What’s Stopping You From Taking the Risk That Could Change Everything?

What’s Stopping You From Taking the Risk That Could Change Everything?

Released Wednesday, 26th March 2025
Good episode? Give it some love!
What’s Stopping You From Taking the Risk That Could Change Everything?

What’s Stopping You From Taking the Risk That Could Change Everything?

What’s Stopping You From Taking the Risk That Could Change Everything?

What’s Stopping You From Taking the Risk That Could Change Everything?

Wednesday, 26th March 2025
Good episode? Give it some love!
Rate Episode

Episode Transcript

Transcripts are displayed as originally observed. Some content, including advertisements may have changed.

Use Ctrl + F to search

0:00

Was there 18 years? Breadwinner for my

0:02

family. Fancy, executive salary. Very, very comfortable.

0:04

Never thought I would leave. But I

0:06

was terrified to leave Google. Terrified. And

0:09

so I would tell myself all sorts

0:11

of tales, right? Tales like, we're going

0:13

to have to downsize. We're going to

0:16

starve. I will never be able to

0:18

get hired again if the book flops

0:20

because I'm 45. And, you know, no

0:23

one's going to hire a 45-year-old. Every

0:25

single thing I just said. tales. So

0:27

what are the truths of this situation?

0:30

I would likely make less money.

0:32

I was leaving to write a

0:34

book. We had a lot in

0:36

savings. My relationship to money is

0:38

one thing, but you know, there's

0:40

other values in life, like time

0:42

with my family being high net

0:44

freedom. So once I was able

0:46

to separate the truths, which are

0:48

verifiable facts, and when you can separate

0:50

the truths from your tales, that

0:53

is what helps you push past the

0:55

fear. by My Latest Book Never Play It's

0:57

Safe. Right now, if you do not have

0:59

a copy of my latest book,

1:01

I want you to listen to

1:03

what Gary Vainerchak said about my

1:05

latest book. Building a life you

1:08

love doesn't happen on accident. It's

1:10

a process. Few people know this

1:12

process like Chase Jarvis does and

1:14

never play it safe is the

1:16

roadmap. Or what Sophia Amarooso said. This

1:18

book is a powerful compass for

1:21

embracing risk and creativity in. all

1:23

the aspects of your life. Chase

1:25

shows us how to step out

1:27

of our comfort zones and become

1:29

who we weren't meant to be.

1:31

Here's a cool fact. All of the best

1:33

stuff in life is on the other side

1:36

of your comfort zone. And Never Play It

1:38

Safe is a blueprint. That's how I

1:40

designed it. It's a blueprint to

1:42

get you there reliably over and

1:44

over again. It's not an accident

1:46

that this was a national bestseller

1:49

on, I think, four best-selling book

1:51

lists. That's because it is a roadmap.

1:53

It's a blueprint, right? It's going to

1:55

reshape how you think about

1:57

attention, time, intuition, constraints, those

1:59

things. feel like hold you back?

2:01

If you're not playing enough, if you're

2:03

working too much, you're working in the

2:05

wrong way, if failure seems too constant

2:07

and you can't see what the benefits

2:09

are, or if you don't have the

2:12

practices and the habits to help you

2:14

achieve the extraordinary results that you seek,

2:16

this is the book that I put

2:18

three years of my life in its

2:20

goal is to help you be more

2:22

creative, fulfilled, and successful in everything that

2:24

you do. And if this hasn't convinced

2:26

you or the blurbs from Gary Vainerchak

2:28

and Seth Godin and Sophia and Damon

2:30

John from Shark Tank, then I get

2:32

it. There's a bunch of other reviews

2:34

at Amazon or wherever you buy books.

2:36

And I'd love it if you pick

2:39

up a copy if never play it

2:41

safe, a practical guide to freedom, creativity,

2:43

and a life you love. Now, let's

2:45

get into the show. Hello

2:49

everybody, what's up, it's Chase. I

2:51

am very happy to welcome you

2:53

another episode of the show, you

2:55

know, the show where I sit

2:58

down with awesome humans and I

3:00

unpack their brain with the goal

3:02

of helping you live your dreams.

3:04

And today's guest is Jenny Wood.

3:06

Jenny comes to us after 18

3:08

years at Google. She grew from

3:10

an entry-level employee to executive and

3:12

has led massive operations to billions

3:14

of dollars in revenue. And a

3:16

few years ago, she started a

3:18

project inside of Google called Own

3:20

Your Career, which ended up growing

3:23

to be a very popular career

3:25

development program inside of Google. And

3:27

it is this program that spawned

3:29

in part one of the things

3:31

we're talking about in today's show,

3:33

an amazing book called Wild Courage.

3:35

And you know, I'm a huge

3:37

believer in owning our creativity in

3:39

pursuit of the dream job, the

3:41

dream career. that that doesn't just

3:43

happen on an accident. And Janie's

3:45

book, Wild Courage, the subhead here

3:48

is Go After What You Want

3:50

and Get It, is a really

3:52

lovely dovetail to my philosophy overall.

3:54

And it actually dovetails really interestingly

3:56

with my latest book called Never.

3:58

played safe. It was really fun.

4:00

It was the first time I

4:02

had met Jenny just this year.

4:04

She and I are part of

4:06

a call it a secret club,

4:08

an author's club that gets together.

4:10

It was really, really fun to

4:13

read an early draft of her

4:15

book. Grateful to have her on

4:17

the show, if you're interested in

4:19

how to be more courageous, if

4:21

you're interested in how to be

4:23

weird, that weird version of yourself

4:25

that you're not sure if you

4:27

should share with others, how to

4:29

do more of that, how to

4:31

be shameless in promoting yourself and

4:33

your work, realizing that you're just

4:35

connecting the world with the work

4:38

that they need, and how to

4:40

air on the side of action.

4:42

overthinking, tells us the next set

4:44

of steps that we need to

4:46

do way more than thinking. Yours

4:48

truly, and Jenny Wood, talking about

4:50

wild courage, enjoy today's show. Jenny,

4:52

thank you so much for joining

4:54

us. Welcome to the show. It's

4:56

so great to be here, Chase.

4:58

Are we gonna get courageous today?

5:00

We're gonna get wild be courageous.

5:02

Wildly courageous. Well, I have the

5:05

distinct opportunity to have you on

5:07

the show today and get to

5:09

pick your brain around a topic

5:11

that my audience, those who listen

5:13

and watch and have tuned into

5:15

the show for a long time,

5:17

know that I'm passionate about and

5:19

that is courage. I often cite

5:21

that you don't need to be

5:23

100% courage to do something. It's

5:25

sort of like 1% more courage,

5:27

51% courage to 49% fear. We're

5:30

going to cover a lot of

5:32

that. today. You have a new

5:34

book. We also need to talk

5:36

about that, not accidentally. It's called

5:38

Wild Courage, the joke that you

5:40

just, the inside joke, if you

5:42

didn't know the title, in our

5:44

little opening mantra there. But for

5:46

the handful of folks who might

5:48

be new to you, your work,

5:50

the book, some of the things

5:52

we're going to talk about today,

5:55

how do you, you know, what's

5:57

your normal sort of introduction to

5:59

you in your work and the

6:01

things that you care about? Yeah,

6:03

well I think my normal introduction

6:05

is, hi, I'm Jenny, tell me

6:07

about yourself, but for the purposes

6:09

of today, a little bit more

6:11

background. I did research at Harvard

6:13

Business School, I then went on

6:15

to have basically grew up my

6:17

entire career at Google, growing from

6:20

entry level to executive. I ran

6:22

an operations team that sat between

6:24

sales and engineering, and just for

6:26

fun as a passion project, I

6:28

founded a program called Own Your

6:30

Career, which grew to be one

6:32

of the largest career programs in

6:34

Google's history. So that was pretty

6:36

fun. And then I was like,

6:38

wait a second. I like my

6:40

operations role, but I really love.

