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Last week, we talked about the original meaning of the Pursuit of Happiness—not as the chase for pleasure, comfort, or constant positive feelings, but as the pursuit of a life well lived. A life shaped by character, responsibility, and a commitment to live a more virtuous life.


Over the next few weeks, I’ll explore some ideas from four remarkable books by Ryan Holiday, each focused on a cardinal virtue: courage, discipline, justice, and wisdom. For more information about his work visit ryanholiday.net

  1. Courage Is Calling explores courage not as fearlessness, but as the daily practice of acting despite fear. 

  2. Discipline Is Destiny focuses on self-mastery—the ability to govern impulses, habits, and attention over time. 

  3. Right Thing, Right Now centers on justice not as abstract ideals, but as everyday choices—telling the truth, treating people fairly, and doing what’s right even when it’s inconvenient or costly. 

  4. Wisdom Takes Work explores the lifelong discipline of clear thinking, good judgment, and humility.


I’ll highlight one essential idea per virtue—something we can practice, and apply right away.


We’ll begin with courage. 


Courage is Calling and So is Fear

Fear and courage are not opposites—they are connected. Fear is a natural human response that shows up whenever something matters: growth, truth, responsibility, or change. Courage isn’t the absence of fear; it’s the decision to take positive action when we’re afraid. Fear asks us to stop and protect ourselves. Courage asks us to move forward. When fear is allowed to influence our decisions, life shrinks toward comfort and avoidance. When courage is practiced, even in small ways, we become healthier and happier.


We don’t often connect fear to happiness. We tend to think fear is about danger or anxiety, while happiness is about emotions or circumstances. But ancient thinkers understood something different: fear is one of the greatest obstacles to a good life—not because it causes pain, but because it keeps us in our comfort zone.


Fear Isn’t the Enemy—Avoidance Is

Fear itself isn’t the problem. Everyone feels it—leaders, parents, and all the courageous people we admire, are afraid from time to time.


The problem is letting fear decide what we will and won’t do.


Fear rarely looks dramatic. It shows up in everyday situations:

  • Avoiding a conversation you know you need to have

  • Staying silent instead of speaking up

  • Choosing comfort over growth

  • Delaying a decision that needs to be made

  • Playing smaller to avoid criticism or failure


Fear doesn’t need to defeat us outright. It just needs us to really believe we mean it when we say, “I’ll do it tomorrow.


”Later” is fear’s favorite disguise, it thrives when we delay. The more we postpone, the more fear grows. Avoided conversations damage relationships. Avoided decisions creates unhealthy stress. Avoided responsibility erodes self-trust.


Courage Is a Practice, Not a Personality Trait

Courage, as Holiday defines it, isn’t fearlessness or bravado. Courage is the daily practice of acting when we are afraid.


It’s not something you either have or don’t have—it’s a skill you train. That means courage doesn’t come before action. Action comes first. Waiting to feel courageous is a trap.


Taking small positive actions every day is what changes our relationship with fear:

  • Speak up sooner

  • Make the call

  • Decide without certainty

  • Step slightly outside your comfort zone


Each small act builds capacity. Each choice restores something essential to happiness: agency—the ability to choose how we live, even when circumstances are uncomfortable.


The Courageous Choice

Happiness, as it was originally understood, was never about avoiding discomfort. It was about living on purpose—choosing growth over safety, values over feelings, and service over self, even when fear is present. That kind of life doesn’t happen automatically. It requires choosing to act with courage—not once, but daily, in small, ordinary moments.


Courage is a muscle. It strengthens only through use—not education or intention.


At some point today, fear and courage will be calling

I encourage you to answer the call that moves you closer to a life well lived—and supports your pursuit of happiness.


Next week, we’ll explore discipline: the steady force that turns courageous intentions into consistent action.


Let's Get Better Together,

Bill Durkin, Founder

One Positive Place


 
 
 

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