When Success Triggers Self-Doubt: What Laura Gassner Otting Calls “Wonderhell”

Success is supposed to feel validating. 

You work for the promotion. You earn the opportunity. You step into a bigger room. And naturally, you expect confidence to meet you there. 

But for many leaders, success does not feel clear at all. 

It feels like pressure. 
It feels like exposure. 
It feels like the unsettling realization that the next level demands a new version of you. 

The accomplishment is real. The opportunity is real. But so is the voice asking, What if I cannot sustain this? What if I am not as ready as everyone thinks? Laura Gassner Otting calls that tension Wonderhell: the emotional space between recognizing your potential and learning how to live inside it.  

It is a powerful idea because it names something so many high performers experience but rarely talk about openly. 

Why success can feel unsettling 

In my work with senior leaders, I have seen this pattern again and again. A capable executive steps into a larger role and, instead of feeling grounded, feels exposed. They have been chosen for their potential, but now that potential suddenly feels like a burden. 

In the conversation, Laura described how leaders and entrepreneurs often hit a moment where they realize there is more inside them, but that realization does not always feel inspiring at first. It can feel destabilizing. The mind races ahead: If I go for the next market, the bigger role, the larger presentation, is this the moment everyone finds out I’m a fraud? 

That is such an important leadership moment. 

Because the challenge is not just external. It is internal. You are navigating possibility while also managing fear, pressure, and a thousand external voices telling you what success should look like next. Bigger. Faster. More. And yet what you actually want may be different. It may be a new challenge. Or more meaning. Or more time with your family. Or a different path altogether. 

Transformational leadership starts with self-awareness. And one of the most important things you can become aware of is this: not every opportunity is asking you to prove yourself. Some opportunities are inviting you to know yourself more deeply. 

Imposter syndrome is not always a stop sign 

One of my favorite moments from the conversation was Laura’s reframing of imposter syndrome. 

She shared a deceptively simple shift. Instead of hearing, “I haven’t done this before” as evidence that you do not belong, hear it as an invitation: “Oh, wow, I haven’t done this before.” Same words. Different meaning. One interpretation creates threat. The other creates curiosity. 

That distinction matters. 

Because when leaders interpret uncertainty as danger, they move into a reactive state. They tighten. Overprepare. Second-guess. Try to control every variable. Their energy goes into managing anxiety instead of creating results. In the interview, I described this as reactive leadership: effort organized around containing fear rather than unleashing possibility. 

But when uncertainty is framed as an invitation, something changes. Leaders become more open, more creative, and more willing to learn. They can access vision instead of just vigilance. 

Your greatest strength can also be your biggest blind spot. For many high achievers, the strength is drive, responsibility, and ambition. The blind spot is believing that worth must always be earned through the next achievement. 

The real question is not “Can I do more?” 

Laura shared a story about running her first mile at age 39. That one mile became a 5K, then a 10K, then a half marathon, and eventually the Boston Marathon. What struck me was not just the progression. It was the question underneath it: What else could I do? Who else could I become? 

That is a beautiful question for leaders. 

But it can become a dangerous one if it is driven only by external validation. 

When every accomplishment automatically becomes a launching pad for the next one, leaders can lose touch with whether the goal in front of them is actually theirs. Laura made that point clearly: you cannot be insatiably hungry for someone else’s goals. At some point, leadership maturity requires separating external expectations from intrinsic motivation. 

This is where so many executives get stuck. They know how to perform. They know how to achieve. But they have not paused long enough to ask: Is this next step aligned with what matters most to me now? 

Self-awareness is not soft. It is strategic. 

When leaders know what truly motivates them, and recognize that others are driven by different things, they make better decisions, build stronger teams, and create cultures with more cognitive diversity. That was another key thread in our conversation: people are not all motivated by the same rewards, and great leadership depends on understanding what drives behavior beneath the surface. 

Action steps you can take this week 

If you are in a season where success feels heavier than you expected, start here: 

First, notice the story you are telling yourself. 
When a bigger opportunity appears, do you interpret it as exposure or expansion? 

