Flawed Giants

We've all been there. You discover someone whose ideas resonate deeply with you - perhaps a philosopher, entrepreneur, artist, or scientist. You devour their books, watch their talks, follow their career. Then, inevitably, you learn something troubling about them. Maybe it's a personal failing, a problematic belief, or a serious transgression. Suddenly, you're faced with a dilemma: Do you disregard everything you've learned from them? Or do you somehow try to separate the wisdom from the flawed vessel that delivered it? It could even be worse - you might have them, their band or their idea tattooed on you (I haven’t but I could definitely have one featuring a band I used to love as a child!)

This question has become particularly thorny in our polarised age. We seem increasingly drawn to placing people on pedestals, only to enthusiastically topple them when they inevitably disappoint us. It's a cycle of idolisation and cancellation that leaves little room for nuance - and potentially robs us of valuable insights that even deeply flawed individuals might offer.

The False Pedestal Problem

Our tendency to idealise thought leaders isn't new. Humans have always sought heroes and sages. But there's something uniquely modern about our current approach. Social media amplifies both adoration and condemnation, creating a whiplash effect where yesterday's guru becomes today's pariah. This binary thinking doesn't serve us well. As philosopher John Stuart Mill observed in On Liberty:

"The liberty of the individual must be thus far limited; he must not make himself a nuisance to other people." John Stuart Mill

Mill himself was a complex figure - advocating for women's rights while also supporting British colonialism in India. His complexities don't invalidate his insights about liberty, but they do remind us that wisdom rarely comes from perfect vessels. The psychologist Carl Jung talked about the concept of the 'shadow' - those aspects of ourselves we prefer not to acknowledge. Our collective tendency to project perfection onto public figures, followed by outrage at their inevitable humanity, might well reflect our own discomfort with imperfection. We demand from others a flawlessness we cannot achieve ourselves.

“Filling the conscious mind with ideal conceptions is a characteristic of Western theosophy, but not the confrontation with the Shadow and the world of darkness. One does not become enlightened by imagining figures of light, but by making the darkness conscious. The latter procedure, however, is disagreeable and therefore not popular.” Carl Jung

Perhaps our cultural struggle with flawed teachers is, at heart, a struggle with accepting our own contradictions.

The Wisdom in Imperfection

What if a teacher's flaws aren't merely obstacles to overcome, but potential sources of insight in themselves? Steve Jobs, one of the Ideas Guys I've written about, is one such flawed giant. His brilliance in design and innovation exists alongside well-documented episodes of cruelty and questionable ethics. Yet his understanding of simplicity, focus, and the intersection of technology and humanities has influenced countless entrepreneurs and designers.

Jobs' flaws weren't incidental to his contributions - in many ways, they were intertwined with them. His uncompromising (and sometimes harsh) pursuit of perfection drove both his worst personal behaviours and his greatest professional achievements. By studying the whole person - shadow included - we gain a more nuanced understanding of innovation itself.

The ancient Greeks understood this complexity. They gave us the concept of "tragic flaw" - the idea that greatness and downfall often spring from the same source. The very qualities that make someone exceptional can also be their undoing. Recognising this pattern helps us develop a more sophisticated understanding of human achievement and failure.

How might we thoughtfully approach learning from flawed individuals? Various philosophical traditions offer useful frameworks.

The Buddhist concept of ‘taking the medicine, not the person’ suggests we can benefit from teachings without necessarily endorsing everything about the teacher. Just as we might take a doctor's medical advice while recognising they aren't perfect in all aspects of life, we can extract valuable wisdom while acknowledging its source's limitations.

Philosopher Immanuel Kant's categorical imperative encourages us to consider whether a maxim could become a universal law. Applied here, we might ask: "Would I want everyone to discard all knowledge from imperfect sources?" The answer is clearly no - we'd lose virtually all human wisdom. Meanwhile, pragmatist philosophy, particularly as articulated by William James, suggests judging ideas by their practical utility rather than abstract purity. James writes:

"The truth is what works." William James

This approach allows us to evaluate concepts independently from their originators.

In my own faith journey, wrestling with this issue has been fundamental. Many aspects of my former evangelical background have been profoundly formative, even as I've moved away from that tradition in many ways. Learning to hold both appreciation and critique simultaneously has been challenging but ultimately enriching. I have fond memories of amazing experiences, a solid community and making a tangible difference with people who needed help. I cannot discard that baby with the proverbial bathwater which I reject. (If anyone wonders, I cannot stand the politicisation of faith, the hypocrisy I witnessed and saw in myself, the logic of passive acceptance despite compelling contrary evidence, the mismatch between belief and practice, and the ‘authentic’ community that I discovered was actually just created through a series of transactional relationships. I don’t blame anyone and hope one day to reconcile back into a faith community but this is a strange place having been fully committed for almost forty years.)

