When Oddball Leadership demands sacrifice

Let’s talk about what really happened in February 2025.

SIMON SINEK MADE ME FEEL LIKE A FRAUD FOR A SECOND — THANKS, MAN.

If you’ve read the “essentials” for emerging leaders — The 7 Habits of Highly Effective People, Good to Great, True North, How to Win Friends & Influence People — then of course you know Simon Sinek.

You know, the Start with Why guy. You have to know him, you must!!

Anyway, I just found out he also wrote Leaders Eat Last.

I’m embarrassed to admit that until recently, I thought that title was just a clever metaphor I could use to roast my bosses at work whenever they led the buffet line at the work picnic — “Way to eat last, boss!”

But then I finally Googled it.

And realized:

SIMON SINEK BASICALLY CODIFIED ODDBALL LEADERSHIP IN 2014!!!!!

For about five seconds, I felt like a fraud.

Then I laughed — because if anything, I feel vindicated.

THE MESSY COST OF ODDBALL LEADERSHIP

What I appreciate most about Sinek is that he doesn’t romanticize leadership. He calls it what it is: a role that demands sacrifice.

And he’s right.

Because sometimes, being the best Oddball Leader you can be means making the ultimate (career) sacrifice — and doing it without regret.

I mean, let’s be fricking for real a moment:

Leading like an Oddball takes guts. It’s not always LEGOs and clay snakes and affirmation circles.

Oddball Leadership requires empathy in an ego-driven world.

Curiosity in a culture addicted to certainty.

Softness in a system that only rewards sharp edges.

It’s the kind of leadership that gets misunderstood.

Because it threatens the overcompensating.

It unsettles the self-important.

It scares the ones who confuse control for competence.

It’s the kind of leadership that gets you fired — which is precisely what happened to me about this time a year ago.

WHAT REALLY HAPPENED IN FEBRUARY OF LAST YEAR

It was early 2025. I’d been running the fundraising shop at St. Patrick Center — part of Catholic Charities of St. Louis — for about 18 months. We had just come out of a record-breaking, year-end fundraising season, even though the deck was especially stacked against us, and we were switching gears to focus our energies on planning the annual gala and golf tournament, and selling tax credits (a popular way for some donors to make charitable gifts in Missouri) before their April and June sell-by dates.

Until I sent an email that would unexpectedly change everything.

Here’s the abridged version of How It All Went Down™️:

I’d been pushing for about a year to restructure my team so we could sell tax credits to donors more quickly and efficiently. The plan included promoting a teammate — a hardworking volunteer coordinator — to a manager role, with a salary increase to match the responsibility. But the ROI would be impeccable!

After months of back-and-forth, I finally got the green light.

Except for one detail:

No raise. Not a cent.

The Chief of Staff had approved the promotion but explicitly denied any pay adjustment.

Of course, that didn’t sit right with me — and it shouldn’t have.

I wasn’t about to promote someone without fair compensation. In fact, during a prior discussion with my boss — the VP of Philanthropy at Catholic Charities — I had even offered to personally take a pay cut to help make this promotion happen.

So I emailed my boss — respectfully, confidentially (or so I thought) — to say I couldn’t in good conscience move forward with an inequitable promotion. I expressed my disappointment, and concern of preferential treatment over the agency’s procedural inconsistencies in regard to promoting staff.

Ultimately, I suggested we revisit the elevated position next fiscal year, while confirming I could not guarantee we would sell off the year’s tax credits given our current structure (though it wouldn’t be for lack of trying).

Two days later, I was sitting in an executive boardroom being told, according to the email I’d sent earlier in the week, I “clearly wasn’t happy.”

No other explanation. No severance. No chance to re-align and find common ground. Just a final decision, delivered swiftly and sloppily — and my team would not find out about that decision until hours later.

So that’s how my career with Catholic Charities of St. Louis ended — not with a conversation, but with a cold goodbye.

WHAT I THINK (PROBABLY) HAPPENED

Look, Oddball Leaders aren’t for everyone.

We ask questions we’re not supposed to ask.

We advocate for fairness even when it’s inconvenient.

We take the servant part of “servant leadership” literally.

And some people in power simply don’t love that.

I’ll never know exactly what happened behind closed doors that led to my termination. Maybe my boss broke my confidence and passed my email around. Maybe the Chief of Staff took it personally. Maybe it was just my turn to be the most expendable reminder of a moral inconsistency.

But here’s what I do know:

When empathy challenges hierarchy, hierarchy bites back.

And when it does, the bite hurts — but it also tells you you’re onto something true.

WHY IT MATTERS

Yes, I still grieve it.

I still get angry sometimes.

I still pray for a new heart and an upright spirit.

But I have zero regrets.

If I knew standing up for my teammate would get me fired, I’d still go down swinging.

Because that’s what Oddball Leaders do.

We lead with curiosity in a world that demands certainty.

We lead with joy when work feels joyless.

We lead with love and humility in the face of ego and power.

And sometimes, we pay for it with our titles, our jobs, and our comfort zones.

It’s hard! It’s not for everyone. And it’s not always safe.

But we don’t lead for safety.

We lead for something better.

And sometimes the bravest, oddest, most sacred thing an Oddball Leader can do is get fired for doing what’s right.

A CALL TO THE ODDBALLS

If you’ve ever been punished for being too kind, too transparent, too human — this one’s for you:

Keep leading with love.

Keep asking the uncomfortable questions.

Keep choosing integrity over approval.

Because the world doesn’t need more compliant leaders.

It needs more Oddballs.

Photo by Jackson Simmer on Unsplash