Revenge vs. Resilience: Why Failing Forward Is the Real Flex (The Edge)

Published Jun 20, 2025, 10:16 AM

While Chip and Kelly take the week off, listen back to one of their all-time favorite episodes: “Revenge vs. Resilience: Why Failing Forward Is the Real Flex.”

In this throwback convo, they dive into society’s twisted relationship with success and unpack why failure isn’t something to hide—it’s something to honor. From Oprah to Steve Jobs, they explore how setbacks shaped some of the most powerful comeback stories of our time.

And with this week’s Wednesday episode exploring revenge as a brain-based addiction, this conversation hits even harder. When we’re hurt or rejected, it’s easy to reach for blame or bitterness—but what if resilience is the real rebellion? What if failure is the first step, not the end?

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Email us: theedge@velvetsedge.com

HOSTS:

Kelly Henderson // @velvetsedge // velvetsedge.com

Chip Dorsch // @chipdorsch

Chip.

Hello, Hi, I'm back in town baby, Welcome home. I had a really early flight today. I always think it's really funny. It's like always the days I have to record on the like the podcast, I don't sleep well or something, and so then it's like half of brains. The poor listeners, I mean, they get this version of me that's like, sorry, guys.

I mean it could have been worse. You could have landed and had to do this right away.

I actually think that might have been better. I was a little more awake earlier at this the day, it's like I'm hitting that maybe I need a nap or something.

I don't know.

We're going to power through though.

We got it.

We got it.

You know what.

It ties into the topic a little bit, you guys. We have been yeah, we've been noticing that our culture has a little bit of an issue with admitting defeat and admitting that they failed at some point in their life. And we were talking about that chip and our data, and now I was like, this feels like a topic. This is like a little bit of the edgy side of the growth mindset to address this, like perfectionism happening in our culture. I'm so guilty of it. I think you are. We talked about like everyone around us. It's like we only want to present this best version of ourselves, which is so not the human process, like at all, Like it's.

Not at all what it means to be a human.

We all fuck up, we all fail, and yet we're sitting here as these people who only want to talk about success all the time.

You know what's funny too, is it's obviously a lot easier to look back when you are successful and admit your failures because of course, right some of the big names, which we'll get into it to some examples, but like that is such a part of their story and it becomes like lore. You know, it's what we talk about about them, Like look what they overcame, and it's all about overcoming things. And even like an example like Lizzo who road to fame by pointing out what she thought everyone would make fun of her for and using it as an asset. That's a really great example of sort of bucking the system. That is, everything has to be perfect and beautifully engineered and filtered and whatever you name it. However, you fix something so that you give a perception of perfection, but I do think it's funny that, like, why is it that until we succeed, we are not able to recognize and admit and embrace our failures. It's I know, personally, I'm fucking terrified.

I was just going to ask you, do you have a certain instance you're thinking about in your life, because I know I'm sitting here thinking about this for me, and that is so true for me. Not on purpose, but it's like I've just felt shame or scared or whatever, So what's yours?

I mean, coming out as gay felt like admitting a failure. My first job was at Atlantic Records, when I knew I wanted to quit in my soul, I knew I had to leave, but I was fucking scared because I thought people would think I had failed. It took a lot of like conversations with people I trusted and really looking deep to realize I hadn't failed, I'd succeeded, and it was time for a new goal. I had gotten everything I ever dreamt of, and I think like suddenly there was like a door that I was opening that was like a black hole because there wasn't another dream on the other side. So to me, it translated as well, you failed, You're not running Atlantic records, and I never set out to do that. I set out to look at Atlantic records. So I mean that's an example. When I was trying to think of examples earlier, I thought to myself, is fear of failure equivalent to fear of success?

Oh?

That's deep, because I do think it is. They do seem to be connected. I'm trying to go through that in my mind right now, though I might need a minute to.

Process that one.

The fear of success is a weird one that I've been bouncing around in my head too, because to me, I think what that equates to is exposure. And like in the past couple of years, I've wanted to retreat because of what I deemed its failures in my life. Right and now it's interesting because to your point that you said earlier, it's like now that I'm like coming out of the haze and finding my stride again and I have some new ideas of new things I want to do, I'm going, oh, well, that had to happen then, because I would have never done it.

