Courage In The Age Of Ai Choosing

Happy Sunday Friends!

Courage is easy when the enemy is in sight, or the truth is obvious. The harder test (the one that defines a leader in this new era) is when the choice isn’t between good and bad, but between bad and bad, between right and right. And harder still: when the decision is clear, but the timing is not.

One Quote I’m Musing

“The bravest are surely those who have the clearest vision of what is before them, glory and danger alike, and yet notwithstanding, go out to meet it.”

| Thucydides

The Stoics understood this. Courage, to them, was not a reckless leap into danger. It was the disciplined choice to act well in the face of uncertainty; sometimes by stepping forward, sometimes by holding back until the moment would matter most.

📝 The Moment That Tests You

Growing into maturity in the military, I learned that action delayed can lose the battle. But in leadership, especially in today’s hyperconnected, AI-driven age, action taken too soon can cause as much damage as inaction.

I’ve sat in rooms with classified intelligence that screamed for action. Every instinct wanted immediate movement. But wisdom and experience, (usually not mine) warned: Not yet. Because the right decision at the wrong time can burn the very ground you’re trying to save.

We’ve all felt a smaller version of this: firing off an email in frustration, only to wish we’d waited a day to send it.

📡 Courage in the Age of AI and Influence

In the times of Stoics, warriors fought with shields and spears (Socrates was a Soldier, FYI). Today, we also fight in the realm of data, algorithms, and narratives.

In this domain, courage isn’t just what you say—it’s when you say it, and into which attention window you release it.

This is where the engagement and influence model comes in. In digital competition, whether it’s corporate strategy, national security, or public opinion, there’s a constant cycle of attention capture, narrative shaping, and sentiment management. Algorithms now predict not just what people will see, but when they will be most persuadable.

In that environment, timing becomes a moral and strategic decision.

Right action at the wrong moment in an influence-driven world isn’t just ineffective, it can be a wasted or even damaging opportunity.

In the wrong moment, even the truth can become a weapon against its wielder.

During the Cuban Missile Crisis, U.S. surveillance photos revealed Soviet nuclear missile sites in Cuba. Had Washington publicized those images too soon, it could have cornered Moscow’s hardliners into launching before diplomacy had a chance to work and risking nuclear war over a news cycle.

Courage, then, is not only about having the truth, but having the discipline to act on it at the moment when it will create the greatest positive impact and the least unnecessary collateral damage.

🪞 Mirror Moment

The online world rewards speed. Hot takes win more likes than considered reflection. And with AI amplifying, boosting, and surfacing the most engaging content (not necessarily the most true), the courage to wait feels like forfeiting the game.

But the Stoics remind us: not all battles are won by charging first. In influence, as in war, often you win by shaping the ground before the fight begins.

🧭 Future Courage Will Look Different

T.E. Lawrence wrote that “All men dream, but not equally. The dreamers of the day are dangerous men, for they may act on their dreams with open eyes, to make them possible.”

I find that especially valuable for the coming years. AI will progress competition and conflict beyond behavioral prediction to predicting decision timing. It will help us model when we are most likely to act and adjust the environment to make opponents act sooner, or later, than optimal.

In that world, the courage to choose your own hour, resisting algorithmic nudges, will become an act of defiance and self-governance.

This is why your influence model matters. It’s not about “gaming” people. It’s about mastering decision timing so that you lead with clarity rather than reflex. The Stoics would recognize this as nothing less than the virtue of courage, evolved for the digital battlefield.

💡 Two Ideas From Me

🛡️ The rarest courage is resisting the pull of urgency when patience is the uncomfortable necessity.

🧭 In an AI-shaped world, clarity comes from asking better questions, not just getting faster answers.

🛠️ A Decision Timing Protocol

A micro-habit to build modern courage:

Before making a decision, write the date and one-line summary.

1. Truth Check – Is my information accurate and complete?

2. Impact Scan – Who benefits and who is harmed by acting now?

3. Timing Test – What changes if I wait one more cycle (day, week, month)?

4. Narrative Alignment – Does this moment match the environment where the message will resonate?

5. Commit or Contain – Act when the benefit outweighs the collateral and the environment is ready.

🔥 Three Favorite Things This Week

🤖 Brain Training Tool – Dual N-Back Game
A brutal little brain workout that pushes your working memory, focus, and pattern recognition. Feels impossible at first, but you can feel your mental clarity sharpen over time.

📘 Podcast – How decision making will change when AI answers are cheap and (too) easy
Cassie Kozyrkov (former Chief Decision Scientist at Google) discusses the paradox of fast AI-generated answers and the new pressure on humans to ask the right questions, not just trust quick outputs.

🛠️ Tool – Fastcap 25-Foot Measuring Tape
No, I’m not affiliated… but I can’t count how many times per day I take a measurement, walk two steps, then can’t remember what I just took… This thing is a crazy-easy godsend.

❓ One Question to Take Into Your Week

What decision am I letting urgency rush when patience might be the more courageous choice?

Until next Sunday, my friends.

Stay courageous.

Think Dangerously.
–e

🔁 Want to follow the Stoic Series?

📩 Over 4 weeks, I’m unpacking each of the four Stoic virtues. Not simply abstract philosophy, but tactical principles for those building and leading in the digital age.