What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want from those who stay stuck waiting for recognition that never comes?

Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career is to keep your head down and let your work speak for itself.

Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries, and she’s the author of Wild Courage: Go After What You Want and Get It. In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals.

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0:00:07.4 Brett McKay: Brett McKay here, and welcome to another edition of the Art of Manliness Podcast. What if the traits you’ve been taught to suppress your entire career are actually the very qualities that separate those who get what they want, from those who stay stuck waiting for recognition that never comes? Today on the show, Jenny Wood argues that most of us are living in what she calls “an invisible cage” created by an overabundance of caution, and that the biggest lie you’ve been told in your career, is to keep your head down and let your work speak for itself. Jenny is a former Google executive who developed a career development program used by 56,000 people in nearly 100 countries. And she’s the author of “Wild Courage: Go After What You Want and Get It.” In our conversation, Jenny explains how traits that have a negative rap can be used for positive ends that will advance your career. We discuss how being shameless, reckless, nosy, manipulative, obsessed, and more can help you overcome your success-hindering fears, take bolder action, and achieve your goals. After the show’s over, check out our show notes at aom.is/wildcourage.

All right, Jenny Wood, welcome to the show.

Jenny Wood: Thanks so much for having me, Brett.

Brett McKay: So you were a successful Google executive. While you were there, you also developed a career development program that helped employees advance their careers by learning how to advocate for themselves, stand out for the crowd. So you’ve made a career for yourself by being unapologetically ambitious, like going after what you want. Have you always been like that? Were you like that as a kid, or was there a moment in adulthood where that switch finally flipped and you’re like, all right, I’m gonna start turning my ambition into action?

Jenny Wood: Ooh, there was a moment, Brett. There was a moment, and it was in 2011 on the New York City Subway, when I was riding the subway home from work, and about 20 feet away from me stands this really good-looking guy, gorgeous blue eyes, thick brown wavy hair, the whole works. And even though I wanted to talk to him, something held me back. The things you would normally think about some stranger on the subway. What if he’s a convicted felon? What if he’s married? What if 100 people stare at me on this packed train? So I sit there, I do nothing while the train passes stop after stop after stop, and his life, frankly, passes me by. But I’m so taken by him that 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, c’est la vie. Well, he gets off at the next stop, which was not my stop, and just as the doors are about to close, I feel this wave of wild courage wash over me and push me out of my subway seat and off the train.

I chase to catch up with him, tap him on the shoulder. I say, excuse me, I’m sorry to bother you, but you were on my subway and I thought you were cute. 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, any chance I could give you my business card? And then I wait for what feels like forever for him to take my card, thinking this was a terrible idea. But he does take the card. He calls the next day. We go on a date a week later, and we’ve now been married for 11 years with two small kids who are nine and seven.

Brett McKay: No, I love that story. I love how you started your book off with that story, ’cause that really captures the title of the book, Wild Courage. So what were you like before that moment? Were you sort of just someone who played it safe, tried to stay in the background?

Jenny Wood: Yeah, I was a confident Google employee on the outside, but scared and timid on the inside, always worried about what my boss was going to think about me walking out of our Tuesday one-on-one, always concerned that nobody would forget that one client presentation I flubbed, always nervous about when I eventually had direct reports and indirect reports as a Google exec, what they thought about me and how they were gonna score me as a leader at Google because there’s a lot of upward and sideways and downward feedback at Google. And it’s funny, just yesterday I gave a keynote to a Google team that happens to be led by the guy who hired me at Google almost two decades ago. And he’s like, Jenny, it’s so interesting and wonderful to see you come into your own because when you first started, you had a hard time having a perspective. You had a hard time sharing your thoughts. I knew that you had smart ideas, but you were too nervous and timid and held back to share those out loud for business impact. And I was like, wow, it’s so interesting because sometimes I think people push back on me and they’re like, it seems like you were just born this way, Jenny.

You seem really confident. You could sell ice to Eskimos. And it was such an interesting moment when I was doing this talk and getting this feedback from the guy at Google who hired me to realize like, yeah, I was not born this way. And you don’t have to be either. You might not be a subway chaser, but wherever you are sitting right now, there is something that you want. And wild courage is what closes the gap between what you want and what you get. And it’s this set of tools that help you go after those things and get them. And it can be learned. It is not an innate skill. It takes practice, it takes reps. It takes building the muscle of wild courage.

Brett McKay: And as you described yourself in the book before you made this jump to wild courage, you remind me of, I was like this in high school too. Correct me if I’m wrong. This sort of describes you how you were in high school and college. You worked hard, you were quietly ambitious, you kind of just like, I’m gonna work really hard, do my best, and then I’ll just wait for people to notice.

Jenny Wood: Yeah, exactly.

Brett McKay: And then if people notice me, then okay, that’s fine. But if they don’t, I’m just gonna stay in the background. I think there’s a lot of people like that. They’re really conscientious. They do good work, but they wait for people to notice before they actually put themselves out there.

Jenny Wood: Absolutely. I was like that. I would almost take it a step further and say that I was really hesitant to stand out, even to acknowledge my own ambitions or share them.

Brett McKay: Yeah, you have this great line in the book that says, “Most existential anxiety in life isn’t about a lack of ambition, but an overabundance of caution.” So the book’s called Wild Courage. What makes wild courage wild?

Jenny Wood: Well, wild courage consists of nine traits that create the bars of an invisible cage that keep you small, that keep you quiet, that keep you following instead of leading. And my goodness, do they raise eyebrows. They are weird, selfish, shameless, nosy, obsessed, manipulative, that’s a spicy one, brutal, reckless, and bossy. And those are not traits we typically think we want to aspire to. So that is the wild piece of it.

Brett McKay: Okay, so your traits of wild courage are weird, selfish, shameless, nosy, obsessed, manipulative, brutal, reckless, and bossy. And what you do in the book is you reclaim these words, which they typically have a bad rap, and you reframe them with new definitions and lay out how they can be used for positive ends. And you say people can use these traits to overcome the three fears you think hold people back. It’s the fear of failure, the fear of uncertainty, and the fear of judgment of others. So let’s talk about some of these traits. The first one is weird. This is all about standing out. Why is learning to stand out such an essential skill and trait to develop if you want success in life?