In line a totally different paths exactly.

But it's not until this point that you can always see it. But I've done it both ways. Like over a decade ago, I was engaged to be married and that fell through three months before the wedding, and I just completely shut down. I wouldn't really talk about it with my friends. Obviously, everyone knew what happened. It happened very publicly, but it was like I couldn't talk about it because I was so ashamed of what it meant or whatever what I thought it looked like for me or meant for me. And then I've done the.

Reverse the last couple years, where it's.

Like I was made into a villain on a reality TV show that I didn't expect, and then COVID happened and I lost some clients I wasn't expecting to lose, and it was just like these things that I really felt ashamed about. I was I love to like over own responsibility. So like maybe it was just like you said, time to move on. Things just played out the way they were supposed to. But I couldn't look at it that way. I just looked at it as like I had fucked up something, I had done something wrong, I had caused something to happen. Blah blah, blah blah blah, And in this case, I tried to work through it by like talking about it as much as I could. I guess I don't know, but like either way, there's this like sense of exposure that I think sends us into this shame spiral because if we feel like we failed, we're just like, why am I not enough? Because everyone else out there seems to be so successful.

And it appears to be that no one else is afraid of failure, right.

I also, let's just not talked about, is it right?

Right? Something that's rooted in my fear of failure is my people pleasing qualities because I feel like if I fail, it affects so many other people, but I rarely give myself the praise when I succeed that it positively impacts other people. So it's weird that I like, yeah, because.

It's like you each out yourself like a yeah, that's like perfectionism one O one, isn't it. It's like you literally expect yourself to be perfect and then when you're a human, you shame.

The shit out of yourself.

Yes, you can't win for trying, But it's interesting because as I was talking about, like you know, talking about when you're going through the failure, And I do think there's something to like we need a certain capacity or a certain level of healing within ourselves to be able to discuss things openly because we're so sensitive and fragulent. It's more painful maybe, but it's almost as if to me, our society has this like intolerance to failure. We can only tolerate perfection or success, and that's really all that we applaud, But we don't really applaud someone's journey. Like I was telling you before the podcast, every time I have a veryous, accessful person on the podcast, the first thing I want to know is what are all the fuck ups? What are all the failures that you had to go through before you got to this point? Because the realist in me is like, I know, you didn't just start Amazon as your first business, you know what I mean? Right, That's a wild example, but it just feels like that is what we expect. We talk about people who go viral on TikTok and they have this amazing song and they blow up really fast, and it's like all of a sudden, they're the most successful thing.

But like, what most of the time The pitfall there is that they're very quickly forgotten because they weren't ready for the success, and the failure there becomes almost insurmountable. Whereas when you're failing on my more micro levels, building your story and learning your lessons and becoming more empathetic to other people who are failing and just figuring out how to navigate failure, which is inevitable, it then makes success easier the closer you get to it. Wow, the success is ever easy, It's just it makes the path a little more navigate navigatable is that a word can be reversible, let's say traversable.

The TikTok thing is an interesting example because, like you did this week on the Wednesday podcast, and I was talking about one of the artists I've been working with as a new artist, and he's talking about the pressure from labels to go get a viral tiktokke, and I said, yeah, that works. But like I've also worked with people who have had that and they have nowhere near the amount of success long term or ultimately. As someone who has come up through the trenches, who has had to make their way playing in the bars on Broadway and all that stuff, because of experience, and what that really means is because they failed in some way, shape or form, and so then they had all of these times where they were like, Okay, that worked, this didn't. This experience was good, this one was bad. And then you pick and choose, and you can craft your own career, your own success, your own life, store, your own relationship, whatever it is, because of the pluses and minuses, the wins and the losses. Right, and in those situations where you have the fast success, which I think is what our culture wants right now, you really don't set yourself up for the long term win or long term goals being fulfilled, the long term success like maintaining right.