Complex Legacies

In my book, I explore 25 Ideas Guys - none of whom are without flaws. Let's examine a few examples that illustrate how we might navigate their complex legacies. I need to mention here again that I absolutely do not endorse these characters in their entirety. I just don’t think it is wholesome nor useful to write people off because some elements of their character, or indeed, the outcome of their actions, is good, bad or indifferent. I believe that we can learn from anyone and anything - and that’s a disposition I am willing to stick my neck out for.

Elon Musk represents a particularly contemporary example of this dilemma. His companies have advanced electric vehicles, space exploration, and renewable energy. Yet his erratic behaviour, treatment of employees, and controversial statements have caused many to question his judgment and character. His recent alignment to US politics has fragmented and polarised whole swathes of American people. 

Rather than choosing between uncritical admiration or total dismissal, we might instead ask: What can Musk's approach to first principles thinking teach us, even while we maintain healthy scepticism about his methods, mission and motivations? 

Yvon Chouinard, founder of Patagonia, offers another intriguing case. His environmental activism and business innovations have inspired many, as well as his decisions to hand the company over to climate action groups. However, his company still participates in consumer capitalism while critiquing its excesses. This tension - between ideal and implementation - offers valuable lessons about navigating complex systems while trying to change them from within. If we are honest, Patagonia may well charge too much for their products and have isolated and disenfranchised whole populations who will never afford their outdoor gear. Despite having their Ironclad Guarantee and their inimitable commitment to tackling environmental issues, there are still question marks about their capitalist position. 

Even Maya Angelou, whom I quoted in my LinkedIn post recently, presents a different sort of complexity. Her wisdom about human dignity emerged directly from her experiences with profound injustice and personal trauma. The hardships she endured weren't incidental to her insights - they were the crucible that formed them. By engaging with her full story - not just the inspirational quotes that circulate on social media - we gain a deeper appreciation for both her resilience and the societal injustices she navigated. The context adds depth rather than diminishing the lessons. Angelou is not the same as Musk, Jobs or Chouinard in terms of her character complexity but the fact still remains that her adversity is complicit in her value to us as learners. Without the racism she suffered, would we have the stories she tells? Now, again, please do not read what I am not saying. I am not justifying systemic racism. I am not saying that the millions of people of colour who have suffered (and continue to suffer) should do so in order for us to have good stories. I am not saying she would not have become an incredible poet and wordsmith if she had experienced nothing but racial harmony. But what I am saying is that the struggle makes the saint. If we whitewash (and I use that term intentionally as this is what my race have tended to do) history and remove pain or poison, I am unsure whether what is left will be anything more than a bland soup of nothingness.

The Nuance Advantage

Embracing a more nuanced approach to learning doesn't just allow us to retain valuable wisdom - it actually enhances our understanding in several ways: Firstly, it develops our critical thinking muscles, which you’ll know is something I think we need to significantly strengthen now more than ever. Rather than outsourcing our judgment to authority figures, we practise discernment - weighing evidence, considering context, and making reasoned assessments about which elements to adopt and which to reject.

Secondly, nuance cultivates intellectual humility. Recognising that even brilliant individuals have blind spots reminds us of our own limitations and encourages a more tentative, questioning approach to knowledge. This counteracts our obsession with perfection whilst navigating our internal struggle for authenticity. “If people really knew what I was like…” is the mantra many of us battle, which leads us to perpetuate a ruse of reality.

Thirdly, nuance models a more humane approach to evaluation. If we can acknowledge that people with significant flaws can nonetheless offer valuable contributions, perhaps we can extend the same grace to ourselves and those around us. When I was thinking about a disposition of grace, something I really want to embody more, I came across this lovely thought from David Zahl,

“...the way you hold a position is very often as important as the position you hold. But it’s especially important when that position begins with the acknowledgment that all of us have significant blind-spots, and that no one ever changes their mind by sheer accusation. Antagonism antagonizes [sic]. And yet, as French writes, “human beings need forgiveness and kindness like we need oxygen.” Amen.” David Zahl

This touched my heart and moved my soul.  All of us have significant blind-spots. 

The philosopher Alain de Botton touches on this in his work on status anxiety as I have mentioned previously, suggesting that our cultural obsession with unattainable perfection creates unnecessary suffering. Learning to appreciate wisdom from imperfect sources might be a step toward a more realistic and compassionate view of human achievement.

A Framework for Learning from Flawed Teachers

So, in light of this worry about babies, bathwater and the pursuit of perfection, I am trying to navigate how we might practically apply this disposition of grace. I hesitate to suggest a framework but I have found some of these ideas to be useful and hope some of them may be to you too. 

