Why Success Still Isn’t Enough
In this episode of The Impostor Syndrome Files, we explore why the success we work so hard to achieve can still leave us feeling like something’s missing. My guest this week is Jason Connell, a licensed therapist whose own experience chasing bigger opportunities led him to question why each accomplishment left him wanting more. He shares how recognizing that pattern changed his career and the way he helps other high achievers navigate their relationships with themselves.
Together, we explore how we learn to connect our worth to what we accomplish and why that belief can keep us searching for reassurance in the next achievement or someone else’s approval. That search often shows up as perfectionism, people-pleasing or a fear of making mistakes, even when we have plenty of evidence that we’re capable. Jason offers a thoughtful perspective on why feeling good enough can remain so elusive and what it takes to begin changing that experience.
Our conversation also explores how these patterns affect our relationships, particularly when we assume everyone around us feels more confident and secure than we do. Jason shares practical ways to work with self-doubt and become more intentional about whose opinions we allow to shape how we see ourselves. We close by discussing how greater self-compassion and more honest conversations can help us feel more connected to ourselves and the people who matter most.
About My Guest
Jason Connell is a Denver-based licensed therapist and author of When Success Isn’t Enough: Why High Achievers Feel Empty — And What to Do About It. His work focuses on high achievers navigating the gap between outward success and how life actually feels.
Before becoming a therapist, Jason built a successful career as a professional speaker and executive coach. He consulted with senior executives at Fortune 500 companies, members of the Bush and Obama White Houses, and professional athletes. On paper, he had built the kind of career he thought would make him feel successful. Privately, he was struggling in relationships, becoming disconnected from friends, and realizing that achievement, validation, and overwork were not changing what was happening underneath.
That realization led Jason into therapy. He later closed his speaking business, went to graduate school, and became a licensed therapist. Today, Jason works with high achievers, including founders, executives, surgeons, hedge fund managers, professional athletes, Division 1 coaches, Marine Corps officers, and clients who are leaders at organizations including Google, Tesla, Stanford, Wharton, and Harvard.
Jason’s work explores the psychology beneath relentless achievement, including why the traits that help people succeed can sometimes make it difficult to rest, feel fulfilled, or know who they are outside of performance.
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Connect with Jason:
Website: https://jasonconnell.co
Book: When Success Isn’t Enough: Why High Achievers Feel Empty — And What to Do About It https://a.co/d/0egpZMhL
Online Consult: https://jasonconnell.co/contact/
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Connect with Kim and The Impostor Syndrome Files:
Join the free Impostor Syndrome Challenge.
Learn more about the Leading Humans discussion group
Join the Slack channel to learn from, connect with and support other professionals.
Schedule time to speak with Kim Meninger directly about your questions/challenges.
Websites: https://kimmeninger.com
Transcript
Kim Meninger
Welcome, Jason. It's so great to have you here today. I would love to start by inviting you to tell us about yourself.
Jason Connell
I am so glad to be here. Thank you for having me, Kim. So, I for first of all, I'm a licensed therapist. I work with people who are really ambitious and, in many cases, very professionally successful, but that success is not bringing them the like happiness, the contentment, the joy that they really thought it would. And I work with people to change that from the inside out. A kind of interesting side effect is like more quote unquote professional success is never my target, but so often when somebody improves their relationship to themselves and their inner lives, they actually start doing better at work. I got there pretty honestly. Unfortunately for me, I for like three decades of my life, I kept taking different paths and winding up at the same wrong place. I first was a professional magician from six to 18. There's either maybe a lot to say about that or not much. We can get into it if you want. And like I had got good at standing on stage and doing magic tricks, and inside I was quite miserable. So I, I left that, and then after college became a professional speaker, and at the beginning of being a pro speaker, I was taking like Greyhounds eight hours across the country, and I was so happy just to have a client and an audience. And then several years later, I got quite lucky, and my career took off, and I just wanted more and more and more, like first class flights and drivers weren't enough. I I never flew private, but I wanted people to fly me private, which that sounds very embarrassing for me to say out loud. And I finally went to therapy myself, and I realized, oh, whatever it is I'm looking for, I need to find inside of me. That's that's going to be the path to happiness, contentment, better relationships, and my therapist helped me build a life that was literally better than I thought was possible for myself. And somewhere along that line, I realized, oh, this is what I want to do. And I closed my speaking and consulting business and went to grad school, become an, became an unpaid intern, and that was about a decade ago. And and now I work full time as a licensed therapist.
