Jay Papasan:
What if I told you that in order to be successful, you needed to be weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, and bossy? Well, that’s what my friend, Jenny Woods, is actually going to tell you. Jenny started out at Google at an entry level, and then built an amazing career over 18 years becoming a senior executive there. And she also led their career development.
And her book, Wild Courage: Go After What You Want and Get It, is all about tapping into those nine traits, like being bossy and being nosy, but actually turning them into positives that we can actually use for greater success. And this is not just in the workplace. This is as entrepreneurs and self-employed people as well. She’s just got years and years of wisdom and lots of practical application.
So, we’re gonna dive into the interview, but really quickly, I’m gonna give you kind of the overview of the traits that she’s talking about and also explain it because we just dive into the conversation. So, weird is kind of code for be authentic, be yourself and be okay being yourself. Selfish, it means that you have to kind of advocate for yourself. Nobody else is going to. As we would say in The ONE Thing, put the oxygen mask on yourself first. You’re gonna be shameless. You’re gonna know your value and promote yourself.
Obsessed, you’re all in. Nosy, insatiably curious. Manipulative, that’s the hardest one for me to say in any kind of positive light, but it’s about tapping into the power of influence. Finally, brutal, hold your standards, reckless, right? We’ve got to have a bias for action. And bossy, you’re going to lead others.
So we’re going to mention some of these. And really quickly, we’ll also start going deeper and kind of tell you what they mean in context. So, I hope you enjoy it as much as I do. Here we go with Jenny Wood.
I’m Jay Papasan, and this is The ONE Thing, your weekly guide to the simple steps that lead to extraordinary results.
So, Jenny, I think probably everybody does this when they read your book. There’s nine traits. They’re all a little provocatively titled, but about halfway through, I went back and I started scoring myself.
Jenny Wood:
Oh.
Jay Papasan:
And I was like, “Where do I have an opportunity to focus? And where am I already good?” And so like I self-assessed myself as, “I’m probably really strong, unobsessed or nosy. Not quite sure which one’s the leader.” But when you think about you, when you went through these, what do you think is the trait that kind of has led you to more success? Is there one that singularly stands out for you?
Jenny Wood:
That’s like asking me to pick my favorite child but-
Jay Papasan:
Yes.
Jenny Wood:
But for today-
Jay Papasan:
In the moment.
Jenny Wood:
In the moment, no less, today, I would say that I think that shameless has helped a lot. Being confident and being proud, like having the courage to stand behind my efforts and abilities and share this book with the world, share my Google leadership and all of that experience with the world. And then, I will also share the one that I would score myself the least, which would be reckless, the courage to err on the side of action and take calculated risks, despite the fact that after 18 years, I just left Google to go bet on myself.
Jay Papasan:
There you go. But I mean, I wonder if you look back, like, “I could have done that three years earlier,” or whatever, but is that economics you studied and then maybe engineering as well?
Jenny Wood:
Economics and international Business. Always a-
Jay Papasan:
International business.
Jenny Wood:
Always a left-brain thinker, always a math person, a pro-con list, always in some kind of analysis role.
Jay Papasan:
But when I think about the people who show up at our door, a lot of them, we could say there’s either dreamers who need more space to do, or doers who need more space to dream. And there are people that kind of fall in that middle that they actually can take action, but they can be very perfectionistic. So, getting out of the gate is just the hardest part for them.
Jenny Wood:
Yeah, absolutely. And that is the reckless trait, actually. It is. And I would call myself a doer who needs more space to dream. But maybe with this shift in my career, going from Google, which was a very high execution role to being a creative and being an author and, now, a keynote speaker and consultant to companies, I would say that it’s helping me tap into the dreamer a little bit more. It’s because I’m leveraging the nosy trait, because I’m getting nosy about what else is out there for me and how can I most help people? How can I leverage my strengths to add the most value to organizations and teams and leadership groups?
Jay Papasan:
Before we came down, you were sharing what you’re considering and what would you do if you were me? Like, yeah, you’ve got that trait in spades because you’re in a transition right now And I’ll try to make it an effort, people who haven’t read the book, definitely read the book. But so, like, shameless, when we talk about that, it’s your willingness to promote your own work, right? To stand behind your product and to value it. And a lot of us devalue our work, we undercharge for what we do.
Jenny Wood:
All the time.
Jay Papasan:
The imposter syndrome shows up, and that hits so many people. Like, I think imposter syndrome is far worse than any competitor you’ll face.
Jenny Wood:
Oh, absolutely because, oftentimes, what stands in our way of going after what we want is not money, or luck, or skill, or talent, or connections, it’s your fear, right? It is the imposter syndrome. But that’s actually such great news because whether it’s fear of failure or fear of uncertainty or fear of judgment of others, when fear is the root, that means that you have agency to push past the fear, right? Because it’s an internal struggle.
