How to Lead With Wild Courage (Even If You’re Afraid) with Jenny Wood – EP 248

Justin Donald: Hey, Jenny, good to have you on the show.

Jenny Wood: It’s so great to be here. How’s it going?

Justin Donald: It’s going great. I’ve been looking forward to this ever since our mutual friend, Hal Elrod, one of my closest friends in the world recommended that I have you on the show. He said, of all the episodes he’s done, you are one of the biggest wow factors that he’s had. So, I’m so thrilled about our time today.

Jenny Wood: No pressure.

Justin Donald: No pressure at all. And by the way, you could screw everything up here, but your message, which you’re not going to, but your message is so right up the alley of so many people that listen or watch it, and so, yeah, I’m just excited to explore your genius here today because you’ve done some really cool things and I want the world to know about it, but I want our audience to be able to take what you say in a tangible way into their professional life.

Jenny Wood: Yeah, definitely. Well, it’s a pleasure to be here.

Justin Donald: Yeah. So, alright, you have quite an impressive background. Your experience with Google, working there 18 years, that’s a long time. Obviously, your early days there and before it became a Mag 7 company and I’m sure you’ve seen a lot of the growing pains, but you have been involved and headed up divisions where you’ve helped drive billions of dollars a year in revenue. So, your expertise on a high level is like, it’s palpable, but at the same time, you’ve kind of created a new initiative under Google and even outside of Google. And you’ve been able to do it starting from step one. And I think that that is powerful for our community, that you have both the corporate experience, kind of moving up the ranks to becoming a high-profile executive there to the entrepreneur part of you, who is mission focused and mission driven. And so, I’m curious where it all started.

Jenny Wood: Well, it all actually started on a moment on the subway in New York City in 2011 where a really attractive guy was standing about 20 feet away from me. It’s probably not where you thought I was going to go here.

Justin Donald: No, but I love it.

Jenny Wood: But about 20 feet away from me was this guy, gorgeous blue eyes, thick, brown, wavy hair, Justin. And even though I want to talk to him, something holds me back. What if he’s a convicted felon? What if he’s married? What if a hundred people stare at me on this packed train? Well, underneath those questions were the fears that I discovered coaching tens of thousands of people directly or indirectly hold so many people back, fear of failure, fear of uncertainty, and fear of judgment by others.

So, I sit there and I do nothing as the train passes a stop after stop after stop, and as life passes me by, but I’m still so taken by him that I make a deal with the universe. You know how that goes, right? We make these deals with the universe, and I say, if he gets off at my stop, then maybe I’ll try to strike up a conversation with him and if not, then say, levy. Well, the universe was not on my side that day because he gets off at the next stop and I slumped down in my seat and then all of a sudden, this wave of wild courage washes over me and practically pushes me out of my subway seat and off the train, as I know exaggeration, pry the doors of the subway open and run off the train.

I chase after him to catch him. I do, as he’s exiting the station, I tap him on the shoulder. I say, “Excuse me, I’m sorry to bother you. You’re wearing gloves, so I can’t tell if you’re wearing a wedding ring, but in the event that you’re not married, you were on my subway and I thought you were cute. Any chance I could give you my business card?” And then I wait for what feels like forever, thinking this was a terrible idea. But then he takes the card, he calls the next day. We go on a date a week later, and we’ve now been married happily for 11 years with two small kids.

So, that moment of wild courage became a habit for me, and I started asking for what I wanted at work, asking to get promoted, asking for raises, asking for higher profile projects, asking for more money. And I ultimately tapped into more wild courage to start this program at Google that was used by 56,000 people in nearly a hundred countries, Own Your Career. Even though it had nothing to do with my day job, but like, that’s wild courage for you, baby. I didn’t go get a thousand approvals from legal and comms and HR and people operations. I just did it and it became massive with one small step at a time.

Justin Donald: Yeah, that’s an incredible story. So, was some of that like out of body experience, where you’re like thinking, but you’re talking and you’re like, oh, my goodness, did I just say that?

Jenny Wood: 100%. I mean, my opening line to this stranger was, you’re wearing gloves, so I can’t tell if you’re wearing a wedding ring. Who says that? I had no plan. This was not premeditated. It was like open mouth, exit, word vomit, and I didn’t intend for it to be so forward, but I had just turned 30, so I looked for wedding rings. I was trying to be respectful.

Justin Donald: Yeah, well, hey, if you showed up with any sort of the same amount of, we’ll call it wild courage, but also just confidence that you just shared that story with, I mean, I think that it probably didn’t matter what you said in that moment.

Jenny Wood: It’s so interesting that you say that because I’m oftentimes asked, were you just born with wild courage? Were you born with this level of confidence? And my answer is not remotely close. It is a learned skill over time, and that’s why anybody can learn this because maybe you’re not a subway chaser, but wherever you’re sitting right now, there’s something that you want. It could be a relationship, a project, an investment, a financial goal. And what sits between you and that thing you want is fear. Wild courage is the process of feeling that fear and going after the thing anyway, without perfect data, without perfect information, without a perfect answer. And it’s the set of tools that help you go after what you want and get it.

But I say that I learned it because I oftentimes get asked, were you born with confidence? Were you born with this wild courage? And sometimes, I feel like, wait, am I lying when I say that I really wasn’t? But just yesterday, I was doing a talk with a bunch of executives at Google because they’re still my number one client. And the person who hired me, Sam Sebastian, I think I can say Sam’s name, right?

Justin Donald: Sure.

Jenny Wood: He’s like, Jenny, when I first met you, you were 26, bright-eyed and bushy tailed, but man, you struggled to have a perspective. You struggled to have a cogent argument about a business initiative. And I was like, thank you for validating the fact that I did use to live in fear. And it’s not like I’m perfect now. I am rife with imposter syndrome. I’m rife with indecision. I really struggle to take a risky move or email a prospect for a keynote because I want to go work with a Fortune 500 company of, I’m still scared of rejection and failure all day long, that it was interesting that Sam reminded me that I really have come into my own voice with the learned skill of wild courage. And if I can do it, anyone can do it.

