3 Stoic Ways To Make Bold Choices (When Fear Holds You Back)

Today's Saturday • 8 mins read

Psychopaths can make any risky choice without a thought, as their brains cannot process fear.

For the rest of us, we often feel frozen before a life-changing decision — by imagining what could go wrong.

“We suffer more in imagination than in reality.” — Seneca

Stoic philosophers had three useful ways to break out of this mental freeze:

  1. Separate the controllable from the uncontrollable.
  2. Force the mind to see opportunity where others see obstacles.
  3. Practice ‘Premeditatio Malorum,’ or anticipation of potential pitfalls.

Surprisingly, they remain as relevant today as they were in ancient Rome.

1. Separate The Controllable From The Uncontrollable

The idea of separating the controllable from the uncontrollable factors helps, especially when fear whispers doubts about a big decision.

Epictetus put it simply: “Some things are in our control and others not.” Marcus Aurelius wrote, “You have power over your mind—not outside events.”

Ask yourself what you can truly influence, such as your effort or attitude. Let go of the rest, like how others react. This shift frees up energy for bold steps, turning paralysis into progress.

Start small by listing out factors in your next choice. Circle what you control, cross out the rest. Over time, this habit builds mental clarity. It reduces anxiety by focusing your mind on actionable parts.

Diana Nyad Story

In 2013, Diana Nyad attempted her fifth swim from Cuba to Florida. She was 64 years old. Four previous tries had failed due to jellyfish stings, asthma episodes, and storms.

Nyad trained herself to withstand cold water for longer periods. She had a support team of marine life experts design a special mask to prevent jellyfish stings.

Then she took to the water and kept swimming for 53 hours, through ocean currents, stormy conditions, and sharks and jellyfish. When Nyad reached Florida, she was the first person to achieve this feat without a shark cage.

She said later. “I just knew I could control my preparation, my attitude, and my response to whatever the ocean threw at me.”

Nyad’s journey shows the Stoic way: mark out the controllable and focus energy on them.

Apply this to your life: Make a list of the elements over which you have control and work to improve them. Ignore factors you cannot control.

2. See Opportunity In The Obstacle

Stoics believe that obstacles are temporary, expected, and nature-given. So they embrace the challenge, adapt themselves, and grow stronger out of the experience.

Philosopher-King Marcus Aurelius said, “The impediment to action advances action. What stands in the way becomes the way.”

Before giving up in a difficult situation, think about the feedback it carries. Ask, “What can I do now? What can this teach me?”

Answering those can help you decide whether you should work on improving your skills or try something new. So you can avoid similar mistakes and future regrets.

Seeing opportunity in your smaller obstacles will build courage for bigger ones. You learn to make bold choices naturally without feeling anxious that you’re taking risks.

A very heartwarming example of this:

Def Leppard Story

Rick Allen, the drummer of Def Leppard, lost his left arm in a car accident in 1984. That simply meant his drumming career was over.

But Allen worked with engineers to design a special electronic drum kit. The system used foot pedals to trigger sounds that his left arm would normally play. He learned to redistribute complex rhythms between his right arm and his feet.

In 1987, Def Leppard released “Hysteria,” their best-selling album ever, with Allen’s new drumming style.

Allen innovated around his loss. Do the same: Try sketching alternative paths when blocked. Search for a window when the door slams shut.

3. Imagine The Tough Times & Prepare Now

“Premeditatio Malorum,” translated as the “premeditation of evil,” seems like a strange way to approach future uncertainty.

But Stoics used it to prepare for uncertainty, transforming imagined fear into proactive strength.

Try it before a major choice. Visualize worst-case scenarios, such as denial or criticism, then plan simple responses. This mental rehearsal builds resilience, so real challenges feel familiar and less daunting.

Over time, it empowers you to act boldly, knowing you’ve already faced the shadows in your mind.

Chris Hadfield Story

In 2009, astronaut Chris Hadfield had to go on a long spacewalk to repair the Hubble Telescope.