So, you can push past the imposter syndrome, you can push past the fear. And that’s such great news, because that means that if you’re able to push past it, then you can realize the joy and the success on the other side of that fear. So, it’s kind of cool if you think about it. Of all the things in the world you can control, you can control your own fears when you have the wild courage to close the gap between what you want and what you achieve.
Jay Papasan:
I love it. I also think of fear as signaling, “This is important to me.”
Jenny Wood:
Yeah, it’s a compass.
Jay Papasan:
You don’t feel fear around things that don’t matter to you. That also signals like, maybe this is something that’s worth exploring my courage around, right? I can go find my wild courage. If I have fear, that means there’s something on the other side worth seeing.
Jenny Wood:
Absolutely, yeah. And gosh, I’m gonna butcher it, but I read something yesterday that was like, growth requires being uncomfortable and being uncomfortable leads to growth or something like that said better than how I just said it.
Jay Papasan:
Early in my career, I get the privilege of having a self-made, kind of, billionaire for my mentor for all these years. And I don’t know if you bumped into the founders of Google in your 18 years or not.
Jenny Wood:
I did actually.
Jay Papasan:
They can be very direct. And I guess we can get to that trait later. I won’t just go off ADHD here on you. But he would just say, “Jay, if you really wanna get ahead, you need to get comfortable being uncomfortable.”
Jenny Wood:
Yes.
Jay Papasan:
And I don’t know, I’m sure there’s a million self-help gurus down the line, but it’s just so true.
Jenny Wood:
It’s so true.
Jay Papasan:
Everything we want is outside of our comfort zone. And if we can get comfortable going there more often, getting a little reckless, or if we’ll get down that path, that really helps us. So, awesome, thank you for picking the one right now, shameless. And that’s one, if it’s serving you right now, I shared that a lot of our people that listen to this podcast are self-employed, right? Maybe they’re consultants, they’re architects, they’re attorneys, maybe they have a small business, whatever. And learning to kind of promote your own work is a skill.
And that’s one of the things I loved about your book. They’re called traits. And we tend to think of traits as being innate things. But you turn them all into skills and frameworks. So, I didn’t prep you for this, but I love the framework around power assets. Is it a power asset or power portfolio?
Jenny Wood:
It’s both. Your power assets are the three things that make up your power portfolio. And just like your financial portfolio, you want to have a mix of assets there. You want to have stocks and bonds. And the mix that I encourage you to have is some business skills and some people skills. So, for me, my three power assets are people leadership, influencing stakeholders or customers, and building things from startup to scale.
But it took me time, Jay, to identify those, to kind of whittle it down from a list of 20 things I enjoyed or felt like I was good at or various strengths, but also expand it from kind of being like a deer in headlights when an interviewer, or a customer, or my boss’s boss would say, “Well, Jenny, what do you enjoy doing,” and not staring at them with a blank stare. So, I encourage people to think about what are your three power assets that you bring to the table? And when was the last time you shared those with your customers or with prospects, whether it was to gain a new customer or to upsell or to continue to strengthen a relationship?
Because people want to know what you’re good at. And I always wince when someone says, “This is a shameless plug but…” You know, like at Google, that happened once in a meeting. Someone said, “This is a shameless plug, but I put together this spreadsheet that’s going to save you 30 minutes when you do XYZ project.” And like, what’s the shame in that? You know, it’s really about standing behind, like, what are those power assets and sharing them with the world because people want to do business with people who are confident.
Total non-business example, but we were hiring a nanny/house manager and she wrote on her application, “I’m an exceptional cook.” And I was like, “What a cool thing to write,” but how often would someone come up to you and say, “I’m exceptional at ABC thing”? Guess what? I hired her. And of course, you have to have the goods to back it up. But like the confidence she showed, the creativity, the swagger, right? People believe what you say.
And so, I think recognizing that we don’t have to be self-deprecating, we don’t have to undermine our value, we don’t have to undermine our talents, and that we can actually shout them from the rooftops and say I am proud that I’m an exceptional cook, or real estate agent, or painter, or architect, or accountant. People want to know what you have to offer the world and they wanna do business with you.
Jay Papasan:
You just gotta get practice in. And I think, like, you used real estate agent, we have a large real estate crowd, obviously, coming from the largest real estate firm. And there’s like 1.2 million of them out there. And like, it’s a joke. Like, you get pulled over in California, you don’t have your drivers license. Do you have a real estate license? Like, there are places where there are just so many people who have them. And the thing is, how do we differentiate yourself?
And so, when I was reading about the power assets, I was thinking in the power portfolio, now that I know, actually, they’re both right, I was like, I was thinking from the term of entrepreneurship, like, what makes you different than all of the other agents? What makes you different than all of the other attorneys? Like professional services, what’s your differentiator that makes you special?
Jenny Wood:
Yeah, the thing is the bar is so low to be just 1% better than your competitor. Because nobody is doing this or people are too nervous or too fearful or too shameful to do this, if you are just one step ahead of your competitor by sharing your power assets with your customers or your prospects or your partners, you are gonna get so much more business.