6:42

coaching people to be better than

6:45

they think they can be. And

6:47

so I went out and wrote

6:49

a book. And then in my

6:51

personal life, I've got two kids.

6:53

I live in Boulder, Colorado. Kids

6:55

are seven and nine. Keep me

6:57

on my toes. Try to hike

6:59

every day and take a little

7:01

nature shower. Gosh, that sounds like

7:03

to checks of most of the

7:05

boxes that I've got on my

7:07

list of things to do. That's

7:10

great. Boulder, Colorado, man. I love

7:12

that place, man. Super special. Yeah.

7:14

Courage is a big deal for,

7:16

as I sort of try and

7:18

connect the dots, looking back on

7:20

my life, the time as to

7:22

where I felt that I wasn't

7:24

living up to my potential, potential,

7:26

felt, you know, shame or guilt

7:28

or frustration, usually had to do

7:30

with fear being more dominant than

7:32

my courage or my ability to

7:35

play through it. So let's start

7:37

there. Why are you writing about

7:39

courage? What role has it played

7:41

in your life such that you

7:43

have become an expert? Yeah. Well,

7:45

it all started on a dirty

7:47

crowded New York City subway in

7:49

2011. I'm writing the subway home.

7:51

I see this really attractive guy

7:53

standing about 20 feet away from

7:55

me or so. gorgeous blue eyes,

7:57

thick brown wavy hair, and I'm

8:00

really taken by him. And even

8:02

though I want to go talk

8:04

to him, something holds me back.

8:06

What if he's a convicted felon?

8:08

What if he's married? What if

8:10

100 people stare at me on

8:12

this packed train? Well, and I'm

8:14

already like a confident Google employee

8:16

on the outside, but I'm scared

8:18

and timid on the inside. And

8:20

I later came to realize that

8:22

those three questions I had about

8:25

him convicted felon, you know married.

8:27

or even just like the fear

8:29

that people might stare at me,

8:31

were underpinned by fears that had

8:33

helped me back so often in

8:35

life and that I saw hold

8:37

so many talented successful people back

8:39

at Google. And those three fears

8:41

were fear of judgment, fear of

8:43

failure, and fear of uncertainty, fear

8:45

of uncertainty, and fear of uncertainty.

8:47

So I sit there, I do

8:49

nothing, the train passes stop after

8:52

stop after stop and life, frankly,

8:54

passes me by. But I make

8:56

a deal with the universe, I

8:58

say, if he gets off at

9:00

my stop, I'll try to strike

9:02

up a conversation with him, and

9:04

if not, then that's the universe

9:06

telling me it wasn't meant to

9:08

be. So we gets off at

9:10

59th Street, and I say, Just

9:12

as the doors are about to

9:14

close, because that is not my

9:17

stop, I say, screw the universe,

9:19

because this wave of wild courage,

9:21

like, washes over me, and it

9:23

practically pushes me off the subway

9:25

train. So I chase to catch

9:27

up with him, I tap him

9:29

on the shoulder, I say, excuse

9:31

me, I'm sorry to bother you,

9:33

you're wearing gloves, so I can't

9:35

tell if you're wearing a wedding

9:37

ring, but in the event that

9:39

you're not married, you're on my

9:42

subway, you're on my subway, And

9:44

then I wait for what feels

9:46

like forever as I think this

9:48

was a terrible idea. But then

9:50

he takes my business card, he

9:52

calls the next day, we go

9:54

on a date a week later,

9:56

and we've now been married happily

9:58

for 11 years with two kids.

10:00

That is the story that we

10:02

all want. And yet, we all

10:04

know that it doesn't always go

10:07

that way. Yeah, that is true.

10:09

And I often get asked two

10:11

things. Well, like, how do you

10:13

recover from the failure when it

10:15

doesn't work out? But also. What

10:17

if I'm not a subway chaser,

10:19

Jenny? Like that sounds like a

10:21

ridiculously unrelatable story. Like what about

10:23

me? How can I have what

10:25

I, then I like guide people.

10:27

You just need like a little

10:29

mini courage deposit on any given

10:32

day, right? Maybe it's raising your

10:34

hand to say something in the

10:36

big town hall where your VP

10:38

is presenting and you want to

10:40

be visible and stand out or

10:42

maybe as an entrepreneur, you know,

10:44

it's about sending, you know, X

10:46

number of emails out to picture

10:48

services or to ask a client

10:50

for an upsell or to say,

10:52

hey, we've got this great client

10:54

testimonial, I wanted to share it

10:57

with you, right? Or maybe it

10:59

is, you know, Do you need

11:01

to get a lot of work

11:03

done on a flight home with

11:05

your family like I did the

11:07

other day and your seats are

11:09

three together and one separate and

11:11

you ask your husband to sit

11:13

with the two kids the entire

11:15

flight while you work on this

11:17

project for this client? Maybe it's

11:19

the courage to ask for something

11:22

from your spouse or your partner.

11:24

So yes, not everyone is a

11:26

subway chaser, but no matter where

11:28

you sit, there is something right

11:30

now that you want, right? Some

11:32

goal, some project, you know, something

11:34

for your business for your business.

11:36

And wild courage is what closes

11:38

the gap between what you want

11:40

and what you get. It's pushing

11:42

past that fear to achieve your

11:44

greatest ambitions. You have identified a

11:47

handful of traits, as you call

11:49

them, and... I'm in love with

11:51

this list, first of all, because

11:53

there it's a little bit subversive,

11:55

right? There's a little, there's some,

11:57

yeah, a little spiciness in there,

11:59

which I really appreciate. And it's

12:01

also, it's a very real list.

12:03

Like, you know, as I'm, first

12:05

of all, I have had the

12:07

opportunity now to read the book

12:09

twice, one with the PDF that

12:12

I read originally, and thankfully you

12:14

and your team sent me an

12:16

advanced copy of, which it's beautiful

12:18

and gorgeous. Congratulations, but genuinely appreciate

12:20

the traits and there are things

12:22

that a lot of people don't

12:24

want to talk about. You've got

12:26

ones, for example, like nosy and

12:28

manipulative and weird. So give us

12:30

the background on how you ended

12:32

up with this selection of traits

12:34

that is certainly not random and

12:36

yet they are very, they seem,

12:39

seemingly far afield and certainly spicy.