Second, separate external pressure from internal truth. 
Ask yourself whether the next goal is genuinely yours or simply the loudest expectation in the room. 

Third, practice a new sentence. 
When you hear, “I haven’t done this before,” add curiosity instead of fear. That one shift can change how you prepare, how you show up, and what you make possible. 

Fourth, get underneath motivation, both yours and your team’s. 
Not everyone is fueled by money, title, or visibility. People want different things in different seasons. The better you understand those drivers, the more effectively you can lead. 

The opportunity inside Wonderhell 

Wonderhell is uncomfortable. But it is also clarifying. 

It reveals where old definitions of success no longer fit. It exposes the inner critic that still wants to keep you safe by keeping you small. And it gives you a chance to choose differently. 

Unlock your potential does not mean chasing more for the sake of more. It means recognizing when you are being invited into a larger version of yourself and responding with intention instead of fear. 

The leaders who grow the most are not the ones who never feel self-doubt. They are the ones who learn how to meet doubt with curiosity, self-awareness, and choice. 

Because the goal is not perfection. 

The goal is to lead from a place that is aligned, grounded, and fully your own. 

The next level of leadership is not just about achieving more. It is about understanding what drives you, what patterns shape you, and how to lead from a more grounded place. For more insights like this, explore The Enlightened Executive podcast. 

Episode Transcript

Susan Drumm: What happens when you reach the next level of success, and instead of pure confidence, doubt quietly creeps in? That uneasy mix of achievement and uncertainty is exactly what my next guest calls wonderhell. I’m Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership evolution. Each week we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life.

My guest today is Laura Gassner Otting, who teaches people to become limitless. Her secret superpower is seeing your greatness and reflecting it back on you so you can get free of yourself and achieve extraordinary results. She’s a regular contributor to the Good Morning America Show, The Today Show, Harvard Business Review, and Oprah Daily.

She’s the Wall Street Journal bestselling author of three books: Wonderhell, Limitless, and Mission Driven. She served as a presidential appointee in Bill Clinton’s White House, helped shape AmeriCorps, and founded, ran, and sold her own global search firm.

Laura, welcome to the show. I’m so excited to have you here.

Laura Gassner Otting: I’m so excited. I know we’ve been trying to get this to happen for a while, so thank you for having me.

Susan Drumm: Absolutely. So, I love your perspective — maybe we’ll start a little bit with your book Wonderhell, because I love this perspective. There are lots of books about how to become successful, and you’re writing from the other side of that: what happens to you when you are successful at something, or you’re given an opportunity you haven’t had before, and what are the emotions and the mindsets and all the things that come into play then.

Your book Wonderhell talks about this. Perhaps you can share a little bit more — what did you mean by the term wonderhell?

Laura Gassner Otting: So wonderhell is this moment where the burden of your potential walks into your psyche and says, “Hey, what have you got for me? What are you going to do with this newfound potential you didn’t even realize you had last year, last month, last week?” And it happens to all of us.

We’re in this moment where we achieve something we didn’t think we could do — whether it’s running a race, starting a business, landing a deal, or wooing someone. Whatever the thing is, we reach this moment where we’re like, “That was amazing. It was humbling. It was exciting. It was wonderful.” The work we did opened more doors than we ever thought possible.

And yet inside of those doors, we see a version of ourselves that we never thought possible. And suddenly we’re like, “Ooh, maybe I want more.” So it’s exciting and amazing and humbling and wonderful, but it also introduces us to self-doubt, uncertainty, anxiety, vulnerability, stress, impostor syndrome, and all these emotions.

So it’s kind of hell, right? Because you’re stuck with this burden — you go, well, now that I know I maybe I can achieve it, if I don’t, I’m stuck with that inconvenient truth that there’s more inside of me and I’m not sure what to do with it. So it’s wonderful, and it’s hell — it’s kind of wonderhell.

