Then zag.

Enter the Book of Experiments

One concept that stuck with me is from David Epstein (author of Range). He recommends tracking your experiments—tiny, purpose-driven actions that help you navigate complexity.

It works like this:

1. Write down what you want to try.
2. Predict what you’ll learn.
3. Reflect & adjust.

I’ve started applying this in my work. It cuts through the noise. You stop asking “What’s the 5-year plan?” and start asking “What’s the next useful experiment?”

The Real Problems We’re Not Talking About

Let’s call out some BS, shall we?

• People are guilt-tripped for not delivering, even though they spend 50% of their week in meetings that should’ve been emails.
• No one has time to build dashboards, because they’re too busy manually compiling reports.
• We hold update meetings about update meetings, where 10 people sit in silence because—spoiler—nothing changed since last week.

This isn’t productivity. It’s theater.

We’re trying to reach business goals while tying our own shoelaces together.

The Call to Action: Less Talk, More Leverage

Want results?

• Replace manual reports with real-time dashboards.
• Kill recurring meetings with no ROI.
• Empower people to run small, smart experiments.
• Give teams the autonomy to finish, not just start.

The truth is: if you want innovation, velocity, and actual outcomes—you need to create space for it. Space to think. Space to try. Space to zigzag.

So next time you feel the weight of everything, pause. Ask yourself:

What’s the next best experiment?

And then—leave me to it, so I can finish.