Why High Achievers Feel Unfulfilled (Even When They’re Winning) | (#010) Beyond Success: Psychology & Philosophy for Achievers, with David Tian, Ph.D.

Welcome to “Beyond Success,” the podcast for high-achievers seeking deeper meaning, fulfillment and purpose. Now, here’s your host, world-renowned leadership coach and therapist, David Tian.

Welcome to Beyond Success: Psychology & Philosophy for Achievers. In this episode, we’re diving into one of the biggest truths that high-achievers rarely talk about, but need to understand: the real, lasting benefits of confronting what’s under the surface of their consciousness. This is about more than just solving your next problem. It’s about unlocking and accessing the core of yourself that has been buried under all that, quote-unquote, “success.” [00:42.1]

By the end of this episode, you’ll understand how getting real with yourself can open up levels of satisfaction, life fulfillment, happiness and clarity that outperform anything that material success can give you, because most people never reach this point. They live and die chasing goal after goal with that gnawing feeling that something is missing, and what they miss is actually really important, true connection, the fulfillment that comes from understanding who you actually are, who you truly are, beyond your achievements and accomplishments.

Failing to confront these inner layers doesn’t just affect your relationships or your sense of peace. It shapes your entire life trajectory. If you don’t get ahead of this now, you risk losing the very thing you’re working so hard to find, a life that actually feels and is meaningful.

In case you don’t know who I am, I’m David Tian. For over the past almost two decades, I’ve been helping hundreds of thousands of people from over 87 countries find fulfillment, happiness and meaning in their personal and professional lives. I’ve got three main points here. Let’s dive into the first, and this is on success and fulfillment. [01:50.7]

We’re often taught to believe that success and fulfillment are one in the same, that once you’ve “made it,” quote-unquote, whether that’s building the company, reaching that leadership position or earning more than you ever thought possible, but the reality is, many of the most successful people feel something very different from that.

The truth is, success on its own can’t fill you up inside. It’s like building a beautiful house on quicksand. It’ll look impressive on the outside, but it has no foundation, no stability. Success could even intensify or amplify that feeling of emptiness. I’ve seen it up close. I regularly have clients come to me who seem to have everything they ever wanted, and yet something gnaws at them, a quiet, persistent unease.

Let me give you an example using one client. I’ll call him Mark. This man had a life that would be the envy of many of our listeners. He was a prominent figure in the finance industry. He had a huge and beautiful home. He had a beautiful family. He had more cars than he ever had time to drive. He had a vacation home in the Caribbean. Basically he had the whole package from the outside in terms of material success. People around him saw him as a symbol of what was possible, a role model, and he actually worked really hard to maintain that image. [03:11.7]

But in our first session together, he hit me with this, “David, I have everything I’ve ever wanted, but I feel nothing. It’s like I built this perfect life and I’m looking at it from the outside like it’s not even mine.” Mark had spent years chasing every external marker of success that society dangles in front of us. He thought the promotions, the money, the lifestyle, would finally give him that sense of purpose. But those things don’t answer the deeper questions, like, “Who am I really at my core? Why am I doing all of this?”

In fact, for Mark, every new achievement only amplified his emptiness, his sense of unease, his existential crisis. Each win brought a momentary high, but it was like chasing a drug that never fulfills you. You’re happy for a little while, and then the emptiness returns even stronger, and you need a stronger dose of the drug to get a little bit more of that happiness, but each time it gets harder and harder, and the emptiness gets stronger and stronger. [04:14.4]

What happens to people like Mark is that, along the way, they start living for external validation, and of course, that’s a slippery slope, because the more you base your worth on what other people think, whether that’s society or your colleagues, or even your family, then the further you drift from what’s actually real for you.

Every time Mark got promoted or bought something new, he felt good for a little while, but only in the way that a kid feels good when they’ve been praised. It was just a surface-level satisfaction, but deep down, he didn’t feel seen, didn’t feel understood for himself, for his core self. He didn’t even feel seen or heard or understood by himself. [04:54.7]

It’s easy to get trapped in this cycle. Society has the script to get the degrees, get the job, the money, the house, and once you’ve got those, then apparently you’ve won the game of life and you’re supposed to be happy. But who wrote that script? More importantly, does it match your own? For so many people, the answer is no. They chase success on autopilot, only to hit midlife and realize they’ve been running in the wrong direction, and that realization can send you reeling.

