June 2, 2026

The Success Wound

The Success Wound
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Why does the title never feel like enough? Why do so many of us hit every goal we set and still go to bed feeling like we came up short? My guest this week has a name for it. Brooke Taylor calls it the success wound, the pain that comes from mistaking our productivity and achievement for our worth. We get into where it comes from, why creative people are especially prone to it, and what it actually looks like to stay ambitious without running yourself into the ground. If you have ever caught yourself answering "How are you?" with "busy" and felt a little proud of it, this one is for you.

In this conversation, we cover

  • What the success wound is, and why Brooke describes it as a cultural wounding rather than a personal failing
  • Why "you are not your work" is so hard to live out when your work carries your worldview and your voice
  • How the meaning of hard work flipped over time, from a marker of the working class to a badge of status
  • The three things Brooke found that nearly all "unfulfilled achievers" share
  • Her own story: managing eighty million dollars in ad revenue at Google by twenty-four, and what it cost her
  • The difference between manic ambition and aligned ambition, and why they can look identical from the outside
  • The "two power sources" behind all ambition, and how to tell which one is running your engine
  • Two questions you can ask yourself this week to spot when you have slipped into the wound

Approximate timestamps

  • 00:00 Welcome and why this phrase stopped me in my tracks
  • 01:00 Defining the success wound
  • 03:00 Creativity as a conversation, and how the industrial age rewired our sense of worth
  • 05:00 How Silicon Valley resets your definition of "enough"
  • 06:00 The three things unfulfilled achievers have in common
  • 08:00 Brooke's story: Google, recovery, and a hard reckoning
  • 09:00 What organizations get out of the success wound, and the high achiever ceiling
  • 11:00 Choice, gears, and the two settings that lead to burnout
  • 12:00 Manic ambition vs. aligned ambition
  • 13:00 The lamp metaphor: the success wound or the true self
  • 14:00 Writing a book at 5 a.m. while pregnant, and why that was aligned, not manic
  • 16:00 Two questions to catch yourself in the wound
  • 17:00 Where to find Brooke

A few lines worth sitting with

Brooke describes the success wound as the pain that comes from tying our worth to what we produce and achieve, rather than to who we are.

On ambition, she offers a simple image: it runs on one of two power sources, the success wound or the true self. Same hard work, very different fuel.

And one telltale sign you are operating out of the wound, in her words, is that you keep repeating the same patterns and expecting them to feel different.

About Brooke Taylor

Brooke Taylor is a transformational career coach, keynote speaker, and the leading authority on the success wound, a phenomenon she pioneered through more than a decade of research. She began her career in Silicon Valley and spent years as a marketing lead at Google, where she earned the Google Global Sales Award. Her work helps high achievers move from manic ambition to aligned ambition so they can do meaningful work as whole people, not depleted ones.

Find Brooke

  • Website: brooketaylorcoaching.com
  • Free book exercises: brooketaylorcoaching.com/book
  • Instagram: @BrookeTheTaylor

Mentioned in this episode:

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00:00 - Untitled

00:34 - Untitled

00:35 - Introduction

02:00 - Todd Henry teaching about accumulation vs. contribution

06:15 - Interview with Brooke Taylor

22:02 - Outro and Summary

Todd Henry [00:00:02]:
A nurse named Bronnie Ware spent years working in palliative care, sitting with people in the final weeks of their lives. Over time, she started writing down what they told her they wished they had done differently. When she gathered those conversations together, one regret rose above all the others. It wasn't I wish I'd worked harder, and it wasn't I wish I'd achieved more. It was I wish I'd had the courage to live a life true to myself and not the life that other people expected of me. That line sticks with me because so much of what we chase the bigger title, the louder launch, the higher numbers, gets handed to us by everyone except ourselves. Many of us are building a body of work that is a reflection of other people's expectations of us, not our own potential. We inherit a definition of success, and then we spend decades sprinting toward that definition without ever stopping to ask whether it was ours to begin with.

Todd Henry [00:00:58]:
So today we're going to have a conversation about how you define. What does that look like for you? What are you actually chasing after? And maybe most importantly, what exactly is the body of work that you're building? This is Daily Creative. Since 2005, we've served up weekly tips to help you be brave, focused, and brilliant every day. My name is Todd Henry. Welcome to the show. There's a question we ask each other a hundred times a week without really thinking about it. How are you? And somewhere along the way, the acceptable answer changed. It used to be fine or good.

