I’ve had a lot of conversations on this show about starting a business, but today’s episode is a little different. I sat down with my good friend and neighbor, Josh Dale, who, by the way, also happens to be my son’s baseball coach, to talk about why he hasn’t taken that leap into entrepreneurship yet.

Josh recently retired after over 20 years in the Navy, and now he’s standing at a bit of a crossroads. The desire to start something is there. The work ethic? Rock solid. But like a lot of smart, capable people, he’s stuck in that space between wanting to build something and not knowing exactly what that “something” is. And more than anything, he doesn’t want to fail.

We talked a lot about what makes people hesitate, how it’s not always about the money or fear of hard work. Sometimes it’s the unknown, the risk to your time, your energy, your confidence. Josh was super honest about where he’s at right now, how having that military retirement gives him peace and security, but maybe also gives him just enough comfort to not feel the urgency to pull the trigger.

If you’ve ever found yourself in a season where you know you’re built for more, but you’re not quite sure what “more” looks like, or how to get there, this conversation might sound familiar. Josh may not have all the answers right now, but his story is one a lot of folks can relate to.

EPISODE HIGHLIGHTS:

00:00 - Introduction

01:17 - What’s holding you back from starting a business?

06:05 - From navy life to civilian questions: What’s next?

08:35 - Should I take the leap or play it safe?

12:29 - The real reasons people don’t start: Doubt, comfort, and waiting for the perfect idea

16:47 - What does success really look like for Josh?

ABOUT OUR GUEST:

Joshua Dale is a recently retired Navy veteran who served over 20 years as a hospital corpsman. With a strong background in discipline, leadership, and service, Josh is now navigating the transition to civilian life and exploring what’s next; whether that’s entrepreneurship, a new career path, or meaningful community involvement. Known for his integrity, work ethic, and commitment to others, Josh brings a thoughtful and honest perspective to conversations about risk, purpose, and redefining success after military service.

RESOURCES:

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