12:41

Yeah, for sure. It's interesting because

12:43

I'm so glad that you appreciate

12:45

the spice. Someone said this morning,

12:47

they gave me some constructive feedback

12:49

initially, but ultimately was a compliment.

12:51

They said when I first started

12:53

reading the book, you know, I

12:55

kind of thought, oh, she's just

12:57

being edgy for the sake of

12:59

being edgy. And then he said,

13:01

but Jenny, like, when I got

13:04

into it, he's like, I loved

13:06

it. you're saying the quiet part

13:08

out loud. And that's ultimately what

13:10

this is, because these are things,

13:12

so the nine traits are weird,

13:14

selfish, shameless. obsessed, nosy, manipulative, manipulative,

13:16

brutal, reckless, and bossy. And it's

13:18

basically, like, breaking the unspoken rules,

13:20

or, you know, again, pushing past

13:22

that fear of uncertainty, failure, judgment

13:24

of others, to achieve things that

13:26

you want to achieve in life,

13:29

but we don't go for it

13:31

because we're scared that someone will

13:33

think of us as manipulative, right?

13:35

But manipulative to me is... the

13:37

courage to build lasting relationships and

13:39

to build influence through empathy. It's

13:41

the idea basically that whether you're

13:43

selling a product or a program

13:45

or frankly yourself, your ability to

13:47

win friends and allies and supporters

13:49

is all about mutual benefits. So

13:51

figure out what people want and

13:54

go get it for them. And

13:56

you know, it's but our fear

13:58

of being seen as opportunistic or

14:00

strategic. or like we're playing chess,

14:02

right? Or we're giving something to

14:04

somebody only because we want something

14:06

in return. You know, that's what

14:08

holds people back from taking those

14:10

generous actions that actually expand the

14:12

pie in business and life in

14:14

relationships versus reslyse the pie. Well,

14:16

I'll tell you, you had me

14:19

at the first trait, which is

14:21

weird. Yeah, because for so many

14:23

people in our audience, this is.

14:25

It's difficult to reconcile. There's a

14:27

phrase that I love to channel

14:29

and it was crafted by a

14:31

friend of my name, James Victoria,

14:33

is an amazing artist and a

14:36

sweet kind, smart human. It says,

14:38

what made you weird as a

14:40

kid will make you great today.

14:42

And it is that individuality, the

14:44

things that make us quirky and

14:46

You know, to me, that's our,

14:48

that's our fingerprint. That's, that's who

14:51

we are. And so many times,

14:53

because of cultures, various inputs and

14:55

pressures, we're taught mistakenly to suppress

14:57

that thing, that thing that differentiates

14:59

us from all the other people

15:02

on the planet. And so, you

15:04

know, I felt right at home

15:06

knowing that it was, I had

15:08

your permission to be weird. So,

15:10

help us. Yeah, well, I love that

15:13

you just used the word permission chase

15:15

because wild courage is about giving yourself

15:17

permission and not waiting for someone to

15:19

give you permission to ask for X,

15:21

Y, Z thing or to take X,

15:23

Y, Z action or to go for

15:25

X, Y, Z goal. And weird is

15:27

the courage to stand out, right? Because

15:29

within your so-called weirdness, lie your greatest

15:31

strengths. So I say, hone every ounce

15:33

of weird you've got. And like I

15:35

was a super weird kid. You know,

15:37

you know, there was one moment where...

15:39

I was at a yoga shop

15:42

and I stood on a table

15:44

which sounds a little bit weird

15:46

in itself in and of itself

15:48

and I sang the national anthem

15:50

or no my country tis of

15:52

me and you know I'm in

15:54

that that that very last line

15:57

to the icing like I would

15:59

just like belted from the top

16:01

of my lungs every line of that

16:03

of that song. And my high school

16:05

friends or middle school friends, you know,

16:08

they were like, Jenny, you are such

16:10

a nut. But I think I intentionally

16:12

took these actions to like build a

16:15

thicker skin of trying to not care

16:17

what people thought about me. Now all

16:19

this said. I still get tons of

16:22

imposter syndrome. I still get really insecure

16:24

when I make a mistake. I still

16:26

get, you know, tingly arms when I

16:29

get an email back. That's a rejection.

16:31

I got one earlier this week that

16:33

like was cringe-worthy and made me lose

16:36

sleep at night. So it's like, yes,

16:38

you want to be weird, but you

16:40

also have to recognize that your frequency

16:43

is not going to resonate with everybody's.

16:45

And if that's the case, then you

16:47

just go plant yourself in more suitable

16:50

soil in more suitable soil, but it

16:52

doesn't mean that you shouldn't take the

16:54

shot take the shot. Let's hear about

16:57

this experience situation. Yeah, please share. Yeah,

16:59

so still working through it, just to

17:01

be clear. Thank you for the real-time

17:04

vulnerability here. We are now stepping into

17:06

therapy. And I share this with a

17:08

little bit of hesitation. I'm pulling up

17:11

an email actually. I share it with

17:13

a little bit of hesitation because I

17:15

actually worry that this person might hear

17:18

it. putting yourself out there and launching

17:20

your ideas and being a thought leader

17:22

and writing a book is asking people

17:24

to help you. And I'm assuming most

17:27

people listening have never written a book,

17:29

but it's a lot of work and

17:31

all of the marketing and the selling

17:34

really falls on the author. And so

17:36

it's just been like endless, you know,

17:38

asking for favors and. giving people talking

17:41

points to talk about in their social

17:43

media posts or in a newsletter or

17:45

a show or whatever it is, it's

17:48

a lot of work. And I have

17:50

had some incredible mentors throughout this process,

17:52

some who are very, very well-known famous

17:55

authors or thought leaders in the space.

17:57

And so one of these people who

17:59

was a mentor of mine who was

18:02

just like really taken me under their.

18:04

I with some hesitation leveraged my weird

18:06

shameless reckless self, right, by, you know,

18:09

kicking my imposter syndrome to the curb,

18:11

just being me, the flavor that I

18:13

am, right, of weird, reckless, taking risks

18:16

and erring on the side of action

18:18

and thinking fearlessly that I can do

18:20

this. And I sent a note to

18:23

this person who has, I mean, if

18:25

I said the name, everybody would know

18:27

this person's name, very, very famous author.

18:30

And I basically said, you know, I'd

18:32

be so grateful if you would consider

18:34

sharing this with your audience. And the

18:37

note that I got back was. Alas,

18:39

I'm afraid that my time and effort

18:41

to teach you my approach didn't get

18:44

through, Jenny. At some point, it's not

18:46

worth the effort. I don't even know

18:48

how to respond to a pitch to

18:50

share your work with my audience. You

18:53

decided to do something you knew I'd

18:55

hate. No one likes to be hustled.

18:57

Good luck, but I think it's best

19:00

for us to move on. Bingo. Rough.