I think too, it's like I never set out with a path other than a one single goal, so I am not even equipped really to think about the steps because what is that quote. I'm going to butcher it, but it's basically like do one rung of the ladder at a time, not the whole ladder or the staircase or whatever it is. Because we are trained to think that all these people that are in our little phone that are suddenly rich and famous or successful or whatever did it really fast. So we want to be at the top of the staircase immediately. But every step is important and if you fall down, you just got to get back up and do the next step. The path to success is painted so clearly for us when we're children, because we have no option but to succeed in learning to walk, learning that the stove is hot, like learning those things that you have to do the look.

But isn't that Isn't that technically a failure?

If you touch a hot sew one hundred percent.

As an adult, I would be like, oh my god, I should have known better instead.

Of like going, oh, that's hot.

Right.

It's interesting how we talk to ourselves. But you bring up a really good point, and we were talking about this before the podcast too. There's a lot of really, really hugely successful people that we can reference here, Oprah Winfrey being one of them, who I'm a massive fan of. But she had so many failings before she actually was able to become the Oprah that we know today. I know early in her career there was a lot of struggles, Like she was fired from her first job as a news anchor. The producers felt she was too emotionally invested in stories. I mean tell me that's not a mead situation or not like, but also, isn't that.

What she wants from a journals exactly?

But you know, maybe they just want someone to read the news and not be emotionally connected to it, and she was. But after she got fired, she bounced back and instead of giving up, she actually found her calling through that. She was like, Oh, I am emotionally invested, and that's how she ended up in daytime TV on the Oprah Show over Winfrey Show. Like we know, she was like, Oh, this is teaching me something about myself. I can't be a news anchor that sits and reads the news without connecting to how tragic that story is.

But I can't sit deep.

Yeah, yeah, I can sit with someone going through their story and telling me the hardships of it and emotionally connect to them and actually have a really powerful conversation. And there's a space for that too. So it was really a teachable moment, an aha moment.

If you want a moment.

I think she used it in the way that we see a lot of successful people do and we don't know about, but in the way of oh okay, this didn't work there, But that is actually who I am, and I'm gonna use it to my advantage.

I didn't know that about her.

Steve Jobs is another one. It says one of the most famous failures in business history. Steve Jobs was fired from Apple, which is hilarious, the company he co founded in nineteen eighty five after a power struggle with the board of directors and then CEO John Scully. Jobs was ousted from his own company. How he bounced back instead of letting the failure define him, Jobs would want to found another company Next and then bought Pixar, which revolutionized the animation industry. Obviously like films like Toy Story and things like that. Eventually Apple bought Next and then Jobs returned to the company. So the failure led him to then create the iPod, the iPhone, and MacBook Apple Like it really actually put Apple way more on the radar than it ever was when.

He came out.

I mean, Apple was viewed as kind of a failing company at that point.

Yeah, and says Jobs firing taught him humility and resilience. It shaped the visionary leadership style he brought to his return to Apple. His biggest failure was his springboard for Apple's greatest successes. Wow, I know, isn't that crazy? So anyway, I think like the reframe that we're talking about here is like just we're asking the question, why are we looking at failures as let's cancel them, let's get them out of here. Not to like get back on my soapbox about Will Smith, but that was obviously not a great moment with him and Chris Rock. We've referenced this a million times. If you guys haven't heard chippin has conversation I'm talking about when it was the Oscars, right, this.

Was two years ago.

Now, I think and yeah, I said, I think it's what he does with it. I think that really what we should look at as the culture is not that moment. That moment was to yes, but then he immediately apologized and went into work on himself. So it's like, how is that moment going to help him evolve as a human and do we don't even know what with his life, with his career, what success could come after such a public, humiliating failing. And that to me is when you find your true leaders, your true success stories, and probably some of the biggest transitions in our culture.