Kim Meninger
That's a huge commitment to make a kind of mid career, right? Because it really is a reinvention.
Jason Connell
Yeah, I had a, at the time I was doing CrossFit, and I had a CrossFit coach that was very influential. He himself was a CrossFit Games athlete, which is like kind of as high in the CrossFit world as you can go. And he was going to school to study psychology, which I was always interested in. That that was my true love. And I had said to him, his name was Gabe. I said, Gabe, like, man, you're at the top of your field as an athlete. Like, why, why are you going back to school? And he said this so lucidly. He said, "If I don't make a change, this is as good as my life will get. And that really hit me like straight in the heart. And I was like, "Oh wow, okay. Like if I want more for myself, I actually have to do something pretty dramatic and make a real change.
Kim Meninger
Wow! Now you talked about. It sounds like you kind of were amping up what you needed in order to feel satisfied from the work that you were doing, right? So, can you talk a little bit about that? Just that experience and how it shows up in people who tend to be high achievers.
Jason Connell
Yeah, I mean, I have a lot of compassion and empathy because I lived it myself, and I'm also curious about how you approach this because I think your clients deal with this too. We, the message that I received in this world and still receive in this world, because marketing works very, very well on me, is that what's between me and everlasting happiness is just a little bit more. It might be more success, or it might be more fame, or it might be more money, or it might be a slightly cooler watch or car or whatever, and that's a pervasive narrative, and what, at least my clients and a lot of my friends too, and I end up doing is we chase more, we get it, we're not satisfied, and we look over the horizon, we notice like, oh, there's a bigger mountain, I'm going to climb that, and the trick is to actually just have a hard conversation with yourself and realize, oh, that's not working. That's not making me happy. That's not bringing me closer to my significant other. If you have one, or it's not leading me to find a significant other. If you want one, I actually have to do something entirely different, and that's sort of an operating level system change that I want to talk about in a sec. But how do you think about this? How do you approach this?
Kim Meninger
Yeah, I think about it very similarly. I love the way you captured the a little bit more standing between us and, and happiness because I think if it were a very wide chasm, right, we might say, oh, that's you know that's for other people, or it just wouldn't feel as compelling to try to even access it. But but it sort of feels it feels like it's dangled out there.
Jason Connell
It always feels so close, yeah, and it's so deeply compelling.
Kim Meninger
Exactly, and especially because of our tendency to compare ourselves to other people, and so if that becomes our frame of reference as well, it makes it all more enticing to go after.
Jason Connell
Yeah, well said. We we and this can be quite hard, but we actually need to shift to an internal point of focus instead of an external point of focus.
Kim Meninger
Yes, and that's where I want to go in this conversation too, because I think that is the hardest part. I think recognizing that it's happening is kind of step one, but then how do we change the paradigm because it is so embedded in so many of us, just from messages that we get, like you said, every day implicitly that we're buying into. But even going all the way back to our childhoods, to school, to all of the pressure points that led us to where we are.
Jason Connell
Totally. So, the deal that excuse me that I was making with myself as a pro speaker, unconsciously and then sort of consciously later on was oh if enough people give me validation if I get enough applause or big enough paycheck or standing ovation then I will believe and feel that I am worthy of love so and that's to sort of cut to the core there I think a lot of people would start with an emotion a little less in close than love, then I'm worthy of respect or dignity. But I think that's what it cuts to at the core. And the operating system there, or the deal that we're making there, is a very transactional deal. And it's if I can do this for me to get a standing ovation, then I am worthy. We're being, we are valuing ourselves for what we can do, and usually that's something that is programmed into us very young. If you have the type of parents that you come home with, you know, three A's and an A minus, and your parent says, "Well, tell me about that A minus. Why? Why? Why did you get an A minus?” You're suddenly learning that, like, there's a little bit of conditionality on your lovability, and that conditionality hinges on what you can do, not who you are. So the shift, and we can talk about strategies for this in a second, is one that is often very psychologically and somatically scary. We have to move from believing that we are conditionally worthy to believing that we are worthy just as we are and really feeling worthy just as we are, and that for many people the first step there is learning to open up to the love and affirmation that is already in your life and feel that. I mean, you can many people can recognize, oh, this person likes me or loves me, but you actually kind of need to like let the wall down a little bit and notice the sensation in your body or in your heart or in your gut. And many of us have become disconnected from our bodies, so the first step is maybe actually just learning to feel. There's a lot more there, but I want to pause.
