Lead Anyway: Field Notes From the Snake Pit
What leading through chaos teaches you that no leadership book will
There's a class nobody tells you you're enrolled in.
It doesn't have a syllabus. It doesn't show up on your calendar.
But at some point in your career, if you're paying attention, you realize the education has long been underway.
The tuition is paid in sleepless nights, in misplaced trust, in the exhaustion of building something meant to last … on quicksand
This is that class.
…
There Are No Free Rides
The first thing the snake pit teaches you is that trust is rarely a two-way street. Even when it looks like one.
You'll extend it generously, the way good leaders are supposed to. You'll bring people in, lean on them, invest in them. And some of them will take what you offer and quietly redirect it. Not out of malice, necessarily, but because they're optimizing for a plan you were never a part of.
The lesson isn't cynicism, it's recalibration.
Watch the patterns, not the words. A person who receives your openness but never reciprocates it isn't building a relationship with you, they're managing your relationship (and likely using you). A colleague who agrees with everything and reflects back enthusiasm isn't an ally, they're a mirror with their own agenda.
Trustworthy, loyal people are hard to come by. That's not pessimism, it’s the Truth.
Don't confuse your all-in with theirs.
Actions speak louder than words.
And trust is earned, not given.
Keep it close to the chest until you know.
Get to Know the Rider
Most people, especially in broken organizations, waste energy trying to fix relationships that were never real, or lean on people who were never built to hold weight.
The more useful discipline is simpler and harder: take honest stock of the people around you.
Not harshly. Not cynically. But clearly.
- Who actually has your back when it costs them something?
- Who means well but folds under pressure?
- Who's smiling to your face and carrying your words somewhere else?
- Who's just trying to survive and can't be counted on because they don't even know which way they're headed?
This isn't a verdict. People are complicated and circumstances change. But you can't lead well if you're lying to yourself about who's standing next to you.
When you find the real ones, the ones whose word and work holds, the ones who show up the same whether anyone's watching or not, fight for them.
Let them feel it. Sing their praises (and mean it). Because if you don't, they'll walk right out the door and take their character with them.
That caliber of person can take years to find.
When they show up, you'll know. Let them in. Keep them close.
They're rarer than you think, and worth more than you know.
Bring a Spare Horse
Every plan you make will get disrupted by something you didn't see coming.
Not sometimes. Almost every time.
People quit. People get hired with agendas. Bosses get let go. Demos get sabotaged. Companies get acquired. The ones you counted on were already halfway out the door.
The lesson isn't to stop planning. It's to kill off wishful thinking and lead with contingencies, not hopes.
Stop building plans that only work if everyone behaves the way you hope they will. That's not a plan, that's a wish. And wishes blow with the wind.
Execution = Preparation / Expectations
Lower your expectations and raise your preparation. Build systems that don't collapse when one person walks. Build teams without single points of failure. Build your own knowledge so deep that when the ground shifts, you keep your wits and your footing.
If it can go wrong, plan as if it will.
That's not pessimism. That's how you stay in the saddle.
A good rider doesn't head into open country without a spare horse, extra water and a read on the weather.
Neither should you.
Play the Long Game
This is the hardest part.
Snake pits have their fair share of short-game players.
The ones who steal credit, redirect blame, feed intel upward for personal gain and smile at you while they do it. They get the room. They get the credit. They win, visibly, in the near term.
And, it’s maddening to watch.
But a snake that moves fast through tall grass still leaves a trail. The people worth impressing tend to see through it eventually. Word travels further than most expect. And snake behavior has a way of following the snake around long after the grass has bent back into place.
You're building something different. A reputation for delivery. A team that actually works. A track record built on substance, not smoke.
That takes longer and is less immediately satisfying. There will be nights it feels like a fool's errand. Like the honest hand always finishes last.
It doesn't.
Real trust, earned slowly through consistent behavior, is the only currency that compounds.
Gold rushes end, gold endures.
Outlast them. Outbuild them. Let your work do the talking.
The long game always settles the score.
Ride Through the Dark
True, honest leadership is genuinely hard.
Not intellectually hard. Emotionally hard.
The kind of hard that costs you sleep. That has you staring at the ceiling running the tape back, wondering if the effort is worth it. That has you cycling between wanting to quit and wanting to prove something (sometimes in the same hour).
Every leader inherits something broken. The systems, the people, the promises that were made before you arrived. The snake pit doesn't care what you walked into. It only watches what you do next. And the only way through is through.
What keeps you going, if you're honest about it, isn't some lofty belief in organizational health or a line item on a strategic plan.
It's something quieter and more stubborn than that.
The refusal to leave a place worse than you found it. The desire to build something you're proud of. To prove, to yourself as much as anyone, that it can be done with your integrity still intact.
Some nights the snake pit wins.
You're tired, you're frustrated and the honest path feels like the curse of Sisyphus.
Ride on anyway.
That stubbornness, that refusal to cut corners or cash in your integrity for a shortcut, that's not weakness.
That's the whole damn point.
Earn Them Spurs
Every organization has a power structure. Every team has its politics. Every role comes with a landscape shaped long before you arrived.
You didn't choose the snake pit. But you're in it.
Learn who you're riding with and who you're riding against. Let trust be earned. Build contingencies where others lay wishes. Keep your integrity like a worn coin — always there, never spent cheaply. And when the trail goes dark and the nights go cold, ride on anyway.
The snake pit is a brutal classroom.
No syllabus. No graduation. No one to tell you you're doing it right.
Just sleepless nights, misplaced trust and the bone-deep exhaustion of building something meant to last on quicksand.
But here's what the pit never tells you: everything it throws at you is making you harder to break.
Harder to fool. Harder to rattle. Harder to stop.
So show up. Every single day.
Read the terrain. Build honestly within it. Move with the quiet confidence of someone who knows exactly what they stand for and exactly where they're headed.
This is roll call.
The snake pit doesn't break people like you.
Ride on.