The cracks in the façade start to show during major transitions in life like divorce or a sudden career shift. That’s when people like Mark who have been living for external markers feel the ground begin to shake. Then he went through a difficult divorce, and he felt like his world was coming completely undone. He had built his identity around being this successful husband, the provider, the guy that everyone looked up to, and suddenly, with his marriage unraveling, he felt like he was unraveling, too. [05:58.2]

Divorce forced him to confront the reality that he’d been ignoring, that his success hadn’t actually addressed his deeper needs. For him, like so many others, success had become a way of covering up a feeling that he didn’t want to face, an old sense of worthlessness that he’d been trying to outrun. But the more success he achieved, the more this feeling of emptiness, of being not enough, gnawed at him from the inside, because success doesn’t solve those emotional issues, and if anything, it will eventually magnify them.

This is a common pattern that I see all the time—you achieve. You excel. You build and grow, and those around you see you as a role model. Meanwhile, inside you know the truth. There’s this unresolved longing for something deeper, and that longing actually isn’t a problem. It’s not a flaw. It’s actually the signpost pointing you to the way out. It’s actually trying to tell you something essential. [07:01.7]

That emptiness is pointing you toward something you’ve been avoiding for very long time, and the longer you avoid it, the more you end up at the mercy of these external but empty markers, things like titles, your net worth, what your, I don’t know, LinkedIn profile says about you, none of which really feed your soul, of course.

What Mark finally came to understand through our work together was that success had become his armor. It had allowed him to hide from his real questions, like, “What do I really want out of life? Who am I actually beneath the achievements? What’s my life about and what do I want it to be about?” These questions don’t get answered simply by your next big external win. They require something very different. They require, at first, at least a willingness to stop running and to sit with the parts of yourself that feel incomplete, that feel vulnerable and aren’t being attended to. [08:01.8]

I totally get it, stopping to ask yourself these deeper questions can feel really scary, like a big risk, especially for people who have built their entire life identity on moving forward, growing and all that. But here’s the other side of it—until you face these deeper questions, no amount of success will bring you lasting satisfaction, fulfillment or meaning, because, actually, it won’t be your real success. It’ll be success by someone else’s standards, by society’s standards, success that looks good on paper, but doesn’t feel right inside because it’s not coming from your core.

For people like Mark, that realization was both terrifying but also liberating—terrifying because it means you have to step off the treadmill you’ve been on for your whole life, to stop chasing in this neurotic, compulsive way, but liberating, freeing, because when you finally face what’s real, you find a level of inner peace that no trophy or title could ever give you. When you’re no longer enslaved by the external markers, you can start achieving in ways that feel aligned and meaningful to your core True Self. Your success becomes a reflection of who you really are, not who you think you need to be. [09:15.3]

So, ask yourself this: “Whose version of success am I actually living? And what part of me or parts of me have I been ignoring in order to keep going, to keep powering through?” The answers may surprise you and they may be the most important answers you ever find.

OK, so let’s get into the second main point, which is the hidden emotional toll of success, the isolation that creeps in as you climb higher and higher. A lot of people don’t expect this. We’re sold on the idea that success is supposed to make our life easier. It’s supposed to bring us closer to people. It’s supposed to open up all these doors to more connection and more satisfaction and meaning. In some ways it does, especially early on, but in other ways, especially later down the line, it will totally start to trap you, because here’s what happens—when you become, quote-unquote, “the successful one,” other people begin to expect things from you and they box you in. [10:11.4]

They start to see you as the strong one, the one who has got it all figured out, and this boxed-in, predetermined, preconceived image of you as the powerful, put-together achiever ends up becoming your default identity. It’s what everyone sees, and after a while, it’s all they want to see. They don’t want to know the real you when you’re struggling. They don’t want to hear that you’re dealing with self-doubt or loneliness. In fact, they may not even believe you if you say it and they may unconsciously block it out of their hearing.

I had a client, let’s call him Ben—Ben experienced this firsthand. Ben was a high-level executive managing a massive team of tens of thousands, and he had the kind of life that from the outside, many people would say, looked perfect. He was married to a beautiful woman, had two kids, a beautiful home, and people who knew him professionally thought he was living the dream, and at first he thought he was living the dream, too. But as the years went by and he hit midlife, something changed. [11:10.5]

The weight of the role that he’d built for himself, not just professionally, but personally, also started to take its toll on him, and Ben told me, “David, I feel like I’m living on a deserted island.” He wasn’t talking about some beautiful private getaway. He was talking about isolation. He felt completely alone, even though he was constantly surrounded by people.

