The Secret Ingredient to a Dream Career and Life | Jenny Wood

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Episode Transcript:

Jenny Wood: [00:00:00] To me, I think of weird as a strategic commitment to not fit in.

Jonathan Fields: [00:00:04] Jenny Wood has lived a life of what she calls wild courage, crafting a stunning 18 year career, leading a team at Google that generated billions, chasing her future husband off a New York City subway to get his number. Even learning to fly planes and really just living a life beyond fear by accessing what she calls wild courage, which is also the name of her groundbreaking new book that reclaims and redefines traits like being shameless, selfless, and nosy as fuel for amazing outcomes in work, relationships and life.

Jenny Wood: [00:00:34] Serendipity isn’t found. It’s made.

Jonathan Fields: [00:00:37] What do you think is the relationship between ambition and serendipity then?

Jenny Wood: [00:00:40] Ambitious people close the gap between what they want and what they get.

Jonathan Fields: [00:00:48] What do we risk losing when we’re not wildly courageous?

Jenny Wood: [00:00:51] We risk losing. It’s 2011, and I’m writing the New York City subway home from work and about 20ft away from me is this really good looking guy and I am really taken by him. It’s like gorgeous blue eyes, perfectly coiffed, 5:00 shadow. And I want to approach him, but something stops me. What if he’s a convicted felon? What if he’s married? What if he. What if I make a fool of myself while 100 people on this packed subway train watch me? And so I still want to talk to him. I made a deal with the universe. And I said, if he gets off at my stop, which was 72nd Street, I’ll try to talk to him. And if not, then say, love you. So we get to the next stop, which is 59th Street. People get off the train, new people get on the train. And all of a sudden, Jonathan, there’s like this wave of wild courage that washes over me and, like, practically pushes me out of my subway seat. And I run off that train thinking, forget the universe. I’m making my own meant to be. And I chase to catch up with him. Tap him on the shoulder I say, excuse me. 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 a slow forever. And then he takes the card, and three years later, we got married. We’ve now been married happily for over 11 years with two little hooligans who are seven and nine years old.

Jonathan Fields: [00:02:33] So was that characteristic for you at that moment?

Jenny Wood: [00:02:37] Yes and no. It’s not like I’d never been bold in my life or, you know, chased after a job, a, um, a goal or a project. But but it was uncharacteristic in that moment in that I live in so much fear of uncertainty. Fear of failure, fear of the judgment of others. And those are those like map to the same things I was initially feeling. Right. What if he’s a convicted felon? Fear of uncertainty. What if he’s married? Fear of failure. What if I make a fool of myself while 100 people watch? Fear of the judgment of others. And so I live in a lot of. I call it lowercase a anxiety. Thinking about what do people think of me and how do I fit in? And you know what? And then how do I overcome those fears consciously? Because everybody is capable of this. How do I overcome those classic fears consciously, to go after what I want in life and get it?

Jonathan Fields: [00:03:31] So in that moment, it wasn’t that you were just super confident and didn’t feel any fear at all. It’s just there was something that overcame you and said, this is a moment, there’s something about it. And if I don’t act now, um, something magical might never happen.

Jenny Wood: [00:03:47] Yeah, I mean, I also I really don’t like uncertainty, I like answers, I like data, I like to know. So in that moment I was like, screw it, I’m getting off this train because I’d rather have him tell me no. And maybe that is in and of itself, more fearless than the average person. I’d rather have him tell me no and have an answer than sit here wondering what could have been. And so that maybe was my motivator in that moment. And by the way, I was like a what’s the word? Dedicated online dater. I had a spreadsheet for all of the Galaxy pending dates I had. I once went on five dates in 24 hours. My spreadsheet had things like name, some classic stats, name, height, age. A snippet of what we talked about in our first online conversation. Is our first date booked? That one was binary. Yes or no? Am I? What’s my excitement? Level 1 to 3. And is he funny? 1 to 5. No pressure gentlemen. So? So like, I think that I was just. Maybe so. I was living so much in my head. And this to me, this, like, is going back to it was an uncharacteristic yes in that I live so much in my head. I’m super analytical, studied economics, undergrad and all, like my role at Google for years and years, was running an operations team that helped drive billions of dollars that sat between sales and engineering. Like always analytical, always in spreadsheets, always data driven, always left brained. And in that moment, I overcame that and I was just like, screw it, let’s give it a shot.

Jonathan Fields: [00:05:14] Yeah, it’s like, I have no idea. Like if any of the boxes are checked here, but something’s something. It’s so funny. I have another friend who for years had, um, 108 item checklists for a potential partner.

Jenny Wood: [00:05:26] And then, okay, so is this person now with their partner, like, is this person in a relationship.

Jonathan Fields: [00:05:31] That they actually are. But but it was like long after they let go of the checklist, right?

Jenny Wood: [00:05:36] Well, I was going to say how many of those how many of those 108 are checked?

Jonathan Fields: [00:05:39] Yeah, probably a solid chunk of them, but a solid chunk of them are not also. Um, yeah. And I think that’s a part of what we learn over time, you know, is that so much of the joy is actually lies in the space of the unknown of what we actually can’t figure out in advance.

Jenny Wood: [00:05:53] Yeah, absolutely. And it’s funny, the New York Times wrote an article about it, a full page article. It went viral. It was one of the most read articles in the 30 years that this reporter has worked at the New York Times. It was called serendipity one spreadsheet zero, kind of riffing on the fact that I live in spreadsheets and in this moment, serendipity one. But I still maintain that serendipity isn’t found. It’s made so. And then also, I also realized in that moment of just going with your gut that you do let go of that 108 checklist. Right? So, John, my husband is five years younger than I am. No one on that spreadsheet was five years younger than I was. They were my age. Maybe they were a year younger, maybe they were ten years older. But I never would have thought like, oh yeah, I’m going to be with a guy who’s five years younger than I am. And that was like, it’s like a bit of an anomaly, I would say, to be with a guy who’s five years younger than I am. But when you kind of just throw caution to the wind and you let go and you release yourself of the pressure of the checkboxes, magic happens.

Jonathan Fields: [00:06:49] Yeah. All right. So you just said something we need to dive deeper into. Serendipity isn’t found. It’s made.

Jenny Wood: [00:06:54] Yeah.

Jonathan Fields: [00:06:56] Tell me more.

Jenny Wood: [00:06:56] Yeah. So, you know, my dad growing up always said, kids, you make your own luck in life. Luck is 11:00 pm at the law library. Luck is working hard. Luck is, you know, putting in the reps. Luck is, um, you know, being strategic in what you pursue in life. Like that’s luck. And so on that day, it was putting in work, right? It was making effort. It was getting out of my comfort zone. It was doing something uncomfortable, something a little bit weird, something unusual. Um, and then I made I made the serendipity. I made the serendipity that created my life, which also gave me the confidence to go after so much else in my career, in my professional life, and my friendships, because it taught me that you really can make your own serendipity.

Jonathan Fields: [00:07:37] What do you think is the relationship between ambition and serendipity, then.