Todd Henry [00:01:39]:
Now the answer that earns a knowing nod is busy. Slammed, buried. So much going on, we say it with a little apology in our voice. But underneath the apology, there's a quiet flex. Because being busy has become one of the ways we tell people that we matter. I want to sit with that for a minute because I think it points to one of the most important and least examined traps in creative life and creative leadership in working with our mind and doing work that matters. It's the slow collapse of two things that are supposed to stay separate. The measure of your work and the measure of your worth.

Todd Henry [00:02:16]:
Now, I know that sounds a little bit self helpish, but stay with me for a minute. Measuring your work is healthy and necessary. It is. Did the project land? Did I move someone? Did it solve the problem it was supposed to solve? These are good questions and they're necessary questions and they're important questions and. And we should keep asking them. But measuring your worth is an entirely different thing altogether. Your worth is not up for review. It's not riding on Your last launch, your engagement numbers, or whether your client loved the second round of concepts.

Todd Henry [00:02:49]:
The problem is for those of us who do creative work, those of us who are putting our intuition into the world, we're putting pieces of ourselves into the world through the work that we do. These two measurements are almost impossible to keep apart. Our work carries our fingerprints. It carries our taste. It carries our worldview, our sense of what matters. So when the work gets praised, it feels like we are being praised. And when the work gets ignored or picked apart, it feels like we are being rejected. So over time, without ever deciding to, we start producing not to contribute something, but to prove something.

Todd Henry [00:03:25]:
And the moment that your output becomes the evidence of your value, you have entered a race with no finish line. There is always another deliverable, another milestone, another level, something else you can win. And you can win all day long and still go to bed feeling like it wasn't enough. So I've written and spoken a lot, going all the way back to my book die empty from 2013, about the difference between accumulation and contribution. Accumulation asks, what can I get and how will it make me look? Contribution asks, what can I give and who is it for? That distinction matters, because accumulation will never fill you up. It simply can't fill you up. You were not built to be satisfied by a scoreboard. Contribution work that flows out of who you are, what you care about, your productive passion, the through line that drives you, is the only thing that does the job.

Todd Henry [00:04:23]:
And the reason I care so much about this is that I've watched so many talented, sharp, bright, ambitious, gifted people, and I've even been this person myself at times, who look enormously successful from the outside while quietly running on empty on the inside. Maybe they have the title, they have the following, they have the awards, they have the income. And they cannot figure out why none of it feels like enough. Well, that's what we're going to talk about today. And that brings me to today's guest. Brooke Taylor is a career coach and a keynote speaker. She started in the high pressure world of Silicon Valley, including years as a marketing lead at Google, where she won the Google Global Sales award. By age 24, she was managing $80 million in ad revenue.

Todd Henry [00:05:08]:
And from the outside, she was on her way. She had it from the inside. However, it was a very different story. And out of that experience and 10 years of research, with thousands of what she called unfulfilled achievers, she gave a name to the thing that so many of us are quietly carrying. She calls it the success Wound. The moment I heard that phrase, I thought, okay, yeah, that's something. There's something there. So I think it's going to do the same for you.

Todd Henry [00:05:35]:
Here's my conversation with Brooke Taylor. Enjoy. When your team reached out about this book and I saw the title of the book, I thought, oh, my gosh. Like, before I even knew, before I even read anything else about it, I was like, oh, my gosh, this phrase is so poignant. Tell us about the success wound. What is the success wound?

Brooke Taylor [00:06:00]:
Yeah, in its most simple term, the success wound is the pain that comes from mistaking success, productivity and achievement for self worth. It's this underlying belief that our worthiness of love and belonging is contingent upon what we produce and achieve and do, rather than the inherent goodness of who we are. And in some ways it's a misnomer because we aren't wounded. I believe deeply that it's a cultural wounding that gets transmitted into us and creates this psychosphere spiritual wound within us that I think so many of us are grappling with today, and especially in the creative space, want to express ourselves through our creativity, through our work. And it can be so challenging to separate how that work and art is received from our own perception as people. And so I've been obsessed with this idea, having grown up in Silicon Valley where, you know, as a kid, you can see through some of the, I don't know, the veil a little bit around achievement. And I was like, oh, I don't know. In its most basic term, I was like, are these people happy or are they operating to.

Brooke Taylor [00:07:11]:
Do they feel inadequate like I do? And then working at Google for many years, being able to peek behind the scenes around, okay, are we operating to prove something, or are we operating to be creative and to collaborate? So I've been obsessed with this concept probably my whole life. But in its research form, the last

Todd Henry [00:07:29]:
10 years, it's so tricky because you hear things like, you are not your work. Don't confuse you're not your work. Don't confuse yourself with your work, or your work is not your worth. And I agree with that. And I believe you, you agree with this as well. And it's tricky because as a creative pro, so much of your work involves your worldview. It involves your perspective, your sense of identity. What you're putting into the work, in many way, in some ways defines your values.