His family looked up to him as the provider. His team depended on him as the visionary and his friends thought he was set. He was the made man, that he figured life out in a way that they hadn’t. But behind the scenes, he was feeling disconnected, lonely, burdened by the constant need to maintain this image of strength, not just to others, but to himself. It took him a long time to even be aware of this and that was a big step for him, and he couldn’t share his doubts or his insecurities or his fears to anyone else, because everyone around him seemed to expect him to have all the answers. [12:02.8]

The pressure to have it all together and to keep it all together had become a wall between him and everyone else in his life, and the irony is that the more successful he became, the higher or thicker the wall got. Ben started to feel like he couldn’t even be honest with himself, let alone with the people around him. His identity as the successful one became a mask that was seared into his face. He couldn’t even take it off, and because of that, he was never really able to connect with people in a genuine, authentic way. Every interaction felt fake, forced. Every relationship felt like he was built on an image rather than who he actually was. In fact, he was disconnected from himself and forgot that he even had that mask on.

Society pushes this message on its leaders, the high achievers. They’re supposed to be the strong ones. They’re the rocks that everyone else depends on. That’s the myth or the story that you’ve bought into as you’ve climbed the ladder to becoming an achiever, and when you’ve finally made it to the top, admitting vulnerability to others who have been looking up to you feels risky. It feels like an admission of failure, like a mistake, even though it’s actually just part of being human. [13:12.8]

But high-performing individuals often end up suppressing their own feelings to fit into the role that is expected of them or that they believe is expected of them, and that, over time, is where this crippling isolation sets in. Ben felt like he was drowning in expectations, not just from others, but from himself. He had this constant voice in his head saying, “You’re not supposed to feel this way. You’re supposed to be the leader. You’re supposed to be strong. Everyone else is relying on you. They won’t like it if you show the true you,” and of course, the irony was that this very voice, that relentless drive to appear strong, was keeping him from actually feeling strong. It was robbing him of his own resilience, let alone antifragility. [13:57.1]

There was one moment with Ben that sticks with me. He told me, “David, sometimes I go through the whole day and not once do I feel like myself. I feel like I’m playing a role and everyone around me thinks that’s real,” and that’s the emotional toll of success that most people don’t even talk about. When your success becomes a mask that you can’t take off, it’s hard to know where the mask ends and the real you begins, and this isolation is really common. People just don’t admit it or they’re not even aware of it.

High achievers, in particular, get trapped by these expectations of themselves that they think society has thrust upon them, and in many ways, society and others have of them, and they believe they should be immune to things like self-doubt or loneliness. They think that expressing these emotions will make them appear weak or incapable, and others will be repelled by that, so they, out of fear, keep pushing those feelings down, burying them, hoping they’ll go away. [14:56.6]

Hey, if you’re an achiever who’s been struggling when it comes to managing your emotions or navigating your relationships, I get it. So many high-performers hit a wall when it comes to emotional mastery. Maybe you’ve noticed that stress, frustration or anger is seeping into your personal or professional life, or you feel disconnected from those you care about.

That’s where my “Emotional Mastery” program comes in. It’s based on peer-reviewed, evidence-based therapeutic methods to help you find happiness, love and real fulfillment. Learn how to break free from the emotional roller-coaster and start thriving in every area of your life. You can find out more at DavidTianPhD.com/EmotionalMastery. That’s D-A-V-I-D-T-I-A-N-P-H-D [dot] com [slash] emotional mastery.

But emotions don’t work that way. Science has proven that. They don’t just disappear when you push them down. You suppress them and eventually repress them unconsciously, so conscious suppression becomes unconscious repression and then these emotions fester. They grow in the dark, and eventually, they come out in ways that you can’t ignore and that you can’t control, and that very likely are far more damaging in terms of consequences than if you had actually expressed them when you first felt them. [16:17.8]

For Ben, all those years and decades of pushing down his emotions led to burnout. He reached a point where he felt physically and emotionally depleted. His marriage was strained because he was constantly distracted, never fully present with her. His relationship with his kids was suffering because he was always too tired and very irritable and snapping at them, and he wasn’t able to connect with him because he was, of course, too exhausted to be present.

Yet, despite everything falling apart around him, he still felt like he couldn’t show what was really going on, his vulnerability, that he couldn’t ask for help, because asking for help felt like admitting that maybe he didn’t have it all together, and for someone in his position, that was terrifying. This made our work together very challenging, and it took a long time to get to these realizations. [17:09.5]

Suppressing these emotions, like self-doubt, loneliness, existential fear, ends up creating a pressure-cooker effect in the achiever, actually, in anyone that does this, because you can only keep this going for so long, and when it finally erupts, it often leads to crises. For many people, especially in midlife, it turns into burnout or a breakdown, or a realization that they’ve lost the relationships that matter most to them, and the more you try to hold up this façade, this mask, this image, the further that you end up pushing yourself away from the people who could actually support you, if only you would let them in. [17:46.6]

One of the most liberating things that Ben did was to start acknowledging his isolation, to admit that he felt alone and disconnected despite all his achievements, and that was really not easy for him. It took a lot of time and it took a lot of courage for him to admit that he wasn’t as put together as others thought he was. But when he finally started showing up and opening up to himself first, then to me and then to those closest to him, he found a new kind of strength, the strength to be real, to show himself fully without the mask, to show his True Self, his authentic him at that moment, and that’s when his relationship started to shift, too, because people finally had a chance to actually connect with the real him.