Jenny Wood: [00:07:41] The relationship between ambition and serendipity? Ambitious people close the gap between what they want and what they get. So that is the creation of serendipity. It’s action. It’s recognizing that you can have perfection, you can have progress, but you can’t have both. And at least progress is possible, right? So like let’s say that John had said no. All right. Well, it was progress in getting out of my comfort zone. It was progress in, you know, taking action around something I want and that that those reps putting those reps in are what create success, what create leaders, what ambitious people become in life and why they oftentimes end up getting a lot of what they want.

Jonathan Fields: [00:08:27] In your book, Wild Courage, You, you reframe what many would consider, um, this is going to be my language. The nine deadly sins of ambition.

Jenny Wood: [00:08:37] Um, can I steal your language?

Jonathan Fields: [00:08:38] Of course. Always. Um, and you reframe that into sort of like the nine superpowers that lead to not only the sense of just deep and profound courage, wild card using your language, but also Oftentimes wild success. Um, and also in nearly any domain of life, we’re not just talking about your job here. Yes, it’s relevant there. Um, so, you know, I just ask you, what’s the relationship between ambition and serendipity in your mind, but I also want to zoom out a little bit because the word ambition itself, um, is dicey, you know, right now. Um, it can land with some people as amazing, and it can land with some people as, you know, like, this is the thing to be snuffed out. Um, talk to me a little bit just about the word ambition in the context of the way you live your life.

Jenny Wood: [00:09:26] Yeah. What the heck is wrong with ambition? I understand, I understand the feeling of like, oh, we’re all going to lean out and we’re going to quietly quit. Sure. Quietly quit if you can get away with it. But, you know, I just feel so much joy and pride and accomplishment and fullness and life when I am ambitious. It’s like being opportunistic. What’s wrong with being opportunistic? Opportunities are amazing. Opportunities are fun. Opportunities are exciting. Opportunities create more serendipity. Create partnerships and lasting relationships and learning and growth. And to me, you know, being ambitious, being opportunistic are a little bit synonymous in, you know, it’s like they’re getting a bad rap these days. But these are good things, at least to me. I enjoy them. And I think that people oftentimes do enjoy that feeling of success or drive or ambition, but it’s unpopular to talk about it. It’s unpopular to put it out there.

Jonathan Fields: [00:10:26] Yeah. Well, I mean, why do you think that is, though? Because the way you just teed it up, it’s like, okay, this sounds awesome. You know, like, I could do all these amazing things and engage in these amazing experiences, like, create all these amazing relationships. Why do you think there’s often a negative frame around the world? The word ambition.

Jenny Wood: [00:10:42] It makes me think when I was in seventh grade and I would study really hard for a test, but then I’d say to my friends. Oh, gosh. Like, I can’t believe I got an A. I barely studied. Like, this is so surprising. Did you ever feel that way? Or do you know anybody who ever did that?

Jonathan Fields: [00:10:55] I was generally on the other side of the conversation. Okay. I was not the studier when I was, like, heading to a test, so.

Jenny Wood: [00:11:03] So I was. And but in high school, I just wanted to fit in. I wanted it was cool to be like, oh, yeah, I didn’t study. It was cool to be, like, rolling my eyes about the homework assignment and being like, yeah, I just read the CliffsNotes. I didn’t read the book, but in reality, the people who get ahead do color code their notes from class. They do read the entire book. That was always a really bad reader. So maybe I, you know, did read the CliffsNotes for real. But, you know, they do say that I worked really hard on this math problem set, and I got an A, and it felt great. And so in school, I think there’s this desire to fit in because standing out feels like suicide, right? Like, the last thing you want to do is stand out and be different than your peers. And if everybody’s trying to play it cool, then that makes you stand out. But in your adult life, in your friendships, your professional life, your relationships, like playing it hot is where it’s at, Jonathan. Like playing it cool. That’s old news. Playing it hot is cool. Like I’m into it. And so I think it’s just overcoming that fear of judgment of others. Because if it’s not expected, oh yeah, everybody should just be chill and, um, and have work life balance. And I’m a huge supporter of work life balance, but I’m also a supporter and an advocate of working really hard to achieve what you want.

Jonathan Fields: [00:12:13] I wonder if part of what goes on with ambition also is this ingrained sense of that everything in life is a zero sum game, that the only way that I’m going to shine. The only way I’m going to actually like, touch the golden ring.

Jenny Wood: [00:12:26] Mhm.

Jonathan Fields: [00:12:26] Um, is if somehow I step on someone else somehow if I take opportunity away from somebody else and that there’s like there’s harm caused by my ambition, because if I’m striving toward something and I achieve it, that means others can. And in some way I’m like doing wrong by them. And I wonder if there’s this, like, moral undertow that stops us from sometimes striving towards things we really want, but we won’t. Sort of like overtly announce or really put energy behind because, like, we have this idea that in some way, shape or form in me getting this thing, um, it’s going to stop others from whatever they want to explore in their own lives.

Jenny Wood: [00:13:08] Yeah. I think you’re bringing up something critical there, which is the perception of a zero sum game. And I feel like life is all about expanding the pie, and it’s about framing it, reframing it away from a zero sum game. So here’s an example. I love this concept of cheering your wins. And it does tap into ambition. It taps into being a little bit shameless and just celebrating yourself and, you know, having the courage to stand behind your efforts and abilities. So as I’ve launched this book, I have about 40 people who are on the team helping everything from my core team to interns to PR to my US publisher, UK publisher, marketing, etc. and I just created, you know, not too long ago, this alias called Wild Courage wins and it’s got 40 people on it. And I was like, I want to share the exciting things that are going on with this book. You know, we just got this big, we just landed this keynote, or we just got this big accolade or whatever it is. And I felt really uncomfortable initially sharing this with that group of people, basically the team working on the book. And I was like, oh, it feels like a zero sum game. Like, why am I talking about my wins? Why am I putting the spotlight on me? But then I was having this meeting with the six interns who were working on the book, and they’re like, Jenny, we’re so passionate about being here.

Jenny Wood: [00:14:20] When you share exciting stuff with us, we feel like we are part of something big. We feel like we’re part of something exciting. We feel like we’re part of something groundbreaking. So, you know, ask us to do things, share your wins with us, make us part of the crew. And I was like, oh my gosh, they don’t see this as a zero sum game. They don’t see this as another email in their inbox saying like, okay, here’s another cool thing that happened with Wild Courage. They see this as like we are part of this movement. We are part of this breakthrough for people. And we want to be we want to know and we want to participate in it. And so I did feel like sharing my own wins and successes was a zero sum game, taking something away from somebody else who had worked on the book. But they’re like, no. When you share that, we feel part of it, we feel behind it, we feel included.

Jonathan Fields: [00:15:03] And that kind of drops us squarely into one of the nine, the nine things that you really tee up. Um, and these are things that, again, they’re often viewed as negatives, um, like when people act in a particular way, you’re told actively not to behave in this way.

Jenny Wood: [00:15:19] Absolutely.

