The Tragedy of Achievement: How Success Undermines Judgment | (#071) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

At a certain level of achievement, decisions don’t explode. They erode. They still look reasonable. They still pass internal review. They still get defended with clean logic in clean rooms by smart people who care. Nothing feels reckless. Nothing feels sloppy, and that’s the problem. What disappears first is rarely intelligence. It’s friction. Shortcuts start to feel earned. Tradeoffs start to feel necessary. Discomfort starts to feel irrelevant. Each move makes sense on its own, and together, they bend judgment. [00:51.8]

If you’ve ever watched a large ship cross open water, then you know how this works. A few degrees off course in the middle of the ocean might feel like nothing. The instruments still look fine. The crew still does its job. There’s no alarm or red flag. There’s no crisis, just a quiet deviation that compounds mile after mile. When the ship finally reaches shore, it isn’t slightly wrong. It’s in the wrong place entirely, and that’s how decision quality degrades at scale.

When your choices affect hundreds of employees or thousands or millions of users and a public narrative that never sleeps, mistakes stop announcing themselves. They don’t arrive as obvious disasters. They arrive instead as reasonable explanations. They arrive as reasons. They arrive wrapped in a logic that protects momentum.

Achievement plays a key role here. It’s an excellent fuel. It drives effort. It sustains pressure. It keeps systems moving forward when most people would stall. What achievement does poorly, though, is govern. Achievement answers the question of how hard to push. It does not answer the question of how to decide when the cost of being wrong becomes invisible at first and then irreversible later. [02:07.0]

This episode is about that distinction, about why achievement keeps engines running while quietly distorting judgment, and about why the higher the stakes, the less obvious this problem becomes, until it has already shaped outcomes that are very difficult to undo.

When achievement rises to the top of the value stack, your other values don’t just vanish. They stay in place, but they change function and they end up getting co-opted. They stop guiding decisions and they start serving outcomes, like integrity turns into brand consistency, like decisions aim to match past statements or public commitments or internal messaging. The question becomes whether the story holds together, not whether the reasoning does or whether it tracks truth or reality. [02:55.2]

A clean narrative replaces clean judgment, and compassion, take compassion, compassion turns into stakeholder optics. Impact gets measured by reactions or sentiment, risk exposure, and the concern shifts toward who might complain or who might leave, or who might write the headline. Attention ends up moving away from lived consequences and instead toward reputational management.

Then take courage. Courage ends up turning into risk tolerance. The focus lands on volatility or downside protection and acceptable loss, and courage stops meaning the willingness to face an uncomfortable truth and starts meaning the willingness to absorb a hit if it pays off later.

On the surface, these substitutions might sound reasonable. They might even sound mature. Consistency matters. Stakeholders matter. Risk matters. The trouble shows up in how decisions get made. Instrumental values ask a different question. They ask, what keeps the system running? They ask, what preserves momentum? They ask, what maintains legitimacy long enough to move forward? [04:01.8]

But intrinsic governing values ask a harder question. They ask, what principle the decision rests on, even if that principle might complicate the story or slow the process. This distinction gets blurred when identity, legacy and responsibility get all muddled up together.

When the work carries your name, your history and the lives of many others, the mind ends up looking for stability. It wants continuity. It wants to avoid rupture, so it starts favoring explanations that protect the system over principles that might challenge it.

This happens very subtly. No one announces this change. Meetings still sound serious. Documents still look thoughtful. The language stays polished, but the center of gravity has moved. Instead of asking whether a decision is clean or tracks reality, or is tracking the truth, the question becomes whether it’s defensible. Instead of asking whether it reflects the stated values and principles, the question becomes whether it can be justified to enough people for long enough. [05:05.7]

That shift will feel very subtle. It rarely feels like compromise. Instead, it feels like responsibility. Over time, though, it trains the mind to treat values as tools rather than anchors, and once values become tools, they stop correcting judgment and they start protecting it. That’s how achievement reorders values without anyone noticing. That’s why decisions can remain impressive on paper while drifting away from the principles that were meant to guide them.

