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Wild Courage, Micro-Actions, and Owning Your Career with Jenny Wood

August 17, 2026

Jenny Wood headshot, Glass Ceilings and Sticky Floors podcast guest
Erica Rooney smiling with a microphone in hand

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I'm Erica Rooney

I'm an ex corporate girl, turned founder, and 2x bestselling author, and I help women get into positions of power - and STAY there - without burning out.

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Wild Courage, Micro-Actions, and Owning Your Career with Jenny Wood

Look at the moment you almost let pass you by today. The email you didn't send, the person you didn't approach, the idea you kept to yourself. My guest this week, Jenny Wood, spent eighteen years climbing from entry level to executive at Google, running an operations team that helped drive billions of dollars in revenue a year. And her boldest career move might be the one she made off the clock. She chased a stranger off a moving subway train in a January blizzard because she refused to let the doors close on what she wanted. Eleven years and two kids later, that stranger is her husband.


Jenny left Google this past summer after almost eighteen years, walking away from a six figure paycheck and the financial comfort that came with it to write full time. She's the breadwinner for her family, and the decision took months of soul searching about what she valued more, the money or the freedom to spend her time on work she loved. That leap became Wild Courage, Go After What You Want and Get It, out March 25, and the whole book runs on the same instinct that got her off that subway seat: meet yourself where you are, then take the next small step anyway.


One of the traps Jenny names in the book is NAP work, an acronym she credits to a kitchen table conversation with her mom. It stands for Not Actually Promotable work. Taking the meeting notes. Planning the off-site. Decorating for the holiday party. It keeps teams running, and it quietly stalls careers, especially women's. Carnegie Mellon economist Linda Babcock has spent over a decade studying exactly this pattern. Her research, later expanded into the book The No Club, found that women volunteer for these low-promotability tasks more often than men, get asked to take them on more often, and say yes more often when asked.


That imbalance compounds. McKinsey and LeanIn's 2025 Women in the Workplace report found only 31% of entry-level women have a workplace sponsor, compared with 45% of men, and employees with a sponsor get promoted at nearly twice the rate of those without one. Jenny's answer isn't a grand gesture. It's what she calls a pencil sharpener: within twenty four hours of getting an overwhelming project, sketch a rough doc (the goal, a self-imposed deadline, the first stakeholders, your open questions) and send it to your boss before the doubt sets in. It's a ping to the VP after their town hall. It's saying yes to the big project and no to the tenth NAP task this quarter. You don't have to jump off a subway train to build wild courage. You just have to take the next small, visible action before you talk yourself out of it.

TRANSCRIPT:

Erica: Hey, girl. By now, you know I have Her Collective, my online community for ambitious women who are done doing it alone. Her Collective is for the women who are smart, capable, and driven, but they find themselves stuck on the sticky floors like self doubt, burnout, and waiting for permission that quite honestly never comes. Inside HER, you get more than motivation. You get real support, real strategies, and real momentum.


Erica: We work on things like clarifying what you want now and what's coming next, building confidence without burning yourself out, navigating hard conversations, career moves, and leadership moments with clarity, and surrounding yourself with women who actually get it. This isn't about hustling harder. It's about moving intentionally with the right tools and the right people in your corner. If you're ready to stop spinning, start choosing yourself, and build a career and life that actually feels aligned, I'd love to welcome you inside Her Collective. You can learn more and join us at www.joinhercollective.com.


Erica: Because honestly, girl, you were never meant to do this alone. What if the secret to unlocking your wildest dreams was a mix of bold moves, big small moments, and the courage to step out of your comfort zone, even if that means chasing a total stranger off a New York subway? Well, today's guest, Jenny Wood, is here to prove that it is. From rising through the ranks at Google to become a career mentor for thousands through her Own Your Career program, Jenny's journey is anything but conventional. She's also a pretty rad person with some crazy hobbies that you're gonna hear about in just a bit, but she's also the author of Wild Courage, Go After What You Want and Get It.


Erica: And y'all, if you have been waiting for a sign to go after what you want, this is it. Welcome to the Glass Ceilings and Sticky Floors podcast, the show that's here to empower you to break free from limiting beliefs, ditch toxic behaviors, and unlock the infinite possibilities waiting for you. This is your time to live your best life unapologetically. I'm Erica Rooney, your host and biggest cheerleader on a mission to get more women into positions of power and keep them there where they belong. If you're ready to shatter ceilings, crush self doubt, and build a career and life overflowing with growth and abundance, you're in the right place.


