Is Aaron Burr my new hero?

I still listen to the Hamilton soundtrack at least once a week. Yes, I realize that it's been 10 years and make no apologies. It's phenomenal.

And I just made a deeply, startling discovery.

I might need to be more like Aaron Burr.

Hamilton on Broadway at the Rodgers Theater

And on the topic of making confessions,

I fight everything.

Not metaphorically. I mean I will walk into a room, identify an injustice, and be halfway through my argument before I've even decided whether this is a battle worth having. I will torpedo a business opportunity because I cannot - physically, constitutionally cannot - pretend I'm okay with something I'm not okay with. I will say the thing. Every time. Without fail.

In a burst of fall cleaning, I set aside items to donate that no longer need. Except I want to make sure they get to people who need them. The most.

I love how convenient they make it, but I've seen the pictures of goodwill clothing pallets drowning communities in South America, so obviously I can't take things there >

> I would love for people who recently immigrated to the US be able to use them, because I know how hard it is to start over in a new country >

> But, also, I know that my backyard patio set probably isn't helpful for someone who just moved to the US and that they probably live in an apartment >

> Maybe I should try to sell the set on Facebook Marketplace, but I stopped using FB because of the privacy and ethical concerns but also, would it be better to use my privilage to gift them to someone who couldn't afford it >

> Or maybe I should hire someone to help me move them to a local community center in need, but then I'm paying to donate them which is less than ideal and they aren't getting to the people who actually desperately need them and would benefit the most from them ........

And it goes on and on.

For most of my life I've worn conviction as a badge of honor. I have conviction. I stand for something. I don't smile and nod when I think something is wrong. I don't play the game.

And then I sit back and look at what I've actually accomplished lately.

I am exhausted. And I'm not sure I'm actually moving anything forward.

And my garage is full of stuff that I am too overwhelmed to deal with.

The Story I've Been Telling Myself

Alexander Hamilton - not the historical figure specifically, but Lin-Manuel Miranda's version, is essentially a portrait of my leadership instincts.

Hamilton is overlooked, underestimated, and has nothing but his intelligence and his hunger. He is going to outwork everyone. He cannot fathom staying quiet when he believes something matters.

I am not throwing away my shot.

I have basically been living by that line my entire career.

Hamilton rises. He becomes George Washington's most trusted aide, builds the architecture of a nation's financial system, shapes history through sheer force of will and refusal to be silenced. The first act of the musical is essentially a sustained argument that this approach to life works.

And then the second act happens.

Hamilton publishes a public confession of his affair rather than let an unanswered accusation stand - burning his marriage, his family, and his political future in the process.

He campaigns against his own ally in a presidential election because he cannot stay quiet when he believes something matters.

And listening to this while cleaning out my garage, I see myself uncomfortably clearly. Not the first act version. The second act version. When Hamilton has destroyed his entire life and career. The one where the same quality that made him extraordinary starts making him ineffective. Starts costing people around him who never signed up to pay that price.

The Icarus Problem

Angelica reminded her sister, Eliza, that the ancient Greeks had a story, "you've married an icarus and he has flown too close to the sun".

Daedalus built wings from feathers and wax so he and his son Icarus could escape their imprisonment. His warning was specific: don't fly too low, the sea spray will weigh the wings down. But don't fly too high. The sun will melt the wax.

Icarus flew. He was made to fly, that the sky was his. The higher he went the more he felt alive, felt like flying was the fullest expression of who he was.

He flew higher.

Icarus didn't fall because he was reckless or ignorant. He fell because flying felt like truth. He was flying. He was overwhelmed by the beauty of the sky and brilliance of the sun. He just couldn't stop.

He ascended higher and higher not from arrogance, but a test of daring...... Right?

Hamilton shows up to a duel he has already privately decided was wrong because he cannot not show up.

He knew. He went anyway.

What This Actually Looks Like In My Life

Let me be honest about what fighting every battle actually costs.

It costs energy I don't have infinite reserves of. Every injustice I charge at - every principle I defend, every wrong I refuse to let slide - draws from the same pool of energy.

It costs focus. The battles that genuinely matter - the ones where my conviction could actually move something important - get the same amount of me as the battles that are honestly just about my discomfort with being in a room where someone said something I disagree with.

It costs relationships. Not all of them, not dramatically, but gradually. People stop bringing me things because they already know what I'll say. Opportunities quietly go elsewhere. Nobody tells you this is happening. You just notice one day that certain doors are less open than they used to be.

Is this costing the people I'm "fighting for"? By being so committed to being right have I been completely ineffective? After all, NO ONE has been using the patio set sitting in my garage for the last 6 months.

Recently I walked away from a business opportunity because I couldn't keep my mouth shut about a company I don't believe in. Morally, I stand by it. They're doing things I think are genuinely harmful and I don't want my name associated with it. That's real.

But my business partner wanted to move forward. And their argument - money is money, use it to create good - isn't terrible. It's actually a question philosophers have wrestled with for centuries.

