Perils of the Podium – The Dangers of Success

By / / Christian Living, Discipleship, History, Leadership, Pastoral Ministry, The Post, Theology

There’s a peculiar irony baked into the human experience of leadership. The very thing leaders spend themselves chasing — success — can become THE most lethal threat to their continued effectiveness. Failure, it turns out, is a reasonably good teacher. It’s humbling, clarifying, and tends to produce in those who allow themselves to learn from it, an admirable sobriety.

Success, on the other hand, is a terrible teacher. It’s intoxicating, distorting, and has a long and distinguished history of turning capable, admirable leaders into cautionary tales talked about for centuries.

Success isn’t inherently bad. Clearly, it is better to win than lose, better to build than destroy, better to flourish than flounder. But success, like food or wine, must be taken with some discipline, or the results get ugly.

History is littered with men and women who climbed the summit of achievement only to discover that summit was crumbling beneath them — because they spent their time at the top gazing at the view rather than watching their footing.

Let’s take a tour, of the various ways success has ruined those who’ve achieved it — and what can be done about it.

The Arrogance Trap: When Confidence Becomes Contempt

The most common trap by which success ruins a leader is also the most obvious: Arrogance.

Effective leaders are confident. It’s that confidence that inspires others to follow and accomplish the leader’s agenda. But the journey from confidence to arrogance is shorter than most realize.  Success greases the wheels of that journey.

A leader who’s made good decisions begins to believe, perhaps unconsciously, that they simply make good decisions. That they’re immune to unwise, bad decisions. They develop a kind of inertia in decision-making that takes it for granted, whatever they decide is great, because past decisions were. They forget about the process, the counsel, the circumstances that fed into earlier, good decisions. Those all recede into a blurry past, barely recalled. The leader comes to think that the variable that matters is just their OWN decision.

Alexander the Great provides the ancient world’s premier exhibit on this theme. By his early thirties, Alexander had conquered more territory than any one before him, had proven himself a military genius of astonishing ability, and had earned the genuine admiration of soldiers who followed him to the ends of the known world.

Then, flushed with victory, he began to insist that he was literally a god. He adopted Persian court customs requiring subjects to prostrate themselves before him. He executed old friends during drunken rages. The man who had been admirably bold became merely insufferable. His empire, lacking any coherent succession plan because gods presumably live forever, splintered into warring fragments immediately upon his death at just 32 years of age. A spectacular rise; and a preventable unraveling.

In the modern era, one thinks of a figure like — Elizabeth Holmes, whose early success in fundraising and in cultivating a mythos around herself apparently convinced her that the laws of chemistry and biology were negotiable obstacles rather than fixed realities.

When success tells you that you are exceptional, there’s a temptation to believe that the rules applying to ordinary people are not really meant for you. This particular temptation has a perfect track record — of eventually being catastrophically wrong.

The Insularity Problem: When the Bubble Becomes a Bunker

Success also tends to insulate leaders from reality in a more structural way. As a leader rises, their access to unfiltered information quietly diminishes. The circle around them shrinks to those who’ve been selected — consciously or not — for their compatibility with the leader’s existing worldview.

Meetings get shorter. The Team around the leader becomes an echo-chamber. Briefings are curated by those who provide them to merely ape the leader’s views. And that leader, who now seems crucial TO continued success, is protected from contrary voices – which may very well be raising alarms about ignored problems.

Napoleon Bonaparte offers a bracing example. The Napoleon of 1805, who was still capable of sitting around campfires with his troops and absorbing the actual state of affairs on the ground, was a very different commander from the Napoleon of 1812, who launched an invasion of Russia with breathtaking confidence but abysmal logistics.

Success had erected walls. His marshals, once bold enough to push back, had learned what happened to men who delivered unwelcome news. The Russian campaign didn’t fail because Napoleon forgot how to think strategically. It failed because the information environment around him had been so thoroughly sanitized by years of success, he was making decisions in a hall of mirrors.

The same pattern plays out in the corporate world with dismaying regularity. Kodak’s leadership in the 1990s was not composed of stupid people. They were, in fact, quite successful — which was precisely the problem. Success had convinced them that their category definition of themselves – “We’re a film company, darn it!” – was a fixed reality rather than a contingent detail. Kodak wasn’t a film company! They were a picture company and ought to have seen the revolution in taking pictures that was coming.

