Under the Influence (with Jo Piazza) - The Wild Courage to Go After What You Want (with former Google Exec Jenny Wood)

00:00:00.140 I want to date with Rawls, Carti says.

00:00:03.440 Rawls? Raka asks.

00:00:05.560 This is the love story of real-hinged couple Carti and Raka.

00:00:09.620 Written and read by me, Nicola Dynan.

00:00:12.380 Listen to the free audiobook now.

00:00:22.700 It's 2011, and I'm riding the subway home in New York City from work

00:00:27.300 when a really attractive guy is standing about 20 feet away from me.

00:00:32.440 So even though I want to talk to him, something holds me back, Joe.

00:00:35.900 What if he's a convicted felon?

00:00:37.560 What if he's married?

00:00:38.760 What if 100 people stare at me on this packed train? 0.95

00:00:41.480 That is former Google executive Jenny Wood.

00:00:45.100 She recently wrote a book called Wild Courage.

00:00:47.920 Go after what you want and get it.

00:00:50.760 And this is the story about how she went after a man on a train

00:00:53.400 and turned him into her husband and the father of her children.

00:00:57.300 Well, I later came to realize that underneath those questions were fears that hold so many people back, because they're the same fears that held me back so much in life. Fear of failure, fear of uncertainty, and most importantly, fear of judgment of others. So I sit there and I do nothing as the train passes stop after stop after stop and as, frankly, life passes me by. But because I'm still so taken by him, I make a deal with the universe. If he gets off at my stop, then maybe I'll try to strike up a conversation with him.

00:01:24.900 and if not, then c'est la vie.

00:01:27.700 He gets off at the next stop, not my stop,

00:01:30.360 and just as the doors are about to close,

00:01:34.060 I swear, Joe, I feel this wave of wild courage

00:01:37.780 wash over me and practically push me out of my subway seat

00:01:41.340 and off the train.

00:01:42.900 I chase to catch up with him.

00:01:44.040 I tap him on the shoulder.

00:01:45.400 I say, excuse me, you're wearing gloves,

00:01:47.840 so I can't tell if you're wearing a wedding ring,

00:01:50.200 but in the event that you're not married,

00:01:51.900 you were on my subway and I thought you were cute.

00:01:53.780 any chance I could give you my business card? And then I wait for what felt like forever thinking

00:01:59.060 this is a terrible idea, but eventually he takes the card. We go on a date a week later,

00:02:04.520 three years later, we're getting married and we've now been married happily for 11 years

00:02:09.180 with two small kids. So that was my first moment of wild courage. And now I applied in all areas

00:02:14.620 of life, relationships, friendships, work, home, et cetera. I love this so much. You say that to

00:02:22.540 be successful. You have to be shameless, obsessed, weird, selfish, nosy, manipulative, brutal, 1.00

00:02:29.300 reckless, bossy. All adjectives that I really like a lot. Love it. Because most people say 0.99

00:02:35.140 these are things I do not like and do not want to be. So you already get it. I totally get it.

00:02:39.700 Well, also, these are adjectives that are often applied to women, but in a very negative way.

00:02:45.060 Yeah. Yeah. And so how how did you get to this this collection of adjectives, all of which I am definitely all of these in a single day? 0.98

00:02:55.600 Why why why this to try to achieve the success that you want?

00:02:59.900 Yeah. Well, I mean, I think why especially as women, it's like we've got the double bind, right?

00:03:05.460 You know, as leaders, we're told you have to be nice. You have to be pleasant.

00:03:08.180 You have to be collaborative, but you also have to be determined and decisive and in charge, right?

00:03:17.400 And so that creates a lot of juxtaposition. 0.99

00:03:19.320 I think what happens is women, especially leaders, feel a lot of cognitive dissonance.

00:03:22.820 And by the way, that's whether you're a leader at home or in work or in the community. 0.67

00:03:27.520 We feel cognitive dissonance when we want to step into our power or step into our authority or step into, most importantly, our ambition.

00:03:33.700 because we feel like, well, gosh, if I ask for what I want, am I going to be called selfish?

00:03:39.120 If I share this project and I think it's awesome with my boss or my team, are they going to think

00:03:44.220 I'm shameless? Or if I take a big risk, like in my case, leaving this awesome Google exec job to

00:03:49.700 go write a book, is that reckless, right? And so owning those words and allowing yourself to step

00:03:56.280 into them and really reclaiming them in ways that no longer feel like they're the bars of an

00:04:02.040 invisible cage that keep you small, that keep you quiet and that keep you following instead of

00:04:06.180 leading, right? Like if I don't take action because I think it might be perceived as selfish

00:04:10.560 or shameless or reckless, I am creating this cage for myself and not stepping into what could be

00:04:15.560 out there for me in the world. Because when used in a sane and savvy way, these nine traits,

00:04:20.640 weird, selfish, shameless, obsessed, et cetera, can supercharge your success.

00:04:26.380 I think they really can. I mean, even just talking to you right before the podcast, 0.84

00:04:29.740 I have a confidence boost. I mean, I pretty much like I'm going to have you coach me throughout

00:04:34.600 this episode on boosting my confidence because it ebbs and it flows. As does mine. Right. I mean,

00:04:40.880 all of ours does. Right. But I love any book and any speaker that says to women,

00:04:48.240 you deserve what you want. Oh, my gosh. And go out and go out and freaking get it. Much like the 1.00

00:04:54.240 story about you and your husband and also the story about you leaving Google to then pursue

00:05:03.980 this dream of being on your own and being a New York Times bestselling author. There's a lot of

00:05:10.620 fear involved in that. And I am a person who leads with a ton of fear. It's interesting. I've been

00:05:15.720 dealing with my own, I call it lowercase a anxiety. And people, someone said to me the other day,

00:05:23.820 Jenny, you could sell ice to Eskimos, which kind of offended me. But I think they were trying to

00:05:28.080 say, you seem very confident. You seem very poised or put together. And I was like, you have no idea

00:05:33.300 what's going on beneath the surface. Like, I'm like a duck that like looks really graceful swimming

00:05:37.480 above the water, but then like underneath the legs are like frantically propelling. Right.