Erica: Here's the real deal. We talk about the real stuff here. Imposter syndrome, perfectionism, fear, burnout, you name it. It's raw, it's honest, and it's exactly what you need to level up.


Erica: So grab a seat, pop in those earbuds, and let's dive in.


Erica: In her eighteen years at Google, today's guest grew from entry level to executive, where she most recently led a large operations team that helped drive billions of dollars of revenue per year. In 2021, she started a passion project within Google called Own Your Career, which grew to one of the largest career development programs in the history of Google. She's an expert on acing a job search, building relationships, personal branding, and so much more. Her work has been featured in Harvard Business Review, Entrepreneur, Inc, and Forbes.


Erica: And y'all, I gotta add in these next tidbits because, damn, you are about to be impressed. She's a licensed private pilot and a tap dancer, and she has the most incredible meet-cute story that was actually featured in the New York Times. But she's a wife, a mom, and the author of the book Wild Courage, Go After What You Want and Get It. So without further ado, Jenny Wood, I'm so excited you're here. Welcome to the Glass Ceilings and Sticky Floors podcast.


Jenny Wood: Hello, hello. It is such a joy to be here today.


Erica: Oh my gosh, I'm so pumped. And the title of your book, we're gonna dive in. It's Wild Courage, Go After What You Want and Get It. And girl, you did that on a subway, chasing after someone you had no idea who he was. Was he married or not? Spoiler alert, y'all, he wasn't, thankfully. But now he is. Can you please tell me this story of chasing your husband off the subway?


Jenny Wood: I most certainly can. Okay, so the story is bananas when you now know how it turned out, which you just shared. This attractive stranger on the subway was standing about 20 feet away from me. I was riding home from work one day in New York City, and I was just really taken by this guy, thinking, what's he all about? Where is he going? Where is he coming from? What does he do? And I made a deal with myself. I said, if he gets off at my stop, then I will try to strike up a conversation with him.


Jenny Wood: But if not, then c'est la vie. So he gets off at the next stop, which is not my stop, and I said, okay, that's the universe telling me it wasn't meant to be. The people got off the train, and people got on the train, and just as the doors were about to close, I said, no, screw the universe, and I ran off that train.


Jenny Wood: So I chased after him to catch up with him, and as he was exiting the station stairs, I tapped him on the shoulder. I said, excuse me, I'm sorry to bother you. And he said, that's okay, you seem nice.


Jenny Wood: And I said, well, this part is so crazy because I had no plan as to what was gonna come out of my mouth. I just knew I didn't want to let this moment pass me by. So what came out of my mouth was, you were on my subway and I thought you were cute. I can't see if you're wearing a wedding ring because you're wearing gloves. It was like a blizzard in January in New York City.


Jenny Wood: I said, I can't see if you're wearing a wedding ring because you're wearing gloves, but in the event that you're not married, I'd love to give you my business card. I guess I was being assertive, if you will, by taking all these steps, but I didn't mean for that to be my opening line. And of course, he's got a great sense of humor, so he kind of chuckled, and I gave him my business card. We went out a week later, and I just knew in that moment, sitting there across from him in this dive bar on Columbus and 75th called Dive 75.


Jenny Wood: I just knew. I was like, this is it, this is the one. And yeah, we've been very happily married eleven years with two kids.


Erica: So good. Well, okay, I gotta know. Have you ever done something like that before? Not just with men, but just in general.


Jenny Wood: Yeah, so I'm definitely on the side of more bold. One example is when I was in middle school, I was with a bunch of friends in this yogurt shop, and they dared me, or I dared myself. Somehow a dare was put out there to stand on a table and sing "My Country 'Tis of Thee." And I was like, okay, sure, why not, what do I have to lose? It's not like I didn't have any moments of embarrassment in life or feeling insecure. I have those moments all the time, but it's almost like I would test myself to see if I could build a thicker skin just by doing one little dare at a time. So just like somebody dared me and I accepted the dare in middle school to do that, I did it.


Jenny Wood: I stood up there and sang all the stanzas, until the very end, of the song. Similar to how, in this flash moment on the subway, I was like, just do it, just go for it. It's not like I would regularly walk up to people on the street and give them my number. There was some inertia that day that pushed me out of my subway seat and told me, no, Jenny, go chase after what you want in life. Because if we sit back and let life idly pass us by, then we'll probably not end up where we would want to if we were choosing our own destiny one moment at a time. And that applies to life. That applies to work.