An example, I grew up in the corporate environment at Google from entry level to executive, but I would say under 10% of leaders who reported to me at Google or my indirect reports or their teams would know their power assets or would send what I call the Monday manifesto, the Monday email that says, “Here are two things I’m proud of from last week, and here are two things that I’m excited to work on this week.” But when people sent that to me, or they would talk about it with me in a one-on-one…
Jay Papasan:
Your Monday manifesto?
Jenny Wood:
Monday… well, it’s a mini-festo, not a manifesto, because it would only take 15 minutes to write. I also call this the Shameless Monday Email. But it’s like there are so few people who are regularly going to their customers and saying, “Here’s the win I had,” or the weekly email that talks about what they bring to the table, or some new properties they have, or whatever it is. It’s like we think everybody’s doing this. 90% of people are not doing this. So, if you can be the one who has the confidence, the wild courage to do it, you will differentiate yourself with very little effort. We’re talking 15 minutes a week.
Jay Papasan:
All I can say is, as someone who manages a lot of people, too, not at the scale that you probably did at Google, when you get emails from people in your group, most of the time, I think that I’m about to either hear about a meeting I’m going to have to attend or a problem I’m going to have to participate in solving. If someone just is dropping in, “Hey, a couple of wins from last week,” that becomes like a breath of fresh air.
Jenny Wood:
It’s amazing. And the thing is people feel like, “Oh, well, I don’t want it to be, ‘Oh, look at me,’ or I don’t want it to be too bold, or maybe it’s, again, too shameless,” right? But as a leader, we know, and again, think of this, what your customers might feel if you’re a solopreneur, or an entrepreneur, or self-employed, it is a breath of fresh air. It is helping them solve a problem. As leaders, we’d hear about a win from a customer or from a team, and we’d be super pumped, like, “Oh, great. This is something that I can bring to my boss,” right, or something that moves the ball down the field. But I think we misinterpret thinking like, “Oh, I don’t wanna be boastful,” or “I don’t want to shout my winds from the rooftop,” or “That looks obnoxious.”
Jay Papasan:
What does that even come from?
Jenny Wood:
I don’t know.
Jay Papasan:
What does that even come from? I know we think about, is there some Jimmy Stewart movie about the humble leader that we’re all now imitating from 70 years ago?
Jenny Wood:
I think what it could be is evolutionary psychology, where back in the caveman days, you didn’t want to stick your neck out, you didn’t want to stand out because the pack was there to protect you. So, staying small, staying quiet, staying safe meant protecting yourself from being the lion’s lunch. If you were the one to be more vocal or to roar too loudly, then you might call the attention to the saber-toothed tiger bounding around the corner.
But the world was just a little bit bigger than those communities back in the caveman days. Now, it’s 8 billion people. The only way that you’re really gonna make a dent in this giant interconnected world is to boldly stand behind your efforts and to share what you have going on.
And I’ve made the shift from corporate leader to entrepreneur now. And I tell you, this eat what you kill environment is totally new to me. I’ve never felt more imposter syndrome, but I’ve had to get nosy, right? I’ve had to… like when I was putting the book out, I sent emails to 300 leaders, and subject line, “Would you like to buy one to 200 books in bulk of Wild Courage? And could I come in and do a 20-minute chat as a thank you with your team, or a Q&A, a fireside chat.” Thinking, “Oh man, I’m just going to get so many responses. My inbox is probably going to crash because of all the people who say yes and all the checks that are written waiting in my mailbox.”
Turns out, not quite that easy when you’re an entrepreneur, but you just keep putting yourself out there. And then you get nosy about, “Okay, how can I tweak this?” So, when I wasn’t getting the response rate that I wanted, I changed the subject line. “Would you like to buy 50 to 75 books instead of 100 to 200?” Or maybe my pricing was off, maybe my positioning was off. And then, some people ghosted me, which was a terrible feeling. And some people flat out said no. And it’s hard, but you just have to push past the rejection because, like I said, the joy and the success is on the other side of that fear of “Nobody likes me. Nobody’s interested. How am I going to differentiate myself among all the other competitors in this space, in the industry, etc.?”
Jay Papasan:
Well, you’re leading towards one of my favorite parts of the book. So, I was kicking around, what are the traits that I feel have the most overlap with The ONE Thing? And so nosy keeps coming up. And there’s something about when you’re reaching out maybe to a customer, maybe to your boss, maybe to a stakeholder, you have this woo with you. And again, I may go crazy on your frameworks, but you have so many of these. How many years did you teach this career development program in Google?
Jenny Wood:
So just the last three or so years that I was at Google. Yeah, I started-
Jay Papasan:
Okay. I feel like there must have been a lot of reps because every chapter has these little frameworks. So I love it.