00:05:41.480 And I'm often saying, yeah, I like I saw a loon the other day on vacation and I'm like, I'm like

00:05:47.240 that loon and just gliding, gliding a lot. And then underneath, I'm just paddling. That's it.

00:05:52.000 It's a shit show underneath. 1.00

00:05:53.620 Wait, do we have a swearing? 1.00

00:05:55.460 No, you can swear as often as you'd like. 1.00

00:05:58.160 It is a bonafide shit show going on underneath the water. 1.00

00:06:01.620 Bonafide shit show under the water right down there. 1.00

00:06:03.700 Yeah, it's terrible. 0.99

00:06:04.980 No one wants to see behind this curtain, under the water, all the places.

00:06:08.680 You don't want to see what 6 a.m. to 7.40 looks like in my household when I'm trying to get my 7 and 9-year-old out to school.

00:06:15.580 and my son who has severe ADHD and my daughter who mostly tries to, you know, take a backseat

00:06:22.580 because my son takes up so much energy and space in the house. But I mean, just between the food

00:06:27.460 challenges, I know we're on a totally different tangent now, but like between the won't eat

00:06:31.220 anything and won't get themselves dressed and won't brush their teeth for two minutes by actually 0.97

00:06:36.400 moving the toothbrush around like bonafide shit show. Bonafide shit show. Bonafide shit show. And 1.00

00:06:42.040 And yet, and yet, I mean, I get this too.

00:06:43.740 I feel like professionally, I tend to present as very put together.

00:06:48.820 People are like, you're killing it.

00:06:50.280 Oh, my God. 0.98

00:06:50.760 And I'm like, I'm so fucking tired. 0.94

00:06:52.580 Yeah. 0.75

00:06:53.240 Yeah.

00:06:53.740 A lot of stuff going on under the eyes.

00:06:56.240 A lot of stuff going on under the eyes.

00:06:57.140 I'm seeing it right here.

00:06:58.000 I'm going to kind of smudge something out right here.

00:07:00.340 Mm-hmm.

00:07:00.780 Mm-hmm.

00:07:01.160 Exactly.

00:07:01.760 That's why I'm trying a new makeup routine right now.

00:07:04.160 I love it.

00:07:04.800 Tell me about it.

00:07:05.820 So I'm trying Ilia Beauty.

00:07:07.940 Oh, cool.

00:07:08.640 Yeah.

00:07:08.840 I mean, it's like one of those concealer things.

00:07:13.200 Instagram served it to me because that's what, they know me.

00:07:16.700 They're like, clearly I can see her under eye circles in all of these photos.

00:07:20.700 We see what's going on under the water, Joe.

00:07:22.300 We know.

00:07:23.920 And we can help.

00:07:25.100 Just give us your money.

00:07:26.700 Exactly.

00:07:27.280 And so I give them all my money.

00:07:28.280 But I'm really into this concealer foundation, whatever it is.

00:07:32.780 I have no idea.

00:07:35.500 I love how off topic we are right now.

00:07:37.980 back to shameless. Very off topic and very fun. Way more fun. So yes. Right. I left Google. I did.

00:07:45.880 It felt very scary. I am the breadwinner for my family. It felt safe to stay. It felt secure to

00:07:52.140 stay. It felt ego driven to stay because it's a nice brand to be associated with, especially after

00:07:59.680 18 years being there. It was like all I knew. And I had honestly a lot of pride and felt status in

00:08:05.260 working as an exec at Google and felt like I'd really earned my place having grown from entry

00:08:09.680 level all the way up to executive. Like I felt like I'd made it right. So I was here going to

00:08:13.540 just throw that all away to go bet on myself and be a starving artist. Now, that's interesting that

00:08:20.040 I say starving artist because that gets me into a tool I share in the shameless trait and shameless

00:08:26.140 is the courage to stand behind your efforts and abilities. It's about finding your swagger and

00:08:30.520 And like you said earlier, like believing that you deserve something.

00:08:34.480 One of the things that holds me back is, as I mentioned, fear.

00:08:38.120 And so I had as I was evaluating leaving Google, there were the things that were true, which

00:08:44.600 I call the the truths.

00:08:46.240 And then there were tales, the stories that I created to make sense of the truth or the

00:08:50.400 verifiable facts.

00:08:51.220 So I created so many tales like I'm going to be a starving artist.

00:08:56.360 We're going to have to move from our nice house in Boulder to the other side of the

00:08:59.740 tracks.

00:09:00.080 We're going to have to, um, dip into our savings. I'm going to, my kids are going to be disappointed

00:09:05.700 in me because they can't come to Google and ride the slide and eat the fun snacks. Uh, so just like

00:09:10.480 tail, tail, tail, tail, tail. But then when I broke it down, what were the truths of the situation?

00:09:15.400 I wouldn't get a paycheck every two weeks, but the Google logo on it. Okay. Another truth I'd

00:09:20.460 be leaving to try something totally different. Um, another truth I would be leaving to write

00:09:27.180 and speak to things I love to do. So once I was able to break down what was truth, what was tale,

00:09:32.900 it was easier for me to cut through the noise. And I'm not talking the external noise. I'm talking

00:09:36.740 the noise within my head of it's too risky. You shouldn't do it. You're going to fail.

00:09:42.020 What happens if, if, if, if, if. And then finally I was able to pull the trigger and do it.

00:09:46.580 Though it was a one particular moment that helped me pull the trigger. I was driving my son back

00:09:50.160 from choir. It's an hour drive on windy roads once we get closer to our house, because we live at the

00:09:54.820 base of the mountains. And I had so much going on at Google. I was leading this team that sat

00:10:01.600 between sales and engineering. I was leading this massive program called Own Your Career,

00:10:06.940 which grew to be one of the largest career programs in Google's history with tens of

00:10:10.660 thousands of people using it in almost 100 countries. There was all this external interest

00:10:14.820 in what I was working on and the content I was putting out there. And then had to be a wife and 0.55

00:10:22.680 mom. And so I was oftentimes up in the middle of the night from two to five, just so anxious about

00:10:28.300 everybody I was letting down and all the things that I was letting fall through the cracks and

00:10:31.940 all the emails I hadn't returned and the piles of laundry in the basement. And I'm driving Ari

00:10:36.560 home from choir. And I was like, did my eyes just flutter closed? Because it was one of those nights

00:10:43.080 that I'd been up a huge chunk of the middle of the night. And I remembered back to this guidance

00:10:46.780 that a mentor of mine, Julie, said, she's like, you can do it all, but not all at the same time.