And the deepest growth internally too. I mean, look, we do live in a cancel culture, and as a society, we lack forgiveness, and to use the Will Smith example, like we put these celebrities on these pedestals that they don't deserve to be on because they're human beings, they probably don't want to be on other than the benefits of fame, right, And so when something like that happens, our initial reaction is to write that person off, aka cancel them, rather than to have empathy for them and recognize that they are humans. The way that we look at them is that we think that they're superhuman because they're famous. And that's silly, right, Like Will Smith works really hard at a job that's public, you know, like, yeah, yeah, it's just a public job. And yeah it's cool that he's famous. Yeah what I want my photo with him? And I saw him. Yeah, But like he's still a fucking human being. And I guarantee you he was the most embarrassed about it. He was the one beating himself up more than any part. Yeah, So there was nothing that anyone could say that would make him feel worse than he already felt. So the job of other humans in that moment would be to lift him up and hope that there's a learning moment there and he comes out of it a better human being.

This is kind of a little side note, but I've been thinking about this a lot lately, Like I do think there's something happening with celebrity in our world, and I think we've gone through this intense moment of cancel culture. But I think what my hope is moving forward is that we look at it as we're describing it.

Celebrity is a public job.

They make a lot of money, They have access to some things that us regular folks might not. However, at the end of the day, they are just as human, if not more than any of us. And I just hope that celebrity starts to be looked at in a different way, and also with that hope that failure starts to be looked at it a different way. I was looking up the words failing forward because I think we deem it as like you're falling back, Like That's how it always has felt to me, is like, oh my god, I was just getting up to where I was like climbing upwards on the mountain, and then it was like, damn, you know, you just slam down and like everything falls apart, you lose everything kind of thing, and it's like no, no, no, no, no.

It's just a redirection.

Like it's terrible in the time, and it does involve a lot of loss sometimes, but like even the downward slope of it, you're always going to go back up if you work at it or try Yeah, if you use it for that. And so the concept of like failing forward and just learning how to take the failure like Oprah did, using it to evolve or just like pivot.

The five o'clock.

News is not going to be my thing, but like she found her alignment in daytime TV and now she's fucking Obrah Winfrey. It's like, right, no one would know who she was if she stayed in the Chicago News network, do you.

Know what I mean?

Right? Or went and got a job doing something else, like working at the newspaper, because like let.

That take TV.

Yeah, you know, it's funny because in our business I heard a lot like that guy hasn't done shit. All he's done is fall up, and let's fall up. Mean, it's like there's someone that's like the CEO of a company and there's like you can't point to any success, which is interesting, Like I hadn't thought of it before until you were just talking about failing forward. Yeah, the people that fall up generally are willing to fail publicly, so when we look at their careers, all we see are the failures. But the resilience that takes to get back on the horse and keep fighting to a position that you feel like you belong in is not for everybody. Like, Sadly, I just don't think, you know, we're all as evolved as everyone else. You know, some people are just aren't. They don't have the composition to keep fighting, like they give up. Yeah, And I don't know, does that is that that like something that could fuel drug addiction because you can't connect with yourself, or alcoholism or whatever it is. If success were a linear straight line, we would all be successful. We wouldn't even be having this conversation. We all be rich and happy.

But didn't you think as a kid it was supposed to be.

And don't look to go to college and then you're successful.

I still look at other adults who are successful and I'm like, I just like look at their story and I forget about anything that I would know of like there's people in our friend group even who I forget about the quote unquote failings, But with mine, I'm like, oh, and you think they're.

On display and everyone's talking about them. But the truth is nobody has time to worry about your failures. Fuck. And that's not to say you should not give a fuck about your failures, because you should because they're stars that you're carrying from the battlefield. True, and they should be they should be what you use to fuel yourself into success. I mean, I think about it all the time. When I'm driving through Nashville, I'm like, who the fuck are all these people that own these multimillion dollar homes? Where do they work? Who are they and how do they do it right? Because I feel like I work my ass off and I've got a nice house, But it doesn't mean that I don't have envy and curiosity to like, what am I not doing that's gonna get me there? And you know, some people just inherited their grandparents' house. You know, it's that simple, Like they were lucky, they were born in the right family. Some people worked really hard and had a lot of failures, and the reason why you can probably hear. I'm kind of excited about this topic because I do think I need to embrace my failures more. I have to be willing to fail more rather than not take the risks that it takes to succeed, because I'm worried about failing, because there is one certainty in that if you don't fucking try, you never willin Well.