Justin Donald: Yeah, I love that. And I remember, I was kind of evaluating, I was doing these values, a values exercise for me, a values exercise for my family. And I remember the word courage came up and I remember researching it. And this is years ago, but I remember my big takeaway from the word courage is not that you’re doing things in the absence of fear, it’s that you’re doing them recognizing fear is there, yet you’re doing it anyway.

Jenny Wood: Yeah, you do it scared, right? You feel the fear and you take action anyway because action, not thinking provides clarity. Action, not thinking provides clarity. But the fear is what blocks us from the action, but if fears, if that’s what’s holding us back, that’s actually such good news because we have agency. We have agency to feel that fear and do it anyway.

Justin Donald: So, you weren’t always this confident, you weren’t always this bold. You didn’t have this wild courage in the early days. Now, if we go back early, you’ve now been featured in the Harvard Business Review and Entrepreneur magazine and Inc. and Forbes, and I remember a time, a day, a place where I, in a million years, couldn’t have imagined that I would ever have articles in some of these publications or that I would have the chance to write for a year for Kiplinger magazine. I remember a timid version of who I was and how I showed up.

So, if we go back to that side for you, where did it click? Was it that story with your now husband? Was there some sort of like apex or impact moment inside of the professional workspace that allowed you to go from, let’s just call it like a low-level worker bee to someone that’s actually moving up the corporate ladder in a pretty quick fashion?

Jenny Wood: Yeah, I do remember this one conversation with my boss at the time, Ted, who we were– he was in New York for an offsite, I was living there at the time. I now live in Boulder, Colorado. And we were sitting at this Greek restaurant and he said, Jenny, not only do I see you moving to the next level at Google, I see you being an executive here. Like, that then shared some accolades and it’s like sometimes we need someone to hold a mirror up to our strengths or our skills or what I call our power assets that make up our power portfolio similar to a financial portfolio. Sometimes you need someone to just believe in you, for you to believe in yourself, and I hope that my work gives people permission to believe in themselves, permission to ask for what they want, permission to chase the person off the subway permission to ask your boss’s boss for a meeting every six months, because those are the things that will move the needle.\

But I recognize that sometimes you’re not able to give that permission to yourself. Like, I wasn’t until Ted, who I held in a really high regard up on a pedestal, who was multiple levels above me, and I thought was just this incredible leader to say those words to me, for me to believe it myself. And I remember sitting there, shaking my head almost in disbelief. And then at first thought, like, oh, you’re blowing smoke. You’re trying to make me feel good. You’re coaching me to be better than I think I can be, which is a great thing a leader can do. I talk about that in the bossy trait of Wild Courage. But then I started internalizing it and I was like, he’s a smart guy. He wouldn’t have said that if he didn’t believe it.

So, for all the leaders out there, for all the people leading teams or leading organizations or leading your community, today, this afternoon, go tell someone that they are going to make it big. Go tell someone that you believe in them. Go tell someone that X, Y, Z skill that they have is exactly what the organization needs, and that they’re going to go far. Like, it makes a massive difference for them and it doesn’t take much of your time.

Justin Donald: Yeah, I love that. And I say this a lot that I think of, if we’re looking to level up and if we’re looking to really live an amazing life, both personally and professionally, it’s really going to come from the power of your peer group and the power of your mentors. And this doesn’t have to be the same person and it could be, but you need people in your life that are going to tell you how it is, the real story, like they will give you the real truth even when it doesn’t feel good. But you need the other people that are the cheerleaders, the encouragers that have belief, they share that belief with you. So, often, this comes in the form of one person can embody both of those things. Usually, I have found that you have a group of people that are a little more critical, a little more cynical, maybe not as diplomatic in delivery, but as you toughen up and you thicken your skin, you can receive that. And at the same time, you’ve got these other people that they just pour into you and they just give you belief in yourself. And because of the success they have or because of the values that they hold, it’s very meaningful.

Jenny Wood: Yeah. And you know what breaks my heart is that, yes, you want to have a mix of the people who are a little bit more critical, the people who fill your cup and encourage you. But I think that 80% of people don’t have anybody, don’t have mentors, don’t have sponsors, and they’re really selling themselves short because you need those relationships. You need to know some of your boss’s peers. You need to know your boss’s boss, right? I call this managing higher and managing diagonally, right?

Managing up, that’s old news. Everyone knows you need to have a good relationship with your boss. Managing hire is having a relationship with your boss’s boss. Managing diagonally is up and to the right on an org chart, right? Your boss is above you to the right and left of them are peers. Let’s say they have seven. Find two that are the intersection of influence and also, people you like and get along with and go get to know them and ask them for feedback on your project. Ask them if you can present thing you’re really excited about for 20 minutes, ask if you can mentor an early career professional on their team, because that’s where you find the greatest opportunity, and that’s when your mentors become sponsors. A mentor talks to you, a sponsor talks about you behind closed doors when decisions are getting made, like promotions or the big, huge projects that the VP is watching, right? And so, that’s what moves the needle.

If I bring it back to your principles actually, so find invisible deals is one of your principles of building wealth and passive income. And I would say that falls under this relationship building trait. Like, how are you going to find those invisible deals if you’re not out there talking to people? And I encourage people to have what I call a dynamic dozen, 12 people you’re going to meet in the next 12 weeks, or if you want to slow it down 12 months. But building those relationships and getting curious, which I call getting nosy and one of the wild courage traits, which we can go into. I’m probably jumping the gun here, teasing all these nine traits before we go into them, but like, that’s how you find the invisible deals. That’s how you find the invisible high-profile work at your organization.