00:10:52.380 And I was trying to do it all the time.

00:10:54.440 All, all the time.

00:10:56.480 And I was like, I have done Google for 18 years.

00:10:59.280 It feels terrifying to leave,

00:11:01.360 but I am going to go bet on myself

00:11:02.720 and call it reckless, right?

00:11:04.020 The eighth trait, the courage to take intelligent risk,

00:11:06.680 to err on the side of action,

00:11:08.540 because better to learn from your mistakes

00:11:10.180 than waste time predicting the consequences

00:11:12.420 of every decision.

00:11:13.380 So think fast and fearless.

00:11:14.700 If you're on the fence, do it.

00:11:16.280 And that is the trait that is the hardest for me

00:11:18.000 because I'm such an overanalyzer,

00:11:20.100 such a pro-con list,

00:11:21.220 such a, you know, death by a thousand mini decisions. And I was like, Jenny, you're not

00:11:25.860 living the values of your own damn book. If you stay at Google, like be reckless, bet on yourself, 0.99

00:11:31.780 learn from your mistakes. If it's a giant bust and you go, you know, keynote speak and, and do

00:11:36.640 consulting and coaching for a couple of years. And if it doesn't work, then go back and get another

00:11:40.040 job in corporate or somewhere else. But I didn't feel like I was living my values. If I stayed at

00:11:44.400 Google, especially with a book called Wild Courage. Yeah, no, I see that. Yeah, that advice

00:11:51.760 about you can have all the things, but not at once. I think about it so often. Like I said,

00:11:57.980 my friend Melissa Arnaud said to me the other day on this podcast, actually, she's the first woman

00:12:03.600 to ever summit Everest without supplemental oxygen. She climbed it six times. You know,

00:12:08.760 just your average, ordinary mom. And she says, I think about all the cups I have to fill

00:12:14.660 on, you know, a daily, a weekly basis. There's my career, there's my family, there's myself,

00:12:20.360 there's my friends. And all I try to do is just put a little in all the cups. They don't have to

00:12:24.920 be full. But is each cup getting just a little bit of me? And that is also something, I put that

00:12:31.400 on a sticky note and I hung it up because that is also something that I think about. Because

00:12:35.140 I think too often as women, we think we have to be and do all of the things at once.

00:12:40.760 And it's impossible. And I know for a fact that my husband does not think that.

00:12:45.080 Yeah. And yeah. And then there's the guilt.

00:12:50.000 So much guilt. So much guilt and so much shame.

00:12:52.540 So much shame. I mean, that's why I'm so excited in particular about the third trait,

00:12:56.820 which is shameless. And it's all about kicking imposter syndrome to the curb. It's all about

00:12:59.860 trying to give yourself permission, right? You know, to go after something big, to do something.

00:13:03.880 but like, I feel it now. I just got an inquiry this morning about a keynote in London. First

00:13:07.980 thing I did was looked up flights and I was like, okay, I could go on Monday, spend one night, do

00:13:11.460 the key, like sleep on the airplane, maybe do the keynote at three 30 PM. I come back the next day

00:13:17.740 and I'm like, okay, I only missed two bedtimes with my kids. But like, I, I, it's not every guy,

00:13:23.680 but I think that a lot of male business owners would just be like, oh yeah, that's just what I

00:13:29.720 have to do. And mom's there to get tuition appointments and to pack the lunches and to 0.99

00:13:34.000 make sure the right snacks are in the right backpacks. And, and, you know, and John, my

00:13:38.500 husband is unbelievable. I mean, this book would not have happened without him. Like he basically

00:13:43.080 single parented for the last huge chunk of time. I get it. And that said, there's still stuff that

00:13:49.360 I feel like will always fall on me because it's just in my mom's spidey sense to plan the play

00:13:55.800 dates and to think about like, I don't know, just a bunch of stuff that, yes, I want to take this

00:14:02.060 trip to London because pardon the expression, my business is now eat what you kill. And it is,

00:14:07.600 it's hard. It's really hard work. I thought Google was the hardest job I ever had. Turns out

00:14:11.980 easiest job I ever had. Just so much harder to be an entrepreneur. If you can do anything in the

00:14:16.720 world, but be an entrepreneur, go do that. And that is a direct quote from Jason Pfeiffer, who's

00:14:21.840 the editor-in-chief of Entrepreneur Magazine because it's really, really hard to be an 0.99

00:14:25.680 entrepreneur and it's really hard to be a female entrepreneur. But we have superpowers as women. 1.00

00:14:30.760 We are able to keep all those plates spinning and all those cups a little bit full. And then I think 1.00

00:14:37.620 the important part is stepping into that power, being obsessed where it makes sense to be obsessed,

00:14:41.780 right? That's the courage to set your own standard, to push, perform, persist because

00:14:47.500 your enthusiasm fuels your effort and nothing makes me sadder than seeing women who dim their 1.00

00:14:52.580 light and who, you know, take a backseat to a big, exciting idea or project because they're like, 1.00

00:14:57.820 oh, I'm sure it'll never work. Or, you know, I don't, I don't know if I have the energy to put

00:15:01.780 into it. And then when people do like the world changes, lives change, projects change, companies

00:15:08.000 change, clients change. And women are incredible leaders, incredible at making things happen when 0.99

00:15:13.440 they let that healthy obsession fuel their projects and their ideas and their processes, 1.00

00:15:19.240 again, whether it's at home or at work. So I hope that everybody continues to give themselves

00:15:23.880 permission to take these large steps or even these small steps, because a lot of it is like,

00:15:27.420 what's the small thing I can do right now just to stay sane? But women are freaking amazing. 1.00

00:15:33.280 And women leaders, a special breed. A special breed. They really are. All right, we're going 1.00

00:15:37.480 to take a quick break. And when we get back, I want to dissect a little bit more about this shame.