The engineers who developed early digital camera technology at Kodak were treated as a nuisance rather than as prophets.

The leaders’ bunker was comfortable. Right up till the foreclosure unit showed up to haul away the furniture.

The Sycophant Problem: Yes-Men and the Slow Death of Truth

If insularity is the structural problem success creates, sycophancy is its human face.

Every successful leader generates a gravitational field, and the objects most easily pulled into orbit are those whose primary motivation is proximity to power rather than honest counsel. These individuals — often intelligent, charming, and useless in a crisis — are the sycophants. They thrive in the ecosystem of success.

The mechanism isn’t complicated. A leader makes a decision. It succeeds. Advisors who enthusiastically affirmed the decision are rewarded with the leader’s warmth and continued access. Advisors who raised objections are remembered as obstacles. Over time, the selection pressure is unmistakable. Be agreeable, or be marginalized. The result is a leadership team that functions less like a board of advisors and more like an enthusiastic Greek chorus, narrating the leader’s greatness back to them in real time.

King Rehoboam, Solomon’s son and David’s grandson, is Scripture’s sharpest illustration of this dynamic.

When he came to the throne, older court advisors who’d counseled his father, urged humility and service-oriented leadership. Rehoboam instead turned to his peers — young men who’d grown up in the courts of Solomon’s success. They told him what ambitious young men usually tell ambitious young leaders: Be bolder, harder. Show people who’s in charge.

Rehoboam did exactly that. The result was the permanent division of the kingdom. The sycophants gave him permission to do what he wanted to do anyway, and the price was catastrophic.

In the twentieth century, the collapse of companies like Enron bears all the fingerprints of sycophancy-at-scale. Ken Lay and Jeff Skilling built an organization where internal dissent was treated not as healthy friction but as personal disloyalty. Analysts who asked pointed questions during earnings calls were famously and publicly insulted. When the actual numbers eventually surfaced, the surprise in some quarters was remarkable — though it shouldn’t have been. When you systematically eliminate the people willing to tell you the truth, the truth does not go away. It simply stops being delivered in advance.

The Entitlement Drift: When Perks Become Permissions

A subtler but equally destructive consequence of success is the Entitlement Drift — the gradual, almost imperceptible process by which a leader begins to treat the privileges of success as moral permissions rather than practical accommodations. The private jet, initially a time-saving tool, becomes a symbol of deserved status. The deference of staff, initially a function of organizational hierarchy, becomes an expectation of personal tribute. The leader’s time becomes precious; everyone else’s time becomes expendable.

This drift is dangerous not primarily because of the obvious ethical problems it creates, but because of what it does to a leader’s perception of reality. A leader who has not waited in a line, received a genuinely critical performance review, or been told ‘no’ without elaborate softening in several years is a leader who has lost touch with the texture of ordinary experience — which is, inconveniently, the experience of the people they are supposed to be leading.

The Roman Emperor Domitian began his reign with genuine competence and some legitimate accomplishments, but success and absolute power produced a man who by the end of his reign was requiring citizens to address him as ‘dominus et deus’ — lord and god — in official correspondence. He executed senators for perceived slights. He surrounded himself with informers. He didn’t end well. The Senate, upon his assassination, voted to erase his name from public records in a formal act of “damnatio memoriae” — history’s version of the world’s most emphatic performance review.

The Complacency Trap: Success as a Sedative

Beyond the psychological distortions success creates in leaders themselves, there’s a simpler and perhaps more imminent danger. Success makes people stop doing the things that produced the success. This is complacency; success functioning as a sedative.

The competitive hunger that drove a leader to excellence; the restless questioning, the willingness to challenge assumptions, the disciplined attention to detail – tends to quiet down once the summit has been reached. Why keep scrambling when you’re already at the top? The answer, of course, is that the mountain is always changing. But it’s difficult to feel that when everything currently looks like roses.