Jenny Wood: Yeah, well. The world is just too busy and competitive for you to be invisible and make a dent in your career or in your life. So weird is about having the courage to stand out and be authentic, because within your so-called weirdness lie your greatest strengths. So hone every ounce of weird you’ve got. And that might be what I call playing it hot, which is respectfully disagreeing with your boss in a one-on-one, or sitting in the front row of your VP’s presentation, or being the first person to raise your hand and ask them a question. Or actually, you referenced this program I started at Google called, Own Your Career. That was kind of weird. I played it hot. I did not ask for any permission. This was not my full-time job. I ran an operations team that sat between sales and engineering and helped drive billions of revenue for the company annually. But people would come to me for mentorship, and this guy came to me, and he was asking, he was one of the many people who came to me for mentorship, and was asking, hey, how do you navigate entry-level to executive here?

And I was like, okay, let me just scale this. Let me write down 10 tips that made me successful here, everything from navigating politics, to stakeholder management, to influence skills, to getting promoted. And I’ll just put together a quick training. I’m sure that maybe 30 people will come. Well, 2,000 people came to that first training, and that grew into Own Your Career, which was used by 56,000 people in nearly 100 countries. But here’s the thing. I was playing it hot. I was being weird. I was not in HR. I was not in people operations. I just decided to go for it without asking for permission from anybody, or running it up the flagpole, only for it to die in committee of approvals. I didn’t ask HR, I didn’t ask legal, I didn’t ask comms. And then all of a sudden, I was writing emails that went to 56,000 people at Google. So it’s ’cause I played it hot. I just went for it, and I begged forgiveness, not permission. And there are so many smart, talented people sitting on brilliant ideas that never see the light of day, because they’re waiting for permission or waiting for perfection, quite frankly. And they don’t just start and put something out there like 10 bullets on a document, hoping that maybe two dozen people will come, and then it ends up being a lot bigger than that.

Brett McKay: All right, so being weird is about embracing your quirks, sharpening them into strengths, standing out in a good way. It’s all about leaning into what makes you unique. And then playing it hot is a stance towards life where you show up with your weirdness, with boldness, and energy instead of trying to play it cool and blend in. There’s risk with this though, with playing it hot, ’cause people could just think you’re weird in an off-putting way, or you might step on some toes. But the benefits will typically outweigh the risk.

Jenny Wood: Yeah, let me touch on that for a moment, ’cause this is critically important. When I was launching this book, Kim Scott was a big mentor of mine. She’s like, “Jenny, this is your time to beg.” This might fall a little bit more into the selfish or shameless trait, but she’s like, “This is your time to beg.” I had built relationships with a lot of authors and influencers, and I asked maybe 100 of them to help promote the book, whether it was sharing it on social media or on their blog or if I could be on their podcast, or it was actually probably closer to 200, or whether they’d write a newsletter about it. And there was one very, very famous author, and if I said the name, I will not for their privacy, but if I said the name, every single one of you would know it. And this person not only said no, but also ended our friendship and our mentorship relationship, and man, did it sting. I lost sleep over it. This was just a couple of days before a pub date, and it was a time when I needed to not be losing sleep, and it stung.

But if I had used that rejection as an indication to just start playing it cool and not asking for help or not being weird or not shamelessly putting myself out there, then this book would not have been nearly as successful as it has been. And so, even though the outcome wasn’t what I would have wanted, and it really felt like a punch in the gut, and it still hurts to this day, it still hurts to be told no from someone you deeply respect and admire because you’ve played it too hot. But it doesn’t mean that the decision was bad. It was just the outcome that wasn’t ideal. And so, I still carry that play it hot mentality with me because, 80% of the other people said, “Yes, we’d be thrilled to help.” And then 20% said no respectfully. And this was like the one outlier who said no, in a way that was painful for me. But it’s okay, because we push past those painful moments and we keep doing great things.

Brett McKay: Besides playing it hot, another way you suggest you can be more weird is sharpening elbows. What do you mean by that?

Jenny Wood: Yeah. Well, this is an example of when I was at Google, and the most senior leadership team, kind of the equivalent of the C-suite of this org of Google, was meeting in London to decide a reorg and the fates of the people below them. Now, the people below them, myself included, were not invited to London for the actual meetings. But lo and behold, a bunch of us showed up in London to rub elbows. It’s like call, sharpen our elbows to be in the same proximity, to have coffee chats, to be present. And again, if you wanna be invisible, you can, but it’s not going to help your career because being in the same room, if you’re not invited, if you don’t have a seat at the table, bring a folding chair, as they say. But I think just showing up makes a big difference. It’s like the classic line, 80% is just showing up. And it was astonishing who decided to fly to London and who decided to not and what the outcomes looked like. Because politics are real, relationships are real. And again, it goes back to the biggest lie you’ve been told in your career is just keep your head down, your work will speak for itself. It won’t.

Brett McKay: At the end of each chapter, you have a section of what you call trait traps. And this is how the quality you’re talking about in that section can turn into a weakness. And for the weirdness section, you say the trait trap there is when you start thinking of weirdness as being rude, annoying, just obnoxious. So the takeaway for weird is that you wanna be weird in a good way. Just by doing the things that other people aren’t doing, doing things that might be unusual or unusually bold, just standing out from the crowd. But it’s in a good way. You’re not being obnoxious about it. Let’s talk about another trait, and that is selfish. Nobody wants to be known as selfish, but let’s talk about this first. How can selflessness be harmful? I think that’s a good way to start this question.

Jenny Wood: Yeah. Well if you give everybody a leg up at your own expense, you’ll end up getting trampled. So start showing up for yourself. I redefined this as the courage to be your own champion. And even when I was running the, Own Your Career program, I feel like I took my eye off the ball on my core job a little bit, and I was almost over-delegating to the leaders who reported to me. And then, I had one conversation with my manager who was basically like, Jenny, get your eye back on the ball on your core job. And then it even meant that I had to kind of reshift some of the priorities to either peers who I delegated to or direct reports because I had to look out for myself. I needed to maintain a good performance course that I could continue bringing this good work to the world. And it’s tough. It’s tough, especially as a leader, to be selfish and say, my career matters too. But at the end of the day, I deeply believe that as much as your manager is supporting you and your career, they’re gonna put their career first.