Kim Meninger
Yes, I'm. I love what you're saying because I think there's absolutely a disconnect in a lot of areas. There's a disconnect from our bodies. There's a disconnect from, like you said, there's sort of an intellectual acknowledgement of what we're talking about, but then the actual experience or the the steps involved in getting to that place don't feel clear, right? And I also think time is a factor because everybody's so busy that it feels like, oh, I'll do that work later.
Jason Connell
Yeah, totally. Yeah, I mean, many of us have very little white space in our lives, and the white space that we have, we want to give to like sleeping or to our kids or to our significant others, and to pause and be like, okay, I'm actually going to work on my relationship to myself is quite a radical decision, even though it's the one that will unlock what people are actually looking for.
Kim Meninger
Yes, yeah, and so can you say a little bit more too about the acceptance of the love that we already have because I think that's something that we tend to take for granted, right? Like I think we're always looking for what we don't have and not necessarily acknowledging what's already there.
Jason Connell
Yeah, well said. I mean, as a side note, like abundance practices go sort of in and out of vogue, and people always talk about imagining a future where you have all this money and these cars and this love. But the actual trick there is to pay attention to the hyperabundance that you already have in the present and feel that. I mean, even if you're not as financially secure as you want, you almost certainly have running water. That is a miracle. So the trick for most people, if you're disconnected, is to hold awareness in the mind, and then notice what happens in the body. There might be a tightening, there might be a warmth, there might be an opening, there might be a numbness, whatever. So we would do that to cultivate a sense of material abundance, but more importantly, we would do that to cultivate a sense of emotional abundance and connection of love and regard and respect from the people around you. Now, a lot of people experience this as sort of having like a plexiglass shield in front of them. They recognize, oh, this person loves me, and one of the ways to penetrate that shield. In addition to searching for the sensation in the body, is to ask the question: Why does this person love me? Now, in a lot of instances, the first response that you're likely to give yourself is something that is kind of BS. Oh, they love me because I'm a good provider, or they love me because I'm funny, or they love me because I'm attractive. And there's a part of your mind and your heart that believes that probably, but there's a bigger part of your mind in your heart that knows that's not true. And it might be very emotional to open up to the sense of, oh, I think this person actually just loves me. I'm really lucky for that, and when you get to that point, you want to stay with that kind of like exercise where you want to be outside your comfort zone for a bit, so the muscle, your lungs can grow, or you can burn calories, and then come back into the comfort zone. Same thing with learning to tolerate the abundance of of love and connection that's already there. You find it, you leave your comfort zone a bit. You stay outside your comfort zone, and then you can come back. And if you need to put the plexiglass back up, you totally can.
Kim Meninger
And so, how do you see the challenge of feeling like even if I can acknowledge that the people who love me love me, I still want more love, right? And and I think about this in terms of people pleasing and the fear that someone doesn't like you, or you know the, the, the need for constant positive validation. You know, like is this something that gradually happens as you start to get better connected.
Jason Connell
That's such a good question. Give me just a moment to sort of connect to that and reflect on it. So the desire for more is like deeply, deeply human. We want more of anything because for so long we lived in environments where scarcity was the name of the game. So if we could hoard more food or more secure connections or whatever, it behooved us to do that. So we want to meet that with understanding of hey, this is kind of how the human mind works. And then in in the instance of like wanting more love or deeper connections. The first step is to connect more deeply to yourself, and that can be through reflection, like asking questions along the lines of, if my doctor called me and she said that I only have six months left to live, how would that change things? Or if I had infinite money, you know, 100 million dollars. How would that change things for me? And then once you have some information from those questions, oh, I would actually move into a different line of work if I had infinite money, or I would spend more time with my my dog or my kids if I only had six months left. You want to start making small movements in that direction, just kind of like shifting the, the compass one degree closer to true north. So in this instance, you're loving yourself more deeply. You're becoming more deeply held in integrity. That is going to make you more deeply available to the people in your life. Whether you want to deepen your existing relationship. Now you're more you. You can connect with them more deeply. Or if you want to expand your social circle, now you have more availability of yourself to be able to give to people. So I would start there. I would start with loving yourself.