Justin Donald: I love it. Yeah, and a question I think everyone should ask themselves is, who is endorsing you when you’re not around? Who’s endorsing you constantly that wants to see better for you? And that is only done by developing a relationship and by time spent. That’s it. Like you have to spend the time, you have to make the effort. And I think the more value you add to other people, the more they advocate for you behind closed doors.

Jenny Wood: Yeah, for sure. And leaders keep lists. Like, you think that when that job is posted on LinkedIn that it’s not already 80% filled because they know who they’ve been grooming for the last several years, whether it’s within the company or outside. You might not like it, like you might be pissed off at me listening to this, right? But it’s true, paternity backfills new roles, people doing international assignments who need to be temporarily backfilled. Like, leaders keep lists. So, what have you done this week to remind your leader or your investment partner or my speaking agent? Because I do a lot of keynote speaking that I exist, that I have new content, that I’m tweaking my keynote to be more about AI, that I’ve got a new leadership track, that I’m talking now about teamwork and collaboration and resilience and change management. Like, what have I done this week today to inform all of my speaking agent partners that that’s how I’m pivoting my keynotes? If I’m not there, if I’m not present, if I’m not reminding them, then they’ll easily go to their list of the five people who did email them this week to remind them what their new hot stuff is.

Justin Donald: Yeah, that’s great. And our audience, the people that watch and listen to this podcast fall in a few different camps, but we definitely have a ton of entrepreneurs and we definitely have a ton of people in the corporate world. And so, I think what you’re going to share is going to be very helpful. And so, just this whole idea, so you founded Own Your Career, right? That was the program at Google. And it sounds like you’ve kind of taken that concept outside of Google and you’ve done coaching and you do keynotes and you really help people, I guess, develop their own wild courage. So, I would love to dig into some of these concepts

Jenny Wood: Let’s do.

Justin Donald: In a practical way where people can actually use them to level up professionally.

Jenny Wood: Yeah, definitely. Well, one of the reasons I left Google was because I wanted to make this sizzly, and I don’t know if Google would’ve loved the way I positioned it internally. So, Own Your Career stays with Google. That is a program that Google owns that they can continue to use. But Wild Courage is the reclaiming of these nine traits that create the bars of an invisible cage that keep you small.

They raise eyebrows, Justin. They are not for the faint of heart because the nine traits of Wild Courage are weird, selfish, shameless, nosy, obsessed, manipulative, that’s a spicy one, brutal, reckless, and bossy. And these are all talked about in a very wholesome way, which sounds a little bit like, okay, prove it, Jenny, right? But I am reclaiming them. So, for example, selfish is the courage to be your own champion. Give everyone a leg up at your own expense and you’ll end up getting trampled. Reckless is the courage to err on the side of action and take intelligent risks, because better to learn from your mistakes than waste time predicting the outcome of every possible scenario. Think fast and fearless. If you’re on the fence, do it.

Manipulative, which I really feel like I have to defend, is the courage to build influence through empathy and craft lasting relationships because whether you’re selling a product, an idea, an investment opportunity, or yourself, your ability to win friends and allies is all about mutual benefit. So, figure out what people want and go get it for them so that everybody wins and you expand the pie rather than redivide the pie. So, that is my in defense of these nine traits because I deeply believe that if used in a savvy, insane way, they can supercharge your success.

Justin Donald: Yeah. And your book is a New York Times bestseller. So, you did, I mean, you sold a lot of copies, obviously, which is great. People are using this. This is practical knowledge, practical wisdom. And one of the things I always encourage people to do as they listen to this show is to take something, one thing every episode that they can use to help them live a life that’s more by design and less by default. And so, what I like is that you actually have applications to all nine of these. And so, let’s dig into some of these.

Jenny Wood: Let’s do.

Justin Donald: So, where do you want to start? What would make the most sense for people that are looking to level up, take more ownership of where they’re going? Not just live a life professionally by default. I mean, I think that’s what most people do. They live life in general by default. So, therefore, the byproduct in the professional world is a professional life by default.

Jenny Wood: Yeah, I think that an interesting place to start could be shameless and especially because you mentioned that I had to leverage wild courage. I had to leverage these nine traits to achieve a huge goal of mine, which unapologetically was to hit the New York Times bestseller list. It doesn’t happen by accident. If I were living life by default, if I were sitting there on the proverbial subway, letting the train pass stop after stop after stop, I never would have achieved that big goal. It’s kind of like the Mount Everest of books. And so, shameless is a great one. It’s about finding your swagger. It’s the courage to be audacious and like to think of audacity as a survival skill.

So, one example is, it took a lot of people to help achieve that goal, but I was not shy about sharing that goal. I was shameless in telling people that I wanted to hit the New York Times. I was shameless in asking 100, maybe 200 authors who I’d spent years building relationships with. Let’s call that manipulative, right, for the intention of helping each other. But I knew I was going to come asking for help come pub week. And of the 200 authors I asked for help and influencers, whether I could be on their podcast or they would mention the book in a newsletter or on their blog, there was one person who’s a very, very famous author where if I said their name, every single person listening would know who this is. And this person not only said no to my request to share about Wild Courage on pub week, they also broke off the friendship and the mentorship relationship with me. And man, did that hurt.

There were a lot of people who said, who either didn’t write me back, or said no politely, like, “No, I can’t do that. I get asked a lot. I can’t do it for anyone. It’s just my rule.” But this person really felt like a punch in the gut. And to this day, I am sad and I lost sleep over it. And this was like a couple days before pub date where I really needed sleep. But does it change how I would’ve approached the wild courage, it took the shamelessness, the selfishness, the recklessness of going out and asking for help? It doesn’t. It doesn’t make my decision bad. It makes the outcome bad in this one particular situation, but if I were then just knocked down by this one negative outcome, I would never have the audacity or the shamelessness to go ask the next person, or I also was trying to sell bulk copies because it’s hard to hit the times selling one by one by one by one copies. And this is the kind of book because it’s about how to thrive in your professional life that corporations really do like. And so, I wanted to sell bulk copies.