And they should, because if we’re not showing up for ourselves, then who is? And for the parents out there, you might say, oh, well, if I were to ask you the question, who’s more important than you? Start showing up for yourself. And if you were to say, oh, my child is more important than I am, but does your child need a martyr who’s exhausted and depleted and hungry and sleep deprived? No, go to that yoga class, go to that golf, Sunday regular session that you do with your buddies, and take the time that you need so that you can replenish and show up for the people in your life in a thoughtful and intentional way.

Brett McKay: So being selfish actually allows you to serve better?

Jenny Wood: Yeah.

Brett McKay: Yeah. So what does positive selfishness look like for you?

Jenny Wood: Well, it’s saying yes to the big and no to the small, at least in a work context, but also in a life context. So what’s big? The Q2 strategy project that your C-suite really cares about. What’s big? Improving customer satisfaction by 12% quarter over quarter. Again, in a work context, what’s small? Being the 18th person to reply all on the happy birthday Jimmy email. Give him a high five when you see him at the water fountain. What’s small? Attending every single meeting where you neither add value nor derive value. And how often do we do that? And what’s small? Being the person who always takes notes in the meeting or always raises your hand to lead the wellbeing pillar. Like, yes, these things are good for community, for culture building. Yes, it’s nice to occasionally plan the company picnic for the summer. But if you did it the last several times, if you took notes the last several meetings, then those small actions constitute what I call nap work, not actually promotable. So avoid more than 10% nap work. Because no one ever gets promoted for being responsive to email. And yes, do a little bit of it.

But if you notice that you’re dialing up to 30%, 40%, and granted this stuff can be easy, it can be simple. Sometimes it avoids the big scary projects of the customer satisfaction increase. But if you do too much of it, it’s just not gonna serve you well. So I say don’t nap at the office because you wanna do the big work that moves the business, because what moves the business is what moves your career. And same thing in your life at home also. Like, what are the things that you need to respond to on a given day and what are the small things you can avoid? And maybe it is not responding to every text that comes in, right?

Brett McKay: Yeah, that nap work, I can see that can be a trap for people in their career. ‘Cause often nap work, it’s easy and it’s concrete and it’s actionable. It’s like, oh, I’m doing something. But if you look at it, it doesn’t really move the bottom line on things. And so, I can see it can put someone in a position where like, I just do so much for the company. No one appreciates what I do, but you’re doing stuff that, it’s nice, but it’s like not necessary.

Jenny Wood: Yeah it invites more work, but it doesn’t invite more responsibility.

Brett McKay: Yeah, so say yes to the big, no to the small. But a lot of people have a hard time saying no. Any advice for people who have a hard time saying no to that sort of rinky-dink stuff because it makes them feel bad?

Jenny Wood: Yeah, so two tools are the agenda avenger and the power postpone. ‘Cause nobody wants to say no, and then feel like a jerk. But there are so many ways you can say no and not feel like a jerk. In fact, I do have a freebie if people wanted it. It’s @itsjennywood.com/sayno. It’s eight scripts tools, tricks to say no to meetings, projects and favors, because we get them all the time and we feel guilty. We don’t have the wild courage to say no. And then sometimes a yes turns into like 20 other yeses. It’s like, can you do this quick thing? Okay, cool. Now can you schedule this thing as a result of it? Oh, we’ve got to reschedule it. Now we’ve got to inform this one person. So one little yes can turn into 20 different yeses. But you can use the agenda avenger, which is, let’s say for example, someone asks you to hop on a call. You could say, I’d love to get a better sense of what you wanna cover. Could you send a quick agenda first?

If you push back, and that’s why it’s the avenger, the agenda avenger. If you ask them for an agenda, they’re gonna have to think real hard if you really need to have that meeting. And by the time they put together that three, five point agenda, they might just realize that can be solved over email. How many times have we been in a meeting that really should have been an email? And then, another one is the power postpone. So I’m planning to take a sabbatical coming up here for six weeks. And so, that’s a natural power postpone where I say, I can’t meet now, but I can meet in about eight weeks. And then, sometimes it just resolves itself. Or if they really, really wanna have that meeting or have you on that project, then they can wait. But oftentimes, it just disappears. And those are two of the eight very practical tools I share with people to thoughtfully say no without feeling like a jerk.

Brett McKay: Yeah, the asking for an agenda, I’ve used that a lot in my career. So I’ll get people who will email me like, “Hey, I got this thing. I’d love to hop on the phone to talk about how we can partner together.” And it’s like, what does that mean? Okay. So I send an email like, hey, this sounds great. What are some concrete ideas you have right now on how we can partner? And then they’re like, oh, I don’t know. Okay, well, once you have some ideas, maybe we can hop on the phone then. But when their ask is kind of vague, it’s like, well okay, I’m gonna have you be a little more specific so we can figure out if there’s actually something here for us to do.

Jenny Wood: Yeah, definitely. Or another version of it is, I’d get tons of people who’d reach out to me and say, “Hey, my nephew would love a job at Google. [laughter] It’s always someone’s nephew would love a job at Google. Another strategy here is yes, if, or yes, when. Yes, we can do that if you put together three job recs that look interesting to you. Or yes, we can do this when you send me your idea of the perfect job or something like that. So again, it’s similar to the agenda avenger. You’re not specifically asking for an agenda, but you’re saying, yes, we can do it if you do this or when you do that. So yes, if, or yes, when, to also see if that meeting really needs to happen.

Brett McKay: Another tactic you have for being more selfish in a positive way is winn. W-I-N-N. What’s that?