19:02

Rough. Go ahead, this

19:04

is for you. I mean, it still

19:06

stings. I've lost sleep that night, like

19:09

a lot of sleep, at a time

19:11

where I don't feel like I can

19:13

afford to lose sleep because I'm in

19:16

this very heavy intense period. I was

19:18

mad at myself, I was disappointed in

19:20

myself that I didn't read the room,

19:23

all these nine traits have something called

19:25

trait traps, which is when you take

19:27

the trait too far, and it really

19:29

made, it was like the dagger of

19:32

the email, and then the second dagger

19:34

I was giving myself of thinking, Jenny,

19:36

you were too shameless, you were too

19:39

selfish, and you didn't prioritize the relationship

19:41

over the request. what's helped me move

19:43

through it. So like to be clear,

19:46

I am still processing this. By the

19:48

way, this conversation helps because good. This

19:50

is what I was for. Yeah. I'm

19:52

still processing it. I haven't responded. And

19:55

then I did the whole. Do I

19:57

respond? Do I not respond? Do I

19:59

respond? Do I respond? to bed, do

20:02

I try to make a pitch to

20:04

like regain this friendship and this mentorship?

20:06

Again, like someone I deeply respect and

20:08

admire. And so, but the lesson to

20:11

me that's coming out of it is

20:13

I have asked a hundred other people

20:15

for help on this launch and they

20:18

have been so excited to help me.

20:20

I mean, you're helping me, right? Like,

20:22

I love it. And so if I,

20:25

if I, if I just, if I

20:27

had a negativity bias, right that social

20:29

psychological Well, that didn't work. I should

20:31

just give up and stop asking people.

20:34

I mean, A, wouldn't be living my

20:36

values of wild courage. I wouldn't get

20:38

any, you know, I would stop doing

20:41

what I do and what I coach

20:43

and help people do, which is live

20:45

with wild courage. And so I know

20:47

that I was living my values. And

20:50

I think the outcome wasn't what I

20:52

wanted, but it doesn't mean that my

20:54

decision to ask was wrong. And I

20:57

did think I'd asked in a really

20:59

thoughtful way. And so, anyway, that's where

21:01

I am with it. No, it's so,

21:04

again, it's beautiful, and I will also

21:06

channel another person I admire and respect

21:08

and appreciate Glenn and Doyle. She has

21:10

a phrase called, Brutiful. which is it's

21:13

such a good phrase right it's such

21:15

a good phrase it's brutal and it's

21:17

beautiful in its own way because you're

21:20

both sharing this lesson that you've learned

21:22

you're sharing it in real time yeah

21:24

and it makes me like I want

21:27

to go to bat and work so

21:29

hard to help you because we've all

21:31

had that experience where we just want

21:33

to crawl into a show and disappear

21:36

for a minute and yet. I felt

21:38

nauseous because of how much I value

21:40

this relationship. Yeah. Yeah. And it's rare

21:43

that someone like breaks up with you,

21:45

right? Like in a platonic business context,

21:47

but like I got fired from this

21:49

person and And of course I go

21:52

to action. What can I do next?

21:54

Like action, not thinking provides clarity, I

21:56

say. And so I'm like, well, what

21:59

do I do? How do I recover?

22:01

What do I say? what's the right

22:03

move, but really I just had to,

22:06

I've had to sit with the sorrow

22:08

and the regret a little bit, but

22:10

also just like the pride that like

22:12

I was living my values and I

22:15

can't control other people's responses. And this

22:17

was a really hard moment, but there's

22:19

like, think about the other moments that

22:22

we have day to day where it's

22:24

maybe not quite this harsh of an

22:26

email or this clear of an outcome,

22:29

but even just like not hearing back

22:31

from a people I've pitched for keynotes

22:33

at their company or consulting projects where

22:35

like I just thought they'd respond and

22:38

they're like, oh, not in the budget,

22:40

maybe later, like it is kind of

22:42

spine straightening for those moments where it's

22:45

like you just got to keep putting

22:47

yourself out there. But it's hard. Let's

22:49

acknowledge that it's hard and yet how

22:51

many people do we know that do

22:54

hard things? Right? We are built for

22:56

hard things. And this is one of

22:58

the reasons I'm sort of mapping the

23:01

fact that we're built for challenge and

23:03

for failure and for struggle. And I'm

23:05

mapping these ideas back on to one

23:08

of the reasons I love your list

23:10

of traits so much. Like, you know,

23:12

weird. There's just the, I think the

23:14

value that connects with actions reckless, right?

23:17

Like, exactly. I talk about action over

23:19

intellect. We can so often paralyze ourselves

23:21

from overthinking. And the reality is as

23:24

soon as you take action, you find

23:26

out a lot. And most of the

23:28

stuff that we try and take, we

23:30

try and intellectualize, that means like create

23:33

a solution from the couch. It's not

23:35

real because we haven't put it out

23:37

in the world yet. And so we

23:40

don't actually learn anything. So, oh my

23:42

gosh. The lens that you have created

23:44

with these list of, again, pretty controversial

23:47

or topics, like again, calling action reckless,

23:49

but it is in a moment it

23:51

feels totally reckless and yet you get

23:53

so much data. from taking action relative

23:56

to inaction, trying to decide the stuff

23:58

from the couch. Yeah, I could not

24:00

agree with you more. Failure is just

24:03

data. And if you wanna double your

24:05

successes, quadruple those failures, right? And look

24:07

at any successful person you admire. Their

24:10

resume is riddled with missteps and failures

24:12

and attempts that didn't pan out, right?

24:14

And boldly asking this person like I

24:16

did, you know, for their support and

24:19

it falling flat. don't just study their

24:21

greatest hits, study the discography of their

24:23

entire career, right? Like it's like we

24:26

focus on, okay, well, they're famous and

24:28

there's not that we all need to

24:30

be famous or want to be famous,

24:32

but whatever it is that you have

24:35

a goal to achieve. You know, I

24:37

do think that the more we can

24:39

take action without living in our heads

24:42

and trying to perfect it is what

24:44

yields that minimum viable product, right? Like

24:46

when I was. There's something I'm sitting

24:49

on right now where I'm just like

24:51

trying to perfect this Google doc and

24:53

like get the images all in the

24:55

right place and the the font to

24:58

be the right size and it's like

25:00

no just send the damn thing out

25:02

Jenny like nobody cares. Get it out

25:05

sooner rather than later and that's what

25:07

reckless is. It's the the courage to

25:09

take calculated risks err on the side

25:11

of action because frankly better to learn

25:14

from your mistakes than waste time analyzing

25:16

the consequences of every decision. Think fast

25:18

and fearless and if you're on the

25:21

fence. do it because there are a

25:23

few things in life that we regret

25:25

because they turned out poorly. I kind

25:28

of regret this one, but I'm still

25:30

learning from it, this, you know, email

25:32

situation. But I think we, there's a

25:34

lot of research supporting we more often

25:37

regret the moves we do make than,

25:39

sorry, we regret the moves we don't

25:41

make than the outcome of the moves

25:44

we do make. Absolutely. All of them

25:46

are learning opportunities. And, you know, what

25:48

does my mom say? She calls it

25:51

like. A-F-L-O. Do we have an explicit

25:53

rating on this show? No, you go

25:55

for it. Okay, she calls it an

25:57

A-F-L-O, another fucking learning opportunity. I love

26:00

it. There you go. Ricky Illis folks,

26:02

Ricky Illis. Thanks Ricky. I love that.

