What is a Stoic? ‘The Obstacle is the Way’ Principle

What is a Stoic? Could I become one? It’s a question that took on new meaning for me as I navigated the labyrinth of life as an expat, facing the dual challenge of acclimating to a new culture while building a career from the ground up. I was wrestling with heartache and rejection, grappling with the weight of inadequacy, stumbling over the cobblestones of self-doubt. Each felt like a stanza pulled straight from Sylvia Plath’s darkest poems. Then, as if guided by a divine hand, I discovered Stoicism, a philosophical lifeboat amidst the tempest, shedding light on the profound idea that “the obstacle is the way.”

We’re all facing our own versions of exile, rejection, and self-doubt.

But these very obstacles could be our greatest teachers.

What if the path to inner peace isn’t about chasing happiness, but about embracing life in all its raw, unfiltered glory?

This is where the Stoic principle “the obstacle is the way” becomes not just a saying, but a transformative way of life!

These are the lessons I’ve learned from the homonymous book “The Obstacle is the Way“, by Ryan Holiday, and from Oliver Burkeman’s insightful “The Antidote: Happiness for People Who Can’t Stand Positive Thinking.”

Stoicism is a philosophy that doesn’t sugarcoat life’s harsh realities but instead offers a way to find strength and purpose within them.

So let’s explore what it truly means when we ask, “What is a Stoic?” and how “the obstacle is the way” principle can lead us to a life of profound meaning and resilience.

What is a Stoic Mindset? Reframing Life’s Challenges

To understand what is a Stoic mindset, we must first confront an uncomfortable truth: life is challenging by design.

As the Roman philosopher Seneca wisely noted, “Sometimes even to live is an act of courage.”

But it’s precisely in this acknowledgment that we find the seeds of Stoic wisdom:

• Acceptance of reality: Stoics don’t waste energy fighting against unchangeable facts. Instead, they focus on what they can control – their reactions and attitudes. This is where “the obstacle is the way” becomes a powerful tool for reframing our challenges.
• Virtue as the highest good: For Stoics, true happiness comes not from external circumstances, but from living according to virtue – wisdom, justice, courage, and self-control. When we ask, “What is a Stoic approach to happiness?” this is at the core of the answer.
• “Negative visualization“: Stoics regularly contemplate worst-case scenarios, not out of pessimism, but to appreciate what they have and prepare for adversity. This practice embodies the principle that “the obstacle is the way” to greater resilience and gratitude.

My own journey into the Stoic mindset began with a simple exercise: each morning I remember I’m one day closer to death.

It sounds morbid, I know.

But paradoxically, this practice fills me with power. I realize that I can still choose how I want to live that day, knowing this truth.

Death is an inevitable part of life, a constant companion that follows our every step. Yet, how often do we exclude it from our thoughts, our plans, our very existence?

Keep reading: “Logotherapy, Viktor Frankl’s Meaning of Life”

The Obstacle is the Way: Transforming Challenges into Opportunities

The phrase ‘the obstacle is the way’ comes from Marcus Aurelius’s timeless work ‘Meditations,’ but it’s been popularized in modern times by Ryan Holiday’s book of the same name

Buy “The Obstacle is the Way” on Amazon:

This concept is at the heart of Stoic philosophy, teaching us that our obstacles are not just challenges to be overcome, but opportunities for growth and self-improvement.

When we ask, “What is a Stoic’s approach to adversity?” the answer lies in this powerful principle.

• Perception: Seeing obstacles as opportunities rather than roadblocks. This shift in perspective is crucial to understanding what is a Stoic approach to life’s challenges.
• Action: Taking decisive steps to address challenges, focusing on what’s within our control. This embodies the Stoic principle that “the obstacle is the way” to personal growth and achievement.
• Will: Cultivating resilience and perseverance in the face of setbacks. This is what it means to truly live by the mantra “the obstacle is the way.”

I still remember the day I was passed over for a job opening as a digital project manager in favor of another candidate whom I considered inept.

Judgments aside, I had done my best, going the extra mile to be noticed by my bosses and to earn what I thought was almost my right: to be integrated into the agency where I had started as an intern at nearly 40 years old.

The fact that the other candidate was accepted instead of me threw me into a near depression, as if everything I had done had been in vain.

However, I didn’t give up because of the lessons of the Stoics. The focus wasn’t on achievement; it was on effort.

The full story here: “My messy midlife career change will inspire you“

What is a Stoic Definition of Success?

In a world obsessed with external markers of achievement – wealth, status, power – the Stoic definition of success stands in stark contrast.

But what is a Stoic take on success?

• Living in accordance with nature and reason
• Cultivating virtue and wisdom
• Finding contentment regardless of external circumstances

I was reminded of the words of Epictetus: “He is a wise man who does not grieve for the things which he has not, but rejoices for those which he has.”

This shift in perspective was liberating!

Success wasn’t about climbing the corporate ladder or accumulating accolades; it was about becoming a decent, dignified human being, irrespective of external circumstances.

