When Is It Time to Leave Your Fleet Job? 6 Signs Fleet Professionals Can’t Afford to Ignore

This article is based on a recent episode of The Fleet Success Show podcast.
Watch the full episode here: 

Let’s face it: Fleet managers are some of the most loyal professionals in any industry. You don’t spend decades managing public sector budgets, navigating compliance regulations, mentoring technicians, and staying ahead of evolving vehicle technology if you’re not committed. But even the most loyal fleet professionals eventually face a hard truth:

Sometimes it’s time to move on.

Whether you’ve been managing a city fleet for 20 years, overseeing transit operations for a utility, or running maintenance for a private vocational fleet, the decision to leave a job isn’t easy. But ignoring the signs can stall your career, kill your motivation, or worse, erode your impact.

In a recent episode of The Fleet Success Show, host Marc Canton sat down with industry veterans Steve Saltzgiver and Scott Rood to unpack the tough, emotional, and absolutely essential question: When should a fleet professional leave their organization?

Here are the 6 signs you might be closer to the exit than you realize, and why ignoring them can cost you more than just job satisfaction.

1. You’ve Lost Trust in Leadership

Leadership sets the tone, culturally, strategically, and emotionally.

If you find yourself constantly questioning your leadership’s decisions, ethics, or direction, it may be time to reassess. Scott shared a turning point in his career when leadership at his base changed during a military deployment. When he returned, the culture had shifted. “I didn’t feel good about the direction,” he said. That gut feeling led to his decision to retire from the Air Force after 22 years.

Steve recounted a similar experience at Utah Transit Authority. After 15 years, toxic leadership behavior and a lack of support made him dread going to work. Despite having a wife, five kids, and a mortgage, he walked away.

Key question: Do you trust your leaders to have your back? If not, why are you still there?

2. You’re No Longer Challenged

In fleet, there’s always another hill to climb, unless there isn’t.

Sometimes, you’ve optimized your fleet, implemented new fleet maintenance software, trained up your team, and achieved award-winning performance. And then... nothing. You hit a ceiling. No next-level projects. No strategic goals. No big challenges.

Steve said it best:

“I was getting ready to break something that was already working well... because I was bored.”

If you’re starting to sabotage success out of frustration, it’s not your team’s fault, it’s time to move on and find your next mission.

3. Training and Development Are Off the Table

Fleet professionals don’t just turn wrenches or manage budgets. They manage change.

Technology in fleet maintenance and fleet management software evolves fast, and staying ahead requires constant training. Yet many organizations cut travel and training first when budgets get tight. Steve, Scott, and Marc agreed: if your organization consistently blocks access to conferences or training, that’s a massive red flag.

Marc put it bluntly:

“If you’ve been in a position for years and you’ve never been to NAFA, NTEA, or another relevant show, something is seriously wrong.”

Training isn't just about the employee; it’s a reflection of how much the organization values continuous improvement.

4. You Dread Going to Work

It’s one of the simplest, and most ignored, warning signs: you just don’t like going to work anymore.

Steve called it “the icky Monday feeling.” You know the one: the dread, the stress, the soul-sapping realization that you’d rather be anywhere else. For passionate professionals, that feeling isn’t normal, and it doesn’t fix itself.

If you used to love fleet and now you’re just surviving it, something has shifted. That internal discomfort could be your gut telling you: “It’s time.”

5. There’s No Career Path in Sight

Not everyone wants to climb the ladder. But for those who do, it’s incredibly demoralizing when there’s no place to go.

Steve shared a powerful moment: After submitting his resignation, the organization’s general manager called him in and said, “I had you on the career track to become our superintendent.” Steve’s response?

“That’s great... but no one ever told me that.”

If your leadership hasn’t communicated a vision for your growth, or you’re unsure how to advance, that’s a problem. Don’t assume a path will be built for you. If it’s not visible, it might not exist.

6. An Opportunity You Can’t Ignore

Sometimes, the reason to leave has nothing to do with frustration. Sometimes, it’s about opportunity.

Scott left Clark County not because he was unhappy, but because an exciting opportunity came through Steve’s network. Marc left his longtime job in New York to take a consulting role in Arizona because he wanted to test himself and expand his reach. They weren’t fleeing, they were growing.

Don’t stay in a job you love so long that you miss the chance to evolve into something greater.

Bonus: Don’t Burn Bridges

This industry is small. Leave with integrity. As Steve shared, the person who once made his work miserable came to him years later... asking for a job.

Stay professional. Keep connections warm. Today’s coworker might be tomorrow’s client, reference, or employee.

What About Regret?

The fear of making the wrong move is real. Marc, Steve, and Scott acknowledged that doubt, but emphasized that regret is usually wasted energy. If you leave for the right reasons, with a plan and purpose, the next step is often better.

And if it’s not? You’ll still grow from it.

What Does This Mean for Fleet Organizations?

If you’re an executive or fleet director, these insights are a wake-up call:

• Support training, or risk losing top talent.
  
  
• Provide a visible career track for technicians, supervisors, and managers.
  
  
• Invest in leadership and communication. Silence is expensive.
  
  
• Create challenge and purpose, or ambitious employees will go elsewhere.

This is especially critical when managing large government fleet management software deployments or optimizing a fleet maintenance system. When people don’t feel invested in, they stop investing in your mission.

Final Thought: Don’t Let Comfort Cost You

Fleet managers are builders, problem-solvers, and innovators. If you’ve stopped building, solving, or growing, you’ve stopped doing what you were made to do.

You deserve more than a paycheck. You deserve purpose.

So ask yourself:
Am I learning? Am I challenged? Am I excited?

If the answer is “no,” then maybe the real question isn’t why leave, it’s why stay?