When Success Works, and You Still Feel Disconnected (#068) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Success did what it said it would do. The career works. The money arrived. The doors opened. The status followed. By most external measures, the strategy succeeded, and yet, somewhere along the way, a quieter question begins to surface. Not loudly, not dramatically, usually in the background between meetings or in the car after a win or late at night when the noise finally dies down. It’s a question success doesn’t answer, and when that question appears, most people make the same assumption. They assume something went wrong. [00:50.2]

They assume the discomfort means they chose the wrong goal or the wrong path, or the wrong life. So, they do what achievers are trained to do. They double down. They optimize harder. They add intensity. They look for the next milestone that might finally settle the unease. But what if that assumption is wrong? What if the problem isn’t failure at all? What if the problem is completion? Because this isn’t a psychological issue in the usual sense. It’s not mainly about trauma or mindset, or motivation. Those can matter, but they’re not the core of what I’m pointing out here. This is a philosophical problem, a moral one.

Modern life makes a very clear promise—if you work hard, become competent and you play the game well, you’ll earn security, freedom and respect. For many of you listening, that promise held up. The system delivered. But that strategy was designed to solve certain problems, like survival, status, independence, control. It was never designed to answer the question of meaning or connection, or love or what kind of person this life is shaping you into. [02:00.8]

When unease shows up after success, it doesn’t actually mean something is broken. It may mean the strategy has reached the edge of where it can take you, not because it failed, but because it worked. That might be uncomfortable, because if the discomfort isn’t a bug, then there’s nothing to fix by pushing harder, no next achievement that resolves it, no upgrade that closes the loop, which leads to a different possibility. What if this feeling isn’t a signal to go back, and it’s not a signal to escape either? What if it’s a signal that a chapter has been finished? Not ended badly, but finished properly, and what comes next isn’t more effort, it’s a new orientation.

I’ve got six points here, and this is the first. To understand why this experience is so common among achievers, we need to look at the modern promise of success and why it’s so convincing. The deal is simple. You work hard, become competent, gain independence, and earn your freedom. [03:02.7]

That deal has powered careers, companies, entire economies, and for many people, it worked exactly as advertised. Competence led to leverage. Leverage led to options. Options feel like freedom. There’s nothing foolish about buying into that modern promise, because security and autonomy aren’t abstract ideas. They do reduce pressure. They buy you time. They give you room to breathe. They let you walk away from bad situations. They let you protect your family and provide for your family. They let you sleep well. So, when I talk about the limits of this strategy, I’m not saying the strategy was pointless. I’m saying it succeeded at what it was supposed to do.

The philosopher Charles Taylor helps explain why this deal feels so natural. He describes what he calls “the buffered Self.” The buffered Self is autonomous and self-directed, protected from the chaos of the world by skill, knowledge, and control. It anchors its own life, sets its own goals, and measures itself by results, and this kind of Self works extremely well in modern societies. [04:07.4]

It builds careers. It survives uncertainty by becoming capable. It gains status by proving value. It creates distance from vulnerability by staying effective. It’s a Self that keeps moving by staying useful. It calms anxiety by becoming sharp. It feels safe by becoming needed. So, when people start questioning success, this isn’t about rejecting competence or criticizing ambition. The modern Self itself isn’t wrong. It’s just incomplete.

Most of the confusion shows up when we smuggle in an assumption that was never part of the deal, that assumption that, once success arrives, it’s supposed to settle the deeper questions, like meaning, belonging, love, who you are when nobody’s watching and nothing needs to be proven, your character. But success never promised to answer those questions. It promised security, autonomy, freedom from certain kinds of fear, and somewhere along the way, we added in the rest. [05:05.3]

We assumed fulfillment would be the natural byproduct of competence, that once the numbers were stable, the heart would naturally catch up, that once the external world stopped threatening us, our internal world would become calm. That assumption is understandable, but it’s also false. The problem isn’t that people believed it. The problem is that nobody tells you what happens when the strategy succeeds, but those questions still remain, because when success works, it trains you to trust the same tools everywhere, continuing to use effort, optimization, control, and problem-solving.