Susan Drumm: Yeah. Yeah. It’s always this feeling like, I saw this potential in myself. Now I’m living up to my potential, but what if I can’t keep it? What if I can’t stay here?

Laura Gassner Otting: Yes.

Susan Drumm: Or — and all those “what if” — what if they find out that maybe I’m not quite up to par, that everyone now thinks I am, because I’ve accomplished something?

Laura Gassner Otting: Yes. This is the moment — now that I’ve achieved something, I have to go for the next thing, and the next thing, and the next thing. I ran the first mile of my entire life when I turned 39 years old. I had never run — I used every single excuse to get out of gym class. It took me six weeks to run that mile without stopping, and literally barfing.

And then once I ran that mile, I turned to the person next to me and said, “You know, if we string three of those together, we can do a 5K.” So we signed up for a 5K because we were all hopped up on endorphins. It took us six weeks to train for the 5K, and at the end of it we said, “If we string two of those together, we can do a 10K.”

And at the end of the 10K, we signed up for a half marathon. I live in Boston, so you know where this is going — I ended up running the Boston Marathon. Now I’m training for my ninth marathon, not because I love running, but because at the end of each one you’re like, “Well, I wonder what else I could do. I wonder what else I could be. I wonder who I can embody and what I can become if only I listen to that voice inside my head.”

So for me, I’m really fascinated by what we do in this moment when we realize there’s more inside of us. I think every leader, every entrepreneur, has gotten to this point — they’ve either launched their own business and thought, “Well, a client hired me for something, I sold a product, maybe I can do more, maybe I can go to another market.” But wait — if I go to another market, is that the moment people realize I’m a fraud?

If I get promoted to the next position and I have to give the bigger presentation, is that the day that I yard sale in front of everybody? We’re always in this moment where we’re excited about our potential but also uncertain whether we have one toe over the edge of incompetence, or nine toes over the edge. And it’s in that space that we really learn who we are and what we want.

But here’s the issue — we’re also told what we want in that moment: bigger, better, faster, more. We’re told we should keep achieving and keep going and keep growing. And sometimes we don’t want to.

Sometimes we’re in a season of our life where maybe we want to take a step back and be around a little more for the kids. Maybe it’s time to retire. Maybe we want to switch careers, or do something totally different.

And we’re given this external pressure that we should keep doing the next thing just because the next thing is there. So I’m really fascinated by the space where the burden of our potential is talking to us, while we’re also balancing these external voices and external expectations, to figure out what we’re truly, intrinsically motivated to do.

Susan Drumm: Yeah, absolutely. And when opportunity knocks — I mean, I swear I just had this happen, where I was coaching an executive who became a C-suite executive after someone left. This is at a public company, and now they’re in the C-suite.

They were first really excited, but then there was this burden of, “I don’t know that I belong here, and now I’m really exposed — because if I don’t do well, what if they fire me now?” So much of the work was dealing with that inner critic, and saying, don’t shrink away from it.

There was almost a moment where she was like, “I’m going to leave so they don’t find out that I’m actually not sure whether or not I belong here.” Fast forward — she absolutely belongs there. She saw the potential and is now thriving in it, and if she had quit too soon, gosh, all that opportunity would have been lost.

So, given that opportunity — you talk a lot in the book about these amusement park rides. We know about impostor syndrome, right? What’s your take on dealing with impostor syndrome — what you call Impostorville?

Laura Gassner Otting: Yeah. So Wonderhell — I organized it as an amusement park. There are three different towns: Imposter Town, Doubtsville, and Burnout City. In my last book, Limitless, I talk about why other people’s definitions of success don’t fit for us.

That was based on twenty years in executive search, having called, you know, the most successful people in the world, trying to recruit them away on behalf of my clients. That was the job as an executive recruiter — you call really successful people and try to recruit them away. It sounds like a hard job, but I would call really successful people, and none of them were that happy. And so they all called me back.

I was so fascinated by this question, and so Limitless is like: here’s why you’re not happy, here’s what I actually learned allows people to be happy in their work so that they can achieve success and happiness, and then here’s how you need to change your career, change your company, or change yourself in order to get there. It was super linear, really easy.