Once achievement or success becomes the governing value, the mind doesn’t become careless. Instead, it becomes selective in a distorted way. The first distortion that often appears is confirmation bias, but with a particular flavor—evidence that protects momentum gets highlighted. Data that supports the current direction feels responsible and pragmatic. Information that threatens coherence feels disruptive, even when it’s accurate. [06:02.5]

Over time, your attention narrows. Dissent starts to sound uninformed. Caution gets labeled as lack of vision. Questions that slow execution begin to feel naive. The issue is not yet that contrary evidence just disappears. It’s that it arrives already carrying a handicap. Then moral licensing enters subtly. Past good decisions start to count as credit. Wins become proof of judgment. Sacrifices made earlier become justification for tradeoffs made now. The internal logic might sound reasonable.

Given everything else that has been done right, this exception might even feel earned. The danger is not one bad choice. It’s the accumulation of small permissions, each one defensible. Each one borrows a little from the future. [06:51.0]

The third distortion is harder to see, because it often looks like leadership. Short-term coherence begins to outweigh long-term integrity. Decisions get optimized for narrative stability. The story must hold together. The system must remain calm. Disruption ends up becoming an enemy, even when disruption is the price of accuracy. Future costs end up getting deferred. They’re not denied. They’re simply placed far enough ahead that they fall outside the current decision window. Clean lines today end up creating fractures tomorrow, but tomorrow belongs to someone else.

All three of these distortions share a common source. They’re not moral failures and they’re not evidence of corruption or bad intent. They are predictable cognitive outcomes of misordered values. When achievement governs, the mind learns to protect motion. It filters information through usefulness instead of truth. It treats discomfort as inefficiency. It rewards explanations that keep things moving. [07:57.7]

This is why intelligent, principled people can drift away from their values without even noticing. Their reasoning might remain sharp. Their intentions might remain intact, but what changes is what their reasoning is taking in, what their reasoning is allowed to consider.

Now, biases don’t take over all at once. They arrive as efficiencies. They feel like maturity. They feel like the cost of responsibility, and because the system continues to function, the distortions remain hidden until the consequences can no longer be contained. By then, the problem is no longer a single decision. It’s a whole pattern.

Once a default pattern sets in, the question stops being who is at fault. The real question becomes what restores clarity before the pattern hardens—and this is where values enter the picture, and values need a reframing. Integrity, compassion, courage, and playfulness, these are often treated as ethical decorations, like nice to have, optional, relevant to character, but not to decisions, but that framing misses their real function. These values do practical cognitive work. They clarify judgment. [09:07.3]

Take integrity, for example. Integrity forces consistency across time. It doesn’t ask whether a decision makes sense right now. It asks whether this decision will still make sense when viewed alongside past choices and future commitments, and that temporal pressure makes rationalizing much harder. Contradictions surface earlier that way.

When a decision quietly violates a principle that’s already claimed, integrity brings that violation into view, while correction is still affordable and possible. Delay makes every fix more expensive and integrity protects against clever inconsistency. It limits the mind’s ability to create a logic that works only to rationalize the present moment. [09:52.4]

Another example could be compassion. Compassion widens the decision field. Power naturally narrows your perspective. Distance turns people into metrics. Abstraction turns consequences into models. Compassion, though, pulls real human experience back into your consideration. This doesn’t mean indulging in feelings or avoiding hard calls. It means restoring missing information. A decision made without input from those affected by it is incomplete.

Compassion adds data that power tends to exclude. It reveals costs that spreadsheets don’t register and timelines don’t capture. When leaders dismiss compassion, they often say it clouds judgment. But in practice, the opposite happens. Decisions made without it rely only on partial evidence. They optimize for efficiency while ignoring friction that will surface later in resistance, disengagement or subtle erosion of trust. Compassion reduces blind spots that are created by distance. It forces the mind to account for realities that abstractions smooth over. [10:59.0]

Another example is courage. Courage determines whether that added information is allowed to matter. Courage allows uncomfortable evidence to stay in the room. It resists the urge to explain it away. It prevents the reflex to label disconfirming facts as edge cases or noise. Courage keeps judgment exposed to reality long enough to adjust.

Or take playfulness as another example. Playfulness does something even subtler. It preserves flexibility. It loosens the grip of our identity. It keeps decisions from becoming self-justifying performances. When playfulness is present, changing course doesn’t feel like humiliation. It feels like adaptation.