Jenny Wood: I love this one. I’m so glad you’re bringing it up. So this is play to winn. What I need now, W-I-N-N, as you said. And this is about being selfish about how circumstances might change. And there’s this wonderful story about a session singer for Pink Floyd named Clare Torry. A session singer is someone who is hired for a very small fee to come in and sing backup vocals or something as part of a track for one individual song for a band. So in London, Clare Torry came in and she was paid 30 pounds to sing these backup vocals for the great gig in the sky on a Pink Floyd album. And so, she collected her 30 pound fee and went home and didn’t even know that the song had made the album until it came out. Well, it turns out that album went 14 times platinum. A little bit more than, and her vocals are legendary. If you know the song, it makes the song. And so, she played to win. She said, what I need now is to sue Pink Floyd and ask for a much significant part of the royalties and a songwriting credit.

And then she was really smart and selfish to do that. And Pink Floyd was smart to settle out of court for an undisclosed sum. So what might that look like for you? Maybe your company has just gone through a reorg or layoffs and you’re now doing the job of two people and you’re overworked and overwhelmed and feel like you’re underpaid. Well, what I need now might be giving yourself the advice that you might give to a friend, which is put together three slides, go to your manager, explain the work that you’re doing, ask for a new title, ask for a raise. And we selflessly say things like, oh, but I’m just happy to have a job. Or, what about Alan and Sarah and Louisa? They’re doing hard work too. What about their raises? Well, being selfish is standing up for yourself. And sometimes what I need now is the permission we need to recognize that it’s okay to ask for something when the circumstances have changed.

Brett McKay: Yeah companies or CEOs, they play to win.

Jenny Wood: Heck yeah, they do. And that’s why they’re so successful.

Brett McKay: Yeah, if they never think, well, we promised this guy this job for a long time. It’s like, well, okay, the situation now is like, we’re losing money and we have to make cuts to keep this company afloat. That’s the situation now. So we got to make the cuts, I’m sorry. It’s not personal or anything. They’re playing to win.

Jenny Wood: Yeah, one of my best managers, Mike, said to me in a one-on-one when I was really being a workaholic and not taking any vacation, he’s like, “Jenny, you are capped out on vacation. When is your next vacation gonna be? I’m worried you’re gonna burn out.” And I said, I know, Mike, I’m just so passionate about this project and this new team. And I just, I love Google so much. And he was like, I think about my saying this and like what a ridiculous, it’s not that, Google’s an amazing company. Don’t get me wrong, but what a funny thing to say to justify me not taking vacation. And I will never forget his retort back. He said, “Jenny, that is great. But I want you to remember that Google doesn’t love you back.” And just like you said, Brett, they’re gonna be selfish. Any organization is gonna be smartly selfish if there’s a financial crisis and they have to have a RIF, a reduction in force, if they need to shift priorities and take a big project away from you, if they need to freeze hiring, if they need to pause promotions or give lower raises or bonuses, they will be selfish left, right, and center.

So you can be selfish too, but there’s this power imbalance. Where we look to our companies or we think that our boss’s boss has so much authority and that we can’t ask for what we want, but the best leaders, the future leaders are the ones who ask for what they want because you’re displaying future leadership skills.

Brett McKay: Are there any trade traps with selfishness?

Jenny Wood: Yeah you want to, with all these traits, be expanding the pie and not re-dividing the pie. So I do advise people to look for ways that are mutually beneficial as opposed to, for example, when I needed to be a little bit more selfish about my career and kind of get my eye back on the ball, if I was going to insert myself more in a project that I delegated to a peer or a direct report, I would think about something else that they could do that would bolster their profile as well.

Brett McKay: We’re going to take a quick break for a word from our sponsors. And now back to the show. All right, let’s talk about shameless and shameless. This is all about leaning into your strengths and not being afraid of showcasing them. It’s all about having some swagger.

Jenny Wood: Yeah.

Brett McKay: What do you think holds people back from promoting themselves?

Jenny Wood: I think that this is the biggest challenge with Wild Courage. I do. I think that people feel insecure. They feel rife with imposter syndrome. They feel like they don’t deserve it as much as somebody else. They feel like they don’t have the skills that somebody else has. But there was a moment in a meeting that I was leading where there were maybe 20 people in the room and this guy came in and he’s like, “This is a shameless plug, but I put together this spreadsheet that might help you.” And he shared it over the group chat. The emojis go flying. The chat explodes. Oh my gosh, this is gonna be so helpful. This is gonna save me 20, 30 minutes every time I need to create this project proposal for clients. And yet he led with, this is a shameless plug. And it’s like, what’s the shame in that? You’re sharing something useful and helpful and a time saver for people. And yet we hesitate to share our wins. And I think one of the most helpful tactics here, is to make it consistent, make it a system. If, for example, you shared every Monday what I call a shameless Monday email with your boss with four bullets, two things you’re proud of that you did last week and two things you’re excited about for this coming week, that is so powerful.

First of all, it makes it a lot easier to put together your performance review at the end of the quarter and your accomplishment bullets. But it also just systematizes talking about your wins and it becomes more natural. It becomes more of an update. There’s huge positive externality of then they might CC their boss. Or if you’re a leader, you could share this with your team and CC your own boss. And then you’re sharing with your team your priorities, which people love to know what their boss is up to that day. So the shameless Monday email can be really effective as you lean into your strengths and not be afraid to showcase them.

Brett McKay: Yeah, that’s a powerful idea ’cause your boss has no clue what you’re doing. He might have a little bit of a clue, but he probably doesn’t know everything. So this just makes it more explicit.

Jenny Wood: Yeah, definitely.

Brett McKay: You also have the power portfolio. What’s that?

Jenny Wood: Oh, I love the power portfolio. So the power portfolio is made up of your power assets. And just like a financial portfolio, you wanna have a mix of soft skills and hard skills or of business skills and people skills like you’d wanna have a mix in your financial portfolio of stocks and bonds. So these are the three strengths you have or the three things that you bring to the table that can move the business forward. So I had a coachee named Martina and she came to me with three power assets. She said, “Mine are communication, organization, and supporting others on launches.” And these were okay, but they needed tweaking because again, we want a mix of business and people skills. So yes, people skills matter, but managers and leaders want to know what business problems you’ll solve, because that’s what their boss is grading them on. So that’s why you wanna diversify your power portfolio and aim for a mix here. So we tweaked it. So communication became executive communication. Organization became project and program management, which she was phenomenal at. And supporting others on launches became go-to-market strategy.