Kim Meninger
I love that response because I do think that that is a big part of the challenge that we're talking about, and whether it is because of deep-rooted experiences or trauma, or just because we're not actively reflecting in the way that you're talking about, so we're not experiencing consciously the disconnect between our values, what we care about, and how we're living-you know-I think that that clarity and that movement towards more of what it is that we want does start to fill the hole, so to speak. Right?
Jason Connell
Yeah, totally. It draws you back into the moment and taps into the abundance that's already there. Which, ironically, when you're in that place, can actually start creating much more abundance, whether that's material abundance or abundance of confidence or abundance of self worth or whatever.
Kim Meninger
Yeah, and I wonder, you know, as you're saying that, I'm thinking about the one of the things that I often talk about is what's the motivation for doing or wanting. Right? Is it coming from a place of fear, scarcity? Is it coming from the place of my values? Like this is what I care about, right? Being able to separate the two.
Jason Connell
Yeah, absolutely. And those are two entirely different like motivators. If it's an expression of like I just love this, I love playing music. I real this is so cool for me. That's going to take you to an entirely different place than I need to play music so I can get people to clap, which was what was motivating me for a long time as a speaker.
Kim Meninger
Yeah, and, and how do you see even perfectionism fitting in here as well?
Jason Connell
I mean, perfectionism is like a museum quality example of I am lovable for what I can do, or I'm worthy of for what I can do, or I am only worthy if I am absolutely top performing without making any mistakes. So the challenge there is to allow yourself to be a little bit messy and see what happens. If you're in a professional environment where you're required to be perfect 24/7, and some people are. You should probably like punch your boss in the face and leave. I mean, don't actually commit assault, but that that's a toxic environment, and it's not one where any of us can flourish. But in most cases, almost all systems that we're in have huge thresholds for imperfection, and it's your job to sort of flirt with being messy. And when you are messy, when you are imperfect, really take in like, oh, okay, I didn't lose my job. My friends don't hate me. I didn't miss a mortgage payment. Whatever, because we're we're rewiring our understanding of what's going on when we do that.
Kim Meninger
That's such a great point too, because I think of you know, in overly simplistic terms, right? We have fears, we have beliefs that aren't serving us, and we don't have data to dispute that or debunk that myth, right? And so what I see a lot with perfectionism is that if you never test the system, right? [Yeah, yeah.] You’re reinforcing this belief that you have to be perfect, and the messiness is what allows for the data to say to you know to tell you actually that's not what...
Jason Connell
Yeah.
Kim Meninger
Other people say.
Jason Connell
Yeah. And I think like one of the great things to do here that I think you are encouraging, and your work is encouraging, is to own like, hey, deep down inside, I feel insecure. I feel like I'm a bit of an imposter, and, and the, the edge to work there would actually be to open up about that and share that with people and start like undoing your aloneness. I mean, I one of the bright insights about the imposter syndrome specifically is the higher up the ladder you go, the more likely you are and your peers are to experience the imposter syndrome. But if you're trying to present as perfect, oh yeah, I'm totally emotionally put together. I got everything just just where it should be. You're that's like an AI. That's like a robot. That's not a real human, and when you flirt with, oh my god, I barely got through that meeting, or I was I was such a jackass to my my significant other this morning, and share that with somebody else, the right person will open up, and suddenly we're undoing the sense of aloneness, and we're undoing this need to be perfect, and we're undoing the sensation of being an imposter because we realize that all the people around us are also having this messy human experience, even though it's walled off through some attempt to project perfectionism.
Kim Meninger
Yeah, I love that point too, because I do think that we only see people's sort of curated presentation of themselves, especially on social media and some of the sources of information that we get about people, and so we have a warped sense of what other people struggle with, or whether they struggle at all. And so there is that pressure to present as perfect because we think everyone else around us too.
Jason Connell
Yeah, totally, and it creates this like horrible illusion where we're all feeling inferior, and the trick would just be to drop the guard a little bit and experiment with doing that safely.