00:15:43.440 and guilt because I've had to get over a lot of it. As an author, I now feel like an entrepreneur

00:15:48.840 because you have to be. You're running a business. Yeah, your book is just a clunky business card.

00:15:54.660 It's just a product that I'm selling, right? Just like anyone is selling leggings or lip gloss.

00:16:00.520 It's a wonderful, magical product. Everyone can reorder. Everyone is lying to you right now

00:16:04.680 because it's awesome. But I feel shameless all the time and that still gets me. So let's talk

00:16:09.420 about that when I get back. Great. I don't think I can be your friend, Isabella said.

00:16:19.320 Rebecca's stomach flipped. This is the love story of real hinge couple Isabella and Rebecca,

00:16:25.160 written and read by me, Temi Denton-Hurst. Listen to the free audiobook now.

00:16:32.080 Chew on this bold question from Dentine Gum. Is it ever okay to compliment a millennial

00:16:38.360 on their skinny jeans in 2026. Dentine, Chew Bold.

00:16:50.660 I want to talk about my shame. Can we unpack my shame together a little bit? Is this just

00:16:55.700 like a live coaching session? Live coaching. Yeah, two ways. On the podcast, I still feel

00:17:03.100 like I am a shameless marketing monster. Every time I promote my own book, even though I know

00:17:10.200 it will not succeed unless I do this. Yeah. How can I get over this? To reframe it as helping

00:17:16.540 people. That you are giving people an opportunity to help themselves, to advance, to make changes.

00:17:28.700 What are you most proud of of your book?

00:17:31.580 What is the part of your book that you get most excited about or that you hear from people helps them most? 0.99

00:17:38.020 Well, this particular one is about trad wives murdering their husbands. 0.97

00:17:42.480 Okay. 1.00

00:17:44.040 So I do think that it's helpful.

00:17:46.300 And I also believe truly that it's what America wants and needs right now.

00:17:50.520 I would really like to get a copy of it to Usha Vance.

00:17:53.980 and uh but but i i also for me i do think that great books are escapism and we need some fun

00:18:03.840 right now this is a bananas thriller and i believe that once people get this one in their hands much

00:18:09.120 like sicilian inheritance which i was shameless about last year it's becoming a lot now that i

00:18:13.480 have a book coming out a year because there's no break right yeah it's just that is a lot it's like

00:18:18.100 there's Piazza going at it again. Yeah. Yeah. Which is incredible. And people admire it. People

00:18:23.920 look up to you. People come to this podcast to get that like shot of adrenaline and enthusiasm

00:18:28.140 and and, you know, leadership and and inspiration. And so you're right. Books. Think about how

00:18:38.560 magical it feels to read. Think about how magical it feels to get in the bath or to take a quiet

00:18:44.000 10 minutes when you're not folding laundry or not doing dishes, because when you're reading,

00:18:47.540 you are, it's one of the only activities where you are solely focused on one thing. You're not

00:18:52.500 multitasking. You're not, you know, trying to battle a thousand different things. Like it's

00:18:58.740 when you sit down and you have quiet and that is a special, special time. So you're giving people

00:19:02.220 that gift. So yes, it can feel uncomfortable. Yes. I mean, do you, let me ask you this. Do you

00:19:08.580 want to have a big impact on the world? Oh my gosh. Absolutely. I'm just trying to dismantle

00:19:14.080 the patriarchy. Yeah. With fiction. One fiction novel at a time. Yeah. I mean, that's a pretty

00:19:22.020 cool goal, right? I think so, right? Yeah. And it won't have a huge impact in this world. Let me

00:19:27.140 ask you a second question. Are you willing to get a little bit uncomfortable in order to have an

00:19:31.880 impact? Yeah, no, I'm willing to do anything. After having three kids, I'm pretty much willing to be

00:19:37.120 naked in any situation or uncomfortable doing anything, really. I have, you know, I have so

00:19:45.180 much shame around the marketing, which is funny because I have no shame in any other aspect of my

00:19:49.800 life. That's interesting. I get it. But no shame. Yeah, I get it. No, I hear you. So here's something

00:19:54.360 that I do that feels shameful. And again, when I'm talking about shame and wild courage, it's a

00:19:59.820 little bit different than the classic definition of shame. It can be smaller, right? So again,

00:20:03.420 lowercase s because I'm big on caps and lowercase in these words. So lowercase s, shame, feeling

00:20:09.940 guilty. Well, I guess that's different. Feeling insecure, feeling like I shouldn't be the one to

00:20:15.960 do this, feeling like I'm bothering people. There's a lot of people pleasing that comes up for

00:20:19.900 me, feeling like I, you know, I'm asking too much of people. So here's a good example. My social

00:20:27.720 media of choice is LinkedIn because, you know, this is a big like business audience, though,

00:20:31.200 of course it's relevant for anybody at any point in their life. And, and so on LinkedIn,

00:20:36.040 I have 30,000 connections and that's the max. I have 92,000 followers, but of the 30,000

00:20:41.480 connections, I can DM them with this automated tool. And, you know, every six minutes it sends

00:20:46.980 out and it's like, I'm talking straight up book marketing, Joe, that feels uncomfortable and a

00:20:52.000 little bit shameful. So every six minutes, a DM goes out that says, Hey, my book just hit the New

00:20:56.580 York Times. I'm so excited to share it with you. This book has helped people, you know, feel like

00:21:01.480 they're better leaders at home, get $30,000 raises, you know, a couple snippets. If you want to order

00:21:06.080 it, send me an email and I'll freak out and blah, blah, blah, blah. And every once in a while, I get

00:21:12.940 an email that says, stop spamming me, or this is annoying. And I have every, it feels like a punch

00:21:19.660 in the gut every time. But I also know that 14% of the DMs I send out convert. And that is a really