Erica: Oh my goodness, a hundred percent. And I love opening with this story because it's the red thread of your life, and it's the red thread of the book, and it's so amazing. But, you know, you were an executive at Google. We talked a little bit about that. Tell me what you're doing now and how this book came to be.


Jenny Wood: Yeah, sure. So I was at Google for almost eighteen years, and I left this past summer, summer 2024, because I was so excited about writing a book that helped people get more of what they want in their career. So to answer your question, I'm doing this full time. I am a full time writer and keynote speaker and corporate facilitator, workshop leader, consultant, and I'm having an absolute ball.


Jenny Wood: It was really, really scary. I'm the breadwinner for my family. It was really scary to leave Google, which is a substantial paycheck as an exec, a lot of financial comfort and benefits, and I've got two kids. It took a lot for me to walk away, a lot of soul searching and thinking and, frankly, reevaluating the value I place on money versus being high net freedom, or just being able to put all of my time and energy into what I am currently loving. So, really, really hard decision. But I'm having an absolute ball, and I am just working on promoting this book full time, which is an absolute blast.


Erica: Oh my gosh, well, I've got the book, I've got an early release copy.


Jenny Wood: I know. Don't be jealous.


Erica: But in your book, you talk about how courage is essential to success, because we are often timid on the inside. I absolutely agree with all of that, but how can someone push through that fear to take action so they can chase a man off the subway or leave a nice six figure job at Google? How do we take that action?


Jenny Wood: Yeah, so I think it's meeting yourself where you are. Not everybody, and we actually have to be really mindful of this in the book. I was asking for feedback early on, like, is this book realistic for people? Because most people are not gonna stand on a table at a yogurt shop, and most people are not going to chase an attractive stranger off the subway.


Jenny Wood: But there's a lot of big small things people can do each day. It's actually the name of my newsletter. Perhaps you want a mentor or a sponsor and you're just too nervous to ask. So the big small thing is sending them that note, or pinging them after, not even asking them to be your mentor, but after your VP at your company leaves the town hall in front of 200 people, just pinging them and being like, that was so helpful, that gave me a lot of information about this upcoming reorg that I didn't have, for example. Even that is the beginning of building a relationship. That's not chasing someone off the subway.


Jenny Wood: That's not following someone into the hall after they deliver a presentation to the company and being like, hey, will you mentor me, I'm Jenny. And yes, I have done things like that. But again, meeting yourself where you are, if you're perhaps more introverted, or you're more shy, or you grew up in a culture that is much more reserved or just different than the American or Western corporate culture.


Jenny Wood: Or even a Google culture, where a lot of latitude is given to people at the very bottom rungs who have great ideas. I'm a product of the culture that allows for these more bold moves, but there are all these little teeny tiny big small things you can do each day, like asking for a one-on-one with your boss's boss, or asking your boss if you can present for twenty minutes in their leadership meeting to showcase the project you're working on, or pinging a leader at your company after their presentation and saying, hey, that was awesome, I learned a lot, and leaving it at that. So what are these micro moments that you can integrate into your day that still help you have more courage?


Erica: I love that idea of the micro moments and big small things, because I think when we're thinking about the big ask or the next big bold step, it's always like this huge monumental thing, and people forget the power of just those tiny moments, like pinging the VP, which then, you've got recognition, they're talking to you, they're noticing you, even if it's just in a small gesture of gratitude like you said.


Jenny Wood: Oh yeah, absolutely. Can I share another one?


Erica: Yeah, please.


Jenny Wood: Here's another example. Occasionally, you'll be in a one-on-one meeting with your manager, and they'll just drop a humdinger on you, a total doozy of a project, and you're overwhelmed and insecure, and you feel imposter syndrome that they're even giving you this project, and you have literally no clue where to start. So mild courage is going back to them and asking for them to clarify, like, hey, what are the goals here, what should I be focused on, and when do you want this by?


Jenny Wood: Wild courage is doing something that I call a pencil sharpener. A pencil sharpener is, within the first twenty four hours of getting that totally overwhelming project, you just open up a blank document on your computer. You can jot it down on pen and paper too, I suppose. And you write down a couple categories. Let's say the categories are goal of the project, self-imposed deadline, first three stakeholders I wanna meet with on this project, questions that I need you to answer, boss, and fill in one other category.


