309: How to Lead With Wild Courage with Jenny Wood

What is the shame in creating something standing behind your efforts and abilities, Having the courage to do that, having the courage to share, having the wild courage to put it out there without bringing shame into the equation.

Right.

And so we just think about how often we downplay our efforts.

Hello everyone, this is Kathy Caprino and welcome to my podcast, Finding Brave. I've created this show for everyone who longs to create something bold and brave in their life. To rise up, speak up and stand up for who they are and to reach their highest and biggest visions. Each week I'll be speaking with inspiring guests from all walks of business, leadership, entertainment, the creative arts and the entrepreneurial world. And they'll be sharing their intimate stories of Finding Brave and offer their best strategies for building your most rewarding, joyful and meaningful life, business and career.

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Hope to see you.

Hello everybody.

Welcome to another episode of Finding Brave. I'm Kathy Caprino and I am joined today. What a, what a conversation we're going to have today with the inspiring, amazing Jenny Wood. My goodness. In the middle of your book launch. And we can see exactly what the book is. Wild Courage. Go after what you want and get it. Jenny, thank you for being here. I know you've got 50 things going on, 500 things. Thank you for taking the time enjoying.

Absolutely. Yeah. It's such a joy to be here.

And we are going to talk about here it is how to lead. And I think we're going to say live too. That's not in your, in your book title, but how to lead and live, I think with Wild Courage and what that really means. And you know, this is called finding Brave. As you know, Jenny, I think you and I probably are going to be nodding our heads constantly about how and I want to hop into this how other career and leadership advice gets it wrong. Not to be snarky here, but I have a sense that you really see it in a very different way per the nine traits we're going to talk about. So let me tell you about Jenny first and then we're going to hop into what is Leading with Wild Courage all about. Jenny Wood is a New York Times bestselling author, speaker, former Google executive, and former Harvard Business School researcher. I've got to hear more about that. Who knows that real success isn't about following the rules or waiting your turn or 50 other things we're going to debunk? She's also the founder of Own youn.

Career, one of Google's largest career programs.

In her new book, Wild Courage, Go after what yout Want and Get It, Jenny breaks down nine bold traits that defy conventional career advice. Obsessed, weird, selfish, selfish, shameless, noisy, manipulative, brutal, reckless, and bossy. Oh my gosh, bring it on. Her practical, no nonsense approach empowers ambitious people to break the mold, be better leaders, build influence, and reach their full potential. Jenny has been featured kind of all over the place, but in NBC, Bloomberg, Harvard Business Review, Forbes, Business Insider, etc. Etc. She lives in Boulder with her husband and two children. And I loved it. Is in constant pursuit of the perfect zucchini bread recipe. If I have one, I know where to send it. There we go. Let's dive in here. Jenny, the very first thing I want to ask you, given all that you've done and all that you've written, why this book now?

Yeah, well, I think that it people need courage more than ever with everything that's going on politically, socioeconomically, with the rise of AI, with corporate jobs changing and evolving and, you know, layoffs, restructures, less satisfaction. And so to me, this is the the book I wish I had when I was 22 and just starting out in my career. Though it's certainly a useful guidebook for leaders, but it's also just about how to push past the fear of everything that's happening the world right now or happening on your team or happening with any transition you're going through when it started in 2011, in this very particular moment, I was riding the subway home from work when about 20ft away from me stands this really good looking guy. Gorgeous blue eyes, thick brown, wavy hair. And even though I want to talk to him, something holds me back. Kathy, you know, what if he's a convicted felon? What if he's married? What if 100 people stare at me on this packed subway? So I sit there, I do nothing as the train passes stop after stop after stop, and frankly, as life passes me by, but yet I'm still so taken by him. So I make a deal with the universe. And I say, if he gets off at my stop, then maybe I'll try to strike up a conversation with him. And if not, then c' est la vie. Well, he gets off at the next stop, not my stop. Shoot and shoot. Exactly. And I slump down in my chair, thinking, okay, I guess you know, it wasn't meant to be. But then all of a sudden, this wave of wild courage washes over me and practically pushes me out of my subway seat and off the train. And I pry the doors open, no joke. I chase after him. I finally catch up with him as he's exiting the station, tap him on the shoulder. I say, excuse me. I'm sorry to bother you. You're wearing gloves, so I can't tell if you're wearing a wedding ring, but in the event that you're not married, you were on my subway and I thought you were cute. Any chance I could give you my business card? And now, if you're listening to this podcast, not watching on YouTube, Kathy's face, like, her jaw is, like, on the floor. And. Okay. And so. And so then I wait for.