Jenny Wood:
Yeah. Well, all of this is brand new material for the book. Like this is… it’s all based on years and years of experience, nearly two decades at Google. But yeah, I love coming up with frameworks, because that’s what helps me the most. So, Woo With You is how you can get nosy about what your customer, or your partner, or your client wants.
So, if you think about an email that you write, because we do so much of our influencing, or we try to over email, it’s rare that we get to sit here face to face and have a conversation. So, think about how many emails you write each day to try to get someone to say yes to you, or to buy from you, or to partner with you, whatever it is.
So, next time you sit down to write an email and you’ve drafted it, count how many of your sentences start with the word I, and how many start with the word you. And I want you to flip as many as you can from I to you. That’s woo with you. Because when you’re getting nosy about what’s in it for the other person, you’re much more likely to build that relationship, to find some value in it for them in a way that expands the pie and allows you to both win.
So, for example, I was doing a keynote for an organization and I wrote my first draft. “Thank you so much. I had a great time doing this. I love the gift box that you sent to me. So, thank you. I am building a new leadership training, and I would love to partner with you to try that out.” And then, I read it and I was like, “Oh my gosh, I have to woo with you. Let me flip them.”
So, I flipped as many as I could. “You sent the most delicious gift box. You and your team were an incredible partner to work with. You might benefit by testing out this new leadership training for your managers.” And that helps them see what’s in it for them. And it just is lovely to read a note that’s more about them than about me.
Jay Papasan:
Your audience was so attentive and receptive. I just like playing that game, flip the I to you. It’s such a simple thing, but it changes the whole frame of the conversation and makes it feel differently.
Jenny Wood:
Absolutely.
Jay Papasan:
I love that. All right. So, we’re about the midway point. Let’s just take a quick moment to break. If people need it, pause and move to the next stage of their day, and then we’ll circle back.
Jenny Wood:
Great.
Jay Papasan:
All right, welcome back, folks. So, here with Jenny Wood, and we’re chatting about nosy. And so, I love the Woo With You framework you discovered for us. I was looking at nosy in general and why I thought it matched The ONE Thing. It’s just about the power of questions. And it’s not always the questions we always ask others. It’s sometimes asking ourselves, like, how did they do that? What’s happening here? And there’s a curiosity. And if we show up with curiosity, and we start there, it’s amazing where we go. So, how would you sum up nosy for folks, just so they know?
Jenny Wood:
Sure. Nosy is the courage to dig deeper. It’s getting insatiably curious and letting that curiosity be your compass and helping you find your one thing, right? Like how it’s all about your focus. And how do you even find that focus if you’re not curious about what all the opportunities are there for you?
So like, let’s say that you find somebody in your industry who inspires you. You mentioned you had a mentor that kind of, you know, you learned so much from. My guess is that when you started, a lot of people, when they think about having someone who they follow or someone who mentors them, it’s like, “Well, what am I going to bring to the table? How could I possibly, at 27 years old, offer them anything? Why would they waste their time on me?”
Well, here’s a way to push past that imposter syndrome. Spin the spotlight. Take the spotlight off of you and what you can offer them and focus on people in leadership positions love to share. They love to teach others how they got there. They love to lift as they climb. So, it takes so much pressure off if you go into that mentorship meeting and say things like, what and how questions, never yes or no questions, yes or no questions, close off the conversation. What and how questions are so much richer. They give you so much more backstory. They’re so much more interesting.
So, some questions you could ask a mentor or someone you admire, what was the biggest struggle in your career? Or how did you overcome this challenging client situation? Or how have you found the industry changing over the last 10 years? Or what’s the worst advice you’ve ever been given? That’s how you get nosy in a way that you can really learn from someone and go deeper. All of them started with what and how.
And the best leaders will exemplify this also. Again, feeling insecure, the younger people in an organization like Google would never be the one to raise their hand and say, “What does that little acronym stand for on that slide?” But the leaders who were always the badass leaders would ask those questions, they’d behold the brilliant basics, that they were nervous that they were almost making everybody else feel comfortable in the room. So, they, as the leader, would be the one that says, “Hey, just to make sure everybody in the room understands, what does this acronym RTO stand for?”
And then, everybody kind of sighs with the relief in their chair that someone had the wild courage to ask that question. And the fact that it was the leader, at least these were the leaders I admired most at Google, it shows you that like there’s so much power in asking the questions. And of course, these leaders were doing it on the behalf of everybody else who was too fearful to ask.
Jay Papasan:
I’ve done that many times, and I’ve done it completely selfishly.
Jenny Wood:
Oh, yeah, sometimes-
Jay Papasan:
Just because I can’t stand not knowing. And what shocks me is how many other people, like, in an executive meeting, the new CEO throws out this acronym, and I’m like, “I’m sorry.” And, like, I usually roll out. We used to say, out behind the barn when we were lost as kids. Mississippi family. I’m out behind the barn. I’m completely lost. And I’d be like, “I’m sorry, I’m out behind the barn. What does that mean?” And then, I realized nobody else in the room did either.