Again, same ideas, different word choice, higher impact, shameless, right? But it’s just being more powerful in your language. And again, like organization versus project and program management does have a very different je ne sais quoi. To me, organization sounds weak. It sounds feminine. Not that that’s a bad thing, but in the context of wanting to show your leadership skills and show more of the value you bring to the customer, project and program management just sounds a lot more powerful. And so, we strengthened them by doing that exercise. But even aside from your specific language choice, a lot of people, don’t know their strengths at all or their talents and can’t articulate them in a bit of an elevator pitch. Like some people might just draw a blank if I say, what are the three things that, often I will say execs draw a blank when I say, what are the three things you bring to your team? And they really have to think about it. So it requires writing down maybe 20 things that you think you are pretty good at, things you’d love to do as a child, things that you’ve helped move the business forward on in the past. It might require bringing them to a coach or a mentor or a boss and triangulating it with other people think, and then you can whittle it down to three.

Brett McKay: And I imagine after you whittle it down to the three, you need to figure out what are some things that, like concrete things I can show, that showcases that I have these traits, be able to show that to people. Hey, I’m great at this thing. Here’s what I’ve done.

Jenny Wood: Oh, absolutely. If you’re talking about these in a resume or again, an accomplishment bullet, preparing for a performance review or promotion, you want to use what I call ROI, not the classic ROI return on investment, though this does give you return on career investment. It’s role, objective, and impact. What was your role in this go-to-market strategy? What was the objective? You wanted to launch the product with 10 million users in the first year. And what was the impact? You exceeded that goal and launched it to 11 million users in the first year. And also double your numbers. In any context, double your numbers. Or even going back to… When I say double your numbers, I mean in that example, I used 10 million. Maybe you could say 10 million by day 90. Use physical numbers. It is so much more powerful. They don’t have to be fancy, like revenue growth percentage or actual dollars. It could be, I cut this email sequence down for onboarding new clients from five emails to three, making it more efficient. Or I’m 70% of the way through the fall athleisure line competitive analysis.

Even just saying, I’m 70%, or I cut this down from five emails to three, has a big impact on showing the concrete, the tangible value that you bring to the table. So double your numbers anywhere you can, whether it’s in your shameless Monday email or a resume or accomplishment bullets or your power portfolio when you’re talking about your strengths in the specific situations with ROI where you demonstrated these power assets.

Brett McKay: How are you being shameless with the promotion of this book you’re doing?

Jenny Wood: Well, a big part of promoting the book is having companies buy the book in bulk. So there are books that are sold one at a time, and there are books that are sold 500 at a time. Because this book is so much about, it’s about wild courage in all areas of life, but there’s a bias toward professional wild courage and really thriving within your company, within your organization, and not saying, hey, go quit your job and be a solopreneur, be an entrepreneur. It’s really helping you feel engaged, feel happy, feel successful, feel motivated within your organization, which companies should love and want to buy. So I think this has the potential to be the kind of book that people buy 500 at a time. So how am I being shameless? I recognize that opportunity, and I sent about 300 emails to leaders, friends, acquaintances, secondary connections, subject line, are you interested in buying 200 copies of Wild Courage? And then I put a bunch of details. I’d happy to do a 20-minute complimentary fireside chat if you did. And I sent the first 100, and Brett, I thought that by the end of the day, those checks would just be rolling in for those bulk purchases.

But as it turns out, the budget is not always there. The timing’s not always right. There was a lot of ghosting, a lot of rejection. So shameless in this context is having the courage to just keep going despite all of that rejection. And this was different than the rejection of the one person who cut off our friendship. This was rejection at scale because there were so many people. I probably didn’t hear back from 90% of the people in that first 100. So what did I do? I tweaked the offering. Rather than 200 copies in the subject line, I put 50 copies. Rather than overwhelming them with too much information about the details of how this partnership could work and me coming to do a fireside chat, I whittled it down to just a few sentences. So you can use that rejection and tweak, dial your shamelessness up and down to what might better appeal to the audience.

Brett McKay: Well, this kind of ties in nicely to one of the other traits of being reckless. Like you’ve been reckless with your being shameless.

Jenny Wood: Yeah.

Brett McKay: Let’s talk about that. What does healthy recklessness look like?

Jenny Wood: Well, it’s the courage to err on the side of action, because better to learn from your mistakes than waste time predicting the consequences of every decision. Think fast and fearless. And if you’re on the fence, do it. And for all of you overthinkers out there, for all of you pro-con list makers and like me, left-brain thinkers who are in a lot of analysis paralysis, just thinking about like, what’s the worst that could happen. Even leaving Google for me took a lot of recklessness. And it was hard for me to get to the point where I knew I wanted to leave. And that was a moment where I felt my eyes fluttering closed when I was driving my son back home from choir practice because I had just taken on too much. I had my day job. I was running the, Own Your Career program. There was all this external interest that was budding about my work, including this book. And I was also trying to be a wife and a mom. It’s like five roles. And I was exhausted. I was struggling with lowercase a anxiety. I was oftentimes up between 2:00 and 5:00 AM. And I just was totally sleep deprived and physically, emotionally, and mentally unwell.

And so, I reached the moment where I felt my eyes closing as I was driving Ari home from choir, that it was probably time to go. But it took me about 12 to 18 months to muster the courage to do it. And that’s ’cause I wasn’t reckless enough. And so, I think I was caught in truths and tales. Truths are facts. They’re verifiable facts. This microphone I’m speaking into is black. I’m holding a piece of paper in my hand. But tales are the stories we tell ourselves to make sense of the facts. And so, part of recklessness is separating the truths from the tales.

And so, I really struggled with that leaving Google. The tales I told myself were, I’m gonna have no identity if I leave Google. Another tale, what if we run out of money and have to move out of our house in Boulder by all the trails that I love so dearly? Another tale I told myself is my parents are gonna be disappointed in me because I’m the breadwinner for my family. But then, when I broke it down to actual truths in that situation, a truth would be, yes, I’m not gonna get a paycheck every other week with the Google logo on it.