00:21:27.200 significant conversion rate. Actually, that is a conversion rate to my newsletter because I've also

00:21:30.820 sent this in the past to newsletters. It wouldn't be that high for book sales. But for a newsletter

00:21:34.880 even, that's a really, really high conversion rate. And I have a goal of growing my newsletter

00:21:39.100 list so I can help more people. So even though, sure, I'm draining the trust battery in some of

00:21:44.280 those cases, I've also given people an opportunity to achieve their goals and to read this book and

00:21:50.540 to feel more confident, more competent, more successful, more emboldened, more alive. And

00:21:55.400 that's something I can stand behind, even though it feels like a punch in the gut anytime someone

00:21:59.200 directly says, I don't like this. I don't like what you are doing. And you just have to kind of

00:22:03.740 live with it. That punch in the gut hurts more than when someone tells you they buys it and it

00:22:09.140 feels good. Oh, well, because we have a negativity bias. That is a social psychological principle

00:22:13.400 that's been around since evolutionary,

00:22:15.240 like, you know, it's an evolutionary psychology idea

00:22:18.600 from the caveman days, right?

00:22:20.260 Where you wanted to stay small

00:22:22.560 and you wanted to not err on the side of risk

00:22:25.220 because sticking your neck out

00:22:26.300 could mean you're a lion's lunch.

00:22:27.900 But now in a world of 8 billion people,

00:22:29.840 it's slightly bigger,

00:22:30.660 there's more opportunity to take risk

00:22:32.320 and we need to overcome that negativity bias

00:22:35.000 by, you know, like recognizing the good

00:22:38.180 we're putting into the world.

00:22:39.180 And just, I do find that, you know,

00:22:41.520 actually, I love this. My former, one of my leaders at Google, Rob, said that his dad said

00:22:48.780 to him, unless you have a few fouls, you're not in the game. And it was like a soccer or basketball

00:22:54.100 reference, whatever it was. But I love that. Unless you have a few fouls, you're not in the

00:22:58.180 game. And that to me is like the essence of healthy recklessness. Because it means you need

00:23:03.140 to play big. You need to put yourself out there. You need to take some risks. You need to push it

00:23:08.600 and make yourself and maybe some other people uncomfortable.

00:23:12.720 Totally.

00:23:13.360 Most of us have imposter syndrome about a lot of things,

00:23:17.020 and yet we seem to think that we're the only person with it.

00:23:20.560 I think that social media inspires us a lot more

00:23:22.860 because we're only seeing the best lives of other people.

00:23:26.140 Yeah.

00:23:26.400 Talk to me a little bit about that.

00:23:27.920 I mean, your leader probably has imposter syndrome too, right?

00:23:31.080 Whoever is managing you.

00:23:32.820 Your leader has more imposter syndrome than you do

00:23:34.820 because whatever you have on your plate,

00:23:36.560 if they have seven direct reports,

00:23:37.980 then they have seven times as much on their plate

00:23:40.100 as you do on your plate.

00:23:41.860 And the higher up we go, the more we feel,

00:23:44.420 am I supposed to be here?

00:23:45.520 Did they make a mistake?

00:23:47.000 You know, what if I mess up?

00:23:48.700 There are all these people looking at me.

00:23:50.600 And I felt this when I started managing managers at Google.

00:23:54.120 I was tasked with shutting down a business division

00:23:56.520 in one part of the world and building it back up in another.

00:23:59.280 And I am on a flight back from Chicago

00:24:02.380 to lead an offsite with these leaders

00:24:04.860 who reported to me the next day.

00:24:06.120 and I am so nervous, so insecure.

00:24:10.680 And because I was in this new senior leadership position

00:24:13.700 and so I just felt like I had to overcompensate, Joe.

00:24:16.560 I just squeezed as much information as I could

00:24:18.660 into this 30 slide deck,

00:24:20.280 North Star mission statement

00:24:21.400 of this big reorg and transition.

00:24:24.660 The three pillars we needed to succeed,

00:24:26.780 a leader for each pillar,

00:24:28.360 the comms plan, the finances, right?

00:24:31.920 Like all this stuff.

00:24:32.920 And I walk into the room the next day,

00:24:34.420 plug in my laptop,

00:24:35.420 excitedly start presenting and the entire energy in the room dissipated. And at Google, we had a

00:24:41.540 concept called psychological safety, which is a great thing. It basically means you should feel

00:24:45.500 free to speak your mind to anybody, whether it's someone below you, across from you, above you.

00:24:50.360 And my, my, my was my team feeling psychologically safe that day because they raked me over the coal

00:24:56.400 and said things like, Jenny, why would you think that you have all the answers? We have a combined

00:25:02.100 35 years of experience on this team. You've been here, what, three months? We know these products

00:25:07.500 and processes and players way better than you do. Why wouldn't you lean on us for what we know?

00:25:13.160 So thankfully, I was able to exhale, recognize I'd completely effed up and say, I'm sorry,

00:25:20.040 guys, you're right. Let's scrap this plan and start over. And by the way, I think two of the

00:25:25.000 best things a leader can say, and I call these the humble two, are I don't know and I was wrong.

00:25:29.820 At least I got the second one, which was in the moment I was wrong, but I failed to have

00:25:33.380 the first one, which was, I don't know.

00:25:34.880 I don't know what the strategy should be.

00:25:36.280 I don't know how we should run this reorg and I need to lean on you to help me understand.

00:25:40.360 But why did I perform among the worst I'd ever performed in my career in that moment?

00:25:46.360 Because I was given this leadership position and I had so much more imposter syndrome than

00:25:50.220 had I been 22 and the stakes would feel really low and I'd feel like it didn't matter if

00:25:53.980 I messed up because no one would expect you to know what you're doing at 22, right?

00:25:57.600 Well, I mean, I would still expect, I think 22-year-olds have very high standards for themselves.

00:26:02.640 And I've worked with incredible people right out of school.

00:26:04.900 But the point being, the more senior I got.

00:26:07.380 Although I will say, when you're 22, you still don't know that much about that many things.