26:04

Hat tip. Hat tip. So this to

26:07

me is really easy for about half

26:09

of our audience. They're like, I'm into

26:11

this, I can do this, and there

26:13

are a half right now that are

26:16

terrified. And you, only the people listening

26:18

right now, know which can't they fit

26:20

in. It doesn't matter, you don't have

26:23

to tell anybody. But it, and it

26:25

doesn't always split along this line, but

26:27

half. half of the people who are

26:30

listening have identified, self-identified as, yeah, but

26:32

these things just aren't me. I am

26:34

an introvert, for example. And this sounds

26:36

very easy for extroverted Google executive Jenny.

26:39

But it sounds terrible. Yeah, it sounds

26:41

terrifying for me. So let's let's talk

26:43

to our introverted, you know, more quieter

26:46

folk who might be doubting that this

26:48

could be, work for them. Okay, I'm

26:50

so glad you're bringing this up because

26:53

it really does work for anyone and

26:55

it can be learned by anyone. These

26:57

are not skills that you're born with

26:59

or traits that you're born with. So

27:02

when I think about how introverts tap

27:04

into their wild courage and make these

27:06

small courage deposits every day, I think

27:09

about, well, what are the steps that

27:11

are purely internal, right, like the ways

27:13

we get in our own way? Because

27:15

when I think about extra version, Reaching

27:18

out to 100 people asking for their

27:20

support, chasing someone off a subway, asking

27:22

for a raise or a promotion or

27:25

that client, all of that is interrelational,

27:27

right? It involves putting yourself out there

27:29

and, you know, let's say, maybe it

27:32

feels to them like an extroverted way

27:34

that they don't have. But let's just

27:36

talk about the conversation within your own

27:38

mind for a minute. And a good

27:41

example of this, this is a tool

27:43

I call truths truths and tales. And

27:45

I'm going to use my example of

27:48

leaving Google. So was there 18 years

27:50

breadwinner for my family? Fancy, you know,

27:52

executive salary, very, very comfortable, never thought

27:54

I would leave for the next 15

27:57

years and that I would just retire

27:59

there. And then all of a sudden.

28:01

and I had all this excitement around

28:04

my ideas and this external interest and

28:06

this like book idea and I was

28:08

like, wait a second, I don't think

28:11

I can do all of this at

28:13

the same time and still be like

28:15

a functional human. But I was terrified

28:17

to leave Google. Terrified. And so I

28:20

would tell myself all sorts of tales,

28:22

right? So tales like, we're gonna have

28:24

to downsize and move out of our.

28:27

house in a great location by all

28:29

the hiking trails in Boulder. We're going

28:31

to starve. I'm leaving to be a

28:34

starving artist who leaves their Google exact

28:36

role to go write a book. I

28:38

will never be able to get hired

28:40

again if the book flops because I'm

28:43

45 and you know no one's going

28:45

to hire a 45 year old right.

28:47

My kids are going to be disappointed

28:50

in me because they can't come to

28:52

Google and ride the slide and get

28:54

the free snacks. My parents are going

28:56

to be thinking I'm nuts to leave

28:59

this, this stability. Every single thing I

29:01

just said is stuff that plagued me

29:03

for a year, Chase. But they're all

29:06

tales. So what are the truths of

29:08

the situation? I would likely make less

29:10

money than at Google in my first

29:13

year. Another truth, I was leaving to

29:15

write a book. Another truth, we had

29:17

a lot in savings. Another truth, I've

29:19

always, I had good guidance from my

29:22

financial advisor. Another truth. My relationship to

29:24

money is one thing, but you know,

29:26

there's other values in life, like time

29:29

with my family, being high net freedom.

29:31

So once I was able to separate

29:33

the truths, which are verifiable facts, right?

29:36

You know, I am leaving to write.

29:38

I will no longer be a Google

29:40

employee, right? Those are truths. But everything

29:42

else I shared was a tale. And

29:45

when you can separate the truths from

29:47

your tales, introvert, man, woman, born in

29:49

India, born in, you know, you know,

29:52

Santa Fe. That is what helps you

29:54

push past the fear because we all

29:56

have these gremlins on our shoulder that

29:58

tell us these stories. But oftentimes those

30:01

stories don't serve us well. So identifying

30:03

the truths and the tales of any

30:05

scary nerve-wracking fear-based... situation, writing them down

30:08

in a column, like one for truths,

30:10

one for tales, and then rewriting the

30:12

tales to be more neutral. You don't

30:15

even have to go nuts and be

30:17

like rose-colored glasses, Pollyanna, just even a

30:19

more neutral tale. Like, I may succeed,

30:21

I may not succeed in this entrepreneurial

30:24

endeavor as a creative, you know, writer,

30:26

influencer, keto speaker. That helps because we

30:28

believe the things we say. And then

30:31

say those neutral tales out loud. Yeah,

30:33

I love this. My friend Tim Ferris

30:35

calls it fear-scaping. And it's so useful

30:37

to say, like, worst case scenario. And

30:40

then when you can actually project that

30:42

worst case scenario under your life and

30:44

it's like, oh, well, if I didn't

30:47

make any money, the first year, my

30:49

savings is X dollars less than it

30:51

would have been if I didn't leave

30:54

Google, or if I wasn't able to

30:56

earn a dollar as an author or

30:58

as an artist or an entrepreneur, or

31:00

whatever the thing is I want to

31:03

want to want to do. And it

31:05

ends up being very valuable. And to

31:07

me, the part that needs refining here

31:10

that I'll ask for refining is why

31:12

is this especially valuable for introverts? Is

31:14

it because there's a thought process which

31:17

is more like considerate and the instinct

31:19

for the extrovert is just to go

31:21

for it? I mean, why introvert to

31:23

this lens? Well, the reason I love

31:26

this tool for introvert is because I

31:28

think it's the least scary for them

31:30

because it all happens internally within you.

31:33

And if extraverts feel more intimidated about

31:35

asking somebody for a raise or a

31:37

new project or a favor, right, because

31:39

it involves somebody else, the reason I

31:42

flag this for introvert is because it

31:44

all happens directly within you. In the

31:46

quiet of your own home or wherever

31:49

you, you know, to me it's a

31:51

good first step is recognizing like what's

31:53

happening within you. that you can control.