So, you see, values like these act as decision clarifiers. They expand what the mind can see. They slow distortion before it becomes structure. They don’t guarantee perfect outcomes, of course. They reduce predictable error. [11:58.3]

When the value of achievement is at the top of your value hierarchy and it governs alone, judgment narrows to protect that, to protect forward motion. When these other values are active, though, like the ones I just mentioned, compassion, courage, integrity, playfulness, then judgment regains depth, and depth, more than just speed, is what sustains decisions when the consequences last longer than the momentum that produced them. [12:26.1]

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To make this more concrete, it helps to slow down and look more closely at the last two values I just mentioned, courage and playfulness. These tend to get misunderstood, and because of that, they’re often the first to disappear.

Courage, as it shows up in decision making, has very little to do with bold moves or public confidence. It’s a lot subtler than that. Courage here means letting disconfirming evidence land without rushing to neutralize it. It means allowing discomfort to inform judgment instead of interrupting it. It means staying present when the story that you prefer begins to wobble. [13:58.5]

Most people think courage is just about facing failure. In practice, it’s about facing information that threatens your identity or a self-image, or a narrative or a plan that’s already in motion. It’s a willingness to pause when momentum is rewarded and to listen when speed feels safer. Courage keeps judgment exposed to reality long enough for reality to matter.

Without courage, the mind becomes efficient at self-protection and rationalizing. It explains away what doesn’t fit. It reframes challenges as misunderstandings. It treats unease as a sign to push harder rather than look closer. That’s how self-deception takes hold while everything still appears competent on the surface.

Playfulness seems like an odd companion to courage, right, especially in serious environments? That’s exactly why it matters even more. Playfulness keeps identity flexible. It loosens the bond between who you are and what you’re currently doing. When playfulness is present, a strategy is something you’re trying out, not something you are, and that distinction matters more than it might sound. [15:08.6]

Without playfulness, revision feels like humiliation. Changing course feels like defeat or a mistake. Admitting uncertainty feels dangerous. Maybe the mind clings to the current plan because letting go feels like losing status rather than gaining accuracy to the truth. Playfulness allows experimentation without ego collapse. It creates room to say, “This isn’t working,” without turning that admission into a threat to your own identity. It keeps judgment light enough to move but grounded enough to stay honest.

For founders and leaders, the pattern is consistent. Loss of playfulness predicts rigidity, and rigidity narrows your perception, and narrowing perception creates blind spots, and blind spots produce damage that looks obvious in hindsight but invisible in the moment—so, courage and playfulness work together. Courage lets reality speak and playfulness lets the Self adjust to that reality. Without them, judgment stiffens under pressure, but with them, decisions remain responsive even when the stakes are highest. [16:15.3]

So, if courage and playfulness keep judgment alive under pressure, the next question is whether they slow things down. Most people assume they do, and that assumption is backwards. Values don’t slow decisions down. They prevent systematic misjudgment. What slows organizations isn’t care. It’s clean up. It’s the cost of reversing decisions that moved fast in the wrong direction. It’s the drag created by mistrust, disengagement, and quiet resistance that follow choices made without full information.

Achievement without governors produces speed, yeah. It pushes action forward with confidence and force. That speed might feel decisive. It might look strong, and it often gets praised in the short term, but speed without governors produces errors that scale. [17:05.0]

When a decision is wrong and large, fixing it isn’t a matter of issuing a correction. It means repairing trust, rebuilding systems, and addressing second and third order effects that no one planned for because no one was allowed to see them fully. Accuracy behaves differently, though. Accuracy compounds. Each clean decision improves the quality of the next one. Fewer exceptions are needed. Fewer explanations are required. Less energy gets spent defending past choices.

Decisiveness feels powerful because it’s visible. Accuracy is quieter. Its payoff shows up over time in stability, trust, and in the absence of preventable crises. When the margin for error is small, speed really matters. When the margin for error involves long-term consequences at scale, accuracy matters a lot more. Getting a decision right early prevents years of downstream damage that no amount of later decisiveness can fully undo. [18:07.4]

The paradox is that values increase true efficiency. They reduce rework. They limit distortion. They keep judgment aligned with reality instead of momentum. In environments where every decision carries symbolic weight and long memory, moving fast in the wrong direction is not leadership. It’s just deferred cost.