Jonathan Fields: [00:15:20] And yet you’re basically saying, no, no, like, let’s reclaim these and reframe them as something that’s actually positive, not just for you, but also like more holistically for those around you. Absolutely. You just offered up the notion of shamelessness, um, and gave an example of how that sort of like showed up in your immediate experience, somebody listening to this and they’re like, you know, await. You’re telling me to be shameless? So? So you’re telling me to show up at my job and to be shameless? To be. And then the brain’s going to go to brag, to basically tout how amazing I am, how good I am, how accomplished I am to, um, take me into this conversation because, you know, this is one of those things where people have a really strong, knee jerk reaction to it.

Jenny Wood: [00:16:03] Yeah, understandably, because all of these nine traits create the bars of an invisible cage that keep you small, they keep you silent, they keep you following instead of leading. They keep you not standing out. Right. And so I understand the knee jerk negative reaction to that, but I want to reclaim them. And shameless is such a great example, because it is just about the courage to stand behind your efforts and abilities. It’s finding your swagger, it’s audacity in the best possible way. It’s frankly a survival skill. Like how will you learn whether you’ve got the goods if you don’t first act like it? And there are. And the reason I love this one is because it can hold you back. The opposite of shameless to me is imposter syndrome, and 75% of people report feeling a lack of confidence at work. That’s a study out of the University of Leeds, and I’ve just seen so many people as I’ve coached Googlers, people outside of Google executives, I’ve seen so many people who are incredibly talented, gifted, skilled, experienced, stay stuck because of their imposter syndrome or lack of confidence or just feeling insecure. And to me, the opposite of that is kicking that shame to the curb. And that shame could be small, by the way. It could be, you know, worried about sending an email because you’re scared of, you know, a typo or spending 62 minutes reviewing the email because you want it to land just right.

Jenny Wood: [00:17:31] And you know that I’ve done this before, right? And so I invite people to reclaim this word. And here’s here’s a perfect example. I was sitting at work and I saw on my calendar that my normal meeting with my manager. My normal one on one meeting was moved from a Tuesday to a Thursday, and then on Thursday it was moved to a Friday. And this was right around the time that Google was doing a bunch of layoffs. And I was like, oh my gosh. I was terrified. I was like, layoffs always happen on a Friday. Someone texted me and said, hey, Jenny, I hear there are a bunch of layoffs going on in your org. I hope that your role is okay. And I was like, this person must know something. Shame, right? Like like insecurity. Um, fear. And then I checked the HR person’s calendar, and I was like, there’s an overlapping meeting at the same time. Aha. This must mean that I’m getting laid off. So here I am. This actually was there’s a tool here that I encourage people to use called Truths and Tales. I’ve I am stuck in the tales of what I’m creating.

Jenny Wood: [00:18:29] Right. I must be getting laid off. I download all of the pictures from my work laptop to my personal computer. I’m thinking, oh my gosh, why wasn’t I pushing the leaders on my team hard enough. Why did I get distracted by the side project? Shame, shame, but also tails. Then I got to the meeting on Friday and my manager says, Jenny, thank you so much for your patience. I’ve been vomiting all week and there you go. Like all of that story and tale is completely erased by the truth. The facts of the story. What were the facts? My manager moved the meeting from a Tuesday to Thursday and from a Thursday to a Friday. Another fact there were layoffs happening at the company. What were the tales that I was creating to make sense of the facts? I’m getting laid off. I’m not doing a good enough job. I am not pushing my leaders hard enough on my team tail. And so that to me, shame at work. Like, you know, that to me is the manifestation of shame happening at work, and also shame doing its job to keep you safe and keep you small. But when you get out of the tails and you focus on the truths, you can live a much happier, more productive and shame free life.

Jonathan Fields: [00:19:31] And we’ll be right back after a word from our sponsors. So that’s one side of shameless dealing with a sense of imagined shame, like the stories that we tell ourselves about how we’ve done wrong, how we’ve failed, how we’re not the person that we want to be. Um, but what about the other side of being shameless? Because I think when a lot of people hear the word shameless, they associate it with, um, with being, um, too bold, taking credit for all these different things. You know, so, like, you’re at work for a year. Um, or maybe let’s say you’re at work for three years. Um, and you’ve been doing all these incredible things. You know, you have a list of accolades and accomplishments that are really following you, and you feel like you’re not getting rewarded for it, either in a promotion or recognition or salary, like whatever it may be. Um, and a lot of folks would love to have this conversation and say like, hey, like, let me show you what I’m worth here. Um, but they view that as being kind of shameless like, I think there’s another like lens on this word, which is like people are like, but I’m not supposed to sit here and say like, because this is like like shameless, like translates to arrogant or egotistic.

Jenny Wood: [00:20:49] Mhm.

Jonathan Fields: [00:20:49] Um, and in the context of me especially being in a situation where I feel like I have less power than a person who I want something from, like, I shouldn’t be that person, I should be humble. I should be like, keep my head down. And I shouldn’t be the person who stands up and says, this is who I am. This is what I’ve done, and here’s what I expect back.

Jenny Wood: [00:21:09] Yeah. So it is so common to feel that way and to think that way. And what’s counterintuitive here, Jonathan, is that your leaders don’t see it that way. And I say this, having been at Google 18 years recently, left grew from entry level to executive. And as a leader, when someone shares their wins with me, I actually talk about this shameless Monday morning email that I love, right? Spend 15 minutes. Send your boss two bullets of what you accomplished last week and what your goals are for this week. I call it the shameless 15 minute Monday morning email, and when someone does that, it is helping me as their leader. Know what they’re working on. Gives me things I can talk about in my meeting with my manager. It shows me that they’re doing awesome stuff. It tells me what their goals are, goals are. It helps me think about how I can support them. And so if done in the right way, and that’s really important, right? You don’t want to take credit for other people’s work. You don’t want to, you know, step on other people’s toes. You want to make sure that you’re giving the right people credit. But there’s so much if we’re talking about a work context, and this applies to other contexts too, right? This can apply to relationships.

Jenny Wood: [00:22:16] This can apply to friendships. There’s so much that we do that people don’t know that we’re doing. And even just highlighting what it is that we’re doing is useful. It’s helpful. It’s valuable to other people. And yes, most people think, oh, well, I don’t want to be arrogant and I don’t want to be, you know, um, obnoxious. But again, to me, the counter-intuitive guidance here is that there are far fewer people who are actually arrogant and obnoxious and both. Think about it. Think about it right now. Think about how many people you know who are obnoxious, over-the-top, arrogant, or too much. And now think about, over the course of your life, how many talented, skilled, smart, experienced people, your friends, your partners, your colleagues you felt were just so talented and capable, but they were unsung heroes, or they didn’t stand up for themselves enough, or they didn’t ask for what they wanted. My hunch and you can tell me if I’m right or wrong. My hunch is that you know far more people in the category of smart, skilled, talented, but they just didn’t speak up enough to showcase their wins versus people. You’re like, oh my gosh, you are so over the top. I’m curious what your reaction is to that.