The British Empire in the late nineteenth and early twentieth centuries might serve as a macro-scale example. Having achieved a position of global dominance so complete that British leaders could speak without irony of ruling a quarter of the earth’s surface, the incentives for serious self-examination evaporated. The military thinking, the diplomatic assumptions, the economic frameworks — all calcified around the success that had already been achieved. Two world wars, and the dissolving of their Empire, were the eventual tuition bill for that complacency.

Safeguards: How to Survive Your Own Success

Given all of that, it might be tempting to assume success is a trap from which there’s no escape. But that would be both theologically and historically wrong. There are leaders who navigated extraordinary success with their judgment and character largely intact, and their stories share some common features.

First, and most fundamentally: Cultivate an inner circle of people who have stated permission to tell you you’re wrong. Not people who are merely brave enough to occasionally offer mild pushback, but people whose relationship with you is grounded in honest counsel.

Abraham Lincoln’s famous ‘Team of Rivals’ cabinet — filled b men who actively disliked him and said so — was not an accident. It was a deliberate structural choice by a man who understood that comfortable agreement is a luxury a leader can’t afford.

Second, maintain practices of deliberate humility. This is not false modesty or performative self-deprecation. It’s the disciplined habit of placing yourself, regularly, in situations where you’re not the expert, where you must listen, might be wrong, and where nobody is impressed by your title.

For many ancient leaders, religion served this function, that is, the regular reminder, formalized and communal, that power is borrowed, not owned, and will one day be returned. The Psalms of David are remarkable in this regard. A powerful king, at the height of his influence, writing with raw honesty about his failures, his fears, and his dependence on something – actually SOMEONE – larger than himself.

Third, institutionalize dissent. The most durable organizations in history have found formal means for generating internal criticism — not as a punishment, but as a feature.

The Roman Republic, at its best, had the tribunate:. These were elected officials whose explicit function was to veto the actions of the powerful.

Medieval universities had formal disputatio — structured debates in which even the most revered theologians were required to have their positions publicly challenged.

These things weren’t accidents. They were deliberate structural choices by people who’d learned, painfully, what happens when dissent is eliminated.

Fourth, keep learning. The leaders who survive their own success tended to be people who never stopped being genuinely curious about things they didn’t already know.

Winston Churchill, for all his considerable faults, was a voracious reader and writer across an astonishing range of subjects well into old age. His mind remained elastic in ways that matter for leadership. The moment a leader stops learning is the moment they begin fossilizing, and fossilized leaders make impressive monuments but poor decisions.

Finally — and most importantly — remember that success isn’t evidence of righteousness. This conflation is one of the oldest and most persistent of human errors. A company that is profitable is not necessarily run by good people making wise decisions; it may simply be operating in a favorable market. A nation that is powerful is not necessarily virtuous; it may simply be well-positioned. A leader who is winning is not necessarily right. Success tells you something about the past. It tells you very little about the future, and almost nothing about your character.

I’m reading through 2 Kings right now, and just this morning read of several kings of the Northern Kingdom of Israel who were militarily successful but were rank idolaters. Omri, Ahab, Jeroboam II, and Jehu all did evil in God’s sight.

The Leader Who Knows What They Don’t Know

The most dangerous words a successful leader can think — though they rarely think them in quite so direct a form — are: ‘I’ve figured it out.’ The moment the learning stops, the descent begins. It may be slow. It may be masked for years by institutional momentum and residual goodwill. But it begins.

The antidote is not to fear success, but to understand it properly – As a temporary condition, a contingent outcome, a result requiring continued attention and honest evaluation. The leader who treats success as a destination rather than a milestone will eventually stop at that destination while the things continue moving without them.

History’s most enduring leaders — the Washingtons, the Lincolns, the Churchills, the figures from ancient Israel who managed to hold their nation together through impossible circumstances — were not people who escaped the temptations of success. They were people who, with varying degrees of grace and struggle, refused to let success do their thinking for them. They kept asking hard questions. They kept listening to inconvenient voices. They kept their identity grounded in something more permanent than their current winning streak.

Success, in the end, is a test of character disguised as a reward. The question it poses to every leader who encounters it is simple, and devastatingly serious: Now that you have everything you wanted, what kind of person are you going to be?

The answer to that question is the real measure of a leader — and it is always, always still being written.

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