So, I sent about 300 emails out to organizations asking them to buy 200 copies in the subject line. I said, if you’re open to buying 200 copies, I’ll come, do a complimentary 20-minute fireside chat. I sent out the first hundred. I figured by the end of the day, there’ll just be checks rolling into my inbox. Turns out not so much, but you have to push past that feeling and continue to be shameless, continue to be reckless, whether you’re asking people to buy your copies of your book, whether you’re asking for a promotion, asking for an investment partnership, because otherwise, like nothing happens.

And so, yes, I tweaked it. I moved it from 200 to 50. I shortened the email, used AI to cut 60% of the text, and I tweaked it. So, failure is just data and I used that data to improve what I was asking for and how I was asking for it. But those are two examples of how wild courage can actually move the needle for your business.

Justin Donald: I love that. Failure is just data. And I do think that until we fail, we don’t really have the chance to succeed at the highest levels. And so, that is a backdrop and that is information that we can process and use to level up, I just think it’s so important. Now, you advocate for unapologetic ambition. I mean, that’s one of your kind of big catchphrases, if you will. But it’s more than just that. And I’d love to hear kind of your thoughts around that. Taking bold steps towards the desired outcomes, because I talk about this every week on the show, and so, I’d love your perspective and I’d love for it to be shared in a way that’s probably different than the way I share it.

Jenny Wood: Sure. Well, let’s talk manipulative. I tell this story about how I met author Vanessa Van Edwards. She is a total hero to me. And I was going to be in Austin where she lives for work and I was going to be there Thursday through Sunday. So, I sent her a note. A friend connected us over email and I said, “Vanessa, I’m going to be in Austin Thursday through Sunday. I would love to take you out for coffee and learn all about the publishing industry.” And she said, “Oh, what are the chances? Those are the exact days I’m going to be gone for a keynote. And then we’re extending it to do some family time.” And she said, “I’m leaving Thursday.” I said, “I’m coming in Thursday and my flight was supposed to arrive at 4 p.m. And it was already booked.” And I said, “What time do you leave on Thursday?” She said 3 p.m. I said, “Perfect. My flight gets in just before 1. I could meet you at your gate and we could have coffee.”

And my flight, as we know, got in at 4, but for 60 bucks to Delta and a change fee via change fee and a little tweak, I could change my flight and get in at 1. So sure, liar, liar pants on fire. But you know, relationships are high reward if you make them high investment. And so, I think there’s nothing wrong with being really intentional about the relationships you build and the strength of the relationship can be predicated by the effort you put into it. And so, I have no qualms about the fact, I fessed up to it later. We laugh about it now that I straight applied to her and said my flight got in at 1 and then went to Delta and changed my flight, right? So, that’s what I mean about kind of creating your own destiny. Serendipity isn’t found. It’s made. It isn’t found. It’s made.

Justin Donald: Yeah. That’s powerful to– I mean, the whole idea, one of my friends, good friend, Brad Weimert, he always talks about one of the most important values that he has in the friends that he spends time with is intentionality. How intentional are you with your time and with the relationships that you have and with what you want to learn, who you want to become? And so, I feel like this falls really into that category. For me, relationships are very intentional. I mean, I literally spend a full day every year planning with my wife who are the couples that we want to get time with together as couples, who are the people, and like what you said earlier, I have 12 people that I want to be intentional, even one-on-one spending time with.

So, we have our group of couples, we have our group of individuals. My wife has her group of friends. And there’s just not enough time for everything. And if you are in the habit of saying yes to everything, like a lot of people are, well, by default, you’re saying no to a lot of things, a lot of people. And so, I think we have to be more intentional with who it is that we want to level up with. And I have a category. Who are the mentors that I can learn from this year? And I make a list of the people that are not in my ecosystem that I need to bring into my ecosystem or somehow get into their ecosystem.

Jenny Wood: Yeah. Or even, who are you going to sunset? Not because you don’t like them or respect them, but who have you already gained enough from that it no longer serves you or them to have a regular monthly 30-minute call with? 30 minutes is a lot. Like, we’re not made of endless time. And also, we think that our friendships are just going to continue to flourish without any intentionality. And I will say I pulled back a lot on friendships in a way I regret as I was winding up things at Google and starting to do this book.

And I have some friendships that I let fizzle and I wish I hadn’t. And now that I’m rebalancing my financial portfolio, my mental portfolio, my emotional portfolio, now that I’m building this new life as an entrepreneur and I am high net freedom, and I’m able to now leverage the high net freedom state that I’m in, I’m thinking about how do I rekindle those relationships, which is another form of manipulative. And this is a good thing, right?

We hear the word manipulative and we think, oh, my gosh, that sounds terrible. You’re trying to harm someone. Well, I don’t want anything to be nefarious here, but think of an artist and a lump of gray, wet clay, right? That artist can manipulate that clay into a beautiful, creative sculpture. Just as good leaders can manipulate teams into doing something creative or doing something innovative. Or you can manipulate your portfolio to be the right mix of stocks and bonds or the right short term versus long term or the right high risk, high reward opportunities that you seek. So, I think that the word manipulate comes from to handle and you can handle the situation and create a process, create something out of nothing, and I think that’s actually really inspiring. And not at all bad.

Justin Donald: Now, let me ask this. We have a lot of people that are in the corporate world that have recently transitioned to entrepreneurship or they desire to, their goal is to do that at some point. You were in the corporate world for at least 18 years of Google. Maybe it was more somewhere else before that. Maybe it was just that. But the longer you’re in corporate America, I think, the harder it is to actually break those golden handcuffs, especially as you’re doing well, you’re building a reputation, you’re moving up the corporate ladder, you’re pot committed to a certain degree if there’s a place you’re looking to go or if you’ve been there for a certain period of time or if you’ve studied and majored in something and this is part of that major. So, it’s hard to abandon a good thing for the unknown, which could be a great thing, but it may not.