Those tools and techniques are powerful. They just aren’t universal. They don’t generate meaning on their own. They don’t create intimacy. They don’t tell you what’s worth caring about once the scoreboard stops changing. So, when the unspoken assumption collapses, the reflex is usually confusion and then self-doubt, and then trying to push again. [06:08.4]

But the issue isn’t that success failed to deliver. It delivered exactly what it was designed to deliver. What’s missing isn’t more effort. It’s a better perspective—and this brings me to the second point. When people hit the stage, they assume the problem is personal. They wonder if they’re ungrateful or spoiled, or broken. Sometimes they don’t say this out loud, but they feel it. They start looking at their lives the way a manager looks at a project, like, What’s the bottleneck here? What’s the missing habit? What’s the mental block? What’s the next fix?

It helps to look at what the research really shows. There’s a well-documented phenomenon here called hedonic adaptation. Wins feel incredible at first, and then your nervous system adjusts, the promotion, the raise, the recognition, the bigger house, the fancier car, I don’t know, the expanded responsibility or the new title that finally gets people to treat you differently. Each one brings a lift, but then the baseline resets. This isn’t your character flaw. It’s just how the human mind works. [07:16.2]

Early gains matter. They reduce stress and increase stability, but after a certain point, that curve flattens. More income still expands options, but its effect on your day-to-day wellbeing becomes surprisingly small over time. That doesn’t mean money itself is meaningless. It means money does one job extremely well and then stops doing extra work.

People get confused when they interpret the flattening of the curve as a personal failure, as if gratitude should erase the question, so they question their mindset. They question their ambition. They question whether something inside them is malfunctioning. But none of that is necessary. Achievement moves external conditions. It reduces certain kinds of fear. It increases certain kinds of freedom. What it doesn’t do is continually increase meaning. [08:07.0]

Meaning doesn’t scale linearly with wins. It doesn’t respond to accumulation. It doesn’t obey performance logic. Once you see that the experience stops being so mysterious. The plateau isn’t a verdict on your character. It’s a signal that the problem has changed, and when the problem changes, one of two patterns usually follows.

Some people look for a steeper curve. They chase bigger stakes, more volatility, more intensity. If the nervous system went flat, they’d try to shock it back to life. Other people start to notice the deeper question underneath the plateau, not “How do I feel this win more?” but “What is this all for?” That question isn’t weakness. It’s contact with reality—this is a third point. [08:56.3]

To understand what happens next, let’s step outside modern psychology for a moment and look at Daoism, not as mysticism, but as observation. Striving is the attempt to bend reality to your will. You choose a goal. You apply pressure. You tolerate discomfort. You stay focused. You keep the machine running, and for a time, this works extremely well.

Daoist thinkers understood discipline and mastery. They weren’t anti-effort. What they noticed, though, was that past a certain point, effort changes character. What once created progress now starts creating friction. What once gave you leverage starts demanding constant maintenance. What once felt like self-control starts feeling like self-surveillance, not because effort becomes bad, because control applied everywhere meets resistance. Careers reward force. Deadlines respond to pressure. Markets reward execution. But relationships don’t. Meaning and purpose don’t. Love doesn’t respond to being managed. You can’t force trust. You can’t optimize real intimacy. You can’t pressure purpose into existence. [10:09.0]

So, the achievers reflex—more effort—backfires at this level. More control creates distance. More pressure creates withdrawal. More monitoring creates numbness, and then people get confused again, because the tool that works everywhere else is suddenly making things worse now.

Daoism sees this as a category error, using the wrong tool for the terrain. Wu wei doesn’t mean doing nothing. It means not forcing what cannot be forced, acting in a way that fits the nature of the situation, and sometimes this still includes effort. Sometimes it includes training. Sometimes it includes hard conversations and tough choices. But it’s effort that fits the grain of reality, not effort that tries to overpower the reality. [10:56.1]

Sometimes, success comes with a hidden cost. You might have built a career, a business, or life you thought you wanted, but inside, maybe you feel burned out or unfulfilled. Or maybe it shows up in your relationships with your partner, your family or your team, where no matter how hard you try, the same painful patterns keep repeating.