Jenny Wood: You then rough it out, a rough sketch. That's why I call it a pencil sharpener. You're just kind of warming up the ideas, but you're creating an artifact. You're creating something that exists on paper that did not exist before, especially in knowledge work, where so much is ephemeral ideas or theoretical discussion.


Jenny Wood: Bosses love things that move the ball forward. And a pencil sharpener, which is just a couple of bullets in three to five categories on a shared doc, shows that you're moving the ball forward. And that's really all you need to get started on a big scary hairy project. And then share it with them. And this part is so, so critical, Erica.


Jenny Wood: Share it with them within twenty four hours. The reason that is important is because then you're not sitting there going, oh my gosh, it's been seven days, we have our next one-on-one coming up, I don't have anything interesting to share with them, I should have had a lot of progress on this in seven days. No. If it's within twenty four hours, the expectations are so low of what you'd be able to put together. Even do it the hour after you leave that meeting. Just get something down and you'll realize two things. One, as you get some ideas down, you come up with other ideas, and it starts to solidify in your mind what they might be looking for. And two, you're giving your boss something to react to, which is always going to show that you are the kind of person who has a bias to action, and it allows them to start the dance with you of, oh, we could tweak this.


Jenny Wood: We could adjust this. Nah, it's not really that goal, let's move this. You put these two stakeholders, those are the right ones, this third one, I disagree with, let me write in on this document who that person should be. And then, boom, you're off to the races. So that is wild courage.


Jenny Wood: Mild courage is asking for more help, because it still takes courage to ask for more help or more direction from your boss, but wild courage is taking those next steps yourself, even if they're wrong, even if they're rough, and that is the pencil sharpener. And that, again, is a big small thing. Not too hard to do. But people think it needs to be perfect before they go back to the boss and have another conversation about it, whatever that scary part is.


Erica: That is so powerful, because I'm thinking back to when I was in corporate America and how impressed I would have been if I threw out this big project for someone to do, and they came back to me by end of day or the next morning with, like you said, the simplest of documents with just some goals and next steps and ideas. It shows you're proactive. It shows you're taking an interest. You're gonna be my go-to person. So there is so much power in that one example you just gave.


Jenny Wood: I'm such a nerd, because when you said that, I had chills.


Erica: I think what's so crazy is, like you said, we think it has to be perfect, we think it has to be this big whole thing, but it's that timing piece. Nobody expects greatness in twelve hours.


Jenny Wood: But everybody's impressed by bias to action, and everybody's impressed by the confidence it shows to take a stab at some ideas even if they're wrong. Another thing I say is give three options, have a POV. Your boss is not some wizard behind a curtain with all the magical answers. If they're giving you this project, they don't necessarily know the best way to go about it, and you can get there together. Let's say the project was figure out if we're gonna do vegan vanilla, strawberry, or chocolate ice cream next year as our big product launch.


Jenny Wood: They don't necessarily have an opinion. You don't have to have the right opinion. You might say, actually, what I know about these three flavors, working in the ice cream industry for a long time, I think we should go with vanilla. Giving three options shows that you're able to look at things from different perspectives. And having a POV, saying, I recommend we go with X, shows that you have the confidence and the future leadership potential to actually have a perspective, and that's the kind of person who gets a raise, who gets a promotion, who gets the leadership role, who gets more responsibility. And the other thing I'm picking up on is that when you were chief people officer, you probably saw these opportunities all the time, and you probably saw how often people don't write that half page, one page, no more than that doc by the end of the day or the next day. And that's why I got chills, because it really does stand out. That's why it's this tiny little move that's not chasing somebody off the subway.


Jenny Wood: It's just putting down a couple of bullets that may or may not be correct and sharing them within twenty four hours, but something concrete, some ink on paper. Nobody does it. Right? Nobody does it.


Erica: They don't. And I love that we are on a scale of zero to chasing someone off a subway. That's our standard here, guys. In the book, you have nine labels that you turn into powerful traits that help you fuel your courage. I'm not gonna have you name all nine here, but what are some of your favorite ones to talk about? Let's dive into, I don't know, just pick one.


