James Hollis: Spirituality, Permission & Living the Questions
Updated: 3 days ago
This is the seventh and final installment in a seven-part blog series exploring the lessons of James Hollis' Living an Examined Life through the lens of CEO Mental Fitness. Hollis is a Jungian analyst, not a business guru. His work may be the most important leadership reading you'll ever do. He explores the hidden drivers of human behavior: the unconscious patterns, inherited expectations, and adaptive strategies formed long before you ever sat in the corner office.
Over 21 LinkedIn posts, I explored one lesson from each chapter. This series brings them together, three at a time, so you can sit with them in a deeper way.
Let's finish this.
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Construct a Mature Spirituality
Chapter 19
James Hollis instructs us to adopt our own spirituality.
One that embraces us and addresses mystery.
And so the challenge is to potentially reject that which has been forced upon us in our formative years or to lie vulnerable to the slick preacher in an Armani suit promising us salvation for a $1,000 donation.
After all, private jets are expensive.
CEOs are often held accountable for outcomes that are completely outside their control.
Markets shift.
Economic changes
Global events
So what holds you when nothing else can?
James Hollis challenges us to move beyond the spiritual hand-me-downs we inherited as kids.
You know: the platitudes, the reward systems, the fear-based beliefs
and to build something personal, resilient, and true.
He writes:
"We are, all of us, still responsible for meeting our needs, not some magical other, someone who will fix it for us, lift the burdens off us, explain what it all means, instruct us in what we are supposed to do, and if we are really lucky, take care of us so that we don't have to grow up after all."
What does that mean for a CEO?
It means developing an internal compass from which to lead.
It means sourcing your sense of worth from something deeper than your company.
It means learning to sit with uncertainty, pain, and paradox, and still lead with clarity.
CEO Reflection Audit:
What inherited beliefs no longer serve the leader you are becoming?
Where do you draw strength when results don't go your way?
What deeper meaning fuels your leadership?
CEO Challenge:
Define your own spiritual architecture.
Not the one you were given.
The one that helps you hold the weight of leadership when it all gets heavy.
You don't have to be religious.
However, you do need something more profound than resilience.
Seize Permission to Be Who You Really Are
Chapter 20
Oh, I know.
We like to think we're above it all.
We've got this.
We don't need a coach.
We don't need a therapist.
We're operating at the top of Maslow's pyramid.
Right?
And that's why mental illness among CEOs is raging.
Burnout
Imposter syndrome
Self-medicating
Because many of us are still waiting for permission.
I know I am and it bothers me.
There is a disconnect between who we are and who we were taught and programmed to believe we are.
James Hollis writes:
"...much comes between us and what we know, still our bones know, our blood knows, our dreams know, and sometimes we have to reach a point where we can no longer not know what we already know. And then the possible life opens before us, waiting only for our courage and resolution, waiting only for us to suit up and show up at last."
As CEOs, this shows up in subtle ways:
Sometimes you don't seem like yourself.
Often, there is an angst that just won't go away
You wonder, "Is that all there is?"
Permit yourself to be who you are and not who you were brainwashed into being.
CEO Reflection Audit:
Is this your life or someone else's?
Whose permission is needed to know what you already know?
What would change if you gave yourself full permission?
CEO Challenge:
You know that there are parts of you that are not truly you.
Prior programming and reinforced adaptation.
Shake it off and stop it.
Live the Examined Life: Live the Questions, Not the Answers
Chapter 21
Here we are, Chapter 21, the end of our walk with James Hollis.
Thank you for taking this journey with me.
I once turned in an assignment at school that was completely plagiarized.
My teacher caught it, of course, and gave me an "F."
And she asked me this question.
"What do you suppose you could have created if you had written your own thoughts?"
Whoa
I never forgot that lesson.
Especially now, as a writer, in the era of AI.
James Hollis challenges us in this final chapter to seek a life of meaning, to answer the summons of why we are here, who we are, and how we are to live our lives.
Hollis closes with this:
"Will we keep the appointment? Many, perhaps the great majority, never keep the appointment, never show up, and thus lead lives of quiet desperation, suffer anesthetized souls, and have to continuously palliate distracted consciousness. Others show up because they have to. Keeping that appointment is where our lives find their purpose, not in the answers but in living large questions that are worthy of the soul's magnitude. And that is why the examined life matters."
So there we have it.
The answers lie not so much in the latest Leadership book or in whatever Gary V or Warren Buffett just said.
Rather, it is the size of the questions we are asking and giving expression to the answers our inner soul wants to express.
CEO Reflection Audit:
Are we sufficiently seeking meaning in our lives?
What are the questions that our prior programming cannot answer?
What would it look like to free our inner soul from its prison?
CEO Challenge:
Remember "The Road Less Travelled?"
Take it.
Summon the courage to look inside and let it out.
Keep confronting the larger questions.
"What is the real issue here?"
You're here to become.
Because the examined life is the only one worth leading.
Series Conclusion
This concludes the seven-part CEO Mental Fitness series on James Hollis' Living an Examined Life. Over 21 chapters and 22 posts, we explored the hidden forces that shape how CEOs lead, love, and live. Hollis doesn't give easy answers. He gives better questions. And for a CEO willing to do the work, those questions are where the real growth begins.
If this series resonated with you, I'd love to hear from you. The examined life is not a solo journey.
Liam Chrismer
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