Kim Meninger
Yeah, I think having those conversations with other people where you realize, oh, it's not just me, and that's one of the things that I, one of the reasons why I even started this podcast is because I had so many people asking me personally before I started it. Am I the only one who said this? Right? Like, is this just me? And I said, "Yo, okay, time out. We got to bring this conversation to a bigger audience.
Jason Connell
I mean, just yesterday. So again, I'm like a full time therapist. That's that's my job, which I feel lucky to do. And just yesterday, I had. Three clients who are in senior leadership in publicly traded companies, and when you're talking to your therapist, like these are legally confidential and privileged conversations. So as long as you're not going to plan to kill yourself or kill someone else, you you can say anything, and it's illegal for the therapist to sort of disclose that. So honoring the, the client's privacy, which I'll do here, but also acknowledging that like it's a space where people can be more safe and vulnerable than normal. Three people, I saw seven clients yesterday. Three of the seven were talking about feeling very insecure at the top of their companies and wishing that other people's opinions impacted them less. Two of them were literally losing sleep because they were worried that they had come off poorly in front of their employees, in front of their their peers. Now these are not interns right out of college at 21 years old, sort of getting their sea legs beneath them. These are people that are total operators and badasses, and they're still dealing with that quietly behind the scenes.
Kim Meninger
I see the same thing, and I feel like one of the questions that people often ask me is, "How do I care less?” Right? It's like it almost feels built into the system to care about what other people think.
Jason Connell
Yeah.
Kim Meninger
And I think that part of what I'm thinking about as you and I are talking too, even the, the distinction between having a you know passion for something that makes us want to continue to do it versus perfectionist about it because we're worried about how we're going to show up and things like I'm always going to care about what other people think because I want to show up with integrity and it's important to me not to not to let other people down, but also when I cross that line, right, and it's too much. And so I think part of it too is figuring out where the right balance is.
Jason Connell
One of my I got so lucky when I was a client in the first chapter of therapy that I did with my first therapist. I've done multiple, and my therapist said to me, her name was Pam. Pam said, you know, Jason, for the most part, you don't want other people's opinions to impact you too much. That's not fully possible, but you want to be really thoughtful about whose opinions impact you a lot, like your deep inner circle, and as you're navigating other people's thoughts and feelings about you, you want to lean on your deep inner circle and let them remind you of who you are. And that can be friends, that can be family, that can be a coach, that can be a therapist, that can be like a grandparent. And I think that's so useful. I mean, being able to turn to somebody is like, I feel like I totally bombed that meeting, and then letting your deep inner circle, whoever that is, reflect back to you. First of all, you have a history of being hard on yourself, so let's ground. Second of all, it's totally fine if you bomb that meeting. Nobody cares. Third of all, you know Tim's perception of you in this meeting doesn't matter. Like come here. Let me give you a hug. Let's go get tacos, and that I think does wonders for people. At least it does for me.
Kim Meninger
I think what you're saying is really important too, because what it's doing is it's differentiating between like the, the masses, right? Like just the average person's perception of us and the people who really do matter to us, and again, it's not like we want to be going around carelessly interacting with other people, but to be mindful of who re whose voice to prioritize, right?
Jason Connell
Yeah, totally. And so often when other people are being difficult, it has nothing at all to do with you. You're just a lightning rod for their rage, as you know, and as people listening to this know. But the reminders can be helpful, at least for me.
Kim Meninger
Yes, absolutely, because yeah, you don't know what you've triggered in them without realizing it, right?
Jason Connell
Yeah, or if something happened before they showed up in the room, like their their cat died, or they got in a fight, or whatever.
Kim Meninger
Yeah, that's a really important reminder too, and I think that's something that I've had to work through a lot too. It's funny, like my therapist once said to me, "Kim, you're the center of your universe, not the center of the universe, right? Like nobody thinks about you as much as you think they do.
Jason Connell
I when as a speaker, so like a professional speaker behind the scenes is actually like it's a very much sales-driven business. Like you're spending much more time, sort of like nurturing relationships, developing leads, etc. than people realize. And I had this epiphany. I was like, "There's this deal I really, really, really wanted to close, and I built like my entire week around being available to the, the client to see if they want to call me and book me, and I had this epiphany of like, oh, my entire professional life revolves around if this client or this lead hires me or not, and their entire professional life has nothing at all to do with hiring me. This is sort of like a vague decision that they make in 10 minutes, and then they alert me either you know that day or. Three weeks later, and realizing that asymmetry was hugely helpful for me. And it sounds like you went through something similar when you're like, "Oh wait, huh? I don't have to be the center of other people's universe. I can just be the center of mine. How sweet.