It's not true. You did this.

100% true, but it keeps going. And so then I wait for what feels like forever, for him to respond, thinking this was a terrible idea.

I mean, he's standing there just looking at you.

Not standing there, just looking at me, not saying anything, because I think he was probably a little bit surprised or shocked.

Stalker boldness, right?

This.

The wild courage of this stalker on the train. But he does eventually take my card and call the next day and ask me on a date a week later. And we've now been married 11 years with two small children.

I have so much to say about this. Bravo to you. That is wild courage. And can I. You may not agree with what I'm about to say, but I have spiritual beliefs. I've seen my own past lives. I Know what Kismet feels like? I also think you listen to your highest self. Yeah.

Yeah.

And do you think Wild Courage in what you talk about, there's a part of that where there's a knowingness inside? I did not prompt you with this.

Yeah.

But I feel there's a knowingness inside of us. But we're scared. We don't want to hear it. We don't believe we're worthy of it.

We're good at.

We think.

Do you agree?

Absolutely. Because I think that when we are scared, we don't think we're worthy or we think it should go to somebody else, or we think we should sit there and wait for the guy to ask us out. And like, this is. This is a career development book. Right. So, you know, it's interesting that I start with this very personal story, but yes, like in. At the root of it, it is all about pushing past the fear and think about how often fear comes up in the workplace. Scared to ask your boss for something, scared to set up time with your boss's boss. Scared to ask somebody to mentor you or sponsor you in a work context. And so, you know, having. By the time I started working on Wild Courage, I'd coached tens of thousands of people, Google execs, you know, people inside, outside the company, either directly or indirectly, on influence, leadership, and success. And the same theme kept coming up when people felt stuck. And it's exactly what you just touch on. That theme was fear. Fear of failure, fear of uncertainty, and fear of judgment of others. And think back to the three things that I thought about this guy in the subway. What if he's a convicted felon, right? Fear of uncertainty. What if he's married? Fear of failure. What if a hundred people stare at me on this packed train? Fear of judgment of others. And that's what almost kept me. That's what did keep me silent and small and still and sitting until this wave of word of wild courage washed over me. But then when it did, and it ended in this incredible result for my life and my happiness and my family, I. I started leveraging Wild Courage as a. As a tool in every other area of life. I started asking for what I wanted at Google and started getting promoted. I ultimately was the C.E. sorry, the COO of different divisions at Google and. And ultimately an executive there. And I one day was thinking, well, I should tap into my wild courage further. Even though I'd never worked a day in HR or people are operations in my life, people would still come to me for mentorship and Say Jenny, how did you grow from entry level? Like what, how do you navigate the politics? Like what's the secret sauce? And I thought well let's just scale it. And rather than talking to people individually, I'll write down, I don't know, maybe like 10, 15 tips that helped me rise to exec at Google. Maybe I'll lead a training and I don't know, 30 people will come, but with wild courage. I put this training out, I advertised it pretty heavily on Google's internal tools and 2,000 people came to this first training. So it taught me, you know, it was very exciting to, to lead that program that became one of the largest in careers, one of the largest career programs in Google's history. But, but really the message to me was oh my gosh, I love my operations team that sits between sales and engineering and helps drive a lot of revenue. But I really love coaching people to be better than they think they can be. And here we are with this book. That is so exciting. And now my goal is to spread insane amounts of this type of wild courage into the workplace through these nine sizzly traits. Can you stay on another seven hours please?