Jenny Wood:
Exactly. And that makes you a strong leader, because you have the courage to ask the question that everybody else is too scared to ask. You have the courage to dig deeper, to get insatiably curious, right? And, you know, that’s the thing about wild courage is it’s like successful people take these actions before they have permission, essentially. And so, those are the leaders that we admire.
And the fact that everybody else sighs with relief saying, “Thank you, Jay, for being the one to ask the question. I didn’t know either,” that is the sign of wild courage. That is the sign of a strong leader, someone who feels like they can ask the question without permission from somebody else.
Jay Papasan:
I’ll just say, like, again, like, I wasn’t doing it to be a great leader. I just had to know. So, this is one where the urge overcame things, but I’ll own it if that helps me be a greater leader.
Jenny Wood:
It does.
Jay Papasan:
Because I want everything that comes naturally that I can have there.
Jenny Wood:
It sounds like a chicken-or-an-egg dilemma, right?
Jay Papasan:
Yes, yes, yes, yes.
Jenny Wood:
Or it’s like that is probably the trait that got you to where you are and vice versa.
Jay Papasan:
But I love the asking, like showing up, and asking whoever your boss is, showing up with curiosity. They have so much to teach us. And in the path to doing that, they will teach us how to think, and probably show us how to serve them as well. Like, there’s so much gets unlocked from those conversations.
Jenny Wood:
Yeah, definitely. And another way you can use it is like everyone’s been jealous of a competitor, of a colleague, of a coworker, right? And something that I also call a nosy tactic is stealing the blueprint.
Jay Papasan:
Oh, I love this. Okay. I underlined, highlighted, I wrote modeling, modeling, modeling, and the side. I love this section.
Jenny Wood:
Yeah, and it can go both ways. You can model, you can discover a process, a tool, you can kind of think out loud, and you can create a playbook for somebody else or a standard operating procedure and model it so that somebody below you or someone who’s more junior can learn from it.
But if, like me, you are someone who in the past has gotten jealous of people who are exceptional leaders like Molly Williams, that’s her real name. Molly’s a good friend of mine now, but I was so jealous of how exceptionally talented she was in her processes, in her communication skills, in her email writing, in her presenting to clients. Well, one option is you’re jealous. The other option is you get insatiably curious, you get nosy, and you literally study those tactics like as if you’re studying a book.
And so, I would have an index card where I would write down Molly’s blueprint. And when she was rolling out a process, she would have this incredible Gantt chart of all the different steps and the dates that she had to accomplish the goals. And so, I literally copied that Gantt chart or that blueprint, Gantt chart meaning basically like a project management tool. And then, she would present to a client, I would write on an index card how many times she said “um” per minute, and I would try to match that. It’s like matching your pace to a faster jogger, right? So, rather than being jealous, I decided I could just get nosy and I could steal her blueprint.
Jay Papasan:
Well, nosy is all about learning, right? If you’re asking questions and you’re curious, you’re learning. And if you have a system, no cards. I mean, how low tech is that at Google? I’ve got no cards-
Jenny Wood:
So low tech.
Jay Papasan:
… but it doesn’t matter. You had a system for remembering so that you could carry forward.
Jenny Wood:
And I had a mindset shift. If I could choose to be jealous, I could choose to live in fear that Molly’s going to get promoted before I do, she’s going to get more customers, she’s going to build more revenue, and that’s a mindset of fear or scarcity. Or I could have an abundance mindset, and I could have this mindset of wild courage of, “I can learn from Molly. Molly’s amazing. I can do what she does with my own special pizazz, and that can be my competitive advantage.”
Jay Papasan:
Did you ever have the wild courage to go up to her and say, “How do you do that?”
Jenny Wood:
100% I did.
Jay Papasan:
Okay.
Jenny Wood:
I was like, “Molly, I admire everything you do.” And that’s probably shameless, right? And maybe I’m trying to think if there’s another trait in there. Maybe weird, right, where it’s like, weird is the courage to stand out. So, maybe it was different and unusual, but I was like, “Molly. I think the world of you. You are a total badass. I want to be as good as you. How do you do some of these things?” And she literally trained me on it.
Jay Papasan:
I love that. Okay, that’s great. So, you’re modeling one of the best and now you’re friends.
Jenny Wood:
Totally. She’s one of my-
Jay Papasan:
This person you totally look up to.
Jenny Wood:
And Molly’s amazing. She’s one of my closest friends now. And I used to feel so insecure around her.
Jay Papasan:
We like to say, like, I don’t know which rapper did it, but it’s the game sees game. But I think that when people notice they’re on the path to mastery and they see someone, even if you’re way behind on the path to mastery, you told them, this is an instinct, they want to pour into people, especially people who are really intent on growing.
