What To Do When Achievement Stops Feeling Fulfilling | (#067) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Imagine this for a moment. You’ve spent years building a life that looks steady on the outside. You’ve pushed. You’ve climbed. You’ve done what everyone told you success required, and then one day, the noise dies down. The inbox slows. The deal is done. The goal is met. The finish line that you thought would feel triumphant arrives quietly, like a door closing in some other room, and you’re left standing there with a question that most people never get to ask out loud—what do you do when the thing that you’ve spent so much of your life building no longer needs you?

I want to begin here in that quiet space, the place where your achievements stop being a shield and start becoming a mirror, a place that can feel almost disorienting, because under all of that effort is a low-grade belief that you aren’t really enough. [01:06.7]

But here’s the part that most of us never prepare for—the moment after the win, the moment after you’ve checked every box that you were supposed to check, because that’s the moment you discover that you don’t actually know how to put the engine down. Your body stays braced. Your hands won’t unclench. In this episode, I want to explore why letting go can feel harder, far harder, than the years that you spent striving, and why that struggle is more common and more human than most people ever admit.

To keep us grounded, I’m going to walk through this in five parts. First, we’ll look at the ache behind achievement and why letting go feels like a kind of death. Second, we’ll turn to some Daoist stories and what they reveal about naturalness and mastery. Third, we’ll connect this to wu wei and modern flow states, and why your nervous system, not your to-do list, is often in charge. [02:01.2]

Fourth, we’ll get into the identity void who you are when your usefulness is no longer your main currency, and fifth and finally, we’ll end with a simple Daoist practice that you can use in real time, plus a quiet invitation for what your next chapter might be.

First, let’s slow down and look directly at the part almost no one talks about, the part that makes letting go feel less like a gentle release and more like a kind of death, because for many people listening, even if you don’t see yourself as an achiever, you know this feeling in your body. The moment you stop pushing, a kind of unease creeps in. Rest doesn’t feel restful anymore. It feels suspicious. Slowing down doesn’t feel safe. It feels like you’re slipping behind, even when there’s nothing to chase anymore, and if you’ve ever walked away from a big chapter in your life, the feeling can hit even harder. [02:53.4]

Post-exit founders know this really well. After years of running on adrenaline and purpose and deadlines, they wake up one morning and the whole structure is gone. The calendar opens up. The investors stop calling. The team no longer needs you to steer the ship, and instead of relief, there’s this quiet, haunting emptiness, a question that floats up before you can push it away: “If I’m not building, then who am I?”

That question isn’t limited to founders. It shows up in anyone who has built their identity around being useful or productive, or reliable or driven. When your value has always come from how hard you work or how much you can carry, letting go can feel like stepping off a cliff.

It doesn’t matter how burnt out you were. It doesn’t matter how desperately you wanted rest. The moment rest actually arrives, guilt walks in with it. Anxiety pulls up a chair. Then there’s that strange shame that appears when something comes too easily, as if effort were the price that you must pay to deserve anything good—and this is where the deeper inquiry begins. [04:00.7]

Letting go doesn’t feel threatening because of what you might lose externally. Letting go feels threatening because of what you fear you’ll lose internally, the identity you’ve spent years polishing, the sense of purpose you’ve tied to your output, the quiet belief, maybe even the unconscious belief, that if you stop doing, the person underneath won’t be enough.

That’s why this isn’t a conversation about productivity or time management. It’s a conversation about identity, about the internal architecture that kept you moving for so long, and why, when the world finally gives you permission to rest, you still can’t grant it to yourself.

Second, I want to bring in a pair of Daoist stories that show us another way of being in the world, stories that reveal what happens when we’re not strangling every moment with self-consciousness. There’s an ancient story from the Liezi, the famous fifth century Daoist text, that captures this whole idea beautifully. [04:58.7]

It’s about a master craftsman who could carve the most delicate and intricate shapes with an ease that made people stop and stare. His hands moved with a kind of quiet confidence, the way a musician forgets their playing and becomes the music itself.