Okay, wait, so let me dissect and ask some questions.

Yeah, of course.

So I have to tell you, you probably don't know, you're too busy but I wrote a book in 2020 called the Most powerful you. And what it emerged from was working with 20,000 and it was women then, now I have male clients. But what I saw were seven damaging power and confidence gaps and they're going to be exactly what you, you know, they're going to dovetail, lots of overlap for sure. Right. But what I did see was two things. When people are not getting what they want, feeling what they want, doing what they want. So often I see that they're missing two things. The bravery to face head on what isn't working and to take accountability for to change what they can. But that's not enough. Yeah, we need power. And what's really interesting to me and I'd love your honest thoughts. Yeah, I, the book was going to be called Closure Power gaps but you know, my publisher said nobody knows my power. Power gaps are call it something else. So it's called the most powerful you. What I didn't understand and this is not going to make be a gender discussion fully but so many women have told me I don't want power and I say to them well what do you want? And they say influence.

Yeah, interesting.

Being a role model, I, I said I Hate to break it to you, you don't have those things without power, but it's a certain kind of power. Not this kind of power that we see every day. Yeah, it's positive influence. Positive power. I. I would just love to ask you this. And again, I didn't prep you. Do you see. How do I want to put it? Wild courage being more of a difficulty for certain groups.

Yeah, absolutely. I think. I mean, I've spent my whole life in tech and historically underrepresented groups in tech, whether it's women or Latinx or, you know, people of color, it's definitely harder to tap into that power. And like, I think I love the COVID I love what you just offered because I think power is an amazing thing. It's how you use that power that, that counts. And, you know, it's like if people are. If your clients are saying, oh, I don't. I don't want to be. I don't. Power is not what I'm looking for. Like, ooh, they're going to really bristle at, like the, the nine traits that we'll get into here. But yeah, for sure. I think even though I. This work is. Is gender agnostic.

Right.

The examples that I talk about are both from males and females, all different walks of life, all different cultures. The reality is that these nine traits, which I feel like I've teased it enough, now I should just share what the nine traits are. I feel like, you know, they. They are labels that can oftentimes be more attributed to women than men. So the nine traits of wild courage.

Yeah.

That create the bars of an invisible cage that keep you small, but when used in a sane and savvy way, can supercharge your success are as follows. Weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, and bossy. And just as you defined, redefined power for these clients. I redefined these traits as well. So selfish, for example, is the courage to stand up for what you want. To be your own champion. Right. Give everyone else a leg up at your own expense, and you'll end up getting trampled. Manipulative. That's a spicy one. Is the courage to. To build lasting relationships and influence through empathy. Because whether you're selling a product, an idea, or yourself, you know, your ability to win friends and allies is all about mutual benefit. So go figure out what people want and get it for them in a way that expands the pie, not redivides the pie. So just two little examples of the reframing and the reclaiming of this language. In the same way you did with the word power.

I love it so much. I want to dig into, say, the top three you feel people struggle with most. But before we do that, as you know, former therapist and I do believe that it's so obvious you're a person when you show up to your career. And what a lot of career coaches and others get wrong is they think that they can extricate the person out of the career discussion. In my view, that's absurd. You are a person when you show up to it. So these are personal growth traits as well as professional growth. If you're going to change them in your. In your work, I guarantee you you're going to change them at home, with your kids, with your spouse, with your parents, with your friends. Right? Would you agree with that?

Oh, absolutely. I cannot stop thinking about something that happened two hours ago when I was at field day for my son. And it is straight up from the shameless chapter. And it has nothing to do with work, but it is absolutely something that I try to coach people through in my book. So they definitely overlap.

Thank you for that. But here's the question I want to ask you. The fact that you had that moment on the subway 11 years ago, you.

Said, We've been married 11 years. So that was four. That was like almost 15 years ago. I was 30. I'm 45 now.