Jenny Wood:
Yeah. And that gets back to knowing your power assets, right? It’s like, give someone a reason to believe in you. Give someone a reason to bring you up. Someone came to me, sent me an email the other day, and she said, “Hey, I’d love to know how you got your agent, and how you got this book deal, and how you hit the New York Times.” And it was a very humble email. And I wrote back, because I get a lot of emails like this. And I wrote back, I said, “Well, I’ve got some questions for you.”
So I got nosy, right? And because she wasn’t shameless in what she brought in the original email, I said, “Do you have any following? Do you have any platform? Do you have a newsletter? Are you on any social media?” She writes back, I am shocked, Jay, she said, “I have 271,000 followers across platforms.” I’m like, “That’s a lot.” I was gonna say no to her. But if she had given me this data at the forefront, then I would have immediately hopped on a call and been like, “How can I help you? You’re already clearly making an effort and you’re already making progress. How can I get behind your inertia, which is clearly already there?”
So another great reason to know your power assets, lead with numbers, double your numbers in your examples to customers or to prospects or to mentors.
Jay Papasan:
I love that. I wanna shift now because we’ve, selfishly… I told you, I think that’s one of my traits, being nosy. And otherwise, like, why would I do this podcast if I wasn’t inherently nosy? I think I want to talk about brutal. That one also lines up really well. There’s so much about saying no to things in here. But let’s give people a simple definition of what brutal means, because you see the title like all of yours, and you’re like, do I really want to be brutal?
Jenny Wood:
Yeah, these are all eyebrow-raising traits at first glance, but when used in a sane and savvy way, they truly can supercharge your success. So, because we’re redefining all of them, let’s redefine brutal. Brutal is the courage to protect your time, energy, and priorities. It’s the power of no because people pleasing pleases no one, least of all you, and it keeps you small, it keeps you quiet, it keeps you following rather than leading. And everyone listening here, I assume, wants to lead in some capacity or advance their career or advance their life, advance their relationships.
So, one of my favorite tools from brutal is as simple because just like The ONE Thing, this is a very simple tactic, it’s say yes to the big and no to the small. So, what’s big? Big is some big keynote that I might want to land next fall, right, with a huge audience. Big, if you’re in a corporate environment, might be leading the 2026 marketing project that you know is a priority for your VP. Big, if you’re an entrepreneur, might be increasing from five clients to 12 clients next year. So, those are big things. Say yes to those, even though they’re going to be scary, and overwhelming, and require you to sit down and lay that first domino, right, as you like to say, like that first thing you need to do every day. Now, that’s big.
What’s small? Small is being the 18th person to reply all on the Happy Birthday Jimmy email, going to every single meeting where you neither add value nor derive value simply because your name happens to be on the calendar invite, or being the person to take notes in every meeting, or to organize the shared drive on the computer just because someone asks you. So, when you say yes to the big and no to the small, you’re able to be more brutal and protect your time, energy, and priorities.
And unfortunately, some of that small is what I call NAP work. In a corporate environment, I’d call this not actually promotable. Hey, Jenny, can you plan the company offsite? Hey, Jenny, can you plan the dinner ’cause our VP is in town? Can you take notes? Can you lead the wellbeing pillar? Now, some of that is good because that stuff adds to our enjoyment, right? But if you’re always doing that or you find yourself doing more than 15% of that small work, that is what constitutes as NAP work, not actually promotable, or we might say for entrepreneurs, not actually productive, right?
And so, don’t NAP at work, don’t NAP in the office. And say yes to the big and no to the small. It’s one of the best ways you can be brutal.
Jay Papasan:
And let’s just acknowledge, a lot of the NAP work in the corporate environment tends to fall on women.
Jenny Wood:
It sure does.
Jay Papasan:
It’s just there’s some inherent bias that we’re still carrying around. And so, it becomes doubly important for us to support the nos and have a culture. I think as a leader, are you willing to have a culture where no is an acceptable answer? Because I think the number one reason a lot of people in those environments don’t say no is they don’t think they have a choice.
Jenny Wood:
Right. And you know what? I respect the people more who say no. So, if I think about my friends who are always the yesers, right? Maybe I want to give them more work but I don’t necessarily want to give them more responsibility. I want to give responsibility to the people who can be discerning, who can separate the wheat from the chaff, who can tell me that, you know, yes, I know you’re asking me to do this, Jenny, but I’ve got these three priorities. Does the bananas project take precedence over the apples project? If so, then I can reshift. But if someone just always says, ‘Yes, ma’am. Yes, ma’am. Yes, ma’am,” that is not a future leader. That is a doer, but that is not someone who’s going to do something remarkable and eventually get promoted or grow their business or, you know, deliver and delight more for clients.
Jay Papasan:
We devoted an entire chapter to the inability to say no-
Jenny Wood:
It’s hard.
Jay Papasan:
… because it’s a big one for a lot of people. And so much of what we try to teach people in our workshops and stuff is nine times out of 10, it’s not a direct no, it’s more likely a not now. Or if this happens, I will. You can do so many little mind games where you don’t have to actually say no to your boss or your teammates, but you’re pushing it into the future and there’s a high probability it’ll go away.