00:26:12.720 Well, you're learning.

00:26:13.460 You're learning.

00:26:14.080 You're a baby.

00:26:15.040 That's the thing.

00:26:15.500 You're still a sponge.

00:26:17.060 You're still learning all of the things.

00:26:19.120 Exactly.

00:26:19.740 So it gave me license.

00:26:21.280 I like myself so much more at 24 than I did at 22.

00:26:26.420 Yeah.

00:26:26.580 so we're just about the same age. I'm 45. And, um, and I, okay, this is interesting. I think I

00:26:32.740 was more confident at 22 than I am at 45. Oh, interesting. I'm definitely, I'm definitely so

00:26:38.320 much more confident now. Interesting. Yeah. And I think it's because of examples like that, like,

00:26:43.640 and maybe it's where I am in my career and in life right now, where I feel like I've completely

00:26:48.320 started over. I feel naked. I feel like I am an entrepreneur for the first time with no training

00:26:54.880 in being an entrepreneur.

00:26:56.220 Not that anyone gets training.

00:26:58.300 I feel like I am a speaker and an author.

00:27:01.400 And despite the fact that I'm getting great feedback

00:27:03.920 about when I go into Fortune 500 companies

00:27:06.580 and lead a team of 150 executives

00:27:08.520 and help them think through change management

00:27:10.280 or through employee engagement

00:27:11.840 or through leadership or through confidence

00:27:13.780 or through all these things that they tell me I'm good at,

00:27:17.660 I still feel like it's going to take so many more reps

00:27:20.580 for me to truly believe that I belong,

00:27:23.020 believe that I'm good at it,

00:27:24.140 believe that I deserve to be here. And that's why I say I think I was more confident at 22 than at

00:27:29.000 45 because the stakes feel higher now and that's hard. I mean, the stakes are definitely higher,

00:27:36.560 but you should just see, I'm going to coach you now. You have to keep telling yourself that you

00:27:40.400 are now a New York Times bestselling author. Let's take one more quick break and then let's

00:27:44.420 get back to that. How can we break these cycles of things that make us feel bad so that we can

00:27:50.620 focus on the things that are actually productive

00:27:52.660 in our lives.

00:27:58.700 I didn't like what you said,

00:28:01.020 Odin pauses, about the

00:28:02.720 future. This is

00:28:04.800 the love story of real hinge couple

00:28:06.720 Odin and Edward, written and

00:28:08.820 read by me, Curtis Garner.

00:28:11.120 Listen to the free audiobook now.

00:28:18.920 Okay, we are back.

00:28:20.620 How can we break these cycles of doing the crappy thing that makes us feel bad?

00:28:26.240 Yeah, I mean, I'm a data, like part of the reason I always look at the data is because I lead with data.

00:28:30.900 I was an economics major.

00:28:32.740 Same.

00:28:33.040 Oh, interesting.

00:28:34.300 Oh, that's fun.

00:28:34.880 I know, yeah.

00:28:36.180 So, yeah, we're clearly cut from the same cloth on this.

00:28:38.900 So I have to, I have to like make it a data game.

00:28:41.420 I have to gamify it.

00:28:42.360 So I have to say something like, I don't know, maybe you and I will make a little, a little, the accountability partners here and say,

00:28:49.880 I'm here for this. But I don't even know what's realistic for me. I was going to say maybe I

00:28:53.780 would make a pact with you that I go one day without checking my Amazon raking or Amazon

00:29:00.040 reviews or just like one day without going on Amazon or Goodreads and looking at my book. I

00:29:03.940 probably need to go to like buy doing the tape or whatever. I'm actually going to tell you not to

00:29:07.100 go on Goodreads. I don't think you should ever. I don't think any author. Oh, tell me why. Oh,

00:29:11.220 I don't think any author should go on Goodreads. Because the reviews are much harsher on Goodreads

00:29:15.100 than Amazon the reviews are much harsher I don't read reviews I look at numbers and I look at data

00:29:20.220 but I no longer read reviews because I also believe that books are such a qualitative oh yes it's like

00:29:26.520 that it's just not for this person it was not the right book for this person there there are so many

00:29:30.760 books that are on the bestseller list or that my friends loved that I don't love I'm also not a

00:29:36.340 person that will actively review if I don't like something because I think it's cruel to the person

00:29:41.800 who put a thing out there unless you're going to be like oh i specifically just don't like this this

00:29:47.120 and this because i'm this kind of person like it's very specific and helpful but no no no i think

00:29:52.660 i think reading your own reviews after having written i've written i think 13 books at this

00:29:57.620 point wow yeah no it destroys your soul there's no there's no reason to do it because like you said

00:30:02.560 the bias is that the bad ones are going to harm us more than the good ones will help us yeah for

00:30:08.440 sure. Yeah. I don't know. How do you try to break these habits? Oh, gosh. Actually, can I add one

00:30:14.900 thing? Because I think most people are not authors, right? Most people listening have not

00:30:18.240 written books. But I think what everybody can relate to is the comparison on social media,

00:30:23.180 the comparison of me versus them, the comparison of everybody else looks so put together and

00:30:27.560 polished and their house looks so perfect and their kitchen looks so adorable and their vacation

00:30:32.880 looks so beautiful and their husband's abs are so six pack. And so I think that even though there

00:30:39.680 might be a lot of people who aren't authors and don't have this type of metric comparison, I think

00:30:44.460 we're all comparing in some way, whether it's with a colleague and how their presentation was versus

00:30:49.780 yours or on social media or a friend or any of those things. So I think it's a broader question

00:30:54.060 of like, how do you cut that out when we find ourselves comparing and keeping ourselves small

00:30:58.660 in that way because comparison is the thief of joy comparison is the thief of joy it really is

00:31:03.260 and it's crazy how much we can compare now with the advent of social media right like we used to

00:31:08.860 only be able to compare with our neighbors with the people we came in direct contact with yeah 0.99

00:31:13.700 now you can go and look up every asshole that you graduated from college with and be like wow 0.98