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Modern life rarely teaches this distinction. We assume competence generalizes to everything, until it stops working, until the push that once moved life forward starts flattening it, until the discipline that once gave structure now crowds out aliveness, until the strategy that once created freedom now starts demanding constant upkeep. [12:17.8]

Once you see where force no longer works, you’re now left with a choice. You can keep pushing anyway or you can learn how to relate to these parts of life differently—and this is the fourth point. A human life unfolds in stages.

Confucius put it plainly. He said, “At fifteen, I set my heart upon learning. At thirty, I took my stand. At forty, I had no doubts, no confusion. At fifty, I understood the will of Heaven.” Okay, what matters here isn’t the poetry of it. It’s the structure. Each stage has a task. There’s a cost if you stay too long in any one stage. [12:54.8]

Confusion, at 25, is expected. You’re learning, experimenting. But confusion at 40, for Confucius, means something different, not because you failed, but because you’ve built enough of a life for deeper questions now to matter. You’ve achieved enough to see the limits of achievement. You’ve accumulated enough to notice what accumulation can’t buy. You’ve become competent enough to realize competence isn’t the same thing as wisdom.

There are seasons for building and seasons for understanding. Modern culture pretends there’s only one season—build, optimize, repeat—so, when someone feels pulled toward a new chapter, the reflex is to pathologize it to make it seem like that’s the problem, burnout, weakness, something wrong from the person or with the person. From a developmental view, it’s a transition. Competence without wisdom ends up becoming brittle. Achievement without wisdom ends up becoming hollow. [13:56.2]

We train people relentlessly only for the first half of life and we offer almost nothing from the moment when success stops answering the deeper questions. So, the moment feels private, even shameful. People think, I have no right to feel this way, or, If I say this out loud, I’ll sound ungrateful or spoiled, or, If I admit this, it means I made a mistake.

But wanting a new chapter doesn’t mean the first one failed. It means it concluded, and here’s where the moral dimension comes in—a society that honors achievement, but neglects wisdom, leaves its most competent people quietly lost, not because they lack intelligence, but because they were never taught how to move from one stage of life to the next.

We give people playbooks for success, productivity and leadership. We give them language for metrics and milestones, but we give them almost no language for the moment when the metrics stop touching the deeper questions, so the only available move is to turn the question into a private defect, which is why this stage so often comes with self-judgment—and this is the fifth point. [15:08.0]

Abraham Maslow is remembered for self-actualization. What’s less known is that he later said it wasn’t the end. After studying highly capable, accomplished people, he noticed something else. The people who felt most fulfilled weren’t just actualizing their potential. They were oriented towards something beyond themselves. He called this self-transcendence, not self-erasure, not moralizing sacrifice. It was orientation, a new orientation.

Here’s the clean distinction; competence is about capability. Fulfillment is about connection and contribution, about who and what your capability is in service of. Competence answers “Can I?” Fulfillment answers “Why does this matter?” You can become extremely effective without ever answering the second question. [16:00.6]

Modern culture trains competence extremely well, but it rarely trains wisdom, so people learn how to win games without asking whether the game is even worth playing, and when dissatisfaction appears in an achiever, it feels to that person illegitimate. But they’re not failing. They’re functioning extremely well. They’re responsible. They’re reliable. They’re the person others depend on. But dissatisfaction here isn’t a rejection of success. It’s a signal that capability has now outpaced meaning.

You can be competent in attaining a goal and still not know what that goal is for. Once you see that, the question changes. It’s not “How do I get better at this?” but now it’s “What is this in service of? And what part of life has been neglected because it didn’t show up on the scoreboard?” [16:53.7]

This is the sixth and final point. The predictable mistake at this stage is acceleration or more intensity, higher standards, tighter schedules, a more demanding version of the same pursuit. That response makes sense. It worked before. Effort has always been the lever, but speed doesn’t provide direction. Acceleration solves problems of momentum. Pressure works when the task is external and measurable. This moment now isn’t about that.