‍1. Contextualise without excusing. Understanding the historical or personal circumstances that shaped someone's views doesn't require us to excuse their errors or wrongdoing. Context enriches comprehension without demanding moral compromise. It’s like the forgiving but not forgetting notion - almost. Context is paramount. But that doesn’t mean content can’t be discovered,

2. Extract principles, not personalities. Focus on identifying transferable insights rather than wholesale adoption of a person's entire worldview or approach. It’s the Buddhist medicine-not-necessarily-teacher approach. If the only people you learn from are people you like (or worse, who are like you), your pool will narrow and I suggest your chamber will echo.

3. Compare across sources. Test ideas against other perspectives. When multiple thinkers from different backgrounds arrive at similar conclusions, we can have more confidence in those insights, even if they are questionable. This is the critical thinking piece and the idea that perhaps better information and harbingers of truth will help us see for ourselves rather than being told.

4. Apply ethical filters. Evaluate ideas not just for effectiveness but for alignment with core ethical principles. Some concepts may be pragmatically useful but morally questionable. And likewise, some people’s ethics might not line up with your own but then refer back to #2! You will have values and non-negotiables but there is still something worth saving in the bathwater.

5. Update continuously. Maintain willingness to revise your assessment as new information emerges. Yesterday's unquestionable wisdom may require significant revision in light of today's understanding. It’s the idea of holding things lightly; something that was an alien concept growing up. I held fast to my core tenets before I realised that much of this was learned bias rather than fundamental morality.

When I was teaching Philosophy and Ethics at A-Level, we would regularly apply these principles to thinkers like Aristotle (whose ethics were groundbreaking but who defended slavery) or Nietzsche (whose insights about power and meaning continue to resonate despite troubling aspects of his writings). My students initially found this ambiguity uncomfortable. They wanted clear heroes and villains. But over time, many came to appreciate the intellectual maturity that comes with embracing complexity. As Oscar Wilde put it:

"The truth is rarely pure and never simple." Oscar Wilde

The Whole of Human Experience as Curriculum

This brings me back to the Maya Angelou quote from my LinkedIn post:

"Find a beautiful piece of art. If you fall in love with Van Gogh or Matisse or John Oliver Killens, or if you fall love with the music of Coltrane, the music of Aretha Franklin, or the music of Chopin - find some beautiful art and admire it, and realise that that was created by human beings just like you, no more human, no less." Maya Angelou

Angelou's insight cuts both ways. Yes, it reminds us that we too have creative potential similar to those we admire. But it also reminds us that those we admire are fully human - with all the messiness, contradiction, and occasional failures that humanity entails.

The value of studying flawed Ideas Guys isn't despite their imperfections - it's partially because of them. Their struggles, blind spots, and failures are as instructive as their breakthroughs and insights. The totality of human experience - the triumphs and the tragedies, the wisdom and the folly - constitutes our true curriculum. When we approach learning this way, we resist both the impulse to uncritically idolise and the equally problematic tendency toward righteous dismissal. Instead, we cultivate a more mature relationship with knowledge itself - one that acknowledges its inevitably human origins while still seeking the truth it might contain.

As Leonard Cohen reminds us:

"There is a crack in everything. That's how the light gets in." Leonard Cohen

Key Takeaways

To add some further takeaway nuance, here are some thoughts we might want to finish with:

1. Embrace critical appreciation. Learn to simultaneously value someone's contributions while maintaining healthy scepticism about their flaws or limitations.
2. Look for transferable principles. Focus on extracting concepts and approaches that can be separated from their flawed originators.
3. Use contrast as a teacher. Sometimes a person's failures illuminate their successes. Look for patterns that reveal deeper truths about creativity, innovation, or leadership.
4. Practise intellectual humility. Recognise that if we demanded perfection from our teachers, we'd have none left - and extend the same grace to ourselves.
5. View complexity as an asset. The messy, contradictory nature of human achievement isn't a bug in the system of learning - it's a feature that develops our critical thinking and moral reasoning.

Learning to extract wisdom from flawed teachers isn't just a practical necessity - it's a profound act of maturity. Our intellectual landscape would be desperately barren if we limited ourselves only to perfect sources. History's greatest innovations, most profound philosophies, and most transformative art have emerged from deeply human, often contradictory individuals. By embracing this complexity rather than fearing it, we don't just preserve access to valuable knowledge - we develop a more nuanced, compassionate understanding of human potential. We recognise that brilliance and blindness often coexist, that the same qualities driving someone's greatest contributions may fuel their most significant failures. This perspective doesn't just make us better learners; it makes us better creators, leaders, and humans - capable of seeing the whole spectrum of possibility in others and in ourselves.