Oh, wow. Don't you look beautiful. All right, here's my question. I'm really interested in the childhood shaping of people who are able to do what you do. So can. I know that could be a two hour discussion, but here's my question. Do you feel like, and this is never to cast aspersion on our families or parents. Everyone's doing the best they can. No parent gets out of bed and says, I'm going to blow it. Going to ruin their kid's life, going to keep them back. So this is not anything about blame, but do you feel that when you look back on what you learned as a child, wild courage, the seeds of that were planted, or the opposite of the seeds of that.

Oh, that's so interesting. The seeds were planted in my case. And then let me think if there's a counterpoint in there. I'm sure there were some ways where they. Where the seeds, you know, where there was. Like, I'm working against it. But no. Yes. Yeah. Thank you. I think of this one time where I was dared to sing the Star Spangled Band, not the Star Spangled Banner. My country tis of thee at a frozen yogurt shop in, like, middle school. And even though I felt like I had thin skin in middle school, I mean, who doesn't, right? Where it's like, middle school, 13 years old, right. I remember just, like, belting at the top of my lungs. Every word until the very last do the icing or whatever was, like, belting it in this crowded frozen yogurt shop. And so why did I do it? I think I was like. I guess my friends dared me or whatever. I, like, took the challenge because I was like, if I can push past this, I don't know that I had this evolved of a. Of a, like, framework around it at that age. But I do remember thinking, it feels uncomfortable, it feels scary, but let's do it anyway. It's like, feel the fear and take the action anyway. Do it scared. And if I can do that, then I can get up, I can. Public speak, you know, in high school for debate.

Do you really think you thought those thoughts?

I do think I thought a version of that. Not as evolved as, like, my looking back three decades later, you know, evolution of it. But I do remember that or other examples where I was like, I'm just gonna do it. I'm just gonna do it. Because it sounds like an interesting challenge. Think about that. Like, even getting off the subway to follow John, like, it almost felt like an interesting, interesting challenge. I've always struggled among those three fears of, like, uncertainty, failure, and judgment of others. I've always struggled the most with uncertainty. So to me, it was almost like on the subway that day. Oh, it's a fun challenge to see, what's this guy all about? Will he take my card? Will he call me? And I'd almost rather know and have it be a no, have the answer be no, than to live not knowing. So I don't think that maps perfectly onto this moment in the frozen yogurt shop. But I think there's something about, like, being a little bit more comfortable than the average person with failure with, you know, getting up on stage and seeing how it goes, because there's something exciting about it. I've always been a bit of an adrenaline junkie, Kathy, and I think that. That, you know.

And did your parents the last thing about childhood? Yeah, because I work with a lot of parents. Do you think your parents modeled that and instilled that?

Yes, I do. I do. They also give me a lot of positive feedback, and I think that that helps, doesn't.

And did your parents the last thing about childhood? Yeah, because I work with a lot of parents. Do you think your parents modeled that and instilled that?

Yes, I do. I do. They also give me a lot of positive feedback, and I think that that helps a ton guard against the fear. Because it's like, who do you look up to the most? It's your parents over your friends, right? Like that their word is everything to you. So if my parents, you know, gave me praise and encouragement and, you know, helped me reframe failure a ton, guard against the fear, because it's like, who do you look up to the most? It's your parents over your friends, right? Like that their word is everything to you. So if my parents, you know, gave me praise and encouragement and. And, you know, helped me reframe failures as just data and helped me recognize that. If you look at any successful leader, don't look at their greatest hits, look at the discography of their entire album, right? Like, they had course corrections, they had failures, and my father was an entrepreneur. So like, even that has some inherent risk and failure and naturally within it, I think yours as just data and helped me recognize that if you look at any successful leader, don't look at their greatest hits, look at the discography of their entire album, right? Like, they had course corrections, they had failures, and my father was an entrepreneur. So like, even that has some inherent risk and failure naturally within it. I think that because I had that cushion of positive feedback at home and it guarded against this negativity bias, which is a classic cognitive bias, you know, script or social psychological principle of, like, overemphasizing the negative. Because I had so much of that positivity at home, I think it gave me that cushion to have more wild courage, because I think that because I had that cushion of positive feedback at home and it guarded against this negativity bias, which is a classic cognitive, you know, script or social psychological principle of, like, overemphasizing the negative. Because I had so much of that positivity at home, I think it gave me that cushion to have more wild courage. Because I figured if I'm failing out there in the world, at least I've always got the safety of home to these people who I put on a beard. If I'm failing out there in the world, at least I've always got the safety of home to these people who I put on a pedestal anyway, and.