Jonathan Fields: [00:23:34] Yeah, I would say that’s probably true. There’s also probably a little bit of a selection bias there in that the people who I perceive as just being over the top arrogant and, um, are not people who I keep in my orbit for very long. So I like good people for sure.

Jenny Wood: [00:23:49] For sure.

Jonathan Fields: [00:23:50] I’m curious also because as you just said, like this also can apply to personal relationships. And I feel like this gets a lot more complicated in that context because like, you know, if you’re talking to your partner or your good friend and you’re having coffee, you know, and maybe you’re talking about your relationship and you start to list out the things that you’re doing. For a lot of people, the other side of that is going to land as an attack, as like, oh, so the implication here is like, those are all things I’m not doing and I’m not contributing in a level. So when you’re in a relationship with somebody where there is like parity, where it’s not like a boss and an employee type of thing, um, but you’re supposed to be equal contributors to the dynamic, and you start saying like, this is all the stuff that I’m doing that’s going to land in a really funky way with your partner.

Jenny Wood: [00:24:40] So it’s it’s teeny itty bitty tiny things. The name of my newsletter is Big Small Things. And it’s like, here’s a, here’s an example. So, you know, I’ve had a lot going on with keynotes and the book launch and everything. And John is doing a whole lot of dishes, a whole lot of dishes. But because I’m always moving so fast and going, you know, in a million directions on Any given Tuesday, I don’t always necessarily like, you know, realize or recognize that like, oh, there were dishes in the sink before, and now it’s beautifully clean and empty. And so if John came to me and said, hey, um, you know, drop the kids off at school, they did a great job this morning, did the dishes and started the dishwasher. That is a little tiny version of shameless. He’s taking pride in what he’s done for the house, for our family, for, you know, me as his wife. And I just don’t know that I would have noticed otherwise. All those things because your manager is busy. Your spouse is busy. Your friends are busy. And so it can be. It’s almost like a little itty bitty version of managing up within your home. And you do something great for the house or for your family, and you let them know. And that’s okay. And frankly, it’s helpful. And then I’m glad for the opportunity to say thank you. John, I so appreciate it. I know I have so much going on right now. I am so grateful for everything that you are lifting up in this house.

Jonathan Fields: [00:25:59] Okay, so I buy that, but I want to zoom the lens out here because everything that we’ve been talking about and we’re literally just talking about like one of these nine traits only right now. Yeah. But I think this applies to everything. So much of what you’re describing assumes that there is a healthy, functional dynamic in place between two people.

Jenny Wood: [00:26:16] That’s true.

Jonathan Fields: [00:26:17] That is not always the case.

Jenny Wood: [00:26:18] That’s true.

Jonathan Fields: [00:26:19] So like talk to me about that a little bit.

Jenny Wood: [00:26:22] Mhm. You’re right. And I think that my experience you know spending the vast majority of my career at Google, except for three years before that doing research at Harvard Business School. Google is such a high functioning, collaborative, thoughtful place that, and I actually worried about it. I worry about this with this work. Jonathan. I actually do worry about this because I think I was in a little bit of a bubble at Google where, you know, everyone loves to help each other out and everyone had most people have everyone’s best interests in mind, and your manager is there to support you and your wins. Don’t take away from anybody else’s wins. And I think there are a lot more relationships or, you know, or organizations where it can be more of a zero sum game where like, well, if I get promoted, this other person doesn’t. And yes, of course, there are always only going to be some number of promotions or raises or opportunities to go around. I think you’re right. I in those situations, to me it’s almost I would say call this a little bit of positive manipulation, you know, but manipulative is influencing people. And in those cases where there’s not a healthy relationship, my best advice is have that awkward conversation for three minutes and get on the same page so that you can have that foundation of psychological safety, that foundation of trust and giving and mutual respect. Because if that’s not there, you’re right. None of this works. And people will often forego that three minute awkward conversation of, hey, let’s get on the same page. Hey, how are you feeling about this dynamic? How are you feeling about this relationship? How are you feeling about the split of our workload? People will often forego that three minute awkward conversation, and they will accept three years of a soured relationship. And that’s unfortunate. It pains me to see that. It frustrates me to see that. And sure call that a manipulative three minutes where you’re trying to get on the same page, but manipulative. Manipulative is just influence in my book. Again, reclaiming it.

Jonathan Fields: [00:28:15] I wonder, tell me how this lands with you. I wonder if you think about, like advocating for yourself. Like basically saying, hey, like, this is what I’m showing up, this is what I’m doing, this is what I’m accomplishing. This is how I’m contributing on a regular basis. I wonder if, you know, like if you want to do that. And then the voice inside of you says, oh, this is going to land terribly. I’m not going to do that because I know there’s going to be retribution. There’s going to it’s going to lead to an argument rather than just an acknowledgement. It’s going to lead to closing doors rather than opening doors. I wonder if feeling that in anticipation of potentially having these types of conversations or sending these types of emails, actually starts to become a little bit of a litmus test for whether you’re in the right place.

Jenny Wood: [00:29:01] Oh for sure. And in that case, go plant yourself in more suitable soil. Absolutely. Although I would say it’s there can be times where you are in a great spot and it’s still worth having that conversation. And everything you said is so true. Like, but what if it’s hard? And you know what if it sours the relationship or sours the relationship more? Um, these are rationalizations, right? These are. These are fears. These are voices in our head that keep us small. These rationalizations are powerful. And rationalization is such a powerful weapon. It should require a background check like it’s so, so powerful. And I’ve lived in rationalization oftentimes in my life. Oh well. Going back to the subway, what if he’s married? What if he’s a convicted felon? What if a hundred people stare at me and make fun of me on this train? And it’s overcoming that fear. It’s the wild courage which is the process of overcoming that fear. It’s this set of tools to help you overcome that fear. Wild courage is what helps you have those productive conversations. Because sometimes, sure, you need to go plant yourself in more suitable soil, but there are plenty of other times that if you just had a moment of wild courage, you could have that conversation. It takes practice. It requires getting the reps in.

Jonathan Fields: [00:30:14] And you bring up such an interesting point there also, and I think important in that, maybe you are thinking that maybe you have that anxiety and that spin about like how this could go sideways. Um, but rather than stifling yourself and then end up suffering in so many different ways, um, or, you know, like if you literally just have the conversation now, at least you’re no longer reacting to only your own internal chatter. You’re reacting to actual data. And now you can say, okay, so this before I didn’t know if this was in my head. Am I just spinning? Am I telling stories about it or is this real? But if I actually do the thing now, I know. Yeah. So, like, maybe you actually get what you want and it was all in your head. Oh. Or maybe you get a really negative reaction and you realize, oh, this is real. There’s something wrong with the dynamic here. And maybe this is a signal for me to actually explore something.