People around him began to see him, not just as this façade, this image, and instead, they were able to see a real human being and that allowed him to connect in ways that he hadn’t been able to for decades, if ever. The lesson here, OK, for your takeaway is that success, when it’s built without emotional transparency, ends up isolating you and you end up living a life of disconnection, not just from others, but from your True Self. [19:00.0]

The first step out of it is simply to acknowledge—first you become aware of it and then you acknowledge that it’s there—to admit that being, quote-unquote, the “successful one” doesn’t mean being invulnerable or that you have no feelings. In fact, true resilience, true strength and true antifragility comes from facing what’s real, from letting yourself be seen, flaws and all, or what you think are flaws, and that’s where genuine connection can begin. That’s where fulfillment begins.

OK, so let’s move to the third and final point, which is that real transformation starts with acknowledging what’s buried, just like Ben did. Now, just stated like that, it might sound really simple, maybe even obvious to you, but many high-achievers avoid this, because facing their own inner struggles can feel like looking into a mirror they’ve spent their whole life avoiding. It’s, of course, not easy for them and it’s definitely not comfortable for them, but it’s the only way for them to grow past the image that they’ve built and step into a life that’s real with true connection. [20:06.0]

There’s a misconception out there that confronting these feelings, whether they’re fears, self-doubts, loneliness, is somehow a sign of weakness. This is especially true for people who have been rewarded for their strength, for their ability to keep pushing forward no matter what. They’re used to thinking, I can handle it on my own, or they think, I don’t have time to dwell on this. But over time, by avoiding these emotions, you’re actually giving them more power over you. They don’t just go away because you ignore them. Again, they build up, they fester, and eventually they show up in ways that you don’t want. They sabotage you unconsciously through burnout, breakdown, snapping or raging, and eventually leading to strained relationships. [20:49.0]

Let me give you an example. I had a client named Sam who went through this exact struggle. Sam was a definition of success in his field. He was co-leading his own company. He was a recognized leader in tech. He was someone his colleagues and friends deeply respected, but he reached a point where he couldn’t keep pretending that everything was fine. He felt drained, disconnected, like he was living a life that didn’t actually belong to him. His relationships felt shallow. His work felt empty, and as much as he didn’t want to admit it, he felt lost.

In our first session, he kept circling around what was really bothering him. He talked about how busy he was, how he couldn’t afford to slow down. But the real issue was much deeper, and once he finally started opening up, the dam broke. He admitted he felt trapped by his own success, that he’d spent years creating this façade, this persona that everyone else admired, but that he didn’t even recognize anymore, and letting himself admit that was terrifying for him, but that moment was also the beginning of his freedom, his transformation. [21:55.0]

Sam’s story isn’t unique. A lot of high-achievers struggle with this. They’ve built up such a strong identity around outward success that admitting any kind of what they think is vulnerability feels like dismantling the very foundation they stand on and the very edifice that they’ve spent their whole lives building—but the truth is, acknowledgement of your emotions doesn’t weaken you. It actually gives you the strength to rebuild in a way that feels a lot more authentic to you, your True Self, and once you step into that, everything in your life, in all these different areas of your life, can change.

When Sam began to confront his buried emotions of fear, doubt, his desire for real, true, genuine connection, he started to understand himself on a much deeper level. He realized that much of his drive was fueled by a need for external validation. He’d been chasing these accomplishments, not because they actually mattered to him deep down, but because they made him feel worthy in the eyes of his family, his friends, his peers, and even people who he never even associated with anymore, but were based in his childhood. [23:04.5]

Until he acknowledged that, he couldn’t start to change it. He couldn’t step out of that endless vicious cycle of achieving more to feel good, until he understood why he had been running it for so long and how he started it in the first place. Acknowledging these feelings is the first step toward real, genuine growth in the right direction towards meaning, but it’s also one of the hardest emotionally, because it requires letting go of the image that you’ve spent years or decades of your life building, that you’ve got so much of your identity invested in.