Todd Henry [00:07:59]:
It defines what you care about. Because you're choosing, you have discretion. There was a time when you or I would just be raising, growing crops, like doing the harvest Nailing shoes on horses or whatever, then it's a lot easier to be like, okay, your work is not your worth. Yeah, of course I know I'm nailing shoes on horses. It's a little different when you're inventing your work every day. So how do we parse between those things? When it does feel like so much of my identity or my values, my. My sense of identity is put into the work itself.

Brooke Taylor [00:08:31]:
Yeah. Creatives back in the 1500s, 1600s, 1700s used to have this idea that creativity was like a conversation with the divine. It was a spiritual conversation. And that these ideas almost had their own entities. The famous quote around the David revealing itself. And the artist was just responsible for removing the marble. And that got. That shifted as we moved from farming into factories, we, as people became the proxy for productivity.

Brooke Taylor [00:09:02]:
It used to be that during the Industrial Revolution, your value as a worker was quite literally how long you could stay on the line to produce. And so even this concept today has shifted. Because what's fascinating when I was doing research for this book is that hard work actually used to be. And working a lot used to be a sign of people who had less. It was like a working class would work, and people who had more were. Was like a leisure class. But that's shifted today. Like when people ask you how you are, the right answer is booked and busy.

Brooke Taylor [00:09:34]:
There's so much going on I have. Because it's an indication of how successful you are. So that's shifted where it's like, almost like people who have the most are supposed to be the busiest and working the hardest. So this I. To answer your question, this isn't how we're meant to live. We're meant to live in conversation with our creativity and to. To feel like what we create is almost like a sandcastle, in a way. We create it and then the tides roll in, they sweep it away, and we create again.

Brooke Taylor [00:10:04]:
And that it. We do it for the joy of it. And I think that's how neurologically we're hardwired. But I think culture has shifted that

Todd Henry [00:10:10]:
for us, definitely has shifted that. And to your point about Silicon Valley specifically, I spent a lot of time with Bay Area companies, and it's almost like your baseline, regardless of what your baseline is, when you enter those environments, your baseline very quickly shifts. And you start in some ways comparing yourself to whatever everybody else is doing or comparing success. You might have a definition of success when you come in, and then suddenly your definition of success is 10x what it was before, even though to the vast majority of the world, you're very successful, even what you're doing right now. Right. So why, in your experience, why do we have this? What is going on here? And how does this relate to the success wound that you have? That phrase?

Brooke Taylor [00:10:54]:
Yeah. As an executive coach, people have come to me every day with the common career issues. I'm putting that in quotes. Burnout, imposter, syndrome, low self worth, low confidence, procrastination, overworking, underworking, working hard and playing hard. All of the litany of hundreds of issues that people face in their career. But when I did research with over 10,000, what I call unfulfilled achievers. So people who have high ambitions and high vision for what they want to achieve in their career, but feel like they can never grasp it, they're dissatisfied no matter what they do. And the research showed a different story.

Brooke Taylor [00:11:30]:
It said that they thought that these were their issues again. Perfectionism, burnout, low self worth. But when I looked deeper, they actually had three things in common. And the first was that they all had a childhood experience of equating success with more love, belonging, freedom, survival, independence, happiness in some way for them, success, their wires got crossed. So let's just give. I obviously have an example of having a privileged upbringing, growing up in the Bay Area. The better grades I got, the more I felt like I belonged to my preppy all girls school and that my teachers liked me more and my parents were proud of me more. I have other clients for whom their parents immigrated from other countries.

Brooke Taylor [00:12:13]:
And for them working hard was about survival. It wasn't about love and belonging. It was like we need this in order to survive. So success equals survival is a really strong story. So they, everyone all has their own kind of success origin story. The second thing that they all have in common is that they all had this empty cup feeling. This feeling like no matter how much they achieved, it never felt like enough. This princess.

Brooke Taylor [00:12:36]:
And the pea sized sinking feeling of inadequacy, is this all there is? And that can manifest as a low grade depression. But they all had this wondering, this yearning for something else. And the third thing they had in common was a habit of chasing more. More external validation, more significance, more approval, more productivity, more shareholder value in order to quell that feeling. And those three things are the success wound. And it's interesting because my success wound took me far to a great job at Google, but it also took me down. And by the time I was 24, not only was I managing $80 million in ad revenue, but I was also a Raging alcoholic on the weekends. And so this all kind of came crashing down in the way that it does.