Jenny Wood:
Of course, yeah. Well, we’ve got the classic 4D model, which is not my model, but it’s when you look at your to-do list, that do, drop, delegate, and delay. And I love the delay, because you’re kind of kicking the, like, “Hey, can’t do it now, let’s revisit in September.” By September, oftentimes it gets solved. Another one I like to share is called the Agenda Avenger. Hey, Jay, can we hop on a call?
Jay Papasan:
The Agenda Avenger.
Jenny Wood:
The Agenda Avenger.
Jay Papasan:
You speak faster. I just wanna make sure, like we’re in Marvel World. But we’re not… yeah.
Jenny Wood:
I speak so fast.
Jay Papasan:
It’s great.
Jenny Wood:
The agenda-
Jay Papasan:
People are like, “I’m gonna have to go from 1.5 down to one for this podcast,” ’cause everybody listens to it like I’m 1.5.
Jenny Wood:
They’re gonna be at 0.9 for me, and they’re gonna, you know, do 1.4 for you. It’s so funny you say that. I was listening to the audio recording of my book just yesterday on the way to the airport. And I was like, “Okay, I was worried I was speaking too quickly,” but I only had to go down to .9, not .5 for myself, so that’s good.
Agenda Avenger. So, you say, “Hey, Jenny, can we hop on a call?” And then, you know, I say, “Happy to, but could you send me what you want to talk about first?” And then it allows you to have to think through the agenda, and that’s the Avenger of, you might realize, like, actually, you can solve this over email. So, that’s another great tool for saying no.
Jay Papasan:
You did some things in there. A lot of times, people won’t even say no and it’s just themselves. Like they’re in a movie theater, and they don’t like the movie, and they just won’t get up and leave. They won’t quit the book that’s not serving them. Like, “Everybody says, I should read this book.” “Oh, this is The ONE Thing. It stinks,” you know? But like, we give you permission to close the book and find one that does serve you.
I think a lot of the yeses that happen and the no’s that don’t happen is from a lack of clarity around what’s actually important. So, so much when I’m reading, like, in Wild Courage, a lot of it’s directly aimed at people more in a career environment. It’s all completely applicable to anybody wanting success. But like, do you understand your objective? You had objectives around your work that gave you clarity. And so, that’s NAP work for what I want to do. I think NAP work can actually be different depending on what your objective is.
Jenny Wood:
Yeah. And sometimes your objectives shift, but we fail to realize that there has been a shift. And one of the things I share with people is that I thought I’d be at Google another 15 years. I thought that was my one thing. I thought that I would retire there and that that would be where-
Jay Papasan:
What shifted for you?
Jenny Wood:
Well, once I started this Own Your Career program, even though I loved my job in operations that sat between sales and engineering and helped drive billions in revenue, like I loved my team, I felt a lot of pride, I felt a lot of identity with Google, I was meeting with my executive coach, Julie, and I said, “But now that I run this program as a passion project, it’s helped 56,000 Googlers in nearly hundred countries, I think that I realized that I now just want to coach people to be better than they think they can be.”
But it was so hard for me to catch up, for my brain to catch up with my heart, because again, I’m such an analytical thinker, but I had to recognize my one thing had changed. And it took me about 12 or 18 months to actually leave Google, but I had to recognize that your goalpost can shift. It can change, and you need to recognize and shed whatever it was in the past. Are you living today’s dreams or yesterday’s dreams? Are you trying to live up to somebody else’s expectations or your own expectations?
And when your circumstances change, like mine had, recognizing that and then recklessly moving forward, having the courage to err on the side of action and take a calculated risk, rather than wasting time analyzing the outcome of every possible consequence, you think fast and fearless. If you’re on the fence, do it. It’s one of the most powerful things that you can do is recognizing when the circumstances has changed. In my case, they had. I discovered there was this new kind of goal I had in life, even though it was completely out of left field.
Jay Papasan:
I’m going to put it as a calling.
Jenny Wood:
I guess you could call it a calling.
Jay Papasan:
Like a profession that became a vocation. And you’ve been called. Like you realized, this work is actually something that’s a much bigger opportunity for my life. And I love those moments where we kind of just have this real clarity. And you can also manufacture them.
Jenny Wood:
You can, but it was very scary for me to recognize that. And I got caught in what I call truths and tales. What are the truths of the situation? What are the tales? The truths were, yes, I’ve had this calling. The truths were yes, if I leave Google to be a writer, I might succeed, I might fail. But the tales I told myself, the stories that were kind of negative that I attempted to have make sense of the truths didn’t serve me well.
My tales were, I’m gonna be a starving artist as an author. We’re gonna have to move out of our nice home in Boulder and downsize into some shack. My parents are gonna be disappointed in me because I’m the breadwinner for my family and it’s going to feel too risky.