NASA required him to imagine every possible disaster. They put him in a massive pool, where instructors would suddenly cut his oxygen supply, tangle his safety lines, and turn off all lights.

His question each morning was, “What could derail me from my mission?” So he imagined every possible disaster, such as a torn spacesuit, a broken tether, or a tool floating away, and devised solutions for each.

During the actual spacewalk, something happened that he didn’t anticipate: his eyes started burning and tearing up because of the anti-fog solution in his helmet. In zero gravity, his tears formed blobs covering his vision.

But Hadfield stayed calm and completed the repair with near-blind vision, falling back on his memory of the equipment’s layout and his practiced movements.

Later, he explained, “By visualizing failure in advance, success becomes less about luck and more about preparation.”

Hadfield proved that preparation tames fear. Role-playing through tough tasks readies you for bold moves with poise.

Stoic Guide to making Bold Choices

Each day of indecision is a day stolen from your most ambitious self.

How To Practice Premeditatio Malorum

Premeditatio Malorum helps us face fears with logic instead of panic. Set aside five minutes daily for this exercise.

1. Be Honest To Yourself

The first step is brutal honesty. What absolute worst could happen? Start by writing down your exact fears.

Name the specific fear, say, “I might fail this project and disappoint my team.” Naming the fear can make it more manageable.

Perhaps AI will take your job. What could happen? You may struggle financially. You may feel embarrassed to meet your successful friends.

By naming these fears explicitly, you strip them of their paralyzing uncertainty.

2. Plan Prevention And Repair

Next comes prevention and repair. For each potential disaster, develop a concrete mitigation strategy.

For each specific problem, create two plans: how to prevent it and how to recover from it.

Fear of public speaking
• Prevention: Practice your speech twenty times.
• Recovery: If you stumble, pause, smile, and continue. The audience often forgets small mistakes.

Fear of job loss
• Prevention: Apply to one new job each week while employed. Join three industry groups. Take one new certification course every six months.
• Recovery: Keep three months of savings ready. Build a list of 50 companies you’d like to work for. Write down all your skills and achievements.

Fear of money problems
• Prevention: Save 10% of each paycheck. Learn one new job skill each quarter. Cut three unnecessary expenses now.
• Recovery: Create a bare-minimum budget. List five ways to earn quick side income. Know which bills you can pause temporarily.

Fear of damaged reputation
• Prevention: Document your successes weekly. Help three coworkers each month. Share credit for team wins.
• Recovery: Keep proof of your good work. Stay connected with past bosses who liked you. Learn to tell your career story well.

3. See Opportunities And Rewards

But the Stoic approach doesn’t stop at risk management. It demands that you also consider the potential rewards.

They taught that every challenge brings a chance to grow stronger. More importantly, they ask us to think of the cost of inaction.

For a moment, stop overestimating external risks. Instead, think about how you might lose out on a big success if you don’t do anything.

When you face a challenge:

  • First, list what you might lose
  • Then, list what you might gain
  • Finally, consider the cost of doing nothing

4. Build Courage

This isn’t about recklessness. It’s about calculated courage.

Each difficulty makes you stronger, but only if you face it directly. Think of courage like a muscle. Each time you face a fear, your courage grows.

True wisdom lies not in eliminating risk, but in developing the resilience to navigate it. Your capacity to respond to a challenge matters more than the challenge itself.

A simple act of courage is to stop whining about things outside your control. Act despite fear, and the fear will dissolve.

Final Words

Premeditatio Malorum is about confronting our deepest fears with clear-eyed rationality.

Innovators aren’t completely fearless. They refuse to let fear have the final word. Each tough decision expands their boundaries of what’s possible.

The next time you find yourself trapped in an endless loop of “what-ifs,” remember the Stoic practice. Define your fears. Plan your defenses. Imagine your potential. Then act.

Because in the end, we regret not the risks we took, but the opportunities we were too afraid to pursue.


√ Also Read: The Stoic Triangle of Happiness

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