You know what they say about your deathbed, right, it's not the things that you've failed. I'm doing air quotes right now, you guys, but like, it's not the things that you failed at that you regret, It is the things you didn't try, right. I think it's just we're all so worried about what everyone thinks about us.

Too one percent. And even though we're in the celebrities, and when I say we, I mean we as a collective human race. Because our lives are now public because of social media. I do think that makes it worse.

Oh for sure, But are our lives really public?

Do you know what I mean?

Over it all, I'm just like, let's stop pretending like anything on social media is actually the full story.

Unless like posting the worst photos of ourselves.

I always post with no makeup one and stuff, in stories because I'm like I need to normalize myself, Like I don't want to be just in the pretty picture all the time, Like all of it's just so unattainable if we only show those pieces or just be honest about, hey, I'm only showing those pieces, like I'm not trying to show you guys the days that I'm crying and like having a hard time or truthfully, like for me, most of the time, the struggle for me with social.

Media is like it's fear.

It's fear of being out there again, like what you're saying, and it's like, wait, actually, I need to look at everything that's happened in the last decade or a couple years or whatever you want to say, and go, I've just been in a lot of like gross, there's been a lot of like lessons. There's been a lot of transitions, and it's been painful some of it, but none of it has been not for my highest good ultimately. So I'm about to adopt this Oprah mentality and go, Okay, well it didn't work, you know, in this situation, but like it actually did bring me closer to myself and understanding who I am versus like maybe who I thought I needed to be or was trying to be, or whatever. Like adopting those things as lessons to just get you on the right past it, then you can.

Just yeah, I mean that acknowledgment of what failure brought you versus what it kept from you actually frees you to go get the thing that is attainable.

Exactly Why do we never think of that though?

I don't know, because shame is heavy. It's a really heavy thing. And yeah, you know, it all then comes down to our soul intentions.

Maybe like who is this little man right now? I am so in love with you right now?

Maybe what you were striving for wasn't realistic anyway, and you were doing it because you thought that other people expected you to have it.

I just don't think I was as connected to who I am as a human as I feel now. But I've had to go through some of those losses. I don't know if you feel like this at all, but like, some of those losses are the things that made me go.

Wait, I don't even like that. I don't even think that way.

I don't even you know, It's like we just kind of get going in the machine and you're just like, oh, success will be over here. Oh you're being offered to be on a TV show. Yeah, you better fucking do that. It's TV, Like, it'll help your other business. That is what we look at instead of going wait, like truly sitting with things and like, when I really ask myself, would I not do things the same exact way if it was offered to me again at that time, I would have that's not really a failure. It's like you try something, Eh, it wasn't really the right thing.

Wait, and it was, you know, it was fun while it lasted, and some of it.

Yeah.

I think back to even my coming out and it's like the struggle between admitting to myself that I was gay and actually finally coming out to my family and friends. The fear that you live in because you think your life is going to be over in that moment, because the expectations that you're letting affect you from the.

External, like everyone's just gonna abandon everyone's your family's.

Gonna hate you, You're gonna be abandoned, You're gonna get big up like no one's gonna love you, blah, all the things. Yeah, but in reality, what it did was it was the start of my life, like I got to be me and I'm still evolving in my sexuality because I still carry some of that shame, of course that I put on myself.

Yeah.

Yes, there are external factors because we're all fed the hate, but I'm the only one who chose to believe it, you know what I mean. Like for me, so I look back and I'm like, every time I meet a new person and I have to come out again to them, it is so freeing. But there are times when it feels like inappropriate. But like I would like say, oh, my ex boyfriend just casually, I would say that now and ten years ago I would have never said that right to a new person. Yeah, And it's really freeing to be able to be that because it's like they're getting the most authentic version of me. Yeah, and that at one point felt like it was going to be a huge failure.

That makes so much sense.