Jenny Wood: Yeah. And so, it requires being reckless, abandoning that thing for the unknown, right? Like I said, it’s about erring on the side of action. It requires being nosy. Nosy is the courage to get insatiably curious because curiosity drowns out the fear and pulls you closer to what matters most to you, so use it as a compass. And man, did I get nosy when I was thinking about leaving Google? First of all, I kind of hit, not rock bottom in a way that like I was a mess, but I was really taking on too much. I basically was trying to do five full-time roles, if you include being a wife and a mom as two of those five. And I was driving my son Ari home from choir one day and I was like, did my eyes just flutter closed? Because I was up from 2 to 5 last night, again, with lowercase a anxiety, thinking about all the people I was letting down as I tried to navigate having my full-time operations role at Google, leading the Own Your Career program, navigating all the external interest in a book and my work and all this stuff that I knew could come if I left. And it was just too much.

So, that moment happened and then it took me 12 to 18 months of back and forth, back and forth, back and forth to feel really ready to leave. But the cure is nosiness. A big part of it for me was what if I run out of money? And this got down to truths and tales. Truths are facts. They’re verifiable facts. We are both wearing collared shirts right now. I’m recording on a black colored microphone. Those are truths. They’re verifiable fact. Tales are the stories that we create to make sense of the facts. So, in this case, I was telling myself a lot of tales. I’m going to run out of money. As the breadwinner for my family, I’m going to let them down. My parents are going to be disappointed in me because they’re so proud of me working at Google. I’m not going to have any identity without Google, right?

But if I break down all of those tales into the truths, my parents have always been really supportive in any endeavor I’ve done. Thank goodness for them. I’m not going to get a paycheck every two weeks that has the Google logo on it, but I have other planned income streams. Yes, I’m the breadwinner for my family, but we’ve just had seven conversations with our financial advisor and we have been told by people who know what they’re talking about that we’ve got plenty of runway. And it gives me the opportunity to go out and be a keynote speaker, do one-on-one coaching, do small group coaching. And if you want, I might even ask for some coaching, Justin, on how I think about my revenue streams as an entrepreneur now.

But again, as I got nosy, as I got curious, as I stopped living in fear and anxiety and a scarcity mindset and started living with an abundance mindset, I was better able to make a thoughtful decision that like, yeah, it’s different than what you thought you might do for the next 15 years because I thought I’d keep those golden handcuffs tightly clasped on my wrists and retire here after 15 years and create incredible generational wealth for my kids. But maybe this can look different and maybe dying with zero is a better way to live and I’ll create memory dividends and I will just have a very different future with more passive income, and again, be high net freedom.

Justin Donald: Oh, I love it. That’s awesome. Before we dig into multiple income streams because that’s one of my favorite things to talk about, we could totally have some fun on this show doing that, I would love for some practical, tangible skills or applications for people that are in corporate America to move up, to get a raise, to get more responsibility, to just level up and create more opportunity for themselves.

Jenny Wood: Okay, amazing. Let’s do three of them. Let’s do woo with you. We’re going to do pull it and bullet and we’re going to do tame the octopus. And these are all ways that you can have more impact, have more influence, increase revenue for the company so that you can get recognized and you can be seen as a leader. Okay, so woo with you, if your emails start– pull up an email you’ve written recently. Anyone listening? And count how many sentences start with the word I versus the word you. Woo with you is to swap as many as you can to you versus I.

So, leader Annabel on my team had just done a product training for a client. We wanted to upsell them at Google, but the email said, I had so much fun doing this training. I would love to come back and do another one. I think that this is a really good product that Google is putting out. I know it’s not perfect yet, but blah, blah, blah, blah, blah. Okay, so all of those sentences start with I.

Then we swapped it to woo with you. You were an amazing team to partner with. You brought so much energy, enthusiasm, and knowledge to the way you’re already running your business. You will benefit from learning this new product that I’d be happy to come in and share with you. So, it’s manipulative, right? Like, it is thinking about what’s in it for them. How are they oriented? What are their goals? What are their objectives? Even tap their ego. Tell them their team is awesome, right? And so, that’s woo with you, a really good way to upsell, which gives you more recognition, right, and shows that you’re moving the business because what moves the business is what moves your career. That is number one.

Justin Donald: That’s good.

Jenny Wood: Should I move on to pull it and bullet?

Justin Donald: Yes, let’s do it.

Jenny Wood: Okay, pull it and bullet. So, if your emails are a bunch of text and paragraphs long, clunky pros, cut 60% of the text and write in bullets instead. So, pull 60%, that’s pull it and bullet. Write in bullets instead. No more than three. Leaders love threes. It’s like a love fest we have with threes because data points don’t add, they average. So, if you want to get seven points across, it’s just going to get muddled in the reader’s brain. And not only should you have only three bullets, but bold the first few words of each bullet, right?

Maybe if I’m pitching you to be on your podcast, Justin, and Hal Elrod was kind enough to connect us, but let’s say I’m pitching you, I might say I bring three things to the table. I bring customized content for your audience, number one. Number two, I bring energy and enthusiasm about my work. And number three, I bring a unique perspective as a female talking about finance, right? Like, maybe it’s those three things. Well, I also want to bold just one word in each of those bullets. So, maybe number one is perspective, number two is enthusiasm, and number three is– I forgot my third one already, but female view. And so, that’s pull it and bullet is cut 60% of the text and write it in bullets instead.

Justin Donald: That’s awesome. I love that. Super applicable. What’s your third one?

Jenny Wood: My third is called tame the octopus. So, if you want to get promoted, if you want to get a raise, one of the most critical skills that you can build to influence is tightening your verbal communication. And this one ain’t easy people, it ain’t easy. It takes practice, but it’s a muscle you can build. So, if you think of an octopus, with all the tentacles moving all around, it’s hard for that octopus to get from point A to point B. Justin, how often have you been in a meeting where someone rambled on and on and on and you couldn’t follow their point?