But then when I sat down to write Wonderhell, which is all about the swirl of emotions we may be feeling in this moment when we’re introduced to our bigger potential — again, vulnerability, impostor syndrome, doubt, uncertainty, stress, anxiety, burnout, envy, exhaustion, all of it — I didn’t really know how to write the book, because everybody experiences these emotions at a different moment in time, depending on what stage and what age and what phase they’re in.

A friend of mine, the author Rahaf Harush, said, you know, it’s kind of like an amusement park — you go in and some people want to ride the roller coaster first, some people want to go to the merry-go-round first. So you just need a map that says, “You are here.” And so Wonderhell is created as this amusement park, with Imposter Town, Doubtsville, and Burnout City.

Each of the towns has five rides, and each ride evokes an emotion you may be feeling in that moment. In Imposter Town, I talk about this feeling of realization that there’s more inside of you, and you’re sort of stuck with, well, now what do I do with it?

In writing the book, I interviewed a hundred different glass-ceiling shatterers, Olympic medalists, startup unicorns, thinkers, creatives, philanthropists, activists — everyday people like you and I and your listeners. And what I learned, which was fascinating to me, is that every single one of them, whether consciously or subconsciously, took impostor syndrome and, rather than seeing it as a diagnosis — “there’s something wrong with me, I don’t belong here, maybe they’re going to figure it out” — instead wore it as a badge of honor.

They congratulated themselves — “look at me, in this place I didn’t even know I could get to, how awesome is that?” In doing that, they changed the voice inside their head from a limitation — “you’re an impostor” — to an invitation: “how awesome that you’re here.”

And I’ve got to tell you, they did it with the simplest tool ever — it’s ridiculous. I get paid money to go to events and give keynotes teaching this tool, and it is bananas easy. They simply changed the way they said the sentence to themselves.

Instead of saying, “Oh, wow, I haven’t done this before,” with dread, they just say, “Oh, wow, I haven’t done this before,” with curiosity. It’s so simple. Oh, wow.

Susan Drumm: It’s the different emphasis, right?

Laura Gassner Otting: “I haven’t done this before” is, “Oh no, it’s going to be terrible, I might fail, everyone’s going to see” — it’s rife with embarrassment and failure, and it’s going to be a disaster. “Oh, wow, I haven’t done this before” is exciting, and curious, and it invites you to learn, to grow, to get educated, to experiment, to test, to try, to learn from your failures.

It’s just — they simply changed the way they interpreted impostor syndrome, from a limitation to an invitation. And doing that, frankly, has changed everything for me. I do things now that I’ve never done before, and I’m like, “This is going to be awesome — how cool that I get to do something new,” and then it works.

And how does it work? It works because we expect that it’s going to work — just like having a lucky rabbit’s foot, just like having lucky socks that you wear to the game. If we think things are going to work out well, we do the things that people do for whom things work out well.

You try an extra rep, you practice an extra time, you go back and reproofread your material, you do an extra rep at the gym — whatever the thing is. And just by nature of expecting that things are going to work out, that you’re invited to this opportunity, we actually do more work that allows us to succeed in the opportunity. So it becomes this self-fulfilling, wonderful, virtuous circle.

Susan Drumm: Absolutely. Absolutely. We talk about how there are two orientations to leadership, right? There’s a reactive orientation, which is reacting to something that creates anxiety, and all you’re doing is working to contain the anxiety. So the effort you’re putting in is about containing anxiety — well, that’s not a structure that works over time. What we see, results over time, is an oscillating structure, because it depends on anxiety to motivate you to try to contain it.

Whereas the switch that you’re talking about is creative leadership, which is: I get connected to something I’m passionate about, and I have the vision of what could be possible. And that’s an energy-unleashing cycle.

