The Ambition Conundrum: What Lane Kiffin Reminded Me About Leadership

If you’ve ever stood outside an Oxford gas station late at night holding chicken-on-a-stick, you know there’s a whole world wrapped up in that moment. It’s tradition, identity, and belonging. Oxford has this way of feeling like a small town with a big heartbeat. So when Lane Kiffin’s rumored jump to LSU hit the news cycle, the Ole Miss family didn’t just react, I think they felt it.

As an alum, watching it unfold was… unsteady. Conflicting reports, press conference posturing, rumor mills spinning so fast you couldn’t refresh social media fast enough. People were frustrated and confused. I think it felt like something foundational was shifting without clarity or respect.

My honest take?

Kiffin didn’t handle it very gracefully. Not because he considered a new opportunity, that’s part of the profession, but because of how the uncertainty played out publicly. Whether intentional or not, the confusion and mixed messaging left a lot to be desired. And I’ll acknowledge, I’m not in his shoes. I don’t know every conversation behind closed doors.

But I do know this: Public perception wasn’t great, and in leadership, that matters.

Ambition isn’t the villain —how you pursue it is.

Watching the Ole Miss family react, I started thinking about careers outside of the circus that is college football coaching. We are all trying to grow, take steps forward, and prepare for bigger things. I’ve lived that story. I think most of us had at some point.

Earlier in my career, I put in for opportunities at Casper College more than once. And more than once, I didn’t get the nod. Those moments hurt, no way around it. It made me question if I was ready, if I was valued, if I belonged in the conversation.

But hindsight has a way of teaching you what emotion can’t.

Those experiences forced me to grow in ways I didn’t yet know I needed, not just in skill, but in intentions.

It taught me:
If you want to move up, you better be building people up.
If you want more responsibility, you better respect the relationships that come with it.
If you’re preparing for bigger things, you better prepare your character just as much or more than your resume.

Because at the end of the day, professional development is not just about ability it is about how you conduct yourself in transition.

Eventually, I Found My Place

Looking back now, I’m grateful those earlier doors didn’t open. Because they weren’t my doors.

The City of Casper became the place where:

My values aligned.
My leadership philosophy resonated.
I could serve and grow at the same time.

It didn’t fall into my lap. It unfolded through preparation, humility, failure, relationships, and timing I didn’t control. And it felt different. It wasn’t like a stepping stone, but like a calling. I found my place. The place to build, not chase. The place where ambition isn’t about leaving, it’s about leading.

So What Did Lane Kiffin Teach Me Even If He Didn’t Mean To?

Leaders don’t get judged just by results — they get judged by how they navigate the in-between.
Rumors, instability, and messages we send — intentionally or not, all have an impact.

The Kiffin situation showed how disconnection, confusion, or ambiguity can strain relationships and trust.

Meanwhile, my own journey taught me that:

Growth without grace damages things.
Growth with the right intentions strengthens them.

Preparation is important. Ambition is healthy. But through it all, good leaders:

Communicate well
Honor people
Are grounded
Let their character keep pace with their career

At the end of the day, the opportunities we pursue may change, but the relationships we build remain. Lane Kiffin’s story isn’t just college football drama, it’s a leadership case study for anyone wanting to know how to handle personal ambition, growth, and career change. It reminded me that leadership is less about the job you get and more about how you move toward it and how you leave where you’re standing. I’m thankful that my missed opportunities, my growth, my waiting, and my refining led me to where I belong, serving the city I care about, alongside people I respect, building something I believe in.

So yes…pursue bigger things.
Prepare for opportunity.
Dream. Grow. Stretch.

Just make sure you do it with clarity, honesty, and respect, because someday, someone will be deciding whether to remember you for your resume or for how you carried yourself on the way there.