00:31:18.740 they're an svp at blah blah blah schmerzenberg corporation and i'm not uh and that's a bummer 0.97

00:31:26.820 but yeah i for me so personally i'm like i've gotten really good at like the social media

00:31:35.260 personal scroll of like not feeling comparison yeah i edit my feed but now i've also started

00:31:43.300 professionally editing my feed if i feel myself getting envious i don't block someone but i do

00:31:48.320 take i do unfollow just because i'm like you don't need this you don't need this drama

00:31:52.240 in your head. It's not in my life. It's in my head, right? So I don't know. I am a work in

00:32:01.240 progress. I am constantly trying to figure out what the hell I'm doing. As we all are. Yeah,

00:32:07.840 for sure. Me too. We are. And then there are some basics that I don't even do. When my kids

00:32:13.660 are going to sleep at night, when it's bedtime, I should just put my damn phone in a drawer in 0.99

00:32:18.640 another room and probably lock it and have my husband set a code because I'm totally addicted. 0.99

00:32:23.520 I mean, that's not like who isn't addicted to their phone, right? But this is a practical tool

00:32:27.500 that my old boss, Michelle, mentioned, and I haven't done it, but I really want to try. She

00:32:33.140 said, you need to charge your phone, not in another room, but on a different floor of the

00:32:38.000 house. If you have, you know, I live in Boulder. We've got two stories here. And I loved what she

00:32:43.900 said because she's like, it needs to be that much harder for you to get it because it also is just

00:32:47.820 so unhealthy when the very first thing you do is you look at your phone before your eyes are even

00:32:52.880 fully open and you're already getting into that negative spiral of shame or comparison or

00:32:58.400 disappointment or fear. I will tell you that the nights where I charge my phone downstairs in the

00:33:06.800 kitchen, I sleep on the third floor, kitchen in the first floor, I sleep better. And maybe just

00:33:14.380 like the psychological knowing that it is not near me. Yeah. And I wake up happier because it's

00:33:22.120 not right there. Unfortunately, my phone remains my alarm clock, but I don't. My husband usually

00:33:27.900 wakes me up most mornings. He's been gone this week. So I have had my phone. But yeah, that is

00:33:34.520 one of the best tips is to put your phone away for the night. The other one that I got, and this

00:33:40.240 one's a little harder but there are days when I managed to do it it's treat your phone like a

00:33:44.580 landline in your house oh I love that so you have to go to it so that it's not like you can use it

00:33:51.800 if you're in in the kitchen cooking dinner dinner and you're like oh what does this recipe say but

00:33:56.300 you have to go to it right you can't bring it back with you so hard for me I know so hard for

00:34:02.500 me I know but just thinking about the fact that we have this appendage attached to us all the time

00:34:06.980 For sure.

00:34:08.120 It's kind of, I mean, when I think about it, it's kind of gross, right?

00:34:10.800 Yeah.

00:34:11.100 Oh, totally.

00:34:11.920 We don't need to carry this thing around with us all the time.

00:34:15.080 It's just stealing so much joy and focus.

00:34:17.360 And then what I'm teaching my kids when I'm constantly on it.

00:34:20.080 And like, I mean, that was one of the hardest things about writing this book was my fractured attention to my kids.

00:34:24.360 And there was this moment where my son had a haircut and I was like, Ari, get in the car.

00:34:30.640 And then he went and like bopped around on his bike for a little bit.

00:34:34.820 And then, of course, we were running late, which I frequently am, because I tried to do one last thing and squeeze in one last email response. And we got in the car and I yelled at Ari. I was like, what? I was like, no, we're going to be late. Why didn't you get in the car when I asked? And he's like, well, because, Mom, I didn't believe that you would actually close your laptop and get in the car because all you care about is work. 1.00

00:34:54.700 Right. And so like, okay, dagger in the soul, right? But he's right that there was so much over the last few years that he saw of me glued to my laptop, glued to my phone, like working on the next day's social media post when it was bedtime.

00:35:10.980 And so that's where I feel like now I have the opportunity to make better choices because I don't have this massive deadline with the book and the book is out there in the world. It's been out for four weeks now.

00:35:19.980 and now it's hard to like honestly reprogram myself

00:35:24.460 to what does it look like to have more space

00:35:26.300 in my life for my kids?

00:35:27.320 What does it look like to like how many days a week

00:35:29.480 do I want to pick them up from school versus zero before

00:35:31.900 because our nanny and my husband would always do it

00:35:34.080 and I just was totally written off

00:35:35.840 as like not part of the equation.

00:35:38.300 And how do I re-enter?

00:35:40.020 It almost feels like in Shawshank Redemption

00:35:41.980 where, you know, the guy leaves jail

00:35:43.680 and he like doesn't even know how to function in the world.

00:35:45.960 I feel like I'm coming off of that level of not trauma

00:35:49.020 because it's fun to write a book and it's exciting.

00:35:51.520 But like between balancing the Google role

00:35:53.840 and, you know, then turning to writing the book,

00:35:56.940 like it was just an unbelievable amount of intensity

00:36:01.240 over the last four years for me.

00:36:03.260 Like I've never experienced in my life.

00:36:05.380 And then I heard this stat

00:36:06.260 that by the time your kids go to college,

00:36:08.100 you will have spent 90% of the time

00:36:11.180 you will ever spend with them. 0.99

00:36:13.100 And I was like, holy shit, I cannot believe that. 0.99

00:36:16.680 What am I doing wrong? 0.99

00:36:17.520 And then guilt, shame, guilt, shame,

00:36:19.020 guilt shame. I also don't believe that. I'm convinced my kids are going to live with me

00:36:22.500 forever. I love it. I love it. I hope mine do too, so I can make up for lost time. But I know

00:36:27.380 that, you know, I could live in the shame and the fear that I spent the last four years deeply

00:36:32.200 engrossed in work. Or I could say the best time to plant a tree was 10 years ago. The second best

00:36:37.540 time is today. And I can start making different choices today. But I will also share that, like,

00:36:41.780 I don't want to be a stay at home mom. I will never be a happy stay at home mom. And it took

00:36:45.720 someone putting a mirror up to me and saying, Jenny, do you, because when I was talking about

00:36:49.000 like the working mom guilt, she was like, do you want to stop all this and be a stay-at-home mom?