One day, the king heard about this artisan and asked him to demonstrate his skill in the palace, and at first everything looked the same. The craftsman picked up his tools, positioned the wood, and began to work, but as soon as he noticed the king watching him, his hands tightened up. His movements stiffened. Cuts that he’d made thousands of times suddenly felt unfamiliar to him, and then he stumbled. He hesitated. He lost the natural ease that had defined his mastery. When they asked him afterwards what had gone wrong, he said, “When I carve in my workshop, I forget myself. But today, I could not forget that the king was watching.” [05:53.5]

Most modern achievers know that feeling, even if we’ve never held a chisel. The moment you become aware of the audience, real or imagined, you stop interacting with the world and you start performing for it. The irony is that the more you care about getting it right, the more your naturalness disappears. You begin editing yourself mid action. You measure every move against some invisible standard. You stop flowing and you start gripping.

This is why letting go is so difficult. It’s not about doing less or caring less. It’s about remembering who we were before the world’s gaze became the reference point for every decision, before you learned to monitor yourself, before you believed your worth depended on how flawlessly you executed. Letting go is, at its core, a return to that earlier way of being, a way of being grounded in presence, not performance.

There’s another story, this one from the fourth century Zhuangzi about a butcher named Ding. On the surface, he’s just carving up an ox, but when you watch him work, it’s nothing like the forceful hacking that you might imagine. Instead, his blade glides. It weaves through joints and openings as if it already knows the path, and what’s really remarkable is that, after 19 years, his knife is still as sharp as the day he bought it. [07:11.0]

When the lord asks him how this is possible, Butcher Ding explains that he doesn’t cut with effort. He doesn’t push his way through the meat. Instead, he follows the natural lines within the ox. He moves with the Dao, rather than against it.

What he’s describing isn’t some magic. It’s mastery without self-consciousness. It’s action that isn’t choked by overthinking or fear, or the need to prove anything—and this is the part that many post-exit founders forget when they look back at their own success. They tell themselves this myth that they powered through, that grit alone carried them, but if they’re honest with themselves, there were moments, important moments, when instinct stepped in, when they stopped wrestling with every decision and allowed the next move to reveal itself. [08:00.0]

Letting go, in this sense, is not an escape from responsibility. It’s a return to the internal state where excellence didn’t feel like a strain, the state where you acted from clarity instead of tension, and where your best work emerged not through force, but through alignment, harmony, and integration.

So, if the first move was naming the ache and the second move is remembering this ancient Daoist picture of natural action, the third move is to look at what’s happening inside your body and mind when you can’t let go, when you grip instead of glide.

If we’re going to understand why letting go feels so unnatural for so many achievers, we have to tell the truth about what drives achievement in the first place. It’s not what most people think. It isn’t pure ambition or greed. It isn’t creativity. It isn’t some heroic internal engine. More often, the drive comes from fear, the fear of becoming irrelevant, the fear of losing momentum, the fear of waking up one day and realizing you’re just ordinary. [09:04.7]

Most of my listeners won’t call themselves high-achievers, and that’s part of the pattern. When you’ve built your life on proving yourself, you rarely pause long enough to notice how much you’ve already proven. You stay trapped in the belief that you haven’t done enough, and that tightening your grip is the only thing keeping everything from falling apart.

This fear-based fuel works in the short term. In fact, it works so well in the short term that it becomes the only fuel you trust. But then comes the moment after the exit, after the promotion, after the intense season where your role defines your value, and for a founder, this moment is especially disorienting. Overnight, the identity they carried for years goes silent. No team to lead, no crisis to solve, no scoreboard to track, and without those structures, the mind scrambles for something to hold on to. [09:55.5]

But this isn’t just a founder problem. Anyone who has spent years living in their heads, managing every variable, bracing for the next challenge, they know this feeling—stillness doesn’t feel peaceful. It feels dangerous. When the noise stops, the uncertainty underneath gets louder, and to avoid hearing this, most people double down on control.

Here’s the paradox. Control starts as a coping mechanism. It helps you handle uncertainty when you don’t yet trust yourself, but over time, control becomes the very thing that blocks your clarity. The tighter you hold on, the less you can see. The more you try to manage every outcome, the harder it is to hear your own natural instincts.

Letting go then isn’t just about releasing the external demands. It’s about recognizing how much of your identity has been wrapped around the need to manage everything, and it’s about asking a deeper question: if you weren’t gripping so tightly, what part of you fears that you would just disappear? [10:59.0]

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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Now, within this third move, we also have to talk about your nervous system, because letting go is not just a philosophical choice. It’s a physiological reality. [12:06.6]

When we talk about letting go, most people imagine it as a mental switch, as if you could just simply decide to relax and your body would fall in line, but that’s not how human beings work. Letting go is not a decision. It’s a physiological state. It’s what happens when your nervous system finally believes you’re safe, and for many achievers, especially those who never see themselves as achievers, that state is almost foreign.