Jenny Wood: [00:31:05] Yeah, absolutely. You just called us back to truths and tales, right? Like when you’re when you’re before the conversation, you’re living in your head and you’re saying, well, they probably think this and that. And this happened to me at work about five years ago. Someone sent an email. It really rubbed me the wrong way. And I was like, this person hates me. This person doesn’t respect my work. They hate the org I’m in. I was in a really tricky org that was like pushing the sales teams, and it was highly operational, and I had to tell them oftentimes to like, do things they didn’t want to do. And so I was like, this person just hates me. Living in my head, waking up between, you know, two and 5:00 in the morning, heart pounding, because it’s often the relationships, you know, that we worry about at night. And often it’s usually not the metrics or the goals that keep us up at night. So I was like, really? In my head, what do they think of me? And do they like me? And, um, do they think that my my org is worthwhile? And then and those are tales, right? And then when I had that conversation, I was like, hey, can we just chat for a few minutes? And we cleared it up. That 100% was not their intention. They were tired and stressed. They told me when they wrote it and that they really valued me and the partnership. And those were facts, right? They wrote an email. There was a sentence that said x, y, z. And then, you know, once I was able to separate the truths from the tales, I was able to have a much more happy, productive, fulfilling relationship with this person exactly like you just described. And now this person is like one of my closest confidants years and years later.

Jonathan Fields: [00:32:31] I think so often that happens when we actually then have those hard conversations about the things that we’re thinking or assuming. And you realize both people realize, oh, wow, um, I kind of want to be in this interaction or this relationship differently. Yeah, I want to touch on a couple of the other sort of like traits of wild cards that you list out, these, these reclamation traits. One of them is you invite people to be weird. Um, that, like, weirdness is a part of wild courage. Tell me more.

Jenny Wood: [00:32:59] Yeah. Weird is basically recognizing that within your so-called weirdness, lie your greatest strengths. So highlight every ounce of weird you’ve got. This one is the courage to stand out. Um, you know, I’m talking about a lot of dating stories on this conversation today, but there was this other guy that I was dating before I met John. We’ll call him Brian. And he wanted a wallflower. He wanted someone petite and blonde and quiet. And he said, someone who is beautiful but doesn’t think that she’s beautiful. Which, by the way, is not like just a red flag right there. But I tried so hard to squeeze my round peg into a square hole, I, I acted more demurely, I, I even changed the way I dressed, he once said, like, I think you should wear tighter jeans. And I was like, okay, sure, I’ll acquiesce to whatever it is that you want. Not recognizing that my own flavor of weird and the bold, outspoken, boisterous brunette, you know, dorky jeans wearing Jenny that I was is is a perfectly acceptable version of myself, and that eventually I would find someone whose weird matched my weird and who accepted me for who I was. But it was a very painful process to get there. There was a lot of, um, a lot of years of heartbreak Break and what the heck is this relationship and friendship? And, you know, whatever it was at different courses of the handful of years that was very damaging to me. And had I earlier learned in life to hold on to my weird, to wear it with pride, I would have been a lot happier and less heartbroken, quite frankly.

Jonathan Fields: [00:34:38] Yeah. It’s funny. I mean, I think this comes up so often in personal relationships and not just romantic relationships, but also friends. Like there is an epidemic of loneliness in this country right now. You know, like the percentage of people who say that they have one good friend that they could call in a time of need is horrifyingly lower than you would want it to be. Um, and, you know, and I feel like so many of us are feeling that and so many people want to reach out and want to build new friendships and want to cultivate a sense of community and belonging and like friendship based love. Um, but in order to do that, we kind of feel like, you know, we can’t be our real selves so often, like we are so driven by just the ability to say, I have that person in my life that oftentimes we won’t show up as who we really are. We hide our weird. Yeah, in order to be able to check the box of having a friend. Yeah. And that is profoundly damaging because that friend, even if they’re there for us all the time, if they’re there for like, the illusion of who we’re presenting ourselves to be, not for the really weird, dorky, whatever creative like, goofy person that we actually are. And so like, like our the essence of who we are is never actually in the friendship. Um, and yet we are so groomed almost to want to hide those parts of ourselves that feel like they’re a little bit spiky or a little bit different because we’re so desperate to fit in and have people.

Jenny Wood: [00:36:08] Yeah. And I think part of it is recognizing that you’re not for everyone. You are not everyone’s cup of tea. Right. There’s this tea called Lapsang Souchong that is, like, really aromatic and very bespoke and unique and like the average person is not going to like it. Right. Arizona tea drinkers shun it. Lipton lovers are like, what is this? This tastes terrible. But for a specific small group of people, they love this tea. And you know, I feel like wherever you’re sitting today, wherever you are, whatever makes your personality, you have some flavor of lapsang. Souchong. Right. So you may as well start the friendship on honest footing. Right. If me chasing John off the subway, it’s like, yeah, I showed my boldness, my over-the-topness, my unusual behavior, my kind of out there characteristics right away. And if I hadn’t been for him, then, fine, he moves on. That’s fine. But at least let’s start the relationship on honest footing. Right. So I think it is trying to find, you know, going back to planting, planting yourself in the right soil, whether it’s a friendship or a relationship or work. I think it is a question of putting your word out there and trusting. So much is about trust, trusting that your frequency is going to resonate with someone and that you will find those someones. But if we just hold ourselves back and try to fit the mold and, you know, try to fit in, you’re just I think you’re losing out on deep friendships and relationships. And so to me, I think of weird as a strategic commitment to not fit in.

Jonathan Fields: [00:37:33] Yeah, I love that. And then if we shift into a work context also, you know, so often the things that make us weird, like our different point of view, we see this problem differently. We see this opportunity differently. Like everybody around the table is saying this and this. They’re all in agreement. And we’re like, wait, what? Like, don’t you see that this is like a completely different thing that we’re talking about here? And then we stifle that because we’re like, oh, that’s going to make me the oddball in this particular moment or group. And it’s going to close doors for me, and it’s going to make me the annoying person in the room. And rather than saying, okay, so maybe that thing that’s making me weird is actually the thing that everybody needs right now.

Jenny Wood: [00:38:14] Yeah. 100%. Like, take a risk and be the oddball, because you’re probably not going to be as odd as you think you’re going to be. Let’s say you’re an intern, right? Interviewing or you’re working at a company for for the summer. Well, if all you want is that company’s name on your resume for the two month stint, great. Go ahead. Where the expected business casual stay quiet in every meeting. But if you want to get that job among a bunch of really highly qualified interns, well tap into your strategic commitment to not fit in. Just diplomatically disagree in that meeting where everyone else is nodding along like bobbleheads, right? Um, say something in the town hall in front of all the VP’s. You might even get three reprimands and three compliments in the same afternoon. Right. But if you’re just trying to fit in, you’re not going to you’re not going to make a name for yourself. You’re not going to stand out. And when you do those things, these little small things like raise your hand to lead the project, even if you’re the intern, you know, do it because you’re the intern, right? Those are the things that people higher up in professional organizations like. Those are the things that signal you as a future leader. Because leaders do make tough calls. They do have to be the naysayer. Sometimes they do have to separate, you know, what we’re going to do and what we’re not going to do.