Justin Donald: Oh, it happens way too often, unfortunately.

Jenny Wood: Right. And be honest. Has that person ever been you? It’s definitely been me.

Justin Donald: Oh, I’m sure. I’m sure it has.

Jenny Wood: Yeah. Because I speak to think, and this helps you shift from speaking to think, to thinking to speak. So, we’re going to do a little role play here if you’re up for it.

Justin Donald: All right, let’s do it.

Jenny Wood: Okay, we’re going to tame the octopus. So, I’m going to have you ask me a question pretending that you’re my team leader, you’re my manager. We’re in our team meeting of 10 people. And you say to me, Jenny, what are your team’s biggest Q2 challenges?

Justin Donald: Jenny, what are your team’s biggest Q2 challenges right now?

Jenny Wood: Oh, my gosh, Justin, well, there’s so much going on because we’re a new team and we’ve got all these goals and all these priorities and we’re trying to integrate AI and we want to separate the important from the unimportant. So, it’s really been tricky, which reminds me that the tools we’re using are part in-house, part API, part third party. Something’s in spreadsheets and it’s just kind of murky and clunky. And the other thing that’s clunky is all the people that we’re trying to herd cats around, because we work in Japan and Tokyo and Europe and Asia and South America, and that’s really hard because we want to work in concert together, not opposed, blah, blah, blah, blah, blah. So, we’ve all been there. That is an untamed octopus. Now I’m going to have you ask me– well, let me check in. How easy or hard was that to understand?

Justin Donald: Super easy, super clear, and unfortunately, so normal.

Jenny Wood: Right. Exactly. Exactly, and I see the sarcasm there with easy and clear. So, that was an untamed octopus. Now I’m going to have you ask me the same question, Jenny, what are your team’s biggest Q2 challenges? And I’m going to answer it in a slightly different way.

Justin Donald: Yeah, Jenny, what are your team’s biggest Q2 challenges right now?

Jenny Wood: Justin, I’m glad you asked. Give me just a moment to think about this. My team’s biggest Q2 challenges are number one, priorities, number two, tools, and number three, global alignment. Priorities because we’re a new team, we need to figure out the important versus the unimportant. Tools because we’re doing some things in-house, we’re doing some things externally, and we should probably button that up. And number three, global alignment, because we sit across America’s APAC and EMEA, we want to be working in concert with each other, not against each other. So, to summarize, my team’s biggest challenges are priorities, tools, and global alignment.

Justin Donald: Yeah, succinct, clear, I mean, easy to understand, and for me, as I’m roleplaying your boss, I’m like, all right, well, she’s got it. Like, she understands, right?

Jenny Wood: Well, that’s the thing. It’s like we think that when we pause, we’re going to sound stupid or unconfident or not buttoned up, but we actually sound more poised and more confident and more buttoned up. And I was doing this exercise in a keynote with a finance company the other day and they said, and I was on the edge of my seat waiting for the answer. It felt like you were really honoring the question.

So, tactically, I paused, right? Don’t forget the power of a pause. I wrote down maybe like 7 or 10 things that I could have talked about. I circled three. Those were priorities, tools, and global alignment. And by the way, there are no wrong answers. Your boss isn’t some wizard behind the curtain with all the answers. Like, you can kind of say any of them. The idea is for you to be cogent and buttoned up and to signpost.

And then when I started talking, I said just those three things, right? Apples, bananas, pears. Then a little bit about each of them, and then summarized with apples, bananas, pears, whatever apples, bananas, and pears are in your particular situation. Works great in a team meeting. Works great in a one-on-one with your boss’s boss. Works great in an interview.

Justin Donald: I love it. Well, let’s wrap things up with some different income streams. This is a question that I think is going to be interesting because you’re going down the path of developing some new income streams. What do you put time and attention on? What don’t you? What’s going to take work? What’s not? For me, my favorite income streams are truly passive income streams. But that doesn’t mean that you start with those right out of the gate. Sometimes you need to have the active income streams that help produce later the passive income stream.

Jenny Wood: Yes, totally. And I want basically your help for me to be brutal, right? Brutal is the courage to say no and to recognize that you can’t do it all, that you have to say yes to the big and no to the smaller, yes to the smart and no to the stupid, right, of all the options I have. So, if I think of the things I can now do as an entrepreneur, there are a number of options. Number one, keynotes. Fireside chats at organizations who write big checks, but it requires being on a plane. Number two, one-on-one coaching, love it. Tough to scale. Number three, small group coaching. Number four, licensing my content, high investment, that’s more passive than the others. Number five, newsletter and LinkedIn sponsorships. I have about a hundred thousand people almost who follow me on LinkedIn. I’ve got 70,000 people on my newsletter. I’m leaving money on the table because I don’t ever have a sponsor for those. What else? Building a community which people say takes work, but again, it would be fulfilling. Okay, that’s six. Maybe that’s plenty to work with right there.

Justin Donald: Well, this is fun. So, for me, and I’m going to probably evaluate this differently than you, I think there are some people that are going to show up and they’re going to say, hey, my number one priority right now is to replace my income. I was earning X at Google. I’d like to get as close to X or exceed X, whatever that dollar amount is, and maybe it’s worth it to put in the time, right? My situation was a little different where I had built the passive income over time in one kind of area, one niche, and then once I had that covered, my decision to like, what am I going to do to create income is going to be different because it’s not going to be based on my time.

Now, let’s unpack this a little bit because with a newsletter, for example, a newsletter, so let’s compare newsletter with keynote. A keynote, that requires you, right? You have to travel, you have to present at some point in time, maybe with enough reps, you can build a team and you can have someone that speaks on behalf of Wild Courage, the Wild Courage org, right? But not in the beginning. And they want you. They want the face of the brand. So, that is a very active income stream, but it could also be a very high paying income stream. So, I’ve done keynotes anywhere from early days, like 5 to 10k on up to 50k for a one-hour speech, right? Sometimes they’re in my own city, I don’t even have to travel. Sometimes they’re elsewhere. And so, early on, I did a bunch of those and I remember getting to a point where I felt like I am working too much. This is actually becoming a job. I don’t want to feel like speaking is a job because I actually like to speak.

