The Unlimited Courage Question: The Single Test That Cuts Through All Self-Deception

I was sitting in my car outside a coffee shop, phone in hand, ready to make a call that would change everything. I’d been “preparing” for this conversation for three months. Research. Strategy. Perfect timing analysis. Risk assessment spreadsheets.

All bullshit.

I wasn’t preparing. I was hiding.

The call was to someone who’d offered me a partnership opportunity that would triple my revenue but require me to step into a level of leadership I’d never attempted. I’d been telling myself I needed to “get ready” when the truth was simpler: I was terrified of succeeding and having to become someone I wasn’t sure I could sustain being.

And in that moment, staring at the contact name on my screen, I realized I’d been asking myself the wrong question for three months.

Instead of “What’s the smart play here?” I should have been asking: “What am I not doing because I’m afraid I might succeed?”

This is the unlimited courage question. And it cuts through self-deception like a blade through silk.

The Cowardice We Call Wisdom

Here’s what I’ve learned about difficult decisions: We’re masters at disguising cowardice as prudence.

We call it “being strategic” when we’re avoiding action. We call it “waiting for the right time” when we’re paralyzed by fear. We call it “gathering more information” when we already know what needs to be done.

We analyze endlessly, but we never ask why we’re avoiding the obvious choice.

The Greeks had a word for this kind of self-deception: the absence of andreia, courage. Not the Hollywood version of courage, charging into battle without fear. Real courage: acting in alignment with what you know to be right, despite the fear.

Marcus Aurelius wrote:

You have power over your mind, not outside events. Realize this, and you will find strength.

But first, you have to stop lying to yourself about what that power requires.

The Question That Changes Everything

Here it is, the question that reveals everything:

“What would I do if I knew I couldn’t fail?”

But that’s just the setup. The real question, the one that cuts to the bone:

“What am I not doing because I’m afraid I might succeed?”

This isn’t about failure. Failure is easy to rationalize. “I tried, it didn’t work, moving on.” Success is terrifying because it demands we become someone different. It requires us to leave behind the identity that no longer serves us.

Success means you can’t hide behind “I’m not ready yet” or “I need more experience.” Success means people expect things from you. Success means the comfortable story you tell yourself about why you’re not where you want to be dies a violent death.

When I finally made that call, it wasn’t because I’d found the perfect strategy. It was because I got tired of being the person who had great ideas and compelling reasons not to act on them. But here’s what I didn’t expect: after it went well, I spent three days in a weird emotional limbo, grieving the version of myself who got to dream about potential without having to live up to it.

The cost of courage isn’t just facing your fears. It’s mourning the comfortable identity of someone who “could have been great” but never had to prove it.

And right now, as I write this, I’m doing it again. I have inventory sitting in my garage and early market validation for an ecommerce opportunity, but I keep finding reasons to delay the launch. “Need better photos.” “Should refine the messaging.” “Market timing isn’t quite right.” Same pattern. Same bullshit. Same question I need to ask myself.

The method is brutal in its simplicity:

Stop strategizing your way out of action
Start asking what you’re really avoiding
Deal with the identity you’re protecting
Watch courage emerge naturally

The Four Ways We Bullshit Ourselves

The Planning Obsession

What it looks like: Endless planning, research, and preparation for something you could start today.

Business Example: Spending six months perfecting a business plan for something you could test with customers in a week.

The Truth: You’re not being thorough. You’re avoiding the vulnerability of putting imperfect work into the world. The Greeks called this the opposite of phronesis, practical wisdom that acts with incomplete information. You’re choosing paralysis over wisdom.

The real issue: You’re not afraid of failure. You’re afraid of discovering you’re capable of more than your current identity allows.

The “Perfect Moment” Lie

The Behavior: Waiting for perfect conditions, the right opportunity, or ideal circumstances.

Career Example: Staying in a job you hate because “it’s not the right time” to make a change, while years pass and nothing changes.

The Truth: There will never be a right time. You’re waiting for permission from circumstances to become who you already know you need to be. Arete, excellence, doesn’t wait for ideal conditions. It creates them through action.

The real issue: You’re not being practical. You’re being cowardly and calling it wisdom.

The Leadership Allergy

The Behavior: Avoiding decisions that would require you to lead, influence, or take ownership of outcomes.

Leadership Example: Staying in roles where you execute other people’s vision instead of creating your own, despite having the skills and experience to lead.

The Truth: You’re not being humble. You’re avoiding the responsibility that comes with your actual capabilities.

The Greek Insight: True andreia (courage) includes the courage to claim your place and use your gifts fully, even when it makes others uncomfortable.