Kim Meninger
Exactly. And I wonder too, are there some practical steps that you would recommend people take to consistently remind themselves of that because I think that again, that's something that people listening are probably thinking. Oh, that's great! But then when the next situation comes up, it's going to start all over again.
Jason Connell
Yeah, let me actually like think and feel through that so I can give you a you and the listeners a good answer here. I mean, one of the first things that comes up here is practicing self-compassion. That can sound a little saccharine and a little vague. So, self-compassion is treating yourself with kindness and tenderness, and like you are somebody that you love, and there's a lot of different ways of doing that. But two ways that I think are particularly effective is one in a moment of intensity, whether you're dealing with insecurity or you have to give a speech and you hate public speaking, is to slow down and just sort of like I will close my eyes, I put a hand over my chest, a hand over my stomach, sort of take a deep breath, and the, the thing that you say to yourself is, "This is hard. This is really hard for me, and that's quite a bit of vulnerability. But when you say or do that, you're surrendering into the moment. You're accepting what's already true, and many people will notice, sort of exhale. They'll notice that the tension that they were holding starts to loosen itself, and all the energy that we were using to try to prop up this sort of false relationship to the world, where we're saying, "Hey, I'm not nervous. I'm not anxious. I'm totally confident. That energy is now available for you to navigate through the moment. So I think one really sweet thing to do, because practice self-compassion. The other kind of rule that I have for myself that started when I was a client in therapy, and I use it today when I am a client in therapy, as well as with my wife and my friends, is if there's something I really don't want to talk about, then I have to talk about it, if I don't want to talk about something, it means that part of me believes that I'm not lovable. If this is witnessed by someone else, and when I have the courage, or when one has the courage to actually talk about it and share it with a safe person, you get the direct experience of taking the shadowy, like I'm afraid this is unlovable or unlikable, or will like get me cast out of the tribe part of you into the light, and you have the direct experience of somebody's like, I still care about you, and more often than not, they'll also say, yeah, me too. I deal with that as well. So I would start there. Those are the two things that came up for me.
Kim Meninger
Those are incredibly powerful. Thank you so much for saying that. I think both of them really speak to me. I actually had goosebumps as you were saying that because I do think that that is a missing piece for so many of us. Is we're relying on other people's compassion, but we're really not giving ourselves our own compassion.
Jason Connell
Yeah, totally. And again, it has to. It is hard to do. It has to start from the inside out. Like whatever we're looking for in terms of a solid sense of self or worthiness, actually has to ultimately come from inside of us. Yeah, we can lean on other people, but still, yes.
Kim Meninger
And then, as you said before, I think when it comes from within us, the relationships with other people look a little bit different too. If they feel more solid, right?
Jason Connell
Yeah, I mean the truth is, almost all of us are feeling a little bit more lonely and alone than we let on, and we're just waiting for somebody to go first and open up a little bit more, so that we can open up and meet them there. And going first is such a gift for you, and it's such a gift for the other person too.
Kim Meninger
I like that as it is its own strategies to go first.
Jason Connell
Yeah, yeah, me too.
Kim Meninger
Yeah. Oh my gosh, Jason, I could just go on and on. This has been so wonderful. But for, for others who want more of you, where can they find you?
Jason Connell
So my website is jasonconnell.co. So J A S O N C O N N E L L dot C O. That's like the clearinghouse for all my work, and then I I have a book When Success Isn't Enough. It goes, it covers a lot of what we talked about, and you can get that anywhere books are sold. But the easiest place would be Amazon. The book has a white cover with a blue tear in the middle, and yeah, either of those would be awesome starting places. And if somebody wants to reach out, there's a contact form on my site as well.
Kim Meninger
Wonderful. I will make sure those links are in the show notes. And thank you so much for being here and having this conversation with me.
Jason Connell
Kim, thank you. It's such an honor. I really, really appreciate the chance. And I appreciate the work you're doing. Thank you.