Jenny Wood: I do too. Yeah.

Justin Donald: And so, I started cutting back and I said, well, I’m only going to speak to these right-fit groups and I’m only going to speak at this price point and I’m only going to travel once a quarter max. And so, I had all these kind of like rules and boundaries around it. Now, let’s take the newsletter, for example. The newsletter is really cool because you can touch a lot of people and you can create a lot of content in one sitting that then can be produced over a longer period of time. And this is where I like getting who’s involved.

So, income streams that have other people that manage it, to me, is the greatest. That’s the greatest form of leverage. And so, with my newsletter, I don’t actually sit down and write out a newsletter each week when we send it out. I create a lot of content, whether it be on podcast or speaking to our mastermind or whatever it is, and I hire people to extrapolate the things that I’ve talked about that I think would be best.

Jenny Wood: As do I.

Justin Donald: And then we put that into play, right? And then I’ll approve the content going out. We’ve even utilized some AI in the process of newsletters and how to organize and how to figure out what topics make the most sense, what gets the highest open rate. And so, those are totally two different things. You probably build the value of your company greater on the newsletter list just based on company valuations than you do on the keynote. But you might need to do some keynotes to build the following on the newsletter, right?

Jenny Wood: Right, exactly. A lot of it works in tandem.

Justin Donald: And so, those are a couple of areas and for me, I do less keynotes today than what I’ve done the last seven years. And that was a choice. That was a concerted effort that I want to travel less and I want to build income that doesn’t require me to need to earn income actively.

Jenny Wood: Yeah, and I think the other thing that I’m thinking through is be smart about your math, right? Like, let’s say someone charges $25,000 for a keynote and $1,000 per hour as a consultant or doing one-on-one coaching. Well, it’s easy for that person to fall into the fallacy, oh, well, I should just do more keynotes because 25 grand an hour versus 1k an hour, like, of course, I’d pick the keynotes. But you know what? That keynote requires you to be gone for 24 hours minimum, most likely, possibly two nights, depending on which coast you’re flying to. And so, I think that thinking about if you’re doing the math the right way matters, especially like I’ve got small kids, right? So, these are things that I’m thinking through as well.

Justin Donald: But there’s just so many ways to make money that, I’ve got a lot of friends that speak. I’m in a community of friends that speak, and they do very well. I mean, these are very highly paid speakers. But I’ve just always had a different mindset around it, and it’s that, if I’m excited to do it and if it’s local, then that’s an easy yes for me, if it’s an audience that I think I really resonate with or that they’ll really resonate with me. But if it’s X hundreds of thousands of dollars or X million dollars that you can earn keynoting, well, how do we create that income somewhere else that doesn’t require as much time? Because there are so many ways, when you have a book, you can have an Audible, you can have an online course, you can have a podcast, you can have a membership community, you can have coaching one-on-one, you can have group coaching. So, instead of just an online course, you could actually have masterclasses on certain topics where you go deep. And so, I mean, that’s eight right there. I’ve got a friend, Kary Oberbrunner that talks about the 18 forms of passive income that you can create once you have a book, and so, there’s a bunch of other books.

Jenny Wood: That’s so great. Yeah, that’s so great. And I have them. I’ve done masterclasses on negotiations, masterclasses on getting promoted, masterclasses on influence, and it’s great. And I love doing them, right? The other thing that’s been a real big mindset shift for me is just thinking about, what do I really need? And this gets down to an abundance versus a scarcity mindset. And you use the example of replacing my Google income. Right off the bat, when I left, I said, “I don’t want to replace it. I want to replace 0.5x of it.”

And now, as I just thought more, I just went to Mexico with my parents and my kids and my husband and I really was able to zoom out. I’m actually having a bit of a huge mindset shift to potentially even think about the goal being a fraction of that 0.5x because there’s generational wealth that could be our North Star, but there’s also memory dividends, as I mentioned before, and time with my kids, and I always thought, well, like, I’ve got lightning in a bottle of this book hit the New York Times. Marshall Goldsmith said to me the other day, a well-balanced life doesn’t mean a well-balanced year. Like, go optimize for this book. You’ve got to strike while the iron is hot.

But then on the other hand, I’m not going to slow down when my kids go to college. If anything, I’m going to have more time and I’m going to want to dial it up. So, based on the fact that by the time your kids go to college, you will have spent 90% of the time with them you will ever spend with them. Honestly, I’d almost rather do 0.1x of my Google replacement salary now or my old Google salary now, and then dial it up more in 10 years when they’re both in college, then try to gun it right now and live under this scarcity mindset of got to act fast, the book is not going to be this hot forever, and then burn myself out and have my kids hate me. Because as we all know, the only people who remember the late nights at the office that you spent are your kids and not in a good way. So, it’s a real soul-searching exercise that I’m doing, which is a dramatic shift away from what I was thinking I might do with this book.

Justin Donald: Well, I think it's the most profound thing you've said is that you don't need to replace your income. It can be a fraction of your income. And this is where I always tell people it's important to figure out what is it you need to make to survive, what is it that you need to make to maintain your current lifestyle, and what is it that you would like to make to have your ideal lifestyle, and what does that break down to in a monthly basis because you don't have to earn what you are earning. And, for me, I want to optimize around relationships and experiences. I do not want to optimize around making more money. I just don't.

Jenny Wood: But it really required me to shift my mindset around the value of money. I think what kept me going back and forth at Google for those 18 months or 12 months when I couldn't pull the trigger and leave was because it was so ingrained in me to have a value of money as the number one thing, not in a bad or smarmy or slimy way, just because I think money is really powerful. Money is really powerful. But I will say, again, think about the truths and the tales. I thankfully had wonderful parents who taught me very good investment advice when I was 22. And like because I always saved more than I spent and invested more than I saved and maxed out my 401(k) every single year starting at 22 years old, I was able to create a situation for myself where I do have runway, where I do have an opportunity to pull from my interest.