Laura Gassner Otting: It is. And I’ll fully admit that this sounds super woo-woo — like, “oh, she’s just a motivational speaker, that’s a bunch of nonsense.” But I’m also a doctoral student. I started my doctorate because, you know, I want to be in wonder all the time too — so why not go back to school at fifty-five and get your doctorate?

There’s actual psychological science behind it. I wrote Wonderhell, and I wrote Limitless, and I know that they’re right, because I spent thirty years thinking about it and twenty years advising leaders — from the corner office to the Oval Office — about leadership, about talent, about potential. I know that I know what I know, and I know that it’s right. I just don’t know why it’s right.

And I think a lot of leaders have that — a lot of entrepreneurs have that. We have this instinct that’s like, “I know it when I see it, I know it when I feel it.” We have this gut instinct to make decisions, we can make decisions quickly, but we don’t always know how to articulate why it’s right.

So I went back to school to do this, and the very first week I read an article and thought, “Oh, this is it.” There are two parts of our brain — the task network and the domain network. In one we get things done, and in the other we dream and imagine possibility. So you have the negative emotional attractor, and you have the positive emotional attractor.

It sounds like negative is bad and positive is good, but it turns out we need both. When we’re in the positive emotional attractor state, we’re dreaming, we’re imagining, we’re thinking about possibility — this is when teams do their best brainstorming, when we get together and jam on ideas. It’s amazing.

But if all you did was jam on ideas, and everyone stayed in that positive emotional attractor space, you wouldn’t get anything done. So you have to get to the negative emotional attractor space, which is the task network — once you’re there, you create plans, task lists, deadlines, and figure out how things get done. So we have to be in both places.

But our brains will naturally pull us to the negative emotional attractor space, which is why people’s immediate reaction is, “this is going to be bad, I’m going to fail.” Studies show that if you want your team to do great brainstorming and creative thinking, you actually need to see them and talk to them and say, “I believe in you, I think you’re great” — show them the shared vision, this is where we’re going, and I see you as part of it.

Once they’re in that space where they feel good and positive and are imagining the future, they can brainstorm really well. Then we can bring them into the negative emotional attractor space — the task network — and have conversations about how it actually gets done. So if we’re in this space where we think things are going to go well, we spend much more time in that imagination space, which allows us to see ourselves in a way we’ve never seen ourselves before. And once we see ourselves this way, it’s hard to unsee it — and then we’re left with, do I want to live into this new me or not?

Susan Drumm: Right. Right. And I think we are hardwired to go to that negative space. But what they’ve found in some of the studies I’ve seen is, if you can have three times as much focus on possibility versus negativity — what could go right versus what could go wrong — you’re really in a mode for exponential growth. Imagine that.

But I think we’re actually hardwired probably for the opposite — depending on your own personal style, you might be at 75/25 looking at what could go wrong, or maybe 50/50. But I was shocked to find out that it should actually be three times as much opportunity in a situation than negativity.

Laura Gassner Otting: You know, when I wrote Wonderhell, I kept circling around this idea of manifestation, and I was like, manifestation is nonsense — I can’t write about manifestation and be taken seriously as a business thinker, as an executive coach, as a keynoter. That’s a little too Coachella-woo for me. I can’t write about it.

And then I started digging into the science of manifestation, and it blew my mind, because here’s what I learned: our brains take in eleven million bits of data every single second. What’s the temperature in the room, how does the waistline of my pants feel, I’m reading this email, I’m thinking about making pancakes for my kids tomorrow — the dings on your phone, everything. Eleven million bits of data. But we can only process fifty of eleven million.

So our brains have to sort through all of the data to figure out what’s important. And I learned that manifestation works. Say you want to go to Tokyo — you’re like, “Oh, I really want to go to Tokyo, I wish there was a sale, I’d love to see the cherry blossoms in spring, it would be so pretty, it would be amazing.”

If you just think to yourself, “I want to do that,” and go on with your day, nothing happens. But if you write it on your vision board in pretty pink swirly font, the next day you’re driving down the street, a bus passes you, and Japan Airlines is having a sale to Japan, and you’re like, “Oh my god, I manifested it.”