Jenny Wood: I'm gonna pick the spiciest one. I'm gonna share them all. So it's weird, selfish, shameless, nosy, obsessed, manipulative, brutal, reckless, and bossy. They're all these powerful words, especially for women, but truly for everyone, that create the bars of an invisible cage that keeps you playing small.


Jenny Wood: And I want all of you listening to stop playing small and start playing smart. These are the traits that are gonna help you play smart when used in a savvy, sane way. Of course, we don't wanna harm anybody, we don't wanna be cruel or abusive. These are obviously plays on words, a reclaiming of language. Manipulative is becoming my favorite one to talk about, because it's the one I was most scared to write about.


Erica: Well, what I love to say too, and just a little plug here, I've been called every single one of those things in the book, y'all. But yes, let's talk about being manipulative. How did you take that and turn it into this powerful, positive thing?


Jenny Wood: So manipulative to me is just build influence through empathy and craft lasting relationships. Because at the end of the day, we are always trying to influence somebody or something, whether it is me trying to influence a publisher to give me a big book deal, or me trying to influence my son, Ari, to get out of the house in the morning, and I give him just enough choice, do you wanna wear the red shirt or the blue shirt, to make him feel like he has agency while not derailing my agenda to be at school in seven minutes. So I think the first part is just acknowledging that it is okay to want to influence a situation.


Jenny Wood: We're doing it right now. We're not speaking just to massage each other's eardrums. We are speaking with the intention to influence your audience to help them get better. Sometimes it's for an altruistic purpose, you purely wanna help somebody else. And it's okay if our purpose is also for you to sell more of your book, or to get people to share the episode and get more monthly listeners. And it's okay if I also have a goal of helping millions of people through my book and having your listeners go out and buy my book, which I encourage you to do. I think it's first just acknowledging that it is okay to want to influence, and then we can start to unpack all the different ways you can wield that influence at work.


Erica: I love that. And you also talk about trait traps. So tell me, what is a trait trap?


Jenny Wood: Okay, great question. So trait traps are when you take the trait too far. For example, obsessed is about push, perform, it's not about grinding yourself into a pulp and overworking yourself till you're numb, it's about a good, strong work ethic, not about taking it too far that you make yourself sick.


Jenny Wood: In manipulative, since we were just talking about that, it's about influencing in the right way. One trait trap in there, for example, is build relationships, but know when you've maybe gone a little bit too far. Here's an example of where that would fall into healthy manipulation. This is when I really wanted, I'll tell you who it is, Vanessa Van Edwards, this all-star author, super well known, and I so admired her. I was going to Austin for a work related event, and I emailed her and said, hey, Vanessa, I'm gonna be in Austin, I'd love to take you out to coffee since I'm working on my first book. And she said, okay, great, the only thing is I've got some travel dates that are just over the time you're gonna be there, here's when I leave, here's when I come back. And I saw that she was going to be leaving Austin just before I arrived. So I said, hey, what time?


Jenny Wood: I guess she'd already shared her flight information, and I said, oh, that is perfect, I get in just a couple hours before you, we're probably gonna be at the airport at the same time. Why don't we just get coffee at the airport when you're about to leave and I've just landed? She's like, that's perfect, sounds great. So we had this awesome coffee, became friends. But, Erica, here's the thing. I actually was not supposed to land a couple hours before her, I was supposed to land a couple hours after her. So I quickly checked the Delta website, and for sixty dollars, I got myself on a new flight that landed earlier and got me there to make my story true. So some might say liar, liar, pants on fire.


Jenny Wood: But in this case, a little white lie, a little bit of healthy manipulation to influence the situation without making it awkward or over the top or telling her how the sausage was made and saying, well, I land later, but I could switch my flight, in which case she'd be like, oh, don't do that, that's absurd, and I'd look a little bit extra. So I think just being smart about how you influence or how you manipulate these situations is also important. And the trait trap here would be just being way over the top, or exposing every single thing that's going on in your head to the person who is the recipient of your thoughtful manipulation.


Erica: I love some thoughtful manipulation, I have done that, I could not even tell you how many times. I didn't love the word manipulation with that. I like to think of it more like orchestrating my future, something like that.


Jenny Wood: Orchestrating your future, strategic. Someone else had another great name for this that is escaping me right now. But if we were to call it strategic, or planning ahead, people wouldn't pay nearly as much attention to it. And I like to do things differently, and I like to be a little bit out there. So I'm calling it manipulation, and we'll see if I get canceled.


