Stepping Into Possibilitty

art of encore living stoicism Dec 08, 2022

Imagine a world where uncertainty and adversity reign. A world that’s torn apart by plague, turmoil, division, and violence.

And imagine in this world a man navigating these challenges with courage, self-control, philanthropy, and clear-eyed purpose who tries to help others do the same.

Do you know to which world and man I refer?

Of course, it’s the Roman Empire, 161 - 180 AD, ruled by emperor Marcus Aurelius.

Marcus was the last of the Five Good Emperors of the Roman Empire and the closest thing to a Philosopher King the Western World has ever known.

At night, after a long day of dealing with corrupt politicians, bloodthirsty enemies, financial ruin, natural disasters, an unfaithful wife, and a petulant son, Marcus would write reminders to himself about cultivating and maintaining a sense of stillness and thriving through life’s persistent challenges.

Over and over again, he would write entries like this in his journal.

“Everywhere, at each moment, you have the option:

  • to accept this event with humility

  • to treat this person as they should be treated 

  • to approach this thought with care, so that nothing irrational creeps in”

In this entry, Marcus is reminding himself about the three disciplines of Stoicism.

Stoicism is an enduring ancient Hellenistic philosophy that asserts that virtue is all that’s required to experience greater joy and equanimity through all of life’s trials and triumphs.

Here are the three disciplines of Stoicism Marcus references in his journal entries.

  1. Perception 

  2. Action

  3. Will

Perception and action are part of what is known as “the Stoic fork,” as expressed by Epictetus, a Stoic teacher Marcus revered.

Put simply, you have agency over your thoughts and actions. Everything else is out of your absolute control. 

The third discipline, will, refers to your ability to be mindful of your judgments about yourself, your situation, and others and respond to them with integrity and intention so that you can influence favorable outcomes.

At the beginning of the pandemic, I wrote a book titled, Onward: Where Certainty Ends Possibility Begins, where I repurposed Marcus’ quote and the three Stoic Disciplines as three questions you can answer to help you make better decisions that get you closer to what you want and who you seek to become.

Here are the questions.

What’s now?

Asking, “What’s now?” Inserts a pause so you can zoom out, name, and acknowledge what’s really happening without any adjectives, adverbs, or value judgments. This eliminates unhealthy and unhelpful emotional reactions or expectations.

What’s next?

Asking “What’s next?” encourages you to frame your options so you can eliminate the ones that don’t align with your values and decide which actually gets you closer to what you want without impeding anyone else’s ability to do the same.

What matters?

Asking “What matters?” reminds you that the content of your character is defined by the integrity of your thoughts and actions. You are not the measure of the outcomes you get. The quality of your decisions and effort are their own reward.

An Example

I’ve been a freelancer for over 30 years. The thing about freelancing is that you only make money when you have a gig. 

Almost every day, I wake up and check my calendar to see how my gig pipeline looks. Sometimes I can tell that I don’t have enough gigs coming up to continue to take care of my financial obligations and responsibilities.

On those days, my internal narrative goes something like this.

“Holy sh*t! I don’t have enough gigs. No gigs, no money. Ahh! I won’t be able to pay all my bills at the end of the month. What happens if I can’t pay the mortgage? My kids will hate me. My wife will leave me. I’ll end up an alcoholic living in a box under an overpass and die alone and hungry!”

Seriously. I go there really quickly (and quite often).

But when I zoom out and state what’s happening more objectively, I can identify and work the problem instead of letting it work me over.

Here’s a more objective reframe.

“I don’t have enough gigs on the calendar to pay my bills.”

Having objectively framed my situation, here’s what I might list as choices and how I might apply the process.

  • I can reduce my expenses by canceling online subscriptions and other conveniences.

  • I can get a part-time job.

  • I can explore bankruptcy.

  • I can raise my fees.

  • I can connect with past clients for new business or referrals.

  • I can sell the guitars I don’t play anymore.

  • I can give up and go back to teaching.

Reflecting on these choices, I first eliminated all that don’t align with my values and who I seek to become.

Of the remaining options, the step that feels like it would move me the fastest and furthest is connecting with past clients to see if they’d like to hire me again or would refer someone to me. 

I might also incorporate some of the other choices. 

Reflecting on these choices, the step that feels like it would move me the fastest and furthest is connecting with past clients to see if they’d like to hire me again or would refer someone to me. 

I might also incorporate some of the other choices. 


Answering the questions “What’s now?”, “What’s next?” and “What matters?” engage your will over your perception and actions, developing character excellence and cultivating the virtues of gratitude, generosity, humility, patience, and resilience. 

This is how you build identity, forge meaning, and find fulfillment through life’s ups and downs. 

The quality of your thinking and effort, not recognition and results, are the real rewards in life. 

I hope the three questions and the principles that inform them inspire you to lead and serve from the inside out with greater purpose and peace of mind.

What’s a challenge you’re wrestling with right now? How might answering “What’s now?”, “What’s next?” and “What matters?” help you step into possibility with greater clarity and confidence?

Scott Perry, Encore Life Coach at The Art of Encore Living

If this resonates, please share it with a friend!