What’s happening here isn’t a lack of drive. It’s a lack of proper orientation, and no amount of speed tells you where you’re supposed to be going. So, when people push harder at this stage, the results are subtle but consistent. More efficient and less alive. More accomplished, but less connected. More disciplined, but more restless, not because effort itself is bad, but because effort is being misused. [17:50.6]

A wiser orientation is not the absence of ambition. It’s the governance of ambition. It answers questions that effort itself cannot, like, “What is this life in service for? Who is this success for? What kind of person is being formed along the way?” Those questions don’t slow you down. They keep you from running in circles at higher speeds.

Now it’s important to hold a clear boundary. Not everyone is at this point. Some people are still building stability. Some are still proving their competence. This conversation isn’t meant to pull anyone out of that phase prematurely. But for those who are here, this is not a crisis. It’s a threshold.

A crisis implies something went wrong. A threshold implies something is ready. Crossing a threshold doesn’t require dramatic change. It requires courage and honesty. Here’s the quiet truth that rarely gets said—most people don’t fail their way into regret. They succeed their way into it. They keep going long after the strategy has stopped making sense, because no one ever told them that it was allowed to stop and ask a different question. This podcast exists to make that question legitimate. [19:05.2]

If you’ve reached this point, there’s nothing to fix. There’s nothing to escape. There’s nothing to prove. There’s simply a decision to be made about how the next chapter will be governed, by momentum or by meaning, and that choice doesn’t announce itself with fireworks. It shows up quietly when the noise drops away and you realize that the old answers might still work, but they’re no longer enough.

Let’s come back to the question we started with. What happens when the strategy that worked actually works and still leaves something important unanswered? Success answered the questions it was built to answer, like how to become capable, how to gain independence, how to reduce certain kinds of fear. It did that job well. What it was never actually designed to do was to answer the deeper questions, meaning, purpose, contribution, connection, love, who you are when there’s nothing left to prove, your character. [20:07.8]

Those questions don’t yield to effort. They don’t respond to optimization. They don’t get quieter when you add more achievement—and that doesn’t make success a mistake. It makes it a tool with a limited range, a tool that works beautifully in one domain but poorly in this new domain. So, when unease shows up after success, the honest response isn’t to dismiss it or drown it out. It’s to recognize what it’s pointing toward that this isn’t failure. It’s the limit of a strategy that was never meant to answer every key question.

If you’re listening to this and thinking, Okay, but what’s next? What’s the alternative? notice the timing of that question. That question is still the achiever’s reflex. It’s the reflex to turn insight into a task, to turn ambiguity into a plan, to turn a threshold into a checklist. [21:00.3]

There will be tools later in this miniseries. There will be practices. There will be ways to reorient yourself. But right now, the first move is simpler. It’s to stop treating the unease as an error message and to start treating it as important information—information that the old strategy has run its course in this domain, information that you’ve outgrown a certain kind of motivation, information that the next chapter will require more than just competence.

That’s why I keep using the word orientation. Orientation is what tells competence where to go. It’s what decides what gets protected and what gets sacrificed. It’s what determines whether discipline becomes a form of self-respect or a form of self-punishment.

Self-transcendence, in Maslow’s sense, doesn’t mean becoming less effective. It means letting effectiveness serve something more real. Sometimes, that something is other people. Sometimes, it’s a craft. Sometimes, it’s a community. Sometimes, it’s a set of principles that you stand by and refuse to violate, even when it would be profitable. Sometimes, it’s the kind of father or mother, partner or leader that you want to be when nobody else is applauding you. [22:14.8]

It’s not about becoming saintly. It’s about becoming self-governed, because without wise governance, ambition doesn’t disappear. It just keeps running. It will run straight through the things that you actually really care about. So, the goal here isn’t to quit the game. It’s to stop letting the game pick your values and your life for you.Now, I want to end the way we began. Success did what it said it would do. The system delivered. The strategy worked, and that’s exactly why the remaining questions matter. In the next episode, we’ll look at something related and often overlooked, what competence quietly costs even as it delivers everything it promises. For now, let the silence do the work. [22:59.7]elf in a new way, to explore what becomes possible when you’re no longer carrying the world alone. [23:34.8]