Jenny Wood: [00:39:33] They aren’t the ones that are just nodding and going along like, that’s not a leader. Leaders make tough choices. Leaders are tie breakers. Leaders have to say the thing that that people sometimes don’t want to hear to effectively lead an organization. So if you signal that early on in your career, whether you’re an intern or you’re, you know, early, early career, professional, first five years of your job, those are the things that actually are going to make you stand out, even if you get your wrist slapped every once in a while. I like to advise people sometimes you got to pay the fine. Great story about this. Michael Jordan created the Air Jordan, right? The first basketball shoe that was breaking rules, right? He was a little bit of a rule breaker. The rule for the NBA was the shoe had to be at least 51% white. And if you recall, when these shoes came out heavily red and black. So the NBA, there’s this article where it says the NBA threw Michael Jordan out of the game. But thankfully they can’t stop you from wearing these shoes. And from that this like marketing bonanza grew. This multibillion dollar company and Air Jordans took off. So sometimes you got to go against the grain. You got to be a little bit of a rule breaker. You have to have a strategic commitment to not fit in. You’ve got to be a little bit weird.

Jonathan Fields: [00:40:44] And we’ll be right back after a word from our sponsors. Is there a sweet spot here? Is there being two? Is there being not weird enough? And then also on the other side being too weird? Or do you just need to say, this is who I am, this is how I’m showing up. Like, you either want all of me or none of me. And if you want. And either one of those is fine, but like, I’m going to need to potentially just keep moving through opportunities until I find the place where I can show up 100%. Me or is the practicality is the reality of this that you’re probably you maybe are never going to find that space where you can just show up and every moment and every time and every relationship and every project, you can just be like, here is big, bold, weird. Me, just like, deal with it. Um, what’s your take on that? Because, um, I feel like a lot of people, they’re like, okay, so I can I can let enough of that part of me out to feel like I’m good. Like I’m not feeling stifled. Like people know me and I’m contributing on a level that I want. But I also know there’s like a 22% reserve of weird that I’m not bringing here, because I don’t think people are going to be ready for. I would love to feel like I could, but like, I don’t want to risk that.

Jenny Wood: [00:42:03] Yeah. So I mean, it’s a great push and a and a great thought exercise Because with all of these traits that I explore, you can take it too far. I call these trait traps and you can be too bold, too much, too out there. And like that, 22% has bitten me in the butt before. In middle school, I was brand new to seventh grade, did not know a soul, and everybody else had been in that same school already in sixth grade. I’m in language arts class. Mrs. Howard starts talking about, you know, her life. She gives her little spiel about who she is and her little introduction to to all these seventh graders and I. And then she says, are there any questions? I raise my hand and tapping in a little too much to my weird I ask, I have a question. Are you a virgin? And that is taking it too far. That is the 22% too much. And that did not work out so well that day and I was mortified. I was going for a laugh. Spoiler alert nobody laughed and I was cringing. I wanted to sink back down in my chair and just hide under my desk. And you learn from these mistakes. You learn from these trait traps.

Jenny Wood: [00:43:21] Like I got caught in a trait trap that day, right? These are the nine traits that I say lead to success in life. I got caught in a trait trap. I took it too far. Ironically or coincidentally, I ran into her at the grocery store that afternoon. She was in the greeting card aisle and I think I got to rectify this. I take the longest ten steps of my 11 year old life and I said, Miss Howard, I’m sorry. I was really inappropriate what I said to you, and I apologize. And she was very gracious and said, I understand, you know, no sweat. Um, but what a lesson. I mean, I, I remember that both those moments in class and in the grocery store, I remember it like it was yesterday. And then you learn, right? You iterate, you launch an iterate. I launched something that was too weird. I iterate back down to, okay, that’s too much. How do you keep this in check? And how do you give enough of yourself like you want to give of your best self? Not say something outlandish or obnoxious just for attention? That’s not the weird we’re going for. And being mindful of that is critical.

Jonathan Fields: [00:44:20] Because, I mean, if your version of weird is you’re just a sarcastic idiot.

Jenny Wood: [00:44:24] Yeah, nobody.

Jonathan Fields: [00:44:25] Wants to be. That’s right. So I guess you have to really sort of like, inquire into this. Oh for sure. And figure out like, what is context appropriate here? Yeah. Um, one of the other things that you talk about, um, as, as one of these traits to reclaim is obsession. And again, this is one of those words where people here are like, okay, like obsession is the thing that destroys life. Um, take me into this.

Jenny Wood: [00:44:47] Yeah. This one’s so good. I love this one. All right, so obsession is the courage to set your own standard. It’s, you know, to push and perform and persist because none of these traits will serve you well if you don’t learn to deliver, right? Not for some company, but to achieve your own ambitions. Not for your partner, but to feel fulfilled in a relationship, not for your friend, but to feel like you are giving your all to the friendship. So funny. I think this is one that that people get. I don’t think it’s the most charged word, but I think the concept is one that just exhausts people. I’m working with this wonderful keynote coach on on, you know, my my corporate talks and fireside chats and corporate trainings. And he’s like, Jenny, you know, I read the book, but I skipped over the obsessed chapter. It just sounded exhausting. And I was like, okay, that’s cool. Like, I totally get it. Um, but then as we were working on the keynote, he was texting me all these speeches to watch. He’s like, oh, you’ve got to watch minute seven of the Steve Jobs Stanford commencement speech. And then he texted me another clip and he’s like, hey, you know what would be really funny is if you did this, I think you’d get a great laugh from the audience. And he’s like, you know, can we set up time tomorrow? Because I’ve got this section almost right, but I really want to iterate with you and see how we can nail the landing and land the plane on this one particular story. And I was like, Mike, do you real? I was like, I know you wanted to skip over the obsessed chapter, but do you realize that everything you’re doing right now is what I call obsessed? It’s the passion to get it right. It’s the enthusiasm about the product. It’s the desire to get it just so. And it gives you energy. It fuels me, Mike. It fuels you. It’s creation. And to me, that is obsessed in the best possible way.

Jonathan Fields: [00:46:31] I can totally see. And because I’ve been that person so many times, and it will be again, like when I lock onto something, especially as a maker. Like I have an idea in my head and I will do anything that I can do to make it real. Um, and at the same time, there’s this really fascinating research on passion, which certainly pairs it with the word obsession, for sure. You know, which shows that there are, you know, they describe passion as, which is kind of like a similar thing to what we’re talking about here as being either obsessive or harmonious, you know, and the like the harmonious passion is described as something that is, um, where you pursue something intensely, like it’s a deep, fierce interest. You love doing it. You want to just lose yourself in it, and you often do, but not at the expense of the other parts of your life that you also, um, hold dear to you. Like your health, your relationships, all these different things. Um, they describe the the flip side of that obsessive passion as that thing where effectively this one thing becomes all consuming. Your entire life gets wrapped around it at the expense of everything else and everyone else who you hold dear. And the fascinating part about that research is that if you said to that person, okay, you know, to somebody, okay, so here are the two different ways that you can sort of like go all in on something, um, you know, which one are you more likely to achieve the thing they’ll probably say, well, and this was my answer when I heard this research.