Brooke Taylor [00:13:21]:
My dad got a terminal cancer diagnosis, among other things. It caused me to really pause and question how I was running my life. And for me, my first step was to get sober. And actually what I learned in the rooms of recovery informed this book and how I proceed in my career, which is that for addicts, the substance isn't the problem. It's what's called the spiritual malady. This yearning, this emptiness, this empty cup feeling, the psycho spiritual wound that's actually universal in all humans. Addicts just wear it worse. So when I went back into the halls of Google after attending these meetings that I did every day, I was like, gosh, all these people are addicts.

Brooke Taylor [00:13:58]:
They're just wearing it differently. And so they're all trying to mask again, this deep inadequacy through more achievement, productivity, and validation. So I set out to explore this both with the research, but also how to fix it.

Todd Henry [00:14:12]:
I would assume that in your research that probably you discovered that it's a. In some ways, we're fighting an uphill battle, right? Because I think a lot of organizations are because they organize around efficiency. They organize around making you the model productive citizen of the organization. In some ways, probably not only leverage the success wound, but actually actively incentivize the success wound. Right. What did you discover in your research about the role organizations can play? In some ways, you're almost calling for a rebellious uprising against what feels like is the natural order of corporate America.

Brooke Taylor [00:14:48]:
In some ways, doesn't my company want me to have a success wound? Yes and no. Because we'll call these insecure achievers unfulfilled achievers are more productive. They're 400% more productive than your average bear. But to a point, they hit a point that's called the high achiever ceiling, where burnout, disengagement, low productivity, resentment, quiet quitting. That's when that hits. And I think we certainly saw that in a big way during COVID when everyone was really fried and like, pouring themselves into work as a distraction. It was the only thing that they could do, among other things, all the other uncertainty. But I see this in organizations, specifically tech, in Silicon Valley today, where the whole ethos is do more with less.

Brooke Taylor [00:15:30]:
And so what's happening is that these people are becoming more productive, but again, to a point. And so my argument and what's a possibility through healing this success wound is that you have a choice. You have a choice in how you work. You have a choice with when you go into full throttle and pour all your energy into something because you care about it, because it matters, because you have a deadline. And then you're able to toggle to other gears, right to more of a little bit of a cruise control or a little bit of keeping the accelerator on a little bit in this day, then spending some time with family when we're either full throttle or falling apart, which is endemic of the success wound, where it's like we only have two gears. That's when we get to a state of burnout. So this healing the success wound is about choice. Knowing how and when to go into a grinding state, go into a people pleasing state to win people over, working hard and playing hard because that feels good.

Brooke Taylor [00:16:23]:
And then how to toggle back and come back into choice and say, okay, this is how I need to work in this season in order for it to feel more sustainable.

Todd Henry [00:16:30]:
For me, this flows right into my next, which is I want to talk about the difference between manic ambition and aligned ambition. Could you describe those terms and then talk to us about what each looks like and how we can engage in the healthier form of ambition?

Brooke Taylor [00:16:43]:
Sure. So manic ambition is the frenzied, frantic need to succeed at all cost. For me, manic ambition looked like again, working really hard Monday through Thursday, closing deals, getting to inbox zero, not letting anything slip through the cracks, being a good soldier, excellent. But it was being powered by my success wound, powered by a deep inadequacy. I need to prove myself. I need to belong to this culture more than I belonged to myself. And so no wonder, by the time Friday rolls around, I was exhausted. I needed to release.

Brooke Taylor [00:17:20]:
I felt like I had worked so hard. I deserve a drink or five. And that's what created this pain pleasure seesaw, this work hard, play hard. For me, for other number of my clients, it might just look like this frenzied, frantic need to hold everything together, to do it all at once, to be the best at home, to be the best with your friends, and to be the best in the workplace too. We all have these ideals around success that we're constantly comparing ourselves to. And again, when it's powered by this success wound, that's when you get that mania. But the thing about our ambition is that it's almost like a lamp. But unlike the lamp in my bedroom or your office, our ambition only has two power sources.

Brooke Taylor [00:17:58]:
So it can be powered by our success wound, or it can be powered by this other part of our psyche called the true Self. And the true self is the part of us that is naturally creative, collaborative, present, playful. It has perspective. It's the part of you that when you're working, experiences flow. You are able to handle difficult situations that maybe at one point baffled you. You're able to do the hard thing from a place of courage. And it's no, this is the person that I want to be. And even though this is difficult, I'm going to proceed.