But it’s in that moment of courage, when you’re finally willing to look at what’s truly real, that that real, genuine transformation can happen. You start to genuinely connect with the true you, and that connection spreads to others. It opens up new possibilities for relationships, for purpose, for a life of meaning that isn’t built on chasing the next goal, but on living authentically. [24:05.8]

Acknowledgement doesn’t just change you. It changes the way you show up in the world. People around you will sense it. When Sam stopped trying to uphold his image and instead started being more real, being more authentic. He noticed his relationship shifting. Friends who had seen him as the strong one finally felt comfortable opening up to him, sharing their own struggles, and that created a depth in his relationships that he had never experienced before. He was no longer just a successful co-founder. He was someone people could relate to, connect with, and that brought a level of fulfillment he had never expected.

Leaders, especially, can benefit from creating spaces where they can explore these different sides of themselves without judgment. We’re taught to believe that success means keeping a tight grip on our emotions, that strength means never showing emotion, because that would be weakness. But the reality is, there’s a whole other higher level of strength that comes from letting yourself be seen, having the courage to do that, from acknowledging the parts of yourself that feel uncertain or afraid, or even broken. [25:13.4]

When you can make space for these parts of yourself, you then also make space for others to feel comfortable doing the same, or to have the courage to do the same. It’s like giving yourself and them permission to be human. When Sam embraced this approach to life, he found that he didn’t have to prove his worth through his accomplishments anymore. He didn’t need to keep pushing himself to the brink in order to feel worthy. He could just be, and that, he found, was enough, for him, first and foremost, and as a result, for all those that he loved or cared for.

This shift didn’t make him less ambitious. It actually made his work more meaningful, because he was no longer working from a place of lack. He was working from a place of genuine purpose that was driving him intrinsically to do the work. [26:02.2]

For anyone listening who might be in a similar place, who has been carrying the weight of expectations, trying to hold it all together, I want to encourage you to start here. Start with acknowledgement. You don’t have to dive into everything at once. Just take a moment to ask yourself, “What am I really feeling that I haven’t allowed myself to feel?” Maybe it’s fear. Maybe it’s loneliness. Maybe it’s a longing for connection that’s been buried under years or decades of striving. Whatever it is, let yourself first notice it, and remember acknowledging doesn’t mean you’re weak. It means you’re courageous. It means you’re stepping onto a path that leads to real resilience and true antifragility. [26:47.6]

When you let yourself acknowledge these emotions, rather than suppress them or repress them, you’ll see everything in life differently. Your close relationships will shift. Your sense of purpose will become clearer. You’ll gain a new appreciation for life that goes beyond material success, because now you’re no longer driven by the need to prove something. You’re now free to live in alignment with who you truly are authentically, and that’s the kind of success that can last. It’s the kind of success that isn’t just about reaching the top, but also about enjoying the journey for its own sake. It’s about building a life that feels meaningful and true to you from the inside out.

So, if you’re ready for that, start by acknowledging what’s real. Give yourself that space, and if you have the courage to do it and to stay in that space, I think you’d be pleasantly surprised at what you discover.

OK, let’s bring it all together. We’ve covered three big insights today. First, the illusion of success as fulfillment, just achieving more, gaining more. That in itself doesn’t fill that inner void. If anything, success, over time, without inner alignment, will deepen the feeling of emptiness. [27:59.0]

The second point was the emotional toll of isolation that so often comes with success. When you’re seen as the strong one, it becomes a prison, keeping you from real, genuine connection with others and yourself, and leaving you feeling more alone, even in a crowd.

The third point was that acknowledgement is the first step towards true transformation. Facing those buried emotions instead of hiding from them is a true path to resilience, strength and antifragility, and this is where real transformation begins. Ignoring these truths can cost you more than you might realize. You risk losing yourself to a life that looks successful but feels hollow. You risk burnout, breakdowns, broken relationships, and maybe most tragically, you risk never truly knowing who you are beneath the success.

But here’s what happens when you take these points to heart. Life becomes deeper, richer. Your achievements don’t just look good from the outside. They feel good from the inside, because they come from a place within you of true authenticity. You actually get to genuinely connect with others without pretense, to feel seen and understood finally, and maybe, best of all, you find true life fulfillment that isn’t tied to your next accomplishment or someone else’s approval. It’s rooted in who you actually are. [29:14.0]

So, start today with this podcast episode. Give yourself the space to acknowledge what’s real for you and watch as your life transforms from the inside out.

Thank you so much for listening. If this has helped you in any way, please share it with anyone else that you think could benefit from it. If you liked it, give it a good review on whatever platform you listened to the song or good rating, and let me know what you thought about it. Leave a comment or send me a message or an email. I would love to get your feedback.

Thank you again for listening. I look forward to welcoming you to the next episode. Until then. David Tian, signing out. [29:44.3]