Now, then I had to shift my mindset because I was like, “I don't want to pull from my interest,” never touching the principal, but I don't even want to pull from my interest because then you don't get the benefit of compound interest. If I want my money to double every 10 years, then I can't touch my interest. But that's where I'm making a shift in mindset. And I'm saying if I just consider a portion of this interest as income and use that to buffer my annual nut, my monthly nut, and we can cover that, then I'm really creating a situation where I'm exceptionally happy and I'm prioritizing things other than money, like relationships and my family and my health. I wasn't even feeling that healthy at Google. My hips were hurting. My eyes were getting worse. I was staring at a computer all day, just stuff that I didn't want at 45 years old.

Justin Donald: Yeah. I think this is all just, it's wonderful content here and I couldn't agree with you more. And I'll just say my favorite type of income is asset income. I love cash flow. This is what we spend most of our time on or a lot of our time on in the Lifestyle Investor Mastermind. Our community, we talk a lot about how do you create the passive income that comes from assets.

Jenny Wood: And do you just mean like income, like interest on your assets and taking it as income?

Justin Donald: Yeah.

Jenny Wood: Right. And that's what I'm starting to do when I never thought I would be able to.

Justin Donald: It's a beautiful thing. And then there are all these different investments out there that exist where most people that were in corporate America have the majority of their wealth inside qualified plans and inside the stock market. But when you look at what the wealthiest people in the world do, it's generally only about 15% to 25% of their net worth. And they buy these other assets that produce cash flow.

Jenny Wood: Real estate, angel investment deals. Yeah.

Justin Donald: Now, you're not stripping the dividends out of the public side. You're buying assets that appreciate and also kick off cash flow at the same time.

Jenny Wood: Right. And again, it requires all the work I did early in my career, which was to save and to live within my means and to not spend money on fancy shoes or fancy handbags or go out to dinner in fancy restaurants. Like for years I would always get the cheapest appetizer, right? So, I think that you want to make sure you're living an enjoyable life. And now I try to push myself to get the medium expensive appetizer. But I do think that there's just this mentality, a mentality of saving that can set you up for so much success and freedom in the second half of your career, which is what I have now, but I wouldn't have had it without the smart decisions I'd made early on.

And you know, is it a privilege? I think, yes, in part, it is a privilege because I had the privilege of my parents teaching me about investment strategy, and actually my grandmother and grandfather taught me about this. My grandma was the CEO of her own financial services company until the age of 92. And she was the one who said things as simple as, "Never spend more than you earn. Always max out your 401(k). Put your investments in well-diversified stocks and bonds.” And it doesn't have to be more complicated than that, right? And, of course, then there are more things that we're talking about that are also smart. But I think, yes, it's a privilege that I had that education early on but it's also…

Justin Donald: You still have to act on it.

Jenny Wood: You still have to act on it and it's trade-offs. And I did trade off fancy vacations and fancy dinners and fancy cars every two years so that I could create this opportunity for myself to now live the life I want to live and be there for my family. Now, whether I act on it, we shall see, because it will be hard to find the right balance, but at least I'm having this mindset shift of going from 0.5X to 0.1X of my Google salary.

Justin Donald: And I love that and I want to leave you with a thought before we wrap up, which is what helped you get to where you want to be is likely not the same strategy to help you get to where you want to go.

Jenny Wood: That's exactly right.

Justin Donald: The whole idea, like if you are not scrimping and saving, then you probably could level up. This is for anyone listening, not just you. When I say you, to anyone listening, if you're not saving at least 15% of what you make, well, you probably should scrimp and save to get to that level. When you get to that level, or you get beyond that level and you start amassing wealth and amassing assets and amassing cash flow, there's a different game. And you don't have to be so scarce with those dollars. And in fact, I would encourage people to say, "What are the things that matter most? Where do you want to spend your money?” If you can survive on less than you're making, great. Now, let's figure out where you splurge, vacations, eating out, healthy food, fitness, time with family and friends. And it's like, actually, I want to set goals of how much I want to spend in these areas.

Jenny Wood: Which is hard for me, really hard because when I have a saver mindset, it is hard for me to say, "Yes. Someone said I should download the Peloton app and stop doing free workouts on YouTube because the Peloton app is much better,” and I'm like, "699 a month?!” I don't know. Whatever it is. I'm like, “I couldn't spend on that.” So, I think those are really good goals. Ramit Sethi, I Will Teach You To Be Rich is really good about pushing people to figure out like, where do you want to invest? Sorry. Where do you want to actually spend and what's important to you? Maybe it's hotels for you, maybe it's restaurants for you, maybe it's fitness for you. And I think that's a really healthy exercise for me as I tumble into this new norm.

Justin Donald: Oh, this has been great, Jenny. Where can people learn more about you and about Wild Courage and all the cool things you're up to?

Jenny Wood: Sure. Well, the book's available everywhere in all formats: e-book, audiobook, hardcover on Amazon and everywhere else. And then, yeah, if you want to partner on a keynote or exec coaching or small group coaching, reach out to me. You can find me at ItsJennyWood.com and I share tips on LinkedIn every single day or five days a week, that is, so you can find me there. And I am like the last person to the party on Instagram. So, if you find me on Instagram, I would love for you to follow me there because I'm actually building that up. So, I'm shamelessly asking you, selfishly asking you, but again, it expands the pie because you'll get good content from me that, yeah, hit me up on Instagram. Follow me there.

Justin Donald: Love it. Well, I always end every episode with a question to our audience. My question is the same each week. What is one step you can take today to move towards financial freedom and move towards living a life that you truly desire on your terms, so again, not by default, but a life by design? Thanks for tuning in this week, and we'll catch you next week.