It's actually also clicking for me the thing about what you were tying together earlier, the fear of failure, but also that being tied to the fear of success. It just kind of hit me as I was listening to you. In terms of my story, I guess but like I do think that the last couple of years, I have been so scared and like you said, feeling like everyone's talking about it. Everyone see it, saw the failure. Everyone's going to leave me, abandon me. Like what you're saying that I just haven't wanted to go out there, but you know what that's been doing is keeping me from success, right like it, so it becomes almost this fear of success because success equals exposure or something.

Right, And you're like, if I get unknown, if yeah, I feel like you've achieved success, which you have.

I know it's ridiculous that we do this to ourselves, but yes, but it is true. It's like, if you have quote unquote success, it does make you more out there, and so then what if it fails again? Then what what does that mean?

Well, the more people that know you, the more exposure you have, the more people want to see you fail, the more people won't like you. I'm not saying like people who already liked you. It's just opening up the population of who is even aware of you, right. You know you can look at the Rolling Stones, one of the biggest rock bands in the world, and I could throw a rock and hit people that say I fucking hate that band. I wish they'd die. You know, like, yeah, they're nothing compared to the Beatles, and you know, there are one of the most successful fucking bands of the whole time, and you just you can't listen to that. I saw a quote the other day that says, if you wouldn't ask them for advice, don't listen to their criticism.

It's so true.

Boom, there you go.

Well, I was thinking about when I was prepping for this podcast. I'm like, so much of the fear of failure I think comes from the keyboard warriors or whatever you want to call them, that are trolling you from their fucking basement on their couch, right, and.

It's like just about failures.

Yes, it's like the Theodore Roosevelt quote about if you're.

Not in the arena, actually out there fighting doing the thing. I mean, Brene Brown talks about this too. It's like, unless you're in the arena, do not weigh in on what I'm out here trying to do, right, And that is the quote that I really kind of want to leave this on and like really try to think about moving forward and just ask ourselves these questions like Chip and I are just sitting here. We're never coming to you guys as these quote unquote experts. We're just sitting here asking these questions like, wait, why, as a society are we only focusing on these massive successes without looking at the whole road and the whole journey, so that we, as humans growing and evolving together cannot feel so much shame about our you know, little setbacks or redirections or things like that, like actually being honest with each other about what the human experience is and what the human journey looks like and what the purpose says.

You can't take it.

With you, so is the purpose really Like I'm sure, yes, it's great to have millions of dollars, but like, probably not what your soul only intended to do in this lifetime.

Right, I would venture to say it's much more valuable to be proud and happy with yourself. Yeah, And you can be broke and poor and still have those feelings for yourself even for trying. I mean, it's shit. The road is paved with failure, you know, Like, and a lot of people reach massive success and then hit a roadblock and they fail again. And whether or not they reachieve success is whatever. But this has been a really freeing conversation for me because it's a nice reminder, like too, I drown in my fear of failure. I really do. Yeah, I could write a book on my successes if I wanted to. You know, if you don't even think about that. Yeah, it's funny because I'll be hanging with friends stone or whatever, and like I'll tell a random story and the people are like, what is your life? Like? How did that happen? How did you do that? And I'm like I had forgotten about it until you said that and made me remember something. Yeah, it's wild.

I'm curious what you guys have, Like, if you have any failure stories that have really helped you to figure out what your next direction is or what your success story what you want it to look like, email us at the Edge at velvetedge dot com. You can also leave us a voicemail. We haven't been really plugging the voicemail as much, so we need to get the voicemail back in action. But if you have a voicemail, I would love to hear your failure stories that ended up becoming successes because they changed you are or helped you get on the right path. That is in the link in my bio on Instagram. At Velvet's Edge Chip.

I'm at Chip doors. It's Chip dr scch.

And as you guys go into the weekend and you're living on the edge, I was going to try to get cute, but it don't have it in me.

I hope you always remembered.

Too, not fail act casual. Bye bye mm hmm.

Velvet's Edge with Kelly Henderson

Kelly Henderson began her career in the Nashville country music scene over 15 years ago, orchestrati 
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