Brooke Taylor [00:18:33]:
And so that's aligned ambition. Aligned ambition is the state of harmony, contentment and flow that comes from pursuing the directions of your true self rather than the directions of your success wound. And just to cut a finer point on this, it's hard to tell from the outside the difference between manic ambition and aligned ambition. When I was writing this book, I wrote it between the hours of 5am and 10am while I was pregnant. So my battery drained really fast. And I also, I didn't want to shut my business down because my husband was starting a business. So I needed to step up for our family. And so I said no to vacations.

Brooke Taylor [00:19:11]:
I said no to weddings, I said no to other people's baby showers. I said no to friends comedy show because I was. I wanted to put all my energy into work. Now people might look at that and be like, she's crazy. That's hustle mentality. That doesn't. That's not healthy. And some people did.

Brooke Taylor [00:19:25]:
They're like, where is she? She's fallen off the face of the earth. No, that was intentional for me. I knew exactly how I needed to spend my time and my energy and why this mattered. So again, my. You're. You can only know if it's aligned ambition kind of from the inside. And so I know I'm not afraid of hard work. It's just what's powering it.

Todd Henry [00:19:44]:
I had a very similar story when I was writing my first book, the Accidental Creative. It was the same thing. It was from 5am I walked with Starbucks and right from 5 to 7am before my regular work began. And I had similar comments, like, hey, this seems like you're overworking. It seems like you're what? And I was saying, no, this is. There is a unique season where I have a chance to do something. And this is a very unique season. And it's aligned around a vision that I have.

Todd Henry [00:20:08]:
It's someplace I want to go, and it's core to who I am and all of the things, things you're kind of talking about, but you're right to, to the outside world, it can just look like. And I certainly have since then, slipped into manic ambition at certain points. Right. But it's funny how it is. You're right. It's such an internal thing. Is there a filter that you recommend to people or is there. Are there some questions they can ask themselves to help them identify where they're operating out of manic ambition versus maybe operating in a more healthy, aligned way?

Brooke Taylor [00:20:35]:
Yeah. So the first thing is, what are the consequences? What are the consequences of my working this way? Is this generating, I would say, on aver, better results than disadvantageous results? For example, another question to ask. Is this causing me to repeat a pattern over and over again? A key sign you're in your success wound is that you're repeating the same patterns over and over again and not getting different results. So I have clients who come to me and they're like, I just, like, can't stop saying yes when I mean no. I can't stop wondering if a client's mad at me or I can't stop being obsessed with if I'm going to get fired the next day or something like that. So some people might say that's healthy vigilance, a good amount of anxiety. No, that's causing her sleepless nights, et cetera. So what are the consequences? And is this repeating the same pattern over and over again?

Todd Henry [00:21:29]:
Brooke Taylor's book, Healing the Success Wound, is available now wherever books are sold. What I love about this conversation is that we're not talking about being less ambitious. We're not talking about caring less or wanting less or moving to a cabin in the woods. The point is noticing what's powering the engine, because here's where we started. There's nothing wrong with measuring your work. The trouble begins when your work becomes the measure of your worth. That's the success wound. And the way out, as Brook describes it, isn't a finish line you finally cross.

Todd Henry [00:22:00]:
It's a choice you get to make again and again about which fuel you will run on. Are you working from the wound? Are you trying to prove that you're enough? Or are you working from your true self? The part of your self that's creative, present already secure, the part that wants to contribute rather than accumulate. So if you want a place to start this week, Brooke handed us two questions, and I put them somewhere where you actually can see them. First, what are the consequences of working the way I'm working right now? Not the results, but the cost? And second, am I repeating the same pattern over and over and expecting it to feel different this time. Those two questions have a way of cutting through a lot of the noise, so let's just leave with this. You were not put here to win a race that has no finish line. You were put here to make a contribution only you can make and to do it as a whole person, not a depleted one. Yes, the work matters and you matter.

Todd Henry [00:22:58]:
Try not to get those two things backwards. Hey, thanks so much for listening. If you'd like all of our interviews in full, you can get them@dailycreativeplus.com just go there, enter your name and email address and we'll send you a private feed where you can listen to all of our interviews in full. My name is Todd Henry. If you want information about my books and my speaking events, you can get them at toddhenry. Com. Until next time. May you be brave, focused and brilliant.

Todd Henry [00:23:28]:
We'll see you then.

Brooke Taylor Profile Photo

Author, Healing The Success Wound