The real issue: You’re not afraid of failing in leadership. You’re afraid of succeeding and having to sustain that level of responsibility.

The Familiar Misery Trap

The Behavior: Choosing familiar misery over uncertain growth, staying in situations that drain you because they’re predictable.

Relationship Example: Remaining in relationships or communities that no longer serve your growth because leaving would mean facing uncertainty about who you are without them.

The Truth: You’re not being loyal or stable. You’re choosing the pain you know over the growth you need.

The Greek Insight: This violates the principle of eudaimonia (flourishing). You can’t flourish while actively choosing stagnation.

The real issue: You’re not afraid of being alone. You’re afraid of discovering what you might become if you stopped settling.

The Diagnostic Questions

Before you dismiss this as another framework, sit with these questions. The answers will tell you whether you’re exercising courage or just bullshitting yourself:

What decision have I been “thinking about” for more than a month without acting?
What lie about my ‘potential’ am I clinging to while scrolling X/Instagram/Facebook/TikTok at 2 AM?
What would I have to grieve if I stopped settling for this version of myself?
Who might I outgrow if I actually succeeded at this, and am I avoiding success to protect those relationships?
What would I have to feel if I stopped using “strategy” as an excuse for cowardice?

The courage question isn’t about eliminating fear. It’s about recognizing when fear is driving the bus while you pretend to be the navigator.

What Actually Works

Here’s what I’ve learned about courage in difficult decisions:

Courage isn’t some noble feeling. It’s getting tired of your own bullshit.

When I finally started making decisions from courage instead of comfort, everything changed. Not because I became fearless, but because I stopped letting fear make my decisions for me.

The process is simple:

Ask the unlimited courage question
Identify which avoidance pattern you’re using
Stop protecting the identity that’s keeping you small
Act from who you’re becoming, not who you’ve been

This isn’t about being reckless. It’s about being honest. Most of what we call “risk assessment” is just fear wearing a business suit.

The Greek Understanding of Courage

The ancient Greeks understood something we’ve forgotten: courage isn’t a feeling, it’s a practice. Andreia wasn’t about being unafraid. It was about acting in alignment with virtue despite fear.

I learned this the hard way when I spent eight months analyzing whether to leave a toxic leadership role. I had spreadsheets comparing options, decision matrices, risk assessments. Pure cowardice dressed as strategy. When I finally acted, it took thirty minutes to resign and two weeks to realize I should have done it seven months earlier. Aristotle’s mean between cowardice and recklessness? I wasn’t even close to reckless. I was drowning in sophisticated cowardice.

We’ve become so sophisticated in our avoidance that we mistake paralysis for prudence.

Phronesis (practical wisdom) doesn’t gather perfect information before acting. It acts with the best information available, knowing that action itself provides the most valuable data.

Arete (excellence) doesn’t wait for ideal conditions. It creates excellence through the practice of virtue, including the virtue of courage.

This is why the unlimited courage question works: it bypasses the sophisticated rationalization and goes straight to the truth about what we’re avoiding.

The Challenge

Here’s your challenge: Stop analyzing your way out of action.

Even when external chains bind you, internal ones are yours to break. The courage question works regardless of your constraints because it reveals where you’re adding unnecessary chains to the ones life already gave you.

Stop bullshitting yourself:

Identify the decision you’ve been avoiding: What have you been “thinking about” instead of doing?
Face what you’re really running from: Ask the unlimited courage question and sit with the answer.
Recognize your avoidance pattern: Which of the four patterns are you using to stay comfortable?
Stop protecting the small version of yourself: What identity would you have to release to act courageously?
Act from courage, not comfort: Make the decision your highest self would make, not your safest self.

Don’t change your strategy. Change your relationship with fear.

Final Thoughts

This reveals something fundamental about human nature: we’re more afraid of our potential than our limitations.

We live in a culture that sells endless preparation as a substitute for action. But transformation happens when we stop preparing for courage and start practicing it.

The person who asks the unlimited courage question never needs perfect conditions.

They have something better: the willingness to become who they’re meant to be, one courageous decision at a time.

That’s the difference between existing and flourishing. Between surviving and thriving. Between protecting who you’ve been and becoming who you’re meant to be.

The question isn’t whether you have courage. It’s whether you’ll stop using wisdom as an excuse for cowardice.

You already know what the call is. The only question left is whether you’ll make it.

Ready to stop bullshitting yourself and start making decisions from courage instead of comfort? MasteryLab is the forge where bullshit gets hammered out and people done playing small become who they’re meant to be.