Well, you didn’t manifest it — the process of writing it down, being intentional about it, seeing it, reading it, just the very act of being intentional signals to your brain: pick out Japan if you see anything about it, in that sea of eleven million bits of data coming in every second. So we just have to signal to our brain: I want to spend more time in the positive space, in the imagination space, dreaming about what can be instead of what might never be.

Susan Drumm: Well, this is interesting, because if we take this concept — I mean, you’re an athlete now, obviously, having done a marathon, but you’ve interviewed athletes — and I always say that athletes visualize crossing the finish line. In their mind they can see what the end state looks like, and they picture that. And the more you can visualize what you’re really going after, the more you’ll be drawn to that — versus if you visualize the pothole that might be there, studies show you actually veer more toward the pothole.

Now, let’s take this concept into one of the interesting things that just happened with the Olympic gold medalist in figure skating. She said she went there not with, “Oh, I’ve got to get this gold medal,” but it was almost, in a way, her detachment from it — or at least in some of the interviews I’ve seen — that allowed her to really shine, because what she focused on was her actual skating in the moment, and just enjoying that, and then whatever happened, happened.

What do you make of this distinction? How was she able to do that and not get too attached to the gold medal, and what happens when that gets in the way?

Laura Gassner Otting: Yeah, it’s very interesting. I can’t put myself inside of her head, but I can put myself inside the head of Alex Ferreira, who just won the gold medal for halfpipe men’s freestyle. Those are the guys who, on two skis, do the halfpipe — they go up, they do like a 1080, four rotations in the air, and then come back down. They go back and forth. It’s an insane sport.

And the reason it’s insane is because it’s so new and so dangerous. As soon as somebody does a 960, it’s, “Okay, well, 960 isn’t going to cut it, somebody’s got to do a 1040” — then, “someone’s got to do an 1180.” I can’t do the math, but they’re making the sport up as they go along, and it’s getting harder and harder.

Alex had won the bronze medal, and he’d won the X Games, and he was so incredibly stressed about winning. He just felt like he had to bring home the gold. So his reaction was, “I’m just going to outperform everybody, I’m going to outwork them, I’m going to out-train them, I’m going to out-perfect them.”

And because he was so focused on being perfect, something little always went wrong every single time, and he was like, “well, I can’t be perfect.” It really got in his head — it was really hard. Then, right before the X Games, about two or three years ago, he hurt his back shoveling snow off his mom’s roof.

You’ve got to love a boy who loves his mom — but he hurt his back, and he went to the X Games in a lot of pain. He didn’t even know if he could do the run. He’d grown up wanting to ski, wanting to do this, having nightmares that he would fall in the most important moment.

His coach said to him, “Don’t worry about being perfect — just do one run, you’re going to be fine.” And he did the first run, and he fell, and he thought, “well, it’s all over.” Then the coach said, “Just do one more run.”

And because he thought, “well, I can’t win now, so I’m released, the monkey’s off my back, I’m totally released, I can’t be perfect” — he went on the run and did the best run he’d ever done in his entire life, and got the highest score that had ever been recorded at the X Games, and won gold.

PS, he just finally won gold at the Olympics too — he won bronze eight years ago, silver four years ago, and this year he brought home the gold medal. He told me, when I reached out to him afterward, “I have worked so hard for this, I have wanted this forever, I’ve done everything I could possibly do to prepare, and just knowing it was the last chance, I had this enormous amount of pressure on me — but also I thought, if it doesn’t happen now, it’s not going to happen. You just go out and do the best that you can.”

So my guess is that for Alysa Liu, she felt so released because she decided not to do things the way she was told — by the trainers, her dad, everyone else — to be perfect, eat these foods, train this way, use this music. She was like, “I’m just going to do it my way, and it’s either going to work or it’s not.” You can’t be insatiably hungry for someone else’s goals, you can’t be insatiably hungry for someone else’s plans.