Jonathan Fields: [00:47:59] Well, like, you’re going to have a better life, more balanced life like a happier, richer life if you have the harmonious passion side of it. But if you’re trying to do this one big thing, I’m guessing you’ll be more successful, more likely to actually succeed at it. If you do the obsessive passion side, you just you forget about everyone and everything else and you make that entirely your life. The research actually shows the opposite, that it doesn’t happen that way because you need those other people and resources and activities as resources for when things get hard and when you annihilate them along the way. When things get really hard with that one obsessive passion, you don’t have anywhere to turn and you kind of collapse, you’re less likely to make it happen. It’s such, but it can be so hard to really delineate when you’re in it.

Jenny Wood: [00:48:44] Yeah, and I would build on that because you’re bringing up a key point about the relationship with others. I would say there’s even damage to the relationship with yourself. This reminds me of research from Barry Schwartz out of Swarthmore University, and he talks about Satisficers versus maximizers, and Maximizers get slightly better results. Right? If you’re, like, so obsessed that you just, like, set every ounce of your energy against something, against a goal so maximizers get slightly better results, but feel worse about the end product. Less happy, less less satisfied. Less fulfilled. Satisfies Satisficers you know, they get slightly, maybe not quite as optimal results, but they’re a lot more satisfied, happier with the outcome. And so that doesn’t even relate to your relationships with anybody else, which is such a good point that you bring up. And, you know, if you’re, like, crushing all the people around you, then of course, you know, you’re not going to be long term successful even if you short term achieve x, y, z goal because you need those people in your life to, to lift you up. And it takes a village. But even just within yourself, the dynamic within yourself can be really damaging if you take it too far. And I’ve done this. I had a talk once that I was giving and I just was beating myself up so much. I was too obsessed that this is another trait trap, right? This is like, is the juice worth the squeeze? I call this and I tried to memorize like 14 different things that I wanted to do in that talk.

Jenny Wood: [00:50:06] The perfect hand position and memorize every one liner and make sure I was stage left for this and downstage for that. And get really quiet here and really excited here. And, you know, the talk ended. I came home and I said to my family, they said, how did it go? I was like, I bombed and I didn’t bomb, but I felt like I had like I’d gotten decent feedback, but I was so exhausted. I came down with a cold the next day. I was so disappointed in like the I set the bar too high for myself, and I was so disappointed in not having hit the bar. And every one of those 14 metrics or goals or tactics that I felt like a failure. And that’s a real trait trap that is, you know, that on that particular day, no, the juice wasn’t worth the squeeze. And being mindful of that, even if it’s your internal relationship with yourself, is so critical in living a good life overall.

Jonathan Fields: [00:50:57] Yeah, that’s so agree. And I think one of the one of the really like more nuanced takes is also that we can there can be moments where the juice isn’t worth the squeeze, where we push ourselves too hard, we become too obsessive in the context of things that we genuinely love to do, and that light us up. This is not about like like being pushed to become obsessive about something you’re not really. I mean, you can have something that it’s really the drive is coming from the inside. You know, when I was a kid, I was a painter, and I was madly obsessed with painting. And I would just pour myself into something and, like, forget my friends and not go outside and not play. Um, and it became like it would take over moments of my life and to a point where I was like, this is actually not healthy. And then I started piling perfectionism on top of obsession. And that was like super toxic to me. But I think, you know, um, obsession. It’s such an interesting thing because I think this is one of those things where I truly do believe there is a sweet spot. And one of the huge red flags is, are you ignoring the other parts of your life that you claim to hold dear?

Jenny Wood: [00:52:01] Yeah, and finding the sweet spot, by the way, can be really hard. Really hard. I would imagine that you could think of ways it’s hard for you and where you’ve taken it too far, you know, driven, ambitious people like like us and everybody listening. I’m guessing because everybody listening wants to improve their life in some way or is, you know, has a growth mindset, is wanting to, um, be happier, be better, be more successful? Whatever it is that you desire to achieve, it can be tough for people like like you and me to dial it back. And I find that when I am so excited about something like, you know, putting my ideas out into the world, right? I took a massive risk to leave my Google exec role and be a full time entrepreneur. And so it’s like I’ve set myself against this goal. It’s like I want to besiege the city until it falls, right? Like I want to conquer, I want to accomplish, and all the best ways. It is very hard for me to balance it. You know, I was my son. Ari came in the other day and he’s like, mom, it’s time to go. Like I think you said, I have a haircut. And then I was like, yeah, yeah, I’ll be right there.

Jenny Wood: [00:53:05] And then Ari went and started like biking outside a little bit, and then I ended up yelling at him on the way to the haircut, and I’m like, we’re so late. Like, why were you biking? And he’s like, because I didn’t trust that you were actually going to leave your computer because you’re always working so much and like dagger in the soul, right? And he was right. And I do feel like it’s very hard for me to moderate when I’m enthusiastic and excited and energized by some goal. And for me, personally, moderation is possible. Abstinence is easier, and so I cannot wait till things slow down for me. And like, I want to take six weeks off and I want to actually zoom out of everything. Because when I’m dabbling a little bit in whatever exciting project or goal or thing is, it’s really hard for me to temper it. It’s almost like I have to be all on or all off. I’m really good at vacation and totally shutting off. But I have to be in that mindset because once I start, I almost can’t stop. Which, by the way, I’m not saying it’s healthy that borders on addiction and work addiction, and I think I have some of that.

Jonathan Fields: [00:54:04] Yeah, and I think so many people do also, um, other traits that you explore, you know, like selfishness, um, manipulation. You talked about that a little bit in our conversation. Be brutal. Um, be reckless, be bossy, be nosy. These are things that you dive into that I would definitely invite people to explore more. I’m curious, do you feel like there’s a connection between you? Talk about wild coverage. So these are nine elements that lead to this experience of wild coverage, which often leads you to like, get the things that you want in life. Do you feel like there’s a connection between physical courage, relational courage? Um, professional courage? Are they all the same thing but just different contexts?

Jenny Wood: [00:54:47] Oh, interesting. I think they’re certainly all related. You know, physical courage is an interesting one, I think. Probably because it all comes down to goal achievement. Someone who wants to run a marathon is probably going to also be the person who wants to get, you know, to go for VP in their company, right? Um, you know, relational courage, someone who’s bold enough to say to their partner, hey, you know, how do you feel about the amount we’re investing in our relationship over the past four weeks? Someone who has the courage to say, to ask that kind of what or how question about the relationship is probably also the person who’s going to have the courage to go to their boss and say, you know, what might it look like for us to partner on me getting promoted? Um, so I think they are all interrelated because it’s like that fire inside that drive, which, by the way, Jonathan can be learned like no one is born with wild courage. These are all things that can be learned with baby steps, small practical tools and actions that help you develop this muscle of wild courage. So yes, I think they are related, though of course I’m sure each one has its own particular nuance. Depending on what type of courage physical, relational, professional you’re dealing with.

Jonathan Fields: [00:56:05] Do you feel like being a parent has influenced your take on Wild Card?