31:56

This makes, to me, this is a

31:58

perfect transition around another one of the

32:00

traits and the. concept of shame, again

32:02

referencing Brine Brown for popularizing this and

32:05

I'm really helpful and I felt like

32:07

an open transparent way that we hadn't

32:09

talked about it culturally ever you know

32:12

10 years ago when she came on

32:14

the scene with this vernacular maybe more

32:16

that the concept in in the circles

32:18

that my listeners travel in it's like

32:21

shameless self-promotion for example and and then

32:23

shame is what if you put your

32:25

you know you wear your heart on

32:28

the sleeve and put your ideas out

32:30

there whether in a book or a

32:32

product that you launch or whatever and

32:35

no one buys nobody likes it nobody

32:37

cares how does that make us feel

32:39

about ourselves and you have shameless as

32:41

the concept of swagger as how do

32:44

we you know help us realize that

32:46

being shameless in sort of the classic

32:48

example and in the tongueing cheap like

32:51

yeah the feisty way that you talk

32:53

about it how relate those to our

32:55

listeners yeah so Shameless I define as

32:58

the courage to stand behind your efforts

33:00

and abilities. And you're right, it is

33:02

finding your swagger. It's audacity or shamelessness

33:04

as a survival skill because how will

33:07

you learn if you've got the goods

33:09

if you don't act like it first,

33:11

right? And so it's recognizing your own

33:14

talent, your own power assets. Like what

33:16

are the three things that you're really

33:18

good at and refining those in a

33:20

way that you feel comfortable talking about

33:23

them? I mean. in an entrepreneurial world

33:25

or a creative world, this might be

33:27

sending, you know, your clients some wins

33:30

that you had last week, like, hey,

33:32

just wanted to let you know, like,

33:34

we had so much fun working on

33:37

this project, and here's what we delivered

33:39

for them, and, you know, we'd love

33:41

to partner with you on something coming

33:43

up. And it's like, we feel shame

33:46

in doing that. We feel like it's,

33:48

oh, it's like. shameless self-promotion, but it

33:50

can actually be tasteful self-promotion because you're

33:53

just sharing things and sometimes people need

33:55

what you have to offer, but it's

33:57

not making... yourself available. They don't know.

34:00

It's like, think about the, you know,

34:02

work. my husband John and I are

34:04

thinking about a remodel for our house.

34:06

And when we see a sign on

34:09

someone's lawn who's doing a remodel in

34:11

the neighborhood, we like take a picture

34:13

of that sign and we're like, ooh,

34:16

we're gonna wanna find a great contractor

34:18

when we remodel. This contractor is being

34:20

helpful by quote unquote shamelessly, putting their

34:22

giant sign in the front of this

34:25

other neighbor's house saying remodel brought to

34:27

you by blah blah blah construction. Right.

34:29

But it's actually quite helpful to

34:31

us. And so we're sharing our.

34:34

superpowers with people or our power

34:36

assets, the three strengths or talents

34:38

that we feel like we can

34:40

offer the world, we think that

34:42

we're being obnoxious or too much,

34:45

right? Or too boastful, but we're

34:47

really just sharing information that actually

34:49

can help people. Yeah, I think

34:51

that is, you know, that was

34:53

a big change for me when

34:55

I realized that there are, well,

34:57

two things. One is that as

34:59

a, I'm going back to my

35:01

days primarily where I identified as

35:03

a photographer and it's like my

35:06

absolute banner year, multi-million dollar

35:08

years were when I was

35:10

hired by maybe 25 people.

35:12

And you're like, there's seven

35:14

and a half billion people on

35:17

the planet and I need 25

35:19

to absolutely crush it. How, like finding

35:21

those 25 people, first of all, 25

35:24

is a very small number relative to

35:26

seven and a half billion. Yeah. How

35:28

am I going to discover those people?

35:30

How am I going to connect with

35:33

those people? If, certainly I provided value,

35:35

otherwise they wouldn't have paid me what

35:37

they paid me. So if you can

35:39

reframe this, you know, the concept of

35:42

shame and guilt around going and being

35:44

proud of the work that you put

35:46

out in the world, like... It has a

35:48

chance to completely redefine your business the

35:51

way you think about putting yourself out

35:53

there. Your goal is to connect with

35:55

your people and most people aren't going

35:57

to be your people. That's actually by

35:59

design. Right. And like, I think, you

36:01

know, I always think of like the

36:03

interviewee feeling like, oh, I don't want

36:06

to be shameless in this. pre-interview email

36:08

or like this pre-client project email by

36:10

saying like these are the three things

36:12

I could bring to the table. But

36:14

when I was in exactly Google hiring

36:17

people, like it is so hard to

36:19

find good talent, Chase. And I would

36:21

like to have interview after interview. So

36:23

if you're the photographer or you're the

36:25

writer or you're the designer or you're

36:28

the marketer who's like, well, you know,

36:30

gosh, I'm sure there are so many

36:32

other people out there who are better

36:34

than I. think of this moment in

36:37

a meeting I was in once at

36:39

Google where someone said in a room

36:41

of maybe 30 people she's like this

36:43

is a shameless plug but I created

36:45

this spreadsheet and I'm just gonna share

36:48

it with you and I wince when

36:50

someone says this is a shameless plug

36:52

because she shared that spreadsheet and I'm

36:54

just gonna share it with you and

36:56

I wince when someone says this is

36:59

a shameless plug because she shared that

37:01

spreadsheet every single time and you've Why

37:03

can't it just be, I'm proud of

37:05

this thing I created and I'm so

37:08

excited to share it with you. And

37:10

then think about how that sounds to

37:12

the world, right? You seem like a

37:14

leader. You seem like someone that people

37:16

are excited to do work with. We

37:19

have a nanny we just hired and

37:21

we had her fill out an application

37:23

on Google, on Google form. And she

37:25

said, I'm an exceptional cook. And I'd

37:27

love to cook for your family. I'm

37:30

like, that is so shameless. I was

37:32

like, exceptional cook and guess what? She

37:34

is. You've got to have the goods

37:36

to back it up. Yeah. But even,

37:38

but like, it's one of the reasons

37:41

she got the job because she shamelessly

37:43

touted one of her superpowers. Yeah. And

37:45

it's different than just saying, I enjoy

37:47

cooking. Very different. And there is. And

37:50

I loved her confidence, by the way.

37:52

I hired her in part because of

37:54

her confidence. That's something that, to me,

37:56

these things sort of parlay off one

37:58

another, one another, which is if you.

38:01

are bringing your skills to the world

38:03

in a, you know, according to your

38:05

vernacular in the book in a shameless

38:07

way. Yeah. Not only are you helping

38:09

the right people find you, but when

38:12

that works out, when you are comfortable

38:14

speaking up about your work, and the

38:16

world reinforces it by hiring you. This

38:18

is sort of the, this is how

38:21

confidence and positive self-talk, this is, this

38:23

is, this is at the root of

38:25

this stuff, right? It's like, of course,

38:27

you've said it several times, you need

38:29

to be able to walk the talk,

38:32

but there are things that every single

38:34

person who's listening right now knows that

38:36

they are great at, that the world

38:38

does not. Yeah, yeah, exactly. You get

38:40

no credit for stories you do not

38:43

tell. Right. And then I've even had

38:45

to, like, again, because I'm an entrepreneur

38:47

and a creative for the first time,

38:49

and I'm learning the ropes and making

38:52

a lot of mistakes. We talked about

38:54

one. But here's another one. I was

38:56

offered a keynote opportunity. I was so

38:58

excited about it. Big Fortune 500 company.

39:00

And then they said, you know, we

39:03

were about to do the deal that

39:05

we were in the contracting stage and

39:07

they said, hey, by the way, most

39:09

of our audience is in Asia and

39:11

Europe. So that's 3 AM my time

39:14

for a virtual talk. And I was

39:16

like, I don't know if I don't

39:18

think I want to say yes to

39:20

this. So there's also something, well, this

39:23

more gets to the brutal trait, which

39:25

is the power of no and setting

39:27

boundaries around your time and energy. But

39:29

I said, well, could we do 6

39:31

AM my time, 8 AM Eastern time?