So I think she just found that intrinsic motivation that allowed her to be so fully herself — her talent, there’s no question, her talent spoke for itself, but her joy, her joy was so contagious. And then in the men’s figure skating, Ilia — the Quad God — there was so much pressure, he wanted to be perfect with everything, and then he totally fell. I feel for this kid, because now he has to live with that — it’s going to sit on him for four more years until the next Olympics. And that’s tough pressure.

Susan Drumm: Yeah. And so, handling all that self-talk — now you have the opportunity to make it to the Olympics, and yet where you go mentally, and how you recover to step up — all the things you’re talking about in your book still apply, right? Because it’s still looking at things as an invitation versus a limitation.

That’s what I think Alysa did — she’s like, “I get to skate at the Olympics, this is awesome, and whatever happens, happens. It’d be nice, great, but I don’t have to have that in order to feel good about me.” Maybe there’s some of that distinction there too.

Laura Gassner Otting: Yeah. One of the hilarious professional hazards of my job is that I know an Olympian in every town — I speak at these events, and there’s always other speakers in the green room, and you can’t swing a dead cat in my industry without hitting a gold medal winner. It’s hysterical — I’m like, “Oh, what was your sport?” Meanwhile, I’m like the least athletic person ever.

One of the recent Olympians I met, a guy named Connor Fields, is the only American ever to win Olympic gold in BMX cycling — those are the guys who cycle little bikes up and down on jumps. It’s an incredibly dangerous sport, but honestly, all these Olympians’ sports are dangerous — Alysa Liu is flying around the ice with blades on her feet. It’s totally nuts.

So I called him up and said, “I’m going to be in Vegas for a keynote — I don’t know if you’re around, but I’m training for another marathon, I have to run thirteen miles on Friday, do you want to run with me?” And his reaction was, “I don’t think I can run thirteen miles, I’m a sprinter.” And I said, “Well, I’m fifty-five, and you’re thirty, and you’re six foot tall, and you have a gold medal from the Olympics — I think you’ll be okay.”

I razzed him a little bit, but we were having this whole conversation about how, when you go to the Olympics, it’s gold or nothing — the difference between winning gold and winning silver is milliseconds. And the most interesting study he and I were talking about is that people who win bronze medals are actually happier than people who win silver medals.

If you win gold, you’re like, “I won gold, amazing, I won the Olympics.” If you win silver, you’re like, “I lost.” If you win bronze, you’re like, “thank God I podiumed — I made it, I got a medal, I got lucky.”

So it’s interesting to think that all of us, in our lives, have these expectations about how things are going to go — we have this idea that it’s either going to be perfect, or it’s not, and there’s so much space outside of perfect. We’re never perfect — Serena Williams isn’t perfect, Roger Federer isn’t perfect, and these are the best tennis players who ever lived.

I saw a graduation speech where Roger Federer talked about how he’s lost more points than he’s won, and yet he’s the winningest male tennis player in history. But we have this idea that it’s perfect or not — so when we give a big presentation and don’t get it perfect, what do we practice? We practice the stuff we got wrong.

And we lie to ourselves, telling ourselves that the stuff we got right, we got right intentionally, when in fact we might have just gotten lucky — and we don’t groove the pattern of that. So I always encourage the people I coach to not just practice the things they get wrong, but to actually groove the pattern of the stuff they got right — because, one, you don’t know if you got it right on purpose, and two, if you did get it right on purpose, doing it again and again teaches you what it feels like to get something right, so you can feel that flexibility, that confidence, that a little more control, so that you can improvise in that moment.

Susan Drumm: Absolutely. And so what would you suggest — let’s get tactical for a moment. What are things that you see leaders could do, let’s say, starting tomorrow, that would help them set the right course to be limitless?

Laura Gassner Otting: For themselves?

Susan Drumm: For themselves — yeah, or the people they lead. I mean, really both.

Laura Gassner Otting: So, I would say the biggest mistake that leaders make is thinking all of their people are incentivized by the same thing. Everybody’s like, “Oh, my staff is unhappy, I just need to give them a raise” — well, maybe.