Can you take compromised resources and wash them through good work? Is the sustained good you do with that money worth the discomfort of knowing where it came from?

I said no. Loudly. Immediately. Without fully sitting with the question.

And now I'm sitting with it.

The Character I've Been Dismissing

There's another figure in the Hamilton story. The one I've always cast as the antagonist.

Aaron Burr is Hamilton's opposite in almost every way. His philosophy, stated plainly early in the musical:

Talk less. Smile more. Don't let them know what you're against or what you're for.

I have viscerally hated this advice every time I've encountered it in any form. It reads to me as cowardice. As a lack of conviction. As the kind of hollow political maneuvering that keeps unjust systems intact because nobody will say out loud what everyone knows is true.

Burr is a cautionary tale. Don't misread what I'm about to say. By the end of the musical he's a hollowed out man who waited so strategically for the right moment that the waiting became his whole life. He traded everything for access to rooms he turned out to have nothing to say in. That's its own tragedy - maybe a quieter one than Hamilton's, but just as tragic.

But.

Here's the thing I've been too proud to admit.

Burr was right about some things.

Not about everything. Not about the emptiness of pure strategy and no conviction. But about this: not every moment is the moment.

Not every room is the room.

Not every battle is the battle that actually matters.

And the leader who cannot tell the difference - who brings the same ferocity to every disagreement, every injustice, every misalignment - eventually becomes noise.

And I don't want to waste my time on noise. I want spend my time and money on what matters. And those are increasingly in tension for me.

I Don't Think the Answer is to Become Burr

A life of strategic ambiguity, of never letting anyone know what you actually stand for, of waiting for a perfect moment that keeps receding - that's not leadership. That's just sophisticated self-protection.

But I'm starting to think my leadership journey right now, is about learning a kind of selectivity I've never had to develop before.

What if the most powerful version of conviction isn't the one that shows up everywhere? What if it's the one that shows up selectively - that has a track record of letting smaller things go, so that when it finally plants a flag, everyone in the room knows this one is real?

What if Burr isn't the enemy?

What if Burr is the mirror - the warning about what happens when you take the necessary skill of choosing your battles and strip out everything else, all the substance and belief underneath it?

What if I need a little more Burr the way a forest fire needs a firebreak? Not to stop burning. Just to stop burning everything.

The Framework I'm Building For Myself

I'm trying - and I want to be honest that I'm trying and not succeeding perfectly - to run every battle through three questions before I charge in.

• Is this my values or my ego?

They feel identical in the moment. The same heat, the same certainty, the same sense that I cannot in good conscience let this go. But they're different things.

A values fight is something that would matter in five years. Something that would quietly corrode me if I conceded it. Something I'd defend even with no audience, even if nobody ever knew I'd defended it.

An ego fight is about being right. About not being dismissed. About protecting the image I have of myself as someone who calls things out and doesn't play along.

Hamilton couldn't tell the difference. Every bridge he burned felt like a values fight from the inside. The duel felt like honor. Looking back it looks like a man who'd lost the ability to distinguish between his principles and his pride.

I'm trying to learn that distinction before I run out of bridges.

• Who else pays if I'm wrong about this?

Hamilton's greatest blind spot. He paid for his battles — but so did Eliza. So did his son. So did everyone who'd bet on him.

When I fight, I'm not the only one in the room. My partners are in the room. My team is in the room. The relationships and opportunities I haven't built yet are in the room.

• Does winning actually change anything?

Sometimes the answer is no.

And I fight anyway because it feels like the fight itself is the point. The witness. The refusal to be complicit.

Sometimes that's right. Sometimes complicity in silence is its own cost.

But sometimes I'm spending real resources - energy, relationships, credibility, opportunity - on a victory that leaves the world looking exactly the same.

And I have to be honest about when that's happening.

Where I'm Landing

I don't have a clean conclusion. This is live wrestling, not a solved problem.

What I know is this: the thing that makes me a strong leader - the refusal to be hollow, the willingness to say what I actually believe, the inability to smile and nod when something is wrong - is the same thing that is currently making me less effective than I want to be.

The wings are real. I know they're real. But there are a lot of suns to navigate in the world in 2026 and I've been flying toward every sun I can find, and I'm starting to notice the wax.

The version of me I'm working toward isn't someone who fights less.

It's someone who fights so selectively and so deliberately that when I finally say this is the line - people believe it.

It's someone who actually has the energy and time to fight the battles that do matter because they haven't burnt out on all of the smaller battles.

Because they've watched me let other things go. Because my conviction has a track record of being attached to things that genuinely matter. Because I've learned to save the full force of what I believe for the moments that actually deserve it.

Maybe that's what growing as a leader actually looks like. Not the dramatic battles. Not the righteous stands.

Maybe it starts with not eye rolling every time Aaron Burr steps on stage.

And bringing that patio set to a local organization with a backyard who provides child care, ESL classes, and job-skills training to refugees.