When you're 40 years old, you're usually thinking about settling into your career, maybe planning for retirement. John, calling into "The Ramsey Show," was thinking about something else entirely: how to stop getting fired.

His track record isn't encouraging. Fourteen jobs in 11 years, none lasting even a full year. The reason? "Behavioral and personality challenges," as John put it. Dave Ramsey did the math quickly: "That's not even a year each."

Now John's sitting on more than $70,000 in federal student loans with no job prospects in sight, and he's weighing two wildly divergent options. Option one: join the Navy as an officer. Option two: start a podcast. One requires strict adherence to hierarchy and military discipline. The other requires a microphone and an internet connection.

The Authority Problem

John explained that he wants to be independent, but employers aren't exactly lining up. Even the entry-level positions Ramsey typically recommends as stopgaps aren't panning out. That's when the conversation took a deeper turn.

John revealed he has narcissistic personality disorder, diagnosed through extensive neurological assessments over the years. "There's no cure for it," he said, attributing it to low gray matter in the brain. The disorder manifests as defiance toward authority, which he acknowledged freely. He described entering new jobs with bitterness from previous failures, creating what he called "a self-fulfilling prophecy" of workplace conflict.

Ramsey tried to understand the practical implications. "What you describe would be normally I would think belligerence," he said. John agreed, admitting he often self-sabotages early in new positions. Even when employers don't know his employment history, he says they can sense something is off.

Why the Navy Plan Doesn't Add Up

When John floated the idea of joining the Navy as an officer, Ramsey didn't hesitate. "The Navy doesn't do well with people who have trouble with authority," he said flatly. "That's going to be a nasty conflict."

Rachel Cruze, Ramsey's co-host and daughter, agreed. This wasn't really about finding the right career path or a clever debt payoff strategy. The real question was whether John had addressed the underlying issues that kept derailing his employment.

"I think that's what I'm wondering," Ramsey said. "Is there therapy or something that helps you hold a job, or have a quality relationship?"

John mentioned he's been given some therapeutic tools, but also brought up the possibility of future treatments like nanobots to fix brain chemistry. Ramsey wasn't following that thread. "You just left me behind at the airport, dude," he said.

Above Their Pay Grade

The conversation reached a point where Ramsey, rarely at a loss for advice, admitted this was beyond his expertise. "This is above Rachel and my pay grade," he said, offering to connect John with John Delony, another personality in the Ramsey network who specializes in mental health issues. "Maybe he can add something intelligent to this conversation because I can't."

Before ending the call, Cruze offered a note of cautious optimism. "People do have serious setbacks, but they overcome them — and we talk to them on this show all the time." It wasn't meant to dismiss John's struggles, but rather to suggest that recovery is possible with the right approach.

The underlying message was clear: personality disorders and employment challenges don't have to permanently define someone's trajectory, but they will continue to create problems until properly addressed. Financial strategy comes after mental health stability, not before.

As for the podcast idea? Ramsey didn't even bother responding to that one. If John really wants independence and financial stability, the path forward probably starts with consistent therapy, not a content creation career or military service. Fix the foundation before building the house.