Zig-Zag to Win: Why Success Doesn't Travel in a Straight Line

Tacking Toward Success

Wouldn’t it be nice if our path toward success were as easy as Google Maps’ directions?

“Turn left at hard work. In 500 feet, arrive at victory.” Boom. Done.

Unfortunately, it’s not this simple, nor easy.

The route toward success actually looks and feels more like trying to sail a boat directly into the wind. The headwinds force sailors to adopt a zig-zag approach (see below), aka a maneuver called tacking.

Their zig-zag pattern helps them make incremental progress, but it can feel frustrating and inefficient. Imagine if it felt like half the time you’re going in the wrong direction.

But in reality, it’s the most effective way to make progress when the wind is against you.

The same goes for the journey toward success. Tacking is a great metaphor because it reminds us:

• The path won’t be straight.

• Progress won’t always look like progress.

• Adjustments (not perfection) are what keep you moving forward.

The best performers? They stop chasing straight lines and start embracing the zig-zags.

Success isn’t about avoiding the wind. It’s about learning how to move with it.

Dips Build Momentum

We all wish the path to success was linear. It looks more efficient. Cleaner. More predictable.

But, in reality, the path is filled with inevitable ups and downs.

The video above serves as a perfect illustration for why the peaks AND valleys both matter. The marble on the bumpy, up-and-down track reaches the finish line first because the downs build momentum.

This clip demonstrates the power of tacking. When athletes expect progress to be a perfectly paved road, every bump feels like a breakdown. But if they expect the zig-zag? Every dip and setback becomes a potential slingshot toward success.

As a coach, you play a pivotal role in helping them see that the journey won’t be linear. Linear thinking might say something like “This shouldn’t be happening.” The experimental mindset says, “This is part of the process.”

It’s not about avoiding failure. It’s about using it. It’s about experimenting. Pivoting. Adjusting. And yes, sometimes doing the exact opposite of what you thought would work.

Learning to Handle Hard

Kara Lawson, head coach of Duke Women’s Basketball, said it best:

“Most people think life is gonna get easier. Basketball is gonna get easier. School is gonna get easier. It never gets easier. What happens is you become someone that handles hard stuff better.”

In her now-famous speech to her team, Coach Lawson tells it straight: Life’s not about waiting for things to get easier. It’s about becoming someone who handles hard well. Because the moment you show you can handle hard? Life levels you up.

Here’s the bottom line: Linear is convenient. Hard is fulfilling.
We don’t remember the easy victories. We remember the setbacks that turned into comebacks. We remember when we had a breakthrough while being on the verge of a breakdown.

And this is where coaches come in.

Your job isn’t to remove the hard. It’s to help your athletes recognize that what’s beyond their control (e.g. the scoreboard, the opponent, the wind) isn’t where their power lives. It’s in what’s within their control: How they show up, how they respond, and how they learn.

Here’s a simple reflection question to bring this to life for your players?

“What was hard today? And what did it teach you?”

It’s a reminder:
Hard isn’t a detour. It’s the curriculum.
When athletes stop chasing easy and start embracing hard, they become the kind of people who can thrive no matter which way the wind blows.

Because growth doesn’t travel in a straight line.
It tacks.

Final Thoughts

Like a sailboat heading into the wind, our progress often comes from adjusting, not forcing. When we stop chasing easy and start embracing hard, we unlock our real potential. The straight line may be convenient, but the zig-zag is where we find true fulfillment.

Inspiration for This Piece:

• Le Cunff, A. (2025). Tiny experiments: how to live freely in a goal-obsessed world. Avery.

• Michalowicz, M. (2024). All in: How great leaders build unstoppable teams. Portfolio/Penguin.