Do-Over: When Oddball Leadership demands sacrifice
Let’s talk about what really happened in February 2025.
[EDITOR’S NOTE: I’m p sure this post is cursed bc 1.) it’s been published more than once before I scheduled it, 2.) it went out via email today without a paywall, and 3.) the original post is nowhere to be found on my website. I think either the universe is against me or the Vatican has gotten involved. 😝😝😝—b.]
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.