A truth would be, I can find other ways to have a new identity. A truth would be, my parents have always supported me and are supportive of me leaving Google as well. So that helps you be reckless when you separate the truths and the tales and really break it down to fact versus fiction.

Brett McKay: So another thing you talk about in this reckless section is this react framework. What’s that and how can that help you overcome failures so you can maintain that bias towards action?

Jenny Wood: Yeah, well, sometimes failures are not big colossal, I lost the project or I lost the deal. Sometimes a failure is just a moment that happens that’s cringeworthy during the day. And we’ve all had those. And one of mine was when I sent an email intended for six people to, I think it was 23,000 people at the time. That’s how big Own Your Career was at the time. And I sent it instead of to the volunteers working on Own Your Career, I sent it to the entire Own Your Career alias. And Brett, this was an unintelligible email. It was just a subject line that was three sentences long with nothing in the body. And it was a testimonial of someone who had said they loved the Own Your Career program and that they’d gotten promoted as a result of it. And so, the subject line was just TT: Atkinson Me, which is the person’s name, but it’s a really unusual name. And then I had typos in the subject line. And this went to 23,000 people, including many in the Google C-suite. So I was mortified. I pressed send and then I slowly dragged the mouse to the unsend only to not get there in time.

And here’s what happened. So React is how I overcame that horrible moment of mini failure. It stands for recognize, empower, apologize, celebrate, and trust. Recognize that not everything you do will be perfect. E, empower yourself to own it quickly and clean it up. Take a deep breath. It happens to everyone. And so, I really just had to put on my big girl pants and say, I can clean it up. I can recover from this. Then I did. A is for apologize. I directly apologized to TT. She was not intending for her feedback about Own Your Career to get broadcast to 23,000 people. C is for celebrate. Celebrate the unexpected goodness that comes out of a mistake. I got hundreds of pings and emails back, and not a single one of them said, you jerk, I can’t believe you distracted me with this nonsensical subject line. No, everybody was checking in on me. Everybody wanted to take care of me. Everybody wanted to help me and empathize with me. And they all said things like, Jenny, I promise nobody cares about this, like you do. Nobody’s paying attention. Everybody understands this. It happens to everyone.

They were so empathetic. So that’s celebrating the unexpected goodness that comes out of a mistake. And that’s also the T is trusting that your fellow employees will have your back. And by the way, the other part of C, celebrate the unexpected goodness is, I wrote up this react framework. I then shared it with the whole Own Your Career alias and said, here’s how I recovered from this mistake. And it ended up being the most popular tip of all time that I had ever sent. So it just goes to show you that you can make lemonade out of any lemon. And that’s the react framework.

Brett McKay: All right. So reckless, just take more action, have a bias towards action, and you can overcome those little setbacks and failure. It’s not a big deal. It’s not gonna be a career ender for you. Another trait is being nosy. And I love this section. ‘Cause you start off that section talking about how your grandmother was nosy and how that probably saved her life during World War II. What happened there?

Jenny Wood: Yeah. So my grandmother was in hiding during the Holocaust in Budapest, Hungary. And she left to get a bucket of water for the other people in hiding with her. And she walked down the street and somebody from the Arrow Cross Party, which was sort of the Nazi equivalent ruling party in Hungary, rounded up her and some fellow Jews at gunpoint. And they marched them to a building and they had them against a wall. And my Bubbie, my grandmother, I called her Bubbie, knew that there was no getting out of this. She was doomed. The options were, basically she was gonna get marched onto a train and taken to Auschwitz, like so many other people had, or she was gonna have a summary execution and get shot right there against the wall. And there were literally dead bodies in the street when this was happening, as she told the story to me, in Hollindale, Florida at the age of 93, when we were recording her Holocaust survival stories. And her only option, she told me, was to get nosy. And so, she asked the soldier, this scared, terrified, timid soldier, a question.

And she asked, what would happen if I were to step out of line? And she wasn’t necessarily looking for the answer. She was looking for his reaction. And he answered with the Hungarian idiom, which I will translate to English, which equals, is the mademoiselle so stupid or just pretending to be? And it was a little bit of a jokey answer. She saw a lightness in his voice. He almost cracked a smile. And she really saw his nervousness. And it made her realize that she had a small window here to step out of line, because he didn’t yell at her. He didn’t hit her with the gun. He didn’t cock the gun. And so, just by being nosy, having the wild courage to ask a question, it was the only way she was able to survive that scrape. So she stepped out of line and started walking down the cobblestone street. And she said she remembered hearing the click of her heels every time she took a step as she just kind of slowly breathed in and breathed out and hoped that nothing would happen. And it didn’t. And she returned back to the attic safely. And so, she really only survived because of her nosiness, because she had the courage to ask a question.

Brett McKay: So this is all about asking questions, what it means to be nosy. Why do you think people have a hard time asking questions in their career?

Jenny Wood: We think it makes us look stupid or uneducated or unknowledgeable. Or think about how many times, for those of you who work in an organization that has a ton of acronyms. You think, oh, well, it’s too late. I’m already in this role for four months. I can’t ask that basic question. I can’t ask that simple question again. But nosy is the courage to get insatiably curious because curiosity drowns out fear and pulls you toward what is most exciting to you. So use it as a compass. And curiosity shows leadership, it shows ambition. It’s a great way to overcome nerves at a networking event rather than feeling like you have to impress somebody. Go ask them a bunch of what and how questions like, what was the most interesting session for you so far? Or how long have you been in the industry and what brought you here? Or how have your peers been responding to these sessions? Or how are you using AI right now? What and how questions are so powerful and they take the pressure off of you in any kind of new relationship or networking situation or a meeting with a mentor where you feel like you’ve got to be all buttoned up and prove yourself.

Just start asking and start listening. And even the best leaders, going back to the person who’s a few months into the role and they’re like, oh, I’m too far in to ask what that three letter acronym stands for. But the leaders who we admire most are the ones who have the confidence, the shamelessness, the boldness, the recklessness to say, “Hey, what does PRT stand for on this slide? I just wanna make sure that for everybody in the room who’s new, we redefine that.” And everyone sighs a sigh of relief that somebody finally, had the boldness to redefine that acronym of the thousands that are used at the company. And when it’s a leader who does that, I really admire it.