If you’ve spent years running on stress, your body doesn’t just shut off the moment the threat passes. It keeps scanning, keeps bracing, keeps waiting for the next problem to solve. Overachievers stay in this sympathetic activation long after the external crisis is over. It becomes the water they swim in, so familiar they barely notice it anymore. [12:57.2]

For post-exit founders, for example, this is even more pronounced. Their internal alarm system spent years firing at full blast. Then the exit happens. The demand falls away, but the alarm doesn’t just turn off. The body never gets the message that it’s allowed to rest, and without that message, stillness feels dangerous, not calming.

This is why strategy alone can’t get you out of this pattern. You can’t plan your way into a regulated nervous system. You have to cultivate inner safety. You have to build a relationship with a part of you that’s convinced the world will collapse the moment that you loosen your grip. So, the real question isn’t “How do I stop?” The deeper question is “What part of me still believes I must not stop?”

Fourth, I want to connect all of this back to wu wei, into something much more familiar in modern psychology, flow. This is the bridge between ancient philosophy and your lived experience. When the Dao De Jing talks about wu wei, people often translate it as non-action, and it sounds like a poetic excuse to take naps all afternoon or something, but that’s not what Laozi meant. [14:07.4]

Wu wei isn’t laziness. It isn’t withdrawal from life. It’s the art of acting without the internal friction that comes from self-monitoring or self-doubt, and the constant pressure to prove yourself. It’s action that arises from integration and harmony, rather than tension and fear.

Think of moments when you were so immersed in what you were doing that time felt different. You weren’t forcing anything. You weren’t performing for anyone. You weren’t trying to manage how you looked or how you came across. You were just in it, fully present. That’s the essence of wu wei. The action is still there, but the struggle isn’t.

For people who have crossed big finish lines, founders after an exit, professionals who’ve reached the top of their fields, wu wei points to an entirely different way of living, a life where your value doesn’t come from constant production, a life where presence carries more weight than output. [15:04.7]

After so many years of grinding, this can feel almost threatening. Ease feels suspicious. If something comes without strain, you question whether it counts, but wu wei reminds us that ease is not the enemy of excellence. It’s often the condition that makes excellence possible.

When you stop gripping so tightly, you make room for intuition, creativity and genuine connection. You become more precise, not less committed, more grounded, not less ambitious, and this is where wu wei becomes a real invitation. Instead of asking how you can push harder, it asks how you can remove the inner obstacles that make everything feel heavy. It asks what your life could look like if your actions arose from alignment instead of anxiety, and it invites you to consider that the person you become in that state may be more powerful, not less, because you’re no longer fighting yourself. [15:58.7]

In modern psychology, we talk about flow states, and for many people, that sounds like a productivity hack that you unlock with the right playlist and a standing desk, but real flow is much closer to wu wei than to any kind of performance tip or hack. It’s what happens when your attention, your body and your intention line up so cleanly that you stop micromanaging your own experience. You’re still doing the work, but the inner critic steps aside. The judging mind quiets. You’re not forcing anything. You’re responding. You’re tracking what’s in front of you without dragging in the weight of who you’re supposed to be.

The irony is that you can’t get into flow by trying harder. Trying harder actually pushes you further away from flow. Flow arrives when effort becomes focused instead of frantic, when you stop bracing against the moment and allow yourself to enter it fully. [16:54.6]

For founders, this is especially important to recognize. You didn’t build your company from a spreadsheet. Yes, the numbers mattered. Yes, the planning mattered. But the heart of the thing, the reason it worked, came from instinct meeting opportunity. You were reading the room or the market, or the people. You were moving in real time, not following some formula, and this is the bridge to the next chapter of your life.

Letting go isn’t the end of your effectiveness. It’s what makes the next level possible. The challenge now isn’t to grind your way forward. It’s to rediscover the inner stance that allowed you to create in the first place. Flow isn’t some luxury. It’s the state where your best decisions come from clarity instead of fear, and where the future starts to take shape again.