Therefore there were always crying on my podcast. And here we go, everybody, I want you to listen to that.

There's pedestal anyway, and therefore there were always crying.

Much truth and impact in that statement and on My podcast. And here we go, everybody. I want you to listen to that. There's so much truth and impact in that statement that if who you have at home is saying to you, well, you did it, I know. That if who you have at home is saying to you, well, you did it. I know that felt like a failure or that was humiliating, but look at what you did. If you've got that at home, what's possible for you outside the home is so much greater. That's my. That's my soapbox. Oh, that felt like a failure, or that was humiliating, but look at what you did. If you've got that at home, what's possible for you outside the home is so much greater. That's my. That's my soapbox. Thank you for sharing that. Now let's talk about kind of like my seven gaps. When people say, what's the biggest one that you think if people can work, you know, it will make a huge difference? And for me, it's power Gap one, recognizing your special talents, abilities, and gift. Thank you for sharing that.

Yeah.

Now let's talk about kind of like my seven gaps. If when people say, what's the biggest one that you think if people can work, you know it will make a huge difference? And for me, it's power Gap one, recognizing your special talents, abilities, and gifts.

Oh, that's great.

My goodness. So many people go, I don't have any talents. I don't have. Oh, my goodness. So many people go, I don't have any talents. I don't have any skills. Or I'm afraid to say it. I'm afraid to say I did that on LinkedIn. Well, did you do it or did you not do it? Well, I had a team, and I know you had a team, but you led the team. Oh, wow. What would you say?

Let's start.

And maybe this is hard, but what would you say? How many skills? Or. I'm afraid to say it. I'm afraid the one trait you're doing the most coaching on.

It's like you're asking me to pick my favorite child. But.

But.

But I'll do it for the purposes of the conversation. So I'll. I'll actually focus it on how I feel today.

Right.

Because they do always change. And some days it's, you know, some days it's reckless, Some days it's brutal. Some days it's shameless. Some days it's weird. But today it really does feel like shameless. And shameless is the courage to stand behind your efforts and abilities it's not so different from what you just shared, is the one that you feel is so critically important. It's about finding your swagger. It's about recognizing your talents and your skills, sharing them with the world. And it's about pushing past the fear of, you know, what people might think of you because. And I, I. So we can talk. Very practical tools, right? But I am going to mention this moment that happened on the field just at. At field day today that I alluded to, because it just. It's so similar to what I think happens oftentimes at work. So the kids were playing, you know, dodgeball, and I wanted to chat with my son's teacher. And my son has pretty severe adhd. I'm always kind of like wanting to get the pulse, but I don't often have the time to email the teacher and get the pulse on how he's doing. So I saw an opportunity to talk to the teacher and she brushed me off. She really did. Like, it was a very clear. Almost just walked away. And I was like, I felt so shameful. I felt embarrassed. I felt like I'd made a mistake. Kind of like wrong time, wrong place, not really the time to be checking in with the teacher about how he's doing. And so I just couldn't shake this feeling of. And again, we don't think of it as shame at work because that has such strong connotations. But think about the last time you felt embarrassed by something at work, someone you spoke to or something you said, or you feel like you made a mistake and you just can't shake it, or you lost sleep at night, but thinking over and over again about this conversation you had or the sentence you said, or your tone of voice, or this thing in an email, whether it's a typo or a wording or something. And that's actually how I feel right now. And so even though, yes, it happened today, right now at school, it was a social setting, not a work setting. Think about how often you feel that with your boss, with your colleagues, with your boss's boss, with a client, with a customer, with a process prospect. And so, you know, an example in the work context is someone was presenting something not too long ago and they walked into the meeting. And someone who reported an indirect report of mine, she reported to a manager who reported to me, and she walked into this meeting of 30 people and she said, this is a shameless plug. But I've created this spreadsheet and I really think it could save people a lot of time. And so, like, sorry to bother you all with it. And I know that's not the topic today, but I just wanted to put it in the group chat here. And everyone went gaga, like, emojis flying. Everyone was so excited. Excited. This is going to save me so much time. This is such a great way to improve the process. And yet she presented it as a shameless plug. What is the shame in creating something standing behind your efforts and abilities? Having the courage to do that, having the courage to share. Having the wild courage to put it out there without calling it shame. Like, without bringing shame into the equation.

