High achievers are trained to climb. 

Get the internship. Land the offer. Earn the promotion. Move up fast. 

But Jonathan Chase, Vice President of Turf & Utility at John Deere, thinks that mindset is flawed. 

He’s watched talented people sprint upward only to look around years later and realize they don’t even like where they ended up. 

Instead, he offers a different picture. 

“I prefer to use the analogy of a pyramid.”  

A sustainable career isn’t built vertically. It’s built wide. 

Build the Base 

Jon didn’t follow a straight line. He started in engineering. Moved into finance. Then marketing. Then operations. He’s worked across regions and functions. None of it was a perfectly mapped plan. 

What fueled it? “Curiosity.”  

He wanted to understand how different parts of the business worked. How marketing thought. How supply chain operated. How engineering solved problems. That curiosity built range and range built resilience. 

That kind of reputation isn’t built by racing up a ladder. It’s built by stretching wide. 

Step Into Roles Before You’re Ready 

Here’s the part perfectionists don’t love to hear: you will not feel ready. 

When asked if he’s ever stepped into a role before feeling prepared, Jon doesn’t hesitate. 

“Most of them.”  

He once transitioned into leading a factory after years in strategic marketing overseas. New function. New environment. New expectations. 

His strategy wasn’t pretending to know everything. He walked the factory floor. Talked to people closest to the work. Grounded himself in reality. Built credibility by listening. 

Choose Challenge Over Easy 

There’s a temptation early in your career to optimize comfort or money or prestige. 

Jon pushes back. Instead, he compares career growth to strength training. 

“You don’t make muscle by just sitting around. You make muscle by going to the gym… you’re actually tearing a fiber in your muscle to make it stronger.”  

The same is true professionally. The stretch assignment. The unfamiliar function. The uncomfortable feedback. Those are the reps. 

They hurt in the moment. They strengthen you long term. 

Now It’s Your Turn 

The truth is, sustainable careers aren’t built on comfort. They’re built on courage. They are the leaders who raise a hand before they feel qualified, step into rooms where you don’t know the acronyms and choose growth over ease. 

Jon’s perspective is simple but powerful: stop chasing the quickest path up. Learn the business from different angles. Ask questions. Be curious. 

Learn more 

Jonathan Chase, Vice President of the Turf & Utility Business Unit at John Deere, joins The Cultivating Leaders Podcast to reflect on his career at John Deere. Serving in many business units, Jon shares how an unconventional, curiosity-driven career path shaped his leadership philosophy.