Fifth and finally, we have to face the identity piece head on, and then I’ll leave you with a practice and an invitation. There’s a deeper layer beneath all of this and it’s the part that most people try to outrun. It’s the identity layer, because once the striving quiets down, once the scoreboard goes blank, a very old question rises to the surface—if your worth is no longer tied to your usefulness, who are you? [18:07.4]

For founders, this question can land with real force. If you aren’t the CEO anymore, what part of you believes that you’re nothing? What part of you decided that your authority, your pace, your decisions, were the only proof that you mattered? When the title disappears, when the team moves on, what’s left inside you? And is that place spacious or is it hollow? If you weren’t striving every day, if you stopped managing, stopped performing, stopped carrying what isn’t yours to carry, what would be left, and would you even know how to recognize the person underneath all that effort?

This is the identity void, the space most people avoid entering because it pulls away the mask they’ve worn for decades. Letting go doesn’t feel like losing control. It feels like losing yourself, not because you’re disappearing, but because the version of you that was built around achievement has nothing solid left to hold onto. [19:03.2]

Here’s the truth at the human core. Letting go isn’t frightening because of the external changes. It’s frightening because it forces you to meet the parts of yourself that you spent your whole life outrunning, the insecurity that you covered up with competence, the fear that you covered up with productivity, the longing that you covered with ambition. When the momentum stops, those parts finally have a voice, and meeting them without judging them, without pushing them away, may be the most honest, courageous work you ever do.

Now, before we close, I want to offer a simple practice drawn from the ancient Daoist lens, and you can use this in everyday life, something small enough to remember, but deep enough, hopefully, to cut through the noise. There’s a practice I often share with people who feel stuck in that inner grip. It’s simple enough that you can use it in the middle of a workday or in your car, or even while staring at a blank screen trying to will your brain into cooperating. I call it the “two questions” practice, and despite its simplicity, it cuts straight through the noise. [20:06.3]

Okay, so the first question is “What am I trying to control right now that isn’t actually mine to control?” Not what you wish you could control, not what you’ve been trained to manage, but what isn’t actually yours. Maybe it’s someone else’s reaction. Maybe it’s the future. Maybe it’s an outcome that no amount of overthinking will change. Just asking this forces you to pause for a moment and see the pressure you’ve been unconsciously applying. It interrupts the automatic tightening up.

The second question is “What part of me is afraid of letting go?” Notice I’m not asking why you’re afraid. I’m asking which part of you carries that fear the most, because the moment you recognize that it’s a younger part of you, a protective part or a tired part, the dynamic changes. You can stop fighting the fear and start understanding it, and understanding creates just enough space for your instincts to return. [21:01.8]

When you put these two questions together, you loosen the inner knot that you’ve been pulling against for years. You return, even briefly, to a more natural way of being, one where your body stops bracing and your mind stops trying to outrun itself. You remember what it feels like to respond instead of force your way through, to act from clarity instead of tension.

This isn’t about abandoning your goals or pretending that you don’t care. It’s about recognizing when your effort has crossed the line into self-interference. It’s about giving yourself the chance to experience what your life could feel like without the constant grip.

If you practice these questions consistently, even for a minute at a time, you might notice something quietly powerful. You might become more grounded. Your decisions come faster, your creativity feels less manufactured, not because you’re trying harder, but because you’re finally allowing the natural intelligence inside you to rise up again. [22:03.0]

As we come to a close, I want to leave you with a quiet thought. Letting go doesn’t mean losing what you’ve built. It doesn’t mean walking away from your talent or your ambition, but the part of your life that matters. Letting go simply means you stop losing yourself inside the thing you’ve built. You stop trading your inner world for the next accomplishment. You stop carrying the weight, as if the weight were the proof that you deserve what you have.

If you’ve crossed a finish line recently, whether it was an exit, a promotion, or even some personal milestone, and you still feel the heaviness in your chest, that doesn’t mean you’re broken. It means you’ve reached the limit of what striving alone can give you. The next chapter of your life might not be about running harder. It might be about learning how to set the weight down without losing any of the deeper meaning behind it. [22:55.8]

There’s a different kind of strength available when you’re no longer bracing against yourself, a steadier kind, a clearer kind, a calmer kind, a kind that doesn’t depend on pressure to function. When you allow even a small part of you to rest, you begin to sense the outline of the person underneath all that effort, and that True Self has far more to offer than the version of you who has been running on adrenaline.

So, consider this a gentle invitation, not to stop, not to retreat, but to meet yourself in a new way, to explore what becomes possible when you’re no longer carrying the world alone. [23:34.8]