Brett McKay: You also talk about how you can use nosiness or asking questions to turn envy into a springboard to success. What does that look like?

Jenny Wood: Well, we’ve all got those people in our life who we’re jealous of. It could be a friend, it could be a colleague. And I say use envy as your engine and steal their blueprint. So, there was someone named Molly who I just deeply admired. She was a peer of mine. We were always competing for promotions and I always thought she was three times as good as I was. But instead of being jealous and having it create a scarcity mindset for me, I thought of it as an abundance mindset where I could learn from her. I could get deeply nosy and I could kind of discover her recipe for X, Y, Z skills. So she was really good at project management. And anytime we were launching a new program, she would have this awesome Gantt chart, which had all of the dates and the accomplishments that needed to happen over a six-month period of time. She was really good at communicating next steps. She was really good at delegating. She would bold the person’s name in each email and put a deadline for what needed to happen next. She would thank everybody and be very positive and empathetic.

And so, rather than just be jealous and say, oh, why am I not good at Molly? Like I resent her. I just went to her and I said, Molly, could I do three 20-minute sessions with you where you review some of these project management skills with me and I can basically steal your blueprint? And I would write down these things on an index card and I would put them by my desk and I would use her strategies. Or I did this with another manager, Ted, who was just such a phenomenal presenter and never said, um, in his presentations. And so, then I would gamify it for myself and I’d say, I’m gonna count how many times Ted uses um, in a 10-minute presentation, and I’m gonna try to beat it. So again, rather than being jealous, I used envy as my engine and I would steal their blueprint. And that is rooted in being nosy. It’s being curious versus jealous.

Brett McKay: This reminded me of Plutarch, the famous Roman biographer, philosopher guy. He talks about two types of emotions. There’s envy, where you see someone who’s better than you and you just feel bad and you wanna bring them down. And then he says, “The opposite of that is zeal.” It’s where you admire someone’s excellence and then you wanna imitate it.

Jenny Wood: I love that.

Brett McKay: So curiosity, being nosy can lead to zeal instead of envy.

Jenny Wood: I love that.

Brett McKay: I really like that.

Jenny Wood: I love that.

Brett McKay: Let’s talk about being manipulative. You had an instance where you used manipulation on a past AOM guest, and that’s Vanessa Van Edwards. She talks about charisma. How did you manipulate Vanessa into helping you achieve one of your goals?

Jenny Wood: Yeah, well, I really wanted to meet Vanessa. We haven’t talked about obsessed, but I’m obsessed. I wanna meet the best people. I wanna do the best work. I wanna help people in the most high-impact way. And I knew that part of that was building those relationships with authors so that I could partner with them around time of book launch, and also just learn from each other and enjoy each other’s friendship and mutual value exchange. So I was headed to Austin for some work meetings. Someone had just introduced Vanessa and me over email. And so I said, I’m gonna be in Austin Thursday through Sunday. I would love to take you out for coffee. And she said, “Oh, what are the chances? I’m actually gonna be out of town those exact dates for a keynote.” And so, I think a lot of people would just take no for an answer and be like, okay, another time. And of course, another time never comes. But I wanted to capitalize on this opportunity. So I said, what time does your flight depart on Thursday?

And she said, “It departs at 3:00 PM. Well, my flight was scheduled to get in later than that. But a quick little switcheroo flight change and $60 to Delta Airlines had me coming in before her flight so I could meet her. And I said, what are the chances I get in at 1 O’clock? And so, what if we met right by your gate for coffee? So, did I lie? Yeah, sure. Liar, liar, pants on fire. But I will stand behind that lie all day long that I wasn’t actually originally getting in at 1:00 PM. And maybe I even said I was getting in at 1:00 to just make sure it worked for her before I made the flight change. So I think I actually did lie about the time my flight landed before I made the change. But I tell you, $60 to meet Vanessa Van Edwards in person, it’s a bargain at twice the price. And so, we feel like everything has to be coincidental or just has to work out or fate. But man, I just believe that serendipity isn’t found, it’s made. And manipulative reclaimed is the courage to build influence through empathy and to build lasting relationships.

Because whether you’re selling a product, an idea, or yourself, the ability to end friends, allies, and supporters is all about mutual benefit. So figure out what people want and go get it for them. In fact, something happened this morning where I got an email from the person who ran the PR campaign for the book. And she said, actually, I got an email a couple weeks ago, but I totally forgot to respond to this. It said, hey, would you be willing to write a testimonial for me on LinkedIn? So I would call that nosy, right? That’s great. And then I forgot to respond because I’ve had a lot going on. And then she followed up. I’d call this bossy. She said, “Hey, I hate to nudge you, but I’d really appreciate this review on LinkedIn. Any chance you could do that?” And so, what I think would have made it even more powerful, is if she’d been manipulative and said, “And by the way, I’ve drafted a couple sentences for you that you can tweak as you see fit.”

Because when I talk about manipulative and how it’s all about finding mutual benefit and figuring out what people want and getting it for them, what I want is time back. So I love doing favors for people, but they take time. And so, had she been manipulative and said, “I’ve already written it for you.” That gives me what I want, which is time back and makes it a lot easier for me to say yes. So I did say yes, but now I have to do the work. And it’s still something I have to add to my to-do list. So that’s where manipulative can be such a good thing and win-win and expand the pie, whether you’re changing your flight to meet somebody because relationships should be high reward, but also high investment, or asking someone to do a quick favor for you, like my PR person did today.

Brett McKay: Yeah, so being manipulative, it’s all about just being influential. That’s what it’s all about. And your definition of just being influential is like, thinking win-win, finding out how you can get what you want and need, and while at the same time delivering what someone else needs and wants. It reminds me of this famous quote from Dwight Eisenhower about leadership. And he said, “Leadership is the art of getting someone else to do something you want done, because he wants to do it.”

Jenny Wood: Oh my gosh, that’s so beautiful.

Brett McKay: Manipulative, but that’s just leadership. That’s being influential.