This is what it means to embody the principle that “the obstacle is the way” to true fulfillment.

Buy “The Antidote: Happiness for People Who Can’t Stand Positive Thinking” on Amazon:

What is a Stoic’s Attitude Towards Death?

Death is the ultimate Stoic teacher

No exploration of Stoicism would be complete without confronting the ultimate reality: our own mortality.

It’s a topic we often shy away from, but Stoics viewed death as a powerful teacher and motivator.

In fact, when we ask, “What is a Stoic’s attitude towards death?” we find that it’s intrinsically linked to their approach to life!

• Memento Mori: Remember that you will die
• Using death as a clarifying force to prioritize what truly matters
• Finding freedom in the acceptance of our finite existence

If death is inevitable, why waste time on petty concerns or pointless pursuits?

This realization became a catalyst for living more intentionally, more authentically.

In facing death, I found a powerful illustration of how “the obstacle is the way” to a more meaningful life.

What is a Stoic Way of Life? Practical Applications in Modern Times

So, what is a Stoic way of life in our fast-paced, technology-driven world?

It’s about applying these ancient principles to our modern challenges:

• Practicing mindfulness and present-moment awareness
• Cultivating emotional resilience through rational thinking
• Focusing on personal growth rather than external validation

One practice that transformed my daily life was the Stoic exercise of “negative visualization”.

Each night, I’d reflect on three things that went wrong during the day and how I could have handled them better.

This simple habit not only improved my problem-solving skills but also helped me maintain perspective when facing setbacks.

It’s a practical application of the principle that “the obstacle is the way” to personal growth and resilience.

The Liberating Power of Accepting What We Cannot Control

Perhaps the most profound lesson I’ve learned from Stoicism is the incredible freedom that comes from accepting what we cannot control.

As Marcus Aurelius wisely counseled, “You have power over your mind – not outside events. Realize this, and you will find strength.”

This principle is at the core of what it means when we ask, “What is a Stoic approach to life’s uncertainties?”

• Distinguishing between what we can and cannot control
• Finding peace in acceptance rather than resistance
• Channeling energy towards productive actions rather than futile worries

The Obstacle is the Way: Embracing Failure as a Teacher

Failure, that great boogeyman of modern life, takes on a different hue when viewed through the Stoic lens.

Remember, “the obstacle is the way” : Failure isn’t just an inevitable part of life; it’s a crucial teacher on our journey of growth.

When we ask, “What is a Stoic’s perspective on failure?” we find a refreshingly empowering view:

• Reframing failure as feedback rather than a final judgment
• Learning to extract lessons from every setback
• Building resilience through repeated exposure to challenges

Finding Joy in the Journey: The Stoic Path to Contentment

Contrary to popular belief, Stoicism isn’t about suppressing emotions or living a joyless existence.

Rather, it’s about finding a deeper, more sustainable form of happiness – one that comes from within rather than from external circumstances.

When we ask, “What is a Stoic’s approach to happiness?” we find an answer that’s both challenging and liberating.

• Cultivating gratitude for what we have
• Finding meaning and purpose in our actions
• Embracing the full spectrum of human experience, both pleasant and unpleasant

More on this approach here: “The Midnight Library: Book Summary and Analysis”

As I walk this path to discover “What is a Stoic”, I find a profound sense of peace and joy—not from achieving specific outcomes, but from living in alignment with my values and embracing life’s challenges as opportunities for growth.

This is the ultimate manifestation of the principle that the obstacle is the way to true contentment.

What is a Stoic? A Conclusion

As we come to the end of this exploration, I’m reminded of a quote from Oliver Burkeman.

He writes, “The negative path to happiness is about taking a radically different stance towards those things that most of us spend our lives trying hard to avoid.“

This, in essence, is the heart of Stoicism.

It’s about embracing life in all its messy, unpredictable glory – the triumphs and the tragedies, the joys and the sorrows.

It’s about recognizing that “the obstacle is the way” and that our challenges are not roadblocks, but stepping stones to personal growth and inner peace.

So, what is a Stoic? A Stoic is someone who faces life head-on, who finds strength in adversity, who seeks wisdom in failure, and who cultivates virtue in a world of chaos.

It’s not an easy path, but it’s one that leads to true freedom and contentment.

As I sit here, reflecting on my journey from a lost expat grappling with self-doubt to someone who finds strength and purpose through Stoic principles, I feel a sense of profound gratitude.

The obstacles I face aren’t just challenges to be overcome; they are the very path that leads me to growth, resilience, and a deeper understanding of myself!

This is what it means to truly understand that ‘the obstacle is the way’

Life will always have its challenges.

But with a Stoic mindset, these very obstacles can become your way to a richer, more meaningful existence.

Let’s welcome the journey, face your fears, and find strength in adversity!

For in doing so, we may just discover a peace and contentment that no external circumstance can shake.

In the words of Marcus Aurelius, “You have power over your mind – not outside events. Realize this, and you will find strength.”

May we find that strength, and may we always remember that the obstacle is the way to your truest, most resilient self!