THE DARKNESS OF LEADING

Part 1: So You Want to Be a Leader, Huh?

Let me guess: you got the title, the office, maybe a few initials after your name. People call you “boss” now. Congratulations! You’ve officially stepped into what I like to call The Beautiful Chaos of leadership. Buckle up, because the glamorous photos on LinkedIn don’t quite capture the whole picture.

You thought leadership was about taking charge of projects, influencing strategy, and, you know, making PowerPoints with words like synergy and innovation. And yes, sometimes that’s part of it. But most days, leadership feels a lot more like holding a flashlight in a haunted house, you’re expected to lead others through the dark while pretending you're not scared yourself.

So, What Is Leadership?

Is it a job? A calling? A cruel prank played by your former self who raised their hand in a meeting and said, “I’ll take this on”?

Historically, leadership was about survival. Someone had to tell the rest of the tribe, “Hey, maybe don’t poke the saber-tooth tiger.” It evolved through war, religion, politics… and now here we are, leading Teams meetings where half the team is on mute and the other half is silently screaming inside.

Let’s be real: leadership today is less about commanding armies and more about navigating a sea of expectations, emotions, and endless Slack messages. And here's the kicker, most people don’t even want to lead. They just want someone else to handle the hard stuff while they sip their oat milk lattes in peace.

But true leadership isn’t about making life easier, it’s about making people better. Which, spoiler alert, often makes your life harder.

Grit Over Glamour

Contrary to popular belief, a leader isn’t someone with all the answers—they’re someone who’s fallen flat on their face enough times to recognize when someone else is about to do the same. And instead of saying “I told you so,” they roll up their sleeves and say, “Let’s try it a different way.”

Grit, resilience, discomfort—these are the real currencies of leadership. And if you haven’t had at least three “What the hell am I doing?” moments this week, congrats, you’re either a liar or heavily medicated.

One of my favorite go-to lines when someone on my team is spiraling in doubt is:

“You’re mostly just disagreeing with the version of yourself 10 days from now. That person? They’ve already figured out the thing you’re panicking about. So breathe, do the reps, and let Future You handle the glow-up.”

Sometimes it lands. Sometimes they just blink at me like I’m the office Yoda. Either way, the seed is planted.

Why It Feels So Lonely

Leaders and followers aren’t all that different, really. We’re all just humans dancing between imposter syndrome and existential dread, trying to look like we’ve got our act together. The difference? Leaders do it with everyone watching.

We are expected to be calm in chaos, wise in confusion, and upbeat even when we’re Googling “how to lead a team when you have no idea what you’re doing.”

And sure, there are some who lead with ego and control—those loud, chest-thumping types who think humility is a weakness and empathy is optional. But the real ones—the ones who lead from the trenches, not the pedestal—they know that true leadership often feels like a lonely mountain climb in a thunderstorm... with a team waiting at the bottom asking, “So, what’s the plan?”

Coming Up Next in Part 2:

“Make the Way, Lead the Way, or Get the Heck Out of the Way”

We’ll talk about the difference between making the path vs. leading the path, and how you might accidentally become the roadblock you were hired to clear.

In the meantime, take a breath, grab a snack (yes, the good kind), and remind yourself: You’re not crazy. You’re just leading in the dark—and doing better than you think.