But once you recognize what are the truths and what are the tales in any situation, you can actually reframe the tales to something more empowering or at least something more neutral, and then push past that fear. Because even though at the outside it looked like, “Oh, Jenny has this calling,” it was terrifying for me to leave Google. It’s still scary. It’s still scary to be an entrepreneur.
Jay Papasan:
Change is always scary.
Jenny Wood:
Exactly, yeah.
Jay Papasan:
And you shared like the reckless, it might be the thing that if you had the biggest opportunity.
Jenny Wood:
Of course.
Jay Papasan:
Right? And you just like, well, congratulations to you-
Jenny Wood:
Thank you.
Jay Papasan:
… stepping away from quote, the dream career to follow the dream.
Jenny Wood:
Yeah. And I have to tell you, it took wild courage. And that was part of the reason that I left because I was like, “If I stay, and I’m putting a book out into the world that’s all about being uncomfortable, and taking risks, and pushing past your comfort zone, and yet I just decide to stay at Google another 15 years, like, that’s such a juxtaposition. I feel like a fraud. I don’t feel like I’m living the values of wild courage versus being reckless and being shameless and being obsessed with how I really want to help people now.”
Jay Papasan:
I love it. Like, you opened the book, and we won’t tell the whole story, with the moment of wild courage that helped you land a husband.
Jenny Wood:
Yeah.
Jay Papasan:
Right? So, like, these moments of wild courage became the times that you leaped forward and found the life that you always wanted. And so, like, one of the things we wrote in one of our first books is, opportunity lies on the other side of fear. And the way to close that gap is wild courage. And you’ve given us a great primer. So, thank you for that. I have one last question for you.
Jenny Wood:
Sure.
Jay Papasan:
So, every week we try to give our listeners a tiny challenge, like a first domino. Based on some of the stuff we’ve talked about, what’s maybe a challenge we could give them to implement? Just go practice this week, one act of wild courage.
Jenny Wood:
Ask for something that feels a little bit uncomfortable. That could be a raise, it could be a promotion, it could be a new customer, it could be revisiting with an old customer and asking, do you want to go catch up and get coffee? I have this-
Jay Papasan:
Send the order back!
Jenny Wood:
Thank you! I was just going to say that!
Jay Papasan:
I’m sorry, it could be so small! I was with someone for their birthday breakfast, and they asked for an ice latte, and got a hot one and they’re like… and it was their birthday. And they’re like, “You know what? I think I’ll enjoy a hot one today.” And I was like, “Send it back.”
Jenny Wood:
You wanted an ice latte. So I’ve got this survey with, you know, I think nearly 7,000 people have filled it out. It’s a quiz that people can take that kind of helps you assess how bold you are. And one of the questions is, do you ask for what you want? And 57% of people say yes, which isn’t that high. But contrast that with, I literally asked the question, are you comfortable sending the cold entree back in a restaurant or the lukewarm entree? And only 38% of people say yes. That’s a 19 percentage point gap.
So, that is a great way to start. So one small thing, whether it’s sending back the entree or asking for something at work or asking something of a customer or asking your spouse to do the laundry this week because you have a heavy travel schedule. Ask for something that you might feel bad asking for, but that-
Jay Papasan:
Because it feels a little selfish to tease another trait, but you’re advocating for yourself.
Jenny Wood:
Yeah, exactly.
Jay Papasan:
I love that. Thank you so much. I mean, we could have talked for an hour.
Jenny Wood:
For sure.
Jay Papasan:
Maybe we’ll have you back and talk about some of the other traits.
Jenny Wood:
Well, thanks so much for having me here.
Jay Papasan:
Thanks.
You know, most weeks, one of my jobs is to tell the guests that we have a challenge at the end of the podcast, because even if they’re preparing, do you always listen to the end of the podcast? And if they’re rushing around, maybe they didn’t get a chance. I thought Jenny nailed it. I hope you’ll take the challenge this week and just step slightly out of your comfort zone. I promise you, you’ll be happier on the other side.
Next week, I’m gonna do a solo episode and we’re gonna talk about something, put it in quotes, quality inflation. I heard it, my friend Nathan talking about it first time, but it’s this idea, everybody around you, whether in the workplace or in the marketplace, every year, a lot of them are getting better. They’re working on what they do, their craft, their value proposition. And the bar for just being average goes up every single year, quality inflation. My question to you is what is your approach to staying competitive from year to year?
Next week, I’ll share some of my favorite strategies and tactics for winning in the long game. Tune in next week. I’ll share some of my favorite strategies and tactics for winning in the long game. Tune in next week. I’ll see you there.
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This podcast is for general informational purposes only. The views, thoughts, and opinions of the guest represent those of the guest and not ProduKtive or Keller Williams Realty LLC and their affiliates and should not be construed as financial, economic, legal, tax, or other advice. This podcast is provided without any warranty or guarantee of its accuracy, completeness, timeliness, or results from using the information.