00:36:53.240 I was like, no, I wouldn't be happy. She's like, then just own the fact that you enjoy doing this

00:36:58.580 and recognize that like this brings you joy and this helps a lot of people and this is exciting

00:37:03.320 and your kids think you're a badass and just rock it. And the other day, my daughter had a play date

00:37:08.840 over after she'd been giving me a hard time about how much I was working. And then she like pulled 0.99

00:37:13.240 this little girl, this other seven-year-old into my office. She's like, look at my mom's book.

00:37:17.640 You're never going to believe this, but it's embossed. I don't know if you know what that

00:37:21.020 means, but embossed means that the words are a little bit raised and only 5% of books have that.

00:37:25.700 And like, so here she is, you know, like clearly absorbing the joy and the excitement and the 0.99

00:37:30.340 success of this book, even though I feel like I'm a shit mom. Right. No, exactly. Exactly. It's, 0.99

00:37:35.640 it's interesting the point that you are at the re-entry because I am at the, the withdrawal

00:37:40.600 right now because i'm on a bunch of book deadlines i am also have this book coming out in a few

00:37:49.420 months and so i am handing over so much more to my husband who is taking on you know the primary

00:37:58.300 parent role right now so he should be doing these things um my mom and our au pair and i feel

00:38:05.180 tremendously. I'm having a really hard time deciding what to do, what not to do and where

00:38:12.660 to put my time, even though I know that this is not a forever thing. It is a right now thing.

00:38:19.020 And I still believe that I'm spending a lot of quality time with my kids. But yeah, it's I'm

00:38:25.060 like, all right, no, I'm not doing drop off or I was up in the middle of the night writing

00:38:28.880 something. So I'm not even going to wake up when you guys wake up. Yes. Oh, I just didn't do

00:38:32.640 mornings for years. I just didn't. I'm not doing mornings right now. That's the thing. Like there

00:38:36.980 are some there's some mornings where I don't see them. And that makes me feel awful. But also no

00:38:44.660 one cares. They actually I don't think they actually care. And when when they needled me

00:38:48.720 about it, I think they're just doing it because they know they can 100 percent. And they know

00:38:52.060 that like it totally gets us under our skin. And also, like, I have a ton of privilege. I have a

00:38:57.340 nanny. I have a husband who works part time. I mean, I have tremendous privilege that I have

00:39:03.960 these resources. So I think that it's probably more productive to just be grateful for the

00:39:08.540 resources. And of course, these take choices like I don't buy shoes. I don't buy fancy purses. I

00:39:13.340 don't like I always get I never get the appetizer at the restaurant. I always have like the cheaper

00:39:18.320 entree between the two so that I can make smart spending choices so that I can afford to get some

00:39:22.840 extra help around the house, because that is my love language. My love language is acts of service.

00:39:26.700 And if there is my husband and, you know, a nanny who works first part time, that can also help. Like, I just need to, again, not feel guilty about it, but embrace the choices I've made about my own spending and savings and just be comfortable with that. But I have to recognize, like, not everybody has that luxury. And the single moms out there who are crushing it and working and being successful and providing for their families, like, you are heroes. And the single dads for that matter.

00:39:52.320 And the single dad.

00:39:52.960 Yeah. 0.67

00:39:53.160 And the same with single caregivers, right?

00:39:54.780 Yeah.

00:39:55.020 I think about that a lot.

00:39:56.120 I do.

00:39:57.460 I actually, I don't want to end our conversation, but I am going to go pick my kid up from school

00:40:00.860 because my husband's out of town.

00:40:02.080 So.

00:40:03.100 So sad.

00:40:04.000 So sad.

00:40:04.460 Because I feel like we could maybe talk for seven hours.

00:40:06.940 We could talk for seven hours straight.

00:40:08.400 Maybe seven days.

00:40:09.080 Do a whole show.

00:40:09.840 Do a whole show with us.

00:40:11.100 Will you tell everyone where they-

00:40:12.060 Would you like a co-host?

00:40:13.160 I'm kidding.

00:40:13.560 I would, actually.

00:40:14.460 Yeah.

00:40:14.720 That would take a lot of pressure off me. 0.94

00:40:17.100 I would accept another wife in my house, to be honest. 1.00

00:40:19.480 Oh, who doesn't want a co-wife? 1.00

00:40:21.300 Who doesn't want a co-wife?

00:40:22.800 People are like, would you get jealous? 0.90

00:40:23.820 I'm like, no.

00:40:24.740 No way.

00:40:25.740 I could care less.

00:40:27.400 So more the merrier as long as you schedule the pediatrician appointment today.

00:40:30.760 Exactly.

00:40:31.240 Did you put away laundry?

00:40:32.680 Did you put away the winter clothes for me and bring out the summer clothes?

00:40:36.620 Because you could do it with my husband. 0.99

00:40:38.460 Oh, you want girl. 1.00

00:40:39.880 I do not care.

00:40:42.280 Will you tell everyone where they can find your wonderful book?

00:40:45.000 Yeah, it's available everywhere.

00:40:46.320 It's available in hardcover, in e-book, audio book, anywhere bookstores sold.

00:40:51.040 And I love helping organizations feel more empowered, you know, improve their employee engagement, create better leaders, better managers, thrive and change. And so you can also find me at itsjennywood.com, I-T-S-J-E-N-N-Y-W-O-O-D.com.

00:41:21.040 We'll see you next time.

00:41:51.040 No Ordinary Love

00:42:21.040 The audio book's out now. Give it a listen.

00:42:25.620 Chew on this bold question from Dentine Gum.

00:42:29.040 Is it ever okay to compliment a millennial on their skinny jeans in 2026?

00:42:38.140 Dentine. Chew bold.

Under the Influence (with Jo Piazza) - May 01, 2025

The Wild Courage to Go After What You Want (with former Google Exec Jenny Wood)

Episode Stats

Transcript