39:34

and figuring we'd meet in the middle,

39:36

they'd come back with 4.30, and then

39:38

I, they just said no. They're like,

39:40

well, we're just gonna go with someone

39:42

else. And then I did get a

39:45

little bit shameless and say, well, no,

39:47

I could do 3 a.m. I just

39:49

thought it would be better, but I'd

39:51

already lost the deal. And so I

39:54

think it's also just recognizing, you know,

39:56

we can renegotiate deals, we can attempt

39:58

to renegotiate deals, like you can stand

40:00

up for what you, I should have

40:02

just done it at 3 a.m. But

40:05

you know, I think there's also, there's

40:07

an element of recognizing that like where

40:09

do you push, where do you not

40:11

push, but I think most people. need

40:13

to dial up their ability to ask

40:16

for what they want and those people

40:18

live with more imposter syndrome or feel

40:20

so bad or they people please and

40:22

that's what I want to help people

40:25

with through wild courage. Yeah I would

40:27

say we all know that person who's

40:29

like wow you are in 11 out

40:31

of a 10. And there are some

40:33

aspects of that we love, some that

40:36

we don't, but I would say 99%

40:38

of people that I know, we need

40:40

to dial up. And I don't know

40:42

if you're familiar with the gentleman named

40:44

Gia Jang, who he took this concept

40:47

of rejection therapy and then went on

40:49

a hundred days of rejection, asking crazy

40:51

requests of people, like ask Krispy Kreme

40:53

if they would make donuts in the

40:56

shape of the Olympic rings and asked

40:58

a police officer if he could drive

41:00

his car. Oh my gosh, I love

41:02

it. And yes, as by the way,

41:04

as a response to both these things,

41:07

they made him the donuts in the

41:09

shape of Olympic rings. And yes, he

41:11

drove a cop car. Amazing. This, as

41:13

people are digesting, again, I want to

41:15

hat-tip, the book is called Wild Courage,

41:18

go after what you want and get

41:20

it. The general. pattern in life is

41:22

not that we have too many go-getters

41:24

and boy, it's just... Or too many

41:27

assholes, you know, like too many obnoxious,

41:29

arrogant, like classically selfish, manipulative, and shameless

41:31

people. Like, I interrupted you, but I'm

41:33

so passionate about the fact that like,

41:35

don't sweat it that you're going to

41:38

turn into an a hole if you

41:40

tap into your wild courage. There are

41:42

way more people who need to dial

41:44

it up, then dial it back. And

41:46

I mean, it's literally like... nine out

41:49

of 10 people who are listening to

41:51

this show right now could benefit deeply

41:53

from, no, there's a practical, that's one

41:55

of the things I loved about the

41:58

book is there's a very practical almost

42:00

sort of like workbook approach. These are.

42:02

I think that's a really important thing.

42:04

They're traits and skills that you can,

42:06

that you develop through the process of

42:09

doing these things and you are thoughtful

42:11

and give us ways to practice them.

42:13

And at the end of the day,

42:15

do you feel like that the, like

42:17

which of these traits? Well, I'm guessing

42:20

you may have a favorite one. And

42:22

two, if you don't have a favorite,

42:24

which do you feel like is a

42:26

good place for the person who's just

42:29

hearing about this for the first time

42:31

to start? Your favorite or maybe both.

42:33

You can answer these questions however you

42:35

want. But that's on the table. Okay,

42:37

so asking me my favorite trait is

42:40

like asking me which is my favorite

42:42

child? So I think it's more about

42:44

like, how do I feel today? Well,

42:46

I love, I love the obsessed treat

42:48

because I think it's misunderstood. Well, they're

42:51

all misunderstood. Sure. But, you know, I

42:53

was working with a keynote coach who's

42:55

just incredible, Mike Pacquion, if anybody needs

42:57

a keynote coach. And he's like, Jenny,

43:00

I read the book and I actually

43:02

skipped over the upset. So the answer

43:04

is obsessed is what I'm thinking about

43:06

right now. Obsessed is the courage to

43:08

set your own standard to. push and

43:11

to perform and to persist because none

43:13

of these traits will serve you well

43:15

if you if you don't take pride

43:17

in your work and learn to deliver

43:19

not for some not for like your

43:22

clients for yourself right yeah because it

43:24

feels so good to do your best

43:26

work and to put your energy and

43:28

your effort into something so Mike read

43:31

the book and prep for our keynote

43:33

and he's like okay you know really

43:35

enjoyed reading it Don't be mad. I

43:37

skipped over the obsessed chapter. It just

43:39

sounded like it was a lot of

43:42

work and tiring and like, you know,

43:44

I just, it sounded like it was

43:46

hard work. And I was like, oh

43:48

my gosh, my good feedback. But then

43:50

the next day, Chase, this shocked me.

43:53

He was like, he's like, Jenny, I

43:55

want you to watch minute seven of

43:57

the Steve Jobs Stanford commencement speech. I

43:59

think there's something you can do very

44:01

similar here. And then you can do

44:04

very similar. at minutes 13 because let's

44:06

think about how we can incorporate that.

44:08

I think you can do that too.

44:10

He's like and then also I I

44:13

built out this story three different ways

44:15

for the keynote, and I think all

44:17

of them could play pretty well, but

44:19

I want to get it just right.

44:21

So we nail it for the audience.

44:24

And he was so obsessed with making

44:26

this the best possible keynote he could.

44:28

He was so excited about the craft.

44:30

You fell into my trap. Right. And

44:32

so I was like, Mike, you do

44:35

realize that you are obsessed in the

44:37

best possible way, and I love you

44:39

for it. But I just think there's

44:41

something really special about and I feel

44:44

obsessed right now with how. I'm sharing

44:46

this material with the world and how

44:48

I'm encouraging people and like it has

44:50

been a lot of work, but I

44:52

have so much pride, so much pride

44:55

in that work. And okay, so if

44:57

we're now I'll relate it to how

44:59

it can how it can help people

45:01

or like what's where to start. Sure.

45:03

Also related to obsessed is something as

45:06

simple as counting. How many of your

45:08

sentences you send to a client, to

45:10

a business partner start with the word

45:12

I versus start with the word you?

45:15

So I drafted this email the other

45:17

day to a client where I'd done

45:19

a keynote, and I said I had

45:21

so much fun partnering with you. I

45:23

loved doing the talk around leadership. I

45:26

would love to come back and pilot

45:28

this other workshop I have around teamwork

45:30

and communication skills, and I'd be so

45:32

thrilled to do that with you too.