Erica: The cancel culture is real. Okay, Jenny, on this podcast, we talk a lot about the sticky floors, which are the limiting beliefs and toxic behaviors that keep you stuck. And I saw so many connections in the work that you do, we're just kind of manipulating our language to talk about a little bit of the same things. When you hear sticky floors and these trait traps, what was one of those that you struggled with the most, and how did you get over that?


Jenny Wood: Easy, easy. So this is again something that can happen to anybody, but I think women can be particularly prone to falling into this. And this is what I call NAP work. NAP work, N-A-P, stands for Not Actually Promotable work. And I gotta credit my mom, we were sitting together at the kitchen table, and she came up with this acronym, which I totally love. So Not Actually Promotable work. What is that? Taking notes in the meeting always. Planning the off-site.


Jenny Wood: Our leaders are in town, can you plan the dinner and the snacks, can you organize the shared drive, or come in early to decorate for the holiday party. That is not actually promotable work. Yes, it is important work for teams to function, and it's great to build culture through these activities. But if you're always doing it, then you are really doing a disservice to yourself, when the stuff you should be doing more of is the stuff that's promotable. This is like the 2025 marketing plan that is the key priority for the head of your company, or the strategy for that ice cream project we talked about before, or anything else that really matters for your career or the company, that you can hang your hat on and write a really solid bullet point in your annual review with numbers and metrics that you helped move. And it's hard to say no to these things. It's hard for someone to say to you, hey, can you hop on a call and can we talk about the logistics for x y z thing.


Jenny Wood: And so owning that no and saying, sorry, heads down now on my h2 marketing project, is something that takes practice but is really worthwhile. Because if you're always getting stuck in the NAP work, you're really not putting yourself in a position to continue to move up in your career. And it's not like you should never do it. I think maybe fifteen percent NAP work is probably fine. But if you find yourself getting tapped over and over and over again, it takes some wild courage to push back and say, I had a great time planning the company off-site last year, and I'm so excited to give somebody else an opportunity to do it.


Erica: Yes, and I can attest to that as someone in HR, which is often the dumping ground for a lot of NAP work. You really do have to be smart in how much of that you take on. And I do think as women, we are so often other-focused, and we don't wanna put others out, that we just take it on ourselves.


Erica: But you're right, start to list that out. If you can't put a number or a metric behind how that moved the business forward, you've gotta limit that.


Jenny Wood: Yeah, and in general, I would broaden this up to saying yes to the big and no to the small. The big stuff is that h2 project on strategy, or the ice cream metric you wanna move, and the small is the taking notes, the planning, the off-site. And even within HR, because I was never in any people operations role, but I have enough experience working with those folks to know that even within there, there is promotable work and non-promotable work. So if you're doing something in the HR capacity, at least find a metric you can tie it to. If your company has an annual satisfaction survey and career development is always in the 40% range or whatever it is, at least say, I'm doing this thing with the goal to move this from 40% satisfaction to 47% satisfaction, as opposed to always taking notes for the meeting, which there's no metric tied to.


Jenny Wood: It's just helping out, and somebody else can help out next time if you've done it too much.


Erica: Absolutely. And I will say here too, I think it's helpful to track that stuff. Because when you sit there and tell your boss, hey, I'm the one always taking the notes, they're gonna be like, no you're not, I asked little Bobby to do it. And you're like, but if you have the metrics, you can put that in a performance review. I took all of the notes on the strategic HR meetings for 87% of the meetings in 2024. Now, it's still NAP work, but when you can document it and put it in that review, you're also gonna bring to light where you're spending your time. So I still think you can find those metrics and make them sound impressive for something that's not that impressive, like note taking, and maybe you'll get your boss to think a little differently. I love it.


Erica: Alright, Jenny, can you tell me about the rock, chalk, talk, walk formula? What is it, and how can we use it?


Jenny Wood: Yeah, for sure. So this is goal setting in a nutshell, essentially. Rock is your big thing you wanna accomplish. And have wild courage when you set your rock. Not like, oh, I wanna make some music and put it on Spotify. No, like, aim for the stars. I wanna have a Grammy award winning album by 2029. Okay, so that's your big rock. And I call it a rock because if you think about filling the jar of your life, the rocks are the things that take up the most space, or should take up the most space.