Right.

And so we just think about how often we downplay our efforts. I talk about. And so, like, what. What would have been a good alternative there? I created this spreadsheet. It's going to save you 20 minutes each. I'm so proud to share it with you. And let me know once you use it if you have any ways to improve it. Right. Like that.

To me.

And even not to correct you. Yeah. But, you know, I know it's not on the agenda, but I think it could be so impactful, you know, I hope you'll take the time to take a look, you know.

Yeah.

Reflecting that we're not just barging in on some other topic. There's a reason I'm bringing it up right now.

Exactly.

And I probably. Yeah, I probably even misspoke there. It was totally natural, and it made it, like, was part of the. Oh, it was. It was totally relevant. So I think I just missed shame when it. There was no shame at all. Right. Or even simple things like, you know, you're one minute late to a meeting and you automatically say, sorry, I'm late, versus thanks for your patience. Right. That's a real easy switch that you can make.

Yeah.

And how many. Now, there are apps that will track how many times you say I'm sorry in an email. And yes, women tend to do that more than men, but those are just easy swaps you can make that can kind of d shame your language. Because we believe what we say and we. We oftentimes walk around feeling bad, feeling insecure, feeling imposter syndrome, feeling like you lose sleep at night because of something you did or someone who's waiting on you. But there's another social psychological principle called the spotlight effect. And that means that we walk around with a spotlight on our head thinking, like, feeling very focused about our actions, our mistakes, our choices, our work product, but everybody else walks around with that same spotlight over their head. And so, you know, Kathy, when was the last time you lost sleep because of somebody else's mistake, or, you know, you were waiting for an email from somebody, you're laughing, never right, but cares.

But it's my mistakes I'm agonizing.

Basically, it's your mistakes you're agonizing over, and that's the spotlight effect. So if you're not losing sleep, agonizing about somebody else's mistakes, or mess ups or wording or tone of voice, they're not losing sleep worrying about your mistakes or mess ups or wording or tone of voice. So that to me, is kind of shameless in a nutshell. And I've. I have a couple tools that I can share to help people, you know, compensate for it at work or push past it.

I would love to hear that, but can I do something with you for a sec?

Of course.

You know, having been a therapist, again, I don't do therapy and coaching, but sometimes people can. And I actually interviewed an amazing guy, David Jurassic, on shame. That's his world. He can feel it, he can sense it. And when we hold it, it's very damaging. But I. Here's what I want to say there. I'll have to write a blog post about this, but there's probably eight different dimensions of shame and why we have it. So I'd like to ask you this just so we can do it right for everyone to listen to. If I asked you what feels most shameful about that interaction with the teacher? Meaning, what does it say about you that you're internalizing so much shame? What would it be?

Can I do this with you?

Because 100% I'm thrilled you're doing this. Okay, so what feels most shameful about it? Is that the question, Kathy?

Yes. Like, if you're feeling humiliated, you got the brush off. It wasn't the time, it wasn't the place. What are you internalizing about you that makes you feel badly for days, hours, whatever?

Yeah, so. And let me know if I'm not taking this in the right way. You interpreted that. You intended the question. But I. I catastrophize it. I go much further than the interaction. I say, she doesn't like me. Here are the reasons she doesn't like me. I am too bold. I annoy her. She's rolling her eyes at me. Everyone is saying, oh, there goes Jenny Wood again.