Jenny Wood: Yeah.

Brett McKay: Yeah. So last one, you talked about obsessed. You’re obsessed with meeting Vanessa Van Edwards. That’s another one of your traits of wild courage. What does positive obsession look like?

Jenny Wood: Well, it’s pushing, persisting, performing, because frankly, none of these traits will serve you if you don’t learn to deliver, not for some company, but to achieve your own ambitions. So obsessed for me was, I wanted a job at Google in 2006. I was bright-eyed and bushy-tailed and I submitted my application online having no clue what the job was that I submitted it for. But I discovered there was maybe sort of possibly a formatting funkiness when I uploaded my resume. And whether there was or wasn’t, when I didn’t hear back from Google, I used that as an opportunity to print out that resume on a piece of paper and hop in my mom’s 10-year-old Honda stick shift and drive to the Google office and sit there on the couch until someone came out and talked to me. And I remember the receptionist, it was a shared office space, was like, no, it’s not really protocol for Googlers to come out and talk to you. You can drop the resume here. And just like firm as a tree rooted to the ground, with my smile kind of like, cheeks quivering as I kept that smile on.

I was professionally persistent and said, oh, it’s okay, I’ll wait. I really do need to talk to somebody because there was a problem with my resume. There’s this study that says, people defer to because. It was a study about people standing in line to make Xerox copies and someone from the back went to the front and said, “I need to go to the front of the line because I need to make copies.” Just because they said the word because, they were more likely to be let into the line, even though of course, everyone was there to make copies. But the research suggests that people defer to the word because X, Y, Z. So I said, because there was a problem with my resume, I need to speak to someone. And eventually someone named Elizabeth came out, and I talked a little bit about how I had just come back from working abroad and backpacking through South America, which I understood were very googly skills or things that people did to be kind of well-rounded and global citizens. And then, then and only then, did I hear back from Google once I showed up.

Actually, not even then. I didn’t hear back. I didn’t get her business card. And then I tried every single permutation and combination of first initial, last name, first name, last name, just last name @google.com. Her name was Elizabeth Kelleher. So I emailed E. Kelleher, Elizabeth Kelleher, Liz Kelleher, [email protected]. And then finally, I found the right combination. And when I followed up, then I heard back. So that is my flavor of obsessed. And it’s okay to be obsessed. It’s okay to stick your neck out. It’s okay to show that you want something deeply, because people like enthusiasm. People like energy, people like positivity. And that’s what I was trying to show, because it didn’t work just submitting my application online. Silly protocols and rules are there to deter the deterrable. But I just decided I was gonna be undeterred. And I got the job. And here we are almost 20 years later.

Brett McKay: Yeah. You got to play it hot. Don’t play it cool.

Jenny Wood: Yes. Definitely.

Brett McKay: So we’ve talked about these different traits. Is there one you think that people would get the most benefit from working on or like the one that people struggle with the most that if they started working on today, they’d see a lot of ROI? .

Jenny Wood: I think shameless. I think there’s just a lot of change in the world right now, a lot of economic uncertainty, a lot of change with, the onset of AI, a lot of layoffs, a lot of reorgs, and that’s hard. There’s this moment where my husband and I were living with my grandmother on her pullout couch in Manhattan while we were job hunting. And John shared some unfortunate news. We sat down to dinner. He said, “I’ve been part of a major company restructure and I got laid off today.” Well, I’m crushed as a newlywed, but I look across the table at Grandma Lila, who was like, a total spitfire at four foot 10 and 90 pounds. She was not just shameless. She was unstoppable. And she said, “John, no is just an opening offer. Don’t sign the paperwork.” And John and I look at each other trying to silently communicate what we’re thinking. And then finally, John sighs and says, uh, I think a layoff is like a one-sided thing, Grandma. They say, you don’t work here anymore. And I say, okay. And that’s when Grandma Lila sighs and says, “Well, sure, it would be more comfortable to take no for an answer, but don’t let fear shape your decision, don’t let shame shape your decision. You both want something, right? They wanna get stuff done, even though they can’t afford to pay you. And you want a job because it’s easier to get a job when you have a job.”

So finally, John relents. And the next day he goes to his VP and he half-heartedly offers to stay on for 10% time and pay, while he job hunts. And shockingly, they accept. Now, I’m not sharing this as some influence tactic per se. The point is Grandma Lila’s lesson. Don’t let fear, don’t let shame shape your decisions. Get shameless.

Brett McKay: Yeah, and it worked out for your husband, ’cause he got some time off. He had a little money to live on, kept his benefits. And then a few months later after this crisis that this company was going through, he kind of abated. The company hired him back full time. And it was all because he’s willing to do something we think of as a bad thing, to be shameless. He had to be uncomfortable and ask for something that apparently wasn’t an option. Well, Jenny, this has been a great conversation. Where can people go to learn more about you and your work?

Jenny Wood: Well, the book’s available anywhere. Electronic, e-book, audiobook, hardcover, Amazon, anywhere books are sold. And then you can find me on itsjennywood.com. And I love helping organizations with keynotes. I love helping execs through one-on-one coaching. I do some small group coaching. And I would love to be in touch and help you find your wild courage wherever you are and whatever you are chasing.

Brett McKay: Fantastic. Well, Jenny Wood, thanks for your time. It’s been a pleasure.

Jenny Wood: Thank you so much, Brett.

Brett McKay: My guest today was Jenny Wood. She’s the author of the book, “Wild Courage” It’s available on amazon.com and bookstores everywhere. You can find more information about her work at her website, itsjennywood.com. Also check out our show notes at aom.is/wildcourage, where you can find links to resources and we delve deeper into this topic.

Well, that wraps up another edition of the AOM Podcast. Make sure to check out our website at artofmanliness.com where you can find our podcast archives, as well as thousands of articles that we’ve written over the years about pretty much anything you can think of. And if you haven’t done so already, I’d appreciate it if you’d take one minute to give us a review on the podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always, thank you for the continued support. Until next time, it’s Brett McKay. Reminding you not just to listen to the AOM Podcast, but put what you’ve heard into action.

This article was originally published on The Art of Manliness.