Jenny Wood: [00:56:09] Um, definitely, because it’s really interesting to see how my kids show up with wild courage and without wild courage, especially my daughter. She’s seven. We were at the bagel shop the other day and they were out of the bagel that she likes. No, sorry, cinnamon sugar, and.

Jonathan Fields: [00:56:25] Which is pretty devastating no matter what your age is, by the way.

Jenny Wood: [00:56:28] Right. The gall of the bagel shop? No, right. No matter what your favorite bagel flavor is, right? Like, they should. They should never be out. Um, and so she’s like, I’ll just have plain. And I said, are you sure you don’t want chocolate chip? Because I know she also kind of likes chocolate chip. And she’s like, no, mom, I want plain. And then we walk out of the bagel shop and she’s like, mom, I actually did want chocolate chip, but I didn’t want people to think that I was eating like a, you know, she’s like a chocolate chip bagel. Sounds kind of babyish. And I didn’t want people to think that I was getting a babyish bagel. And I’m like, oh my gosh, you are seven and you are. You’re showcasing shame. You’re showcasing the shame like you have shame in a chocolate chip bagel. So you lied and said that you wanted a plain bagel instead. And just think about how we carry that judgment of others. Like who cares what the you know, College students at the bagel shop work in the counter, care about about, you know, think about your bagel choice. But to her, she didn’t want to be perceived as babyish. And these are things that just get harder and harder in life as we care more and more about what people think about us.

Jonathan Fields: [00:57:34] Yeah, it’s like the grooves start young, and the more we just keep rolling down those same groups, the harder it is to like to get out of those. You just become ruts. And I think we’ve all felt that and probably still feel it in different parts of our lives.

Jenny Wood: [00:57:45] Absolutely.

Jonathan Fields: [00:57:46] Um, big question. What do we risk losing when we’re not wildly courageous.

Jenny Wood: [00:57:53] We risk losing who we authentically are. We risk losing opportunities to do incredible things in the world. We risk losing the joy and the beauty of deep relationships and stories, and we risk losing. Staying in fear of failure, fear of discomfort, fear of the judgment of others. And when we get past that fear, we realize that no matter whether we win or lose in any particular thing, nothing feels as purposeful or powerful or productive as pushing past that fear to the joy and success on the other side of it. Because everything you’ve ever wanted is waiting for you on the other side. It is right there waiting for you. So when you reach for it, when you tap into your wild courage, you are giving yourself the opportunities to live a good life, to live with joy and fulfillment and success and deep, meaningful relationships. That’s what you’re losing. When you don’t live with wild courage, you’re losing all of those opportunities.

Jonathan Fields: [00:59:06] That makes so much sense to me. And it’s like when you do act, not only do you potentially achieve the thing you want to achieve, but like there’s a subtext which is also you achieve the unspoken thing, which is, I was really scared, but I did it anyway and look what happened. And that is like, you know, I think we discount sometimes, like we point to the, the external like goal and the like. Well, this is the thing I accomplished. But the real thing is like, you know, there was this voice in my head and I was able to hear it and still take action. And and that’s a win too.

Jenny Wood: [00:59:41] Yeah. Can I tell a quick story about my grandma? Yeah. Okay. So for because this reminds me of my grandma and she was just, like such a badass. So my my grandma is not any ordinary grandma. Grandma Lila was famous for saying things like no is just an opening offer. So, um. And we all looked up to her for, like, her fearlessness. And not only was she a bridesmaid in my wedding, she was the CEO of her own financial services company until the age of 92. Okay, when John and I first got married, we were living in her New York City apartment on her pull out couch for a couple of months while we were apartment hunting. One night, we sit down to dinner and John delivers some unfortunate news. He says, I’ve been part of a major company layoff today, and so I’m crushed, right? Newlywed and feels so sad for him. And I look across the table and grandma gets this gleam in her eye and she says, no is just an opening offer. Don’t sign the paperwork. And so John and I look at each other like trying to silently communicate what we’re thinking. And then finally John sighs and says, grandma, I don’t think it works that way. A layoff is like a one sided thing. They say you don’t work here anymore. And I say okay. And then grandma sighs and she says, don’t let fear shape your decisions, right? Like, sure, taking no for an answer would be more comfortable, but the discomfort will pass.

Jenny Wood: [01:01:09] Get your ego out of the way and find a compromise, right? You both want something. You want to keep your job because it’s easier to find a job when you have a job and they want to get work done even though they can’t afford to pay you. And so finally, John relents, and the next day he calls his VP and he offers to stay on for 10% just 10% time and pay while he looks for other jobs. So, surprisingly, they accept. And you know, the moral of the story here is grandma’s. Leila’s lesson is, again, don’t let fear shape your decisions. And not only can it give you success and happiness and joy and relationship and, you know, and your job or, you know, prevent you from getting laid off, which, by the way, he went back to 50% and then went back to 100%, went the financial crisis passed, which is just an unbelievable story. But the greater lesson is, you know, that when you take these actions, you really can overcome the fear to all the good stuff on the other side. And you also inspire people, like when people live fearlessly, it inspires other people to do things like that. And that’s kind of cool.

Jonathan Fields: [01:02:21] Yeah, don’t disagree with any of that. Feels like a good place for us to come full circle as well. So in this container of Good Life Project., yes. If I offer up the phrase to live a good life, what comes up to.

Jenny Wood: [01:02:33] Feel the fear and to go for it despite that fear, because that fear is going to remain. It’s part of life. It’s part of who we are. It’s part of what keeps us safe. It’s part of what kept us safe on the savanna, where, you know, sticking your neck out there could mean appetizer for a lion, right? Like stay small, stay. You know, um, protected by the pack. But in this crowded, competitive world of 8 billion people standing out, feeling the fear and going for it anyway is what’s going to create that good life for you. Serendipity isn’t found. It’s made. And the success that you strive for, whatever it is you want today, wherever you’re sitting right now, whatever goal or relationship or project you want to pursue or achieve, nothing feels as exciting and fulfilling as pushing past that fear to the joy and success on the other side. That, to me, is what comes up when I think about a good life.

Jonathan Fields: [01:03:36] Thank you. Before you leave, if you love this episode safe bet, you’ll also love the conversation that we had with Dan Pink about experiencing regret. You’ll find a link to that episode in the show notes. This episode of Good Life Project was produced by executive producers Lindsey Fox and me, Jonathan Fields. Editing help by Troy Young. Kristoffer Carter crafted our theme music and special thanks to Shelley Adelle Bliss for her research on this episode. And of course, if you haven’t already done so, please go ahead and follow Good Life Project in your favorite listening app or on YouTube too. If you found this conversation interesting or valuable and inspiring, chances are you did, because you’re still listening here. Do me a personal favor. A seven-second favor and share it with just one person. And if you want to share it with more, that’s awesome too. But just one person even then, invite them to talk with you about what you’ve both discovered to reconnect and explore ideas that really matter, because that’s how we all come alive together. Until next time, I’m Jonathan Fields signing off for Good Life Project.