Leadership at that level means building decisions that could survive their own consequences. Speed helps you arrive, but accuracy determines whether where you arrive is right. That’s the counterintuitive point, and it’s why the most dangerous mistakes are rarely made by people who hesitate too much, but by those who move quickly without the right values governing where they’re going. [18:55.2]

Okay, that brings us to the uncomfortable question of timing. If this problem is real. Why does it show up later rather than earlier? Early on, reality pushes back. Constraints are obvious. Mistakes get corrected quickly, because failure is visible and costly. Feedback arrives unfiltered. If a decision is wrong, the market responds. The team pushes back. The consequences are hard to ignore.

Success changes that environment. With success, external correction weakens. Systems start absorbing errors instead of exposing them. Advisors become too careful. Teams learn what lands well and what creates friction, and so information gets packaged. Sharp edges get smoothed over. Feedback doesn’t just disappear. It gets filtered.

Confidence meanwhile gets rewarded. Decisive language travels faster than careful reasoning. Certainty sounds like leadership. Ambiguity sounds like weakness, and over time, the leader who speaks with confidence receives reinforcement, while the leader who pauses to question assumptions risks looking uncertain or weak. [20:04.0]

The system begins protecting the decision maker from reality, from the truth, not out of malice, but out of loyalty, fear, incentives, and habit. People downstream depend on stability. They want the machine to keep running, so they adjust how they speak. They bring solutions instead of the real problems. They translate inconvenient truths into safer language, and this is where this drift really hits.

Intelligent, well-intentioned leaders don’t lose their values. They lose contact with unfiltered feedback. They keep making decisions, but those decisions are informed by a narrower and narrower slice of reality. The danger isn’t arrogance. It’s insulation. When the environment stops providing accurate signals, judgment quietly degrades. Errors no longer hurt right away. They get delayed. By the time consequences surface, they’re embedded in systems, culture and public commitments that are much more expensive to unwind. [21:06.2]

This is why experience alone doesn’t protect against misjudgment. In some cases, it actually makes it worse. Past success becomes proof of correctness. The system learns to defer, and the tragedy is that this drift feels like competence. Everything still seems to work. Meetings still happen, metrics still move along, but the distance between decision and reality and truth grows. The later the stage, the harder this is to detect, and the higher the position, the fewer people are willing to bring you what they see plainly. That’s not a failure of character. It’s a predictable outcome of success reshaping the environment in ways that subtly starve judgment of being exposed to the truth. [21:55.0]

So, where does this leave us now? It leaves us with a tension that will actually never go away. Achievement will always push upward. Judgment requires grounding. We’ve walked through how achievement excels as fuel but fails as a governor, how values get repurposed into tools to protect achievements momentum, how predictable biases then follow, how integrity, compassion, courage and playfulness function as cognitive clarifiers rather than mere moral accessories, and why all of this becomes harder, not easier after success.

To make this concrete, let me describe a client I started working with a while back, very senior role, intelligent, disciplined, and widely respected. On paper, everything seemed to be working. He came in because decisions that used to feel clean now felt muddled. Every option had a justification. Every path had support, but each choice left behind a residue of unease that he couldn’t understand or explain. [22:56.3]

As we traced his recent decisions, a pattern emerged. He wasn’t making reckless calls. He was making defensible ones. Each choice protected continuity. Each choice minimized disruption. Each preserved confidence in the system around him. What had quietly disappeared was contradiction. No one brought him information that challenged the prevailing direction, and when they did, he felt an immediate urge to rationalize it away, not because it was wrong, but because it threatened the coherence they’ve worked so hard to build.

Once we identified that, something shifted in an important way. He began holding decisions open longer, not to hesitate, but to let all the discomfort speak. He asked questions that made meetings feel awkward. He invited perspectives that complicated the narrative. He allowed himself to revise without treating revision as some kind of failure. [23:52.2]

The result wasn’t slower execution actually. It was fewer reversals, fewer cleanup operations, less internal strain. Judgment regained depth because it was once again anchored to reality instead of momentum.Achievement will keep pushing. It always does. The work is building governors strong enough to keep direction true, because the higher the stakes, the less you can afford values that merely sound good. They must actually do real work, or they will quietly fail when you need them the most. [24:26.6]