In 2019 we started a global workforce engagement study — we have about ten thousand responses from a hundred and thirteen different countries, every possible demographic, every possible industry. When I was in executive search, we used to listen for eight motivating factors on a phone call about whether somebody might want to leave to consider a new job — things like: Am I inspired by the leader? How big is the challenge? How deep is the impact? What’s the mission of the organization? Where is it located? How prestigious will it look on my résumé? How much money will I make?

In the survey we did — this fifty-question assessment, again ten thousand responses, a hundred and thirteen countries, every demographic, every industry — we found that thirty-six percent of people said money is the most important factor. Which leaves sixty-four percent of people who are incentivized by something else.

The issue is, we think our people know we like them because we pay them, because we give them compliments — but we don’t actually know what incentivizes them. So the first thing leaders need to do is really understand what drives their people, what their people care about.

Because if you’ve got that salesperson who’s crushing it, making their goals all the time, and they keep showing up in your office like, “What have you done for me lately, where’s my bonus?” — they might care about the money, but they also might care about manifesting their values on a daily basis at work. Putting them in charge of your corporate philanthropy program might make them the happiest person in the world, but you don’t know that, because you’re assuming everybody’s not only incentivized by the same thing, but the same thing as you.

Susan Drumm: Exactly. That’s exactly why, in the work that I do, I’m a big believer in — we use the Enneagram a lot. The Enneagram looks at what drives you or motivates you — not behavior, which a lot of other assessments do, but underneath it, why you do what you do, not what you do.

And when you get to that level of why, you start to realize not everybody sees the world the way you do. In fact, that’s actually a good thing, because we want people motivated by different things — because of that motivation, they bring a different perspective and lens to the situation. Having that level of cognitive diversity is really what makes the difference.

Laura Gassner Otting: Absolutely. Some people want to be home at six o’clock every night to have dinner with their kids. Some people want to be on the road because they want to see the world. Some people are interested in maximizing their profitability.

Right now, at this moment in time, everybody has a different reason for what they do — and by the way, everybody’s reasons change throughout their career. So just because you think somebody was incentivized by something ten years ago, when you hired them, doesn’t mean that’s where they are today.

Susan Drumm: Yeah, absolutely. Well, where can people learn more about you and your work, and what would you recommend they take as the next step?

Laura Gassner Otting: So, my website is LauraGassnerOtting.com — but all my friends call me LGO, because Laura Gassner Otting is a lot of name. You can find me on all the socials at Hey, It’s LGO — reach out to me there.

If people are interested in finding out where in Wonderhell they are, they can go to WonderhellQuiz.com. And if you want to take that assessment I mentioned, that’s at LimitlessAssessment.com.

Susan Drumm: Excellent. Well, thanks so much for bringing your wisdom. I’m excited for you getting a doctorate — what is the doctorate in, by the way?

Laura Gassner Otting: It’s a doctorate of business administration — a terminal business degree. I’m hoping my dissertation will be around the use of intuition in hiring decision-making.

Susan Drumm: Oh, I like it — I like it so much. Well, I’m looking forward to it — I imagine out of that you’ll probably write another book about what you discover, so we’ll look forward to seeing that at some point in the future. How much more time do you have before you finish?

Laura Gassner Otting: I have two and a half years — it’s a three-year program, and I’m in the spring semester. So I’d say I have two and a quarter years, but I’m in the middle of quantitative reasoning, which feels like a whole lot of time, so I’m just giving myself that extra room.

By the way, if you are listening to this and you run human resources for your company, or you’re an executive whose success depends on hiring the right people, reach out to me — I’d love to interview you for my dissertation.

Susan Drumm: Excellent, all right, great. Well, if you like this episode, you’re not going to want to miss my interview with Heather Hansen, who discusses how charisma — which isn’t just charm — is a skill that leaders can build.

Let’s all lead the way. Hope you enjoyed today’s episode, and I’d like to point you to the next important step: hit the subscribe button and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.