Jenny Wood: The pebbles are gonna then fill up the next amount of space, and the sand is like little bitty things, but your rocks are the big ones, those big things that you wanna continue to push. And then chalk is write it down. I oftentimes, on my monitor right in front of me here, have a goal, and that goal will be, you know, Grammy award winning album by 2029, or whatever it is, so I can keep reminding myself of what that big rock is. And be specific there. That's when you can say, I want to get there, I gotta put some pebbles in there as well and some sand in there as well. So I wanna record my first three practice tracks by June, and I want to reach out to seven producers by August. So that's where you can get a little bit more granular in these micro goals, because we're also talking about what are these baby steps you can take if you're not gonna chase someone off the subway.


Jenny Wood: So that's rock, what is our goal. And then chalk, write it down.


Jenny Wood: We're talking about you saying it out loud. So sometimes, I am not a manifest-it-into-the-world kind of person, but I am a we-believe-what-we-say kind of person. And the more we say these words out loud, the more we feel comfortable having that goal versus feeling foolish having that goal. For example, in 2006, when I wanted to work for Google, I was living with my parents at the time, and I walked around the house with this nutty mantra. I'm gonna work for Google, I'm gonna work for Google, I'm gonna work for Google. And Google was, like, the hottest thing then, with the lava lamps and the beanbag chairs and all these sizzling news segments promoting it as the best company to work for ever. And I was like, I'm gonna work at Google. So I was talking this goal out loud so that I wouldn't shy away from it and just have it kind of stew around in my brain, in my heart, in my stomach, but never really believe that it could happen.


Jenny Wood: By saying it out loud, you have people who can keep you accountable. And, frankly, more importantly, you keep yourself accountable. And then, finally, walk is you gotta walk the walk. You gotta reach out to those seven producers, you gotta record those three tracks, you've gotta send that resume to Google, you gotta jump off the subway train. And that is rock, chalk, talk, walk, goal setting in a nutshell.


Erica: I love that. My favorite step in all of that is the talk portion, because I have found that that is what makes me do the thing. I can dream it all day, I can write it in my planners, I can journal about it. But if I don't tell somebody else in my circle that I know will hold me accountable, that dream will eventually wither and die.


Erica: I just know myself. And so for me, talking about it, when I wanted to start this podcast, I didn't do it for a very long time. And I know myself, so I did the thing to set it in motion. I did the thing I couldn't take back, and I sent an email to just 10 women who I knew would support me.


Erica: And boom, it was out there. It had to be done. I love it.


Jenny Wood: That is so, so great. And then as you say that out loud, you start to believe it. Or you get other ideas, it becomes an iterative process. Talking it is almost like your own little pencil sharpener, where you put the idea out there and other people might say, oh, well, what about this woman? Or, you'd be awesome, Erica, or you were born for this, and then that builds the confidence and reduces the imposter syndrome.


Erica: I love all of that. Jenny, if you could go back in time to the young Jenny walking around her parents' house mumbling, I'm gonna work for Google, I'm gonna work for Google, and you think about all the things you've learned in your time and your experience, what piece of advice would you give that Jenny today?


Jenny Wood: Chill the fuck out.


Erica: Oh, there's a round of applause for that one, because I need to get on that bandwagon.


Jenny Wood: And other people have told me this too. I remember sitting on the couch with Kim Scott in her house, and she's just been an angel helping me. Kim Scott, who wrote Radical Candor, has been a really wonderful mentor. And we were talking about this, like, okay, what else should I be doing on the book launch? And she's like, relax. And I was like, okay, yeah, point taken.


Erica: Oh my gosh, well, that actually vibes very much with who she is, and I'll give her a shameless plug here, she was on this podcast about a year ago.


Jenny Wood: Yeah, she's so great.


Erica: Head back and listen to the Kim Scott episode, y'all, she can do it.


Jenny Wood: She's the best.


Erica: Oh my gosh, she's amazing. Jenny, if people wanna work with you, where can they find you? We're gonna link the book for the preorders in the show notes. First of all, when does the book launch? Let's start with that.


Jenny Wood: Yeah, March 25.


Erica: Okay, March 25, coming for us, I love it. Where can people find you?


Jenny Wood: Yeah, to bring me into your organization for a keynote or any kind of speaking engagement, fireside chat, or workshop, it's jennywood.com/speaking.


Erica: I love it. Jenny, this was so fun, thank you so much, and best of luck on the book launch and everything else, it's gonna be amazing.


