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.
Playing the part
One of the most amusing comments someone has made about my “office aesthetic” was made late last year.
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.