September 02, 2025

💪🏽 Resilience at 30: Drew Keske on Building a Career with Breadth Before Depth

58 minutes

What does it look like to build a career with curiosity, creativity, and resilience—before you’ve even hit 30?

On this episode of The Underswell, I sit down with Drew Keske, Manager at the K-Bar Ranch in Texas, handyman, project foreman, and supporter of sustainability and social entrepreneurship to find out. Drew brings a younger career perspective, but his story carries timeless lessons for anyone navigating their own path.

Drew’s career has already wound through nonprofits, farming, business operations, event management, sustainability, and now—back to his roots on the family ranch. Along the way, he’s faced setbacks, seized opportunities, and learned how to balance dreams vs. reality with a thoughtful, intentional approach.

In this conversation:

Coming full circle: Returning to the family business and what it’s like working alongside his dad.

Resilience & tenacity: He survived setbacks like a six-month battle with lupus and had his job literally washed away by Hurricane Helene in Asheville.

Breadth before depth: Why Drew chose to build a wide foundation of skills in his 20s before specializing in his 30s.

The crossroads: How he built a card game around the decisions we face in life—and how he’s navigated his own.

Being 30 in 2025: His generational perspective on AI, community, and career-building in uncertain times.

Not letting life overwhelm you: Finding perspective, fun, and gratitude—even when plans collapse.

Timeless advice from Drew:

“Confidence comes through doing the work, just showing up.”

“Have engaged detachment: put in the work, but don’t cling to a specific outcome. Stay open to the doors that open for you.”

“Know what it means to do what it takes, remember to have fun, and take care of yourself.”

Drew’s story is proof that career-building isn’t about a straight ladder climb—it’s about resilience, curiosity, community, and creating your own path, one step at a time.

Can you guess what his Underswell is? What force underneath the surface, drives him to improve continuously? The answer is in the episode.

🔗 Connect with Drew on LinkedIn at https://www.linkedin.com/in/drewske/

💪🏽 Resilience at 30: Drew Keske on Building a Career with Breadth Before Depth

58 minutes

What does it look like to build a career with curiosity, creativity, and resilience—before you’ve even hit 30?

In this conversation:

Coming full circle: Returning to the family business and what it’s like working alongside his dad.

Resilience & tenacity: He survived setbacks like a six-month battle with lupus and had his job literally washed away by Hurricane Helene in Asheville.

Breadth before depth: Why Drew chose to build a wide foundation of skills in his 20s before specializing in his 30s.

The crossroads: How he built a card game around the decisions we face in life—and how he’s navigated his own.

Being 30 in 2025: His generational perspective on AI, community, and career-building in uncertain times.

Not letting life overwhelm you: Finding perspective, fun, and gratitude—even when plans collapse.

Timeless advice from Drew:

“Confidence comes through doing the work, just showing up.”

“Have engaged detachment: put in the work, but don’t cling to a specific outcome. Stay open to the doors that open for you.”

“Know what it means to do what it takes, remember to have fun, and take care of yourself.”

Drew’s story is proof that career-building isn’t about a straight ladder climb—it’s about resilience, curiosity, community, and creating your own path, one step at a time.

Can you guess what his Underswell is? What force underneath the surface, drives him to improve continuously? The answer is in the episode.

🔗 Connect with Drew on LinkedIn at https://www.linkedin.com/in/drewske/

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💪🏽 Resilience at 30: Drew Keske on Building a Career with Breadth Before Depth

💪🏽 Resilience at 30: Drew Keske on Building a Career with Breadth Before Depth