Jenny Wood: Thank you so much. What a fun conversation to have today, and I hope all of you listening got something out of it, and thank you for giving us an opportunity to contribute to your goals.


Erica: Jenny just gave us the blueprint for breaking through. From her signature pencil sharpener technique that can change how you show up at work, to reframing manipulative as building influence with empathy, this conversation was packed with game changing insights, y'all. Jenny's story reminds us all that courage isn't about waiting for the perfect moment.


Erica: It's about making the move that scares you and showing up again and again and again. Her book, Wild Courage, hits shelves on 03/25/2025, but you can preorder it now, and you should. If you're ready to stop playing small and start building a life you love, this is your permission slip. Until next time, y'all.


Erica: Keep chasing those dreams, even if it means jumping off the train. Thanks for tuning in to the Glass Ceilings and Sticky Floors podcast. If this episode lit a fire under you, go ahead and hit that five star review, it's how this message lands in the hands of the women who need to hear it most. And don't stop now.


Erica: Head to Amazon, order the book Glass Ceilings and Sticky Floors. Follow me on Facebook, Instagram, LinkedIn, and TikTok for daily doses of inspiration and all the tools you need to keep smashing those ceilings.

​RESOURCES MENTIONED IN THIS EPISODE:

- Ready to close your own gap and get more women into rooms of power? Join HER Collective, Erica's community for women in corporate America.

- Never miss an episode. Follow Glass Ceilings & Sticky Floors on Apple Podcasts.

- Get closer to closing your own AI gap. Grab The AI Gap by Erica Anderson Rooney.

- Wild Courage: Go After What You Want and Get It by Jenny Wood, out March 25.

- Book Jenny Wood for a keynote, workshop, or fireside chat.

- Big Small Things, Jenny Wood's newsletter.

- Own Your Career, the career development program Jenny founded at Google.

- Radical Candor by Kim Scott.

- Vanessa Van Edwards, author and body language expert.

- Four lies that will keep you stuck in your career.

RELATED EPISODES:

Stuck in Your Career? The Moves That Took Me to Chief People Officer

Wild Courage, Micro-Actions, and Owning Your Career with Jenny Wood

The Sales Rookie Who Cried Every Night and Became a 3-Time Forbes Top Advisor

FREQUENTLY ASKED QUESTIONS:

What is NAP work, and why does it hold women back at work?

NAP work stands for Not Actually Promotable work, a term Jenny Wood coined with her mom for tasks like taking notes, planning off-sites, or organizing office parties. It keeps teams functioning but rarely earns credit in a performance review, and Carnegie Mellon research shows women get asked to take on this kind of work, and say yes to it, more often than men.


What is the pencil sharpener technique for handling a big work project?

The pencil sharpener is Jenny Wood's method for tackling an overwhelming project. Within twenty four hours of getting the assignment, open a blank doc and rough out a few categories, the goal, a self-imposed deadline, the first stakeholders, and your open questions. Sharing that rough draft with your boss fast, even if it's imperfect, shows a bias to action and gives them something concrete to react to.


What is the rock, chalk, talk, walk framework for goal setting?

Rock, chalk, talk, walk is Jenny Wood's goal-setting formula from Wild Courage. Rock is the big, ambitious goal you set for yourself. Chalk is writing it down somewhere visible. Talk is saying the goal out loud to build accountability, and walk is taking the concrete daily action, sending the resume, recording the track, jumping off the subway train, that actually moves you toward it.

MORE FROM ME

Follow me on Instagram @ericaandersonrooney and @joinhercollective

SUBSCRIBE & REVIEW

If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts. Your support helps us reach more women who need these insights. Thank you for tuning in to the Glass Ceilings and Sticky Floor podcast. See you next week!

Hi, I'm Erica!

In the last 15 years, I climbed to Chief People Officer, 6x'd my income, walked away from a culture that stopped matching my values, wrote two books, and built HER Collective to help thousands of women rise to power and lead in the age of AI. I've learned a thing or two about smashing ceilings and closing gaps, and Glass Ceilings & Sticky Floors is where I open the playbook, the receipts, and the real stories to share it all with you.

Erica Rooney in a pink vest, holding a microphone in front of a director's chair with a podcast mic and her two books, The AI Gap and Glass Ceilings & Sticky Floors, smiling
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