45:34

Okay, so there were like four sentences

45:37

in there that started with I. obsessed

45:39

is, I call this tool, woo with

45:41

you by the way, woo your client,

45:43

your audience, your partner, by putting the

45:46

focus on them and being obsessed about

45:48

what's in it for them or, you

45:50

know, their skills or their talents. So

45:52

I rewrote it, wooing with you. And

45:54

rather than I loved partnering with your

45:57

team, I changed it to a sentence

45:59

that started with you, you were an

46:01

incredible team to partner with. Rather than

46:03

I had so much fun doing this

46:05

leadership keynote, I said, your team was

46:08

top notch and responded so well to

46:10

these concepts which lit me up. You

46:12

know, I have this new communications training

46:14

that I'd love to pilot, changed it

46:17

to your team might benefit from being

46:19

better communicators and, you know, having better

46:21

teamwork skills, let me know if I

46:23

can help you and add value to

46:25

your organization. So that is an obsessed

46:28

way to write an email, but it's

46:30

really effective. Wu with you. Well, the

46:32

concept of obsession is also not new

46:34

to the ears and the eyes of

46:36

our listeners and watches here because it's

46:39

true. You sort of can't stand out

46:41

and fit in at the same time

46:43

or our social creatures. So we desire

46:45

to fit in and yet, you know,

46:48

our ability to be the best in

46:50

the world of what we want to

46:52

be in any craft requires obsession in

46:54

the classical sense, but also just being.

46:56

So, um, detail driven. I do not

46:59

know a person who I would describe

47:01

as, you know, among the best in

47:03

the world at their craft. Let's go

47:05

back to Mike around the keynote, who

47:07

would not absolutely delight in telling me

47:10

very, very specific feedback about why this

47:12

particular thing is better than that particular

47:14

thing. And if you deconstruct. there have

47:16

been a lot of studies done on

47:19

the patterns of very successful founders. And

47:21

I think it was Ben Horowitz, who

47:23

I just recently saw this, he was

47:25

like, the pattern that we see is

47:27

they're obsessed with the tiniest details early

47:30

on the process, where someone else, like,

47:32

oh yeah, we'll figure that out later,

47:34

or it's an MVP or whatever, it's

47:36

like, truly great founders are obsessed with

47:38

the right things. And that's probably, you

47:41

know, a hat tip to the Steve

47:43

Jobs part that Mike wanted to, you

47:45

to tap into or something. It doesn't

47:47

strike me, I mean I guess I'm

47:50

going to frame this in the positive,

47:52

it strikes me that when I'm, you

47:54

know, consuming the book, there is that

47:56

truth. The truth just sounds different and

47:58

you. said these things in a way

48:01

that I can't ignore because I can

48:03

reflect on my own life. That's what

48:05

we're doing when we're reading a book

48:07

is we're like, wow, of course. It's

48:09

like, man. The truth hits different and

48:12

you've just you've spent a lot of

48:14

truth in the how many pages is

48:16

your book today. 220. There you go

48:18

and 220 pages. So first of all,

48:20

thank you. Again, I got to remind

48:23

the folks, Wild Courage, go after what

48:25

you want and get it. And I

48:27

also want to leave room in today's

48:29

conversation for you to tell me some

48:31

of the things that I missed. Like

48:34

what do you feel like is an

48:36

area of the book that you find

48:38

surprising or that most people. don't realize

48:40

and then what's the. the Trojan horse.

48:42

Okay, so there are two things I'd

48:45

love to share. One is the importance

48:47

of trait traps and the other is

48:49

a story about my grandma Lila. So,

48:51

okay, so when you bring up obsession,

48:54

when I brought up obsession, I think

48:56

it's actually pretty important to

48:58

address a critical part of the book,

49:00

which is called trait traps. It's when

49:02

you take them too far and maybe

49:04

I mentioned that already, but I want

49:07

to double down on it. Great. I

49:09

have been plagued by being too obsessed

49:11

and not having the right balance around

49:13

like when is the MVP the minimum

49:15

viable product appropriate and when do you

49:17

go whole hog and perfect minutes 17

49:19

of the keynote. And so I share

49:22

one story oftentimes with people where I

49:24

was prepping for a big presentation at

49:26

Google and I had this presentation coach

49:28

and she gave me like 14 things to

49:30

think about like the perfect hand position, where

49:32

to walk across the stage and where to,

49:35

you know, talk quietly for a fact and

49:37

where to be more excited. I did this

49:39

big presentation to a bunch of customers and

49:41

it went well, classically, but I walked off

49:43

stage and I just felt like I had

49:46

failed. And I came home to John, my

49:48

husband, and I was like, I bombed. And

49:50

he's like, what do you mean you bombed?

49:52

Like you said the feedback was good. And

49:54

I was just like, I just feel like

49:56

I failed because I was so overwhelmed with

49:58

all the things. I was trying

50:01

to do right, that I didn't

50:03

even enjoy the process. And Barry

50:05

Schwartz, a professor at Swarthmore University,

50:07

has a name for this. It's

50:09

called Maximizers and Satisfizers. And Maximizers

50:11

are always trying to, like, squeeze

50:13

out every last possibility of, you

50:15

know, perfection and optimization. And they

50:17

do get slightly better results, but

50:19

they're a lot less happier. you

50:21

know, maybe they get slightly worse

50:23

results, but they're happier with the

50:25

outcome. And I know that sounds

50:27

almost like the, um, the antidote

50:29

or sorry, the, um, like working

50:31

against my argument of wild courage,

50:33

but it is important to know

50:35

the context and to know, like,

50:37

when do you take it too

50:39

far? And how can you be

50:41

mindful of that and, and, um,

50:43

and pushing and drive to the

50:45

situation. So that's trait traps. To

50:47

your, but hat tip to you

50:49

because I think you do a

50:51

masterful job and as we already

50:53

sort of reviewed this. is not

50:55

about constraining the 110th percentile of

50:57

courage seekers here. This is, we,

50:59

so many of us are so

51:01

scared of so many things. And

51:03

what we really do need is

51:05

a dose of courage. And it's

51:07

not 100% courage, 0% fear. Exactly.

51:09

It's 51, 49. The courage to

51:11

actually, you know, ask your. than

51:13

stranger on the subway car, now

51:15

husband John. Yes. We all need,

51:17

not all, 99.99% of us need

51:19

a healthy dose of that, especially

51:21

in a world that's having us

51:23

be, you know, more quiet, more

51:25

fearful, more aversion towards our goals

51:27

than what we really ought to

51:29

be doing, which is chasing them

51:31

and unleashing the best version of

51:33

ourselves. Yeah, absolutely. Should I talk

51:35

about grandma Lila? I was just

51:37

going to say we can't not

51:39

hear about grandma now so please

51:41

do. Well we talked a lot

51:43

about being shameless and so this

51:45

is like such a great button

51:47

on what was a heavy dose

51:49

of the conversation. today. So, okay,

51:51

grandma, Lila was like a total

51:53

badass at four feet ten and

51:56

ninety pounds. She was like such

51:58

a maven. So not only did

52:00

she agree to be a bridesmaid

52:02

in my wedding at the age

52:04

of 88, she was also the

52:06

CEO of her own financial services

52:08

company until 92. And when John

52:10

and I first got married, she

52:12

had an apartment in Manhattan, rent

52:14

control, three bedrooms, three bathrooms, like

52:16

total, total locks. And so we

52:18

were staying with her on her

52:20

pullout couch when we were apartment

52:22

hunting early on. And we all

52:24

sit down to dinner one night

52:26

and John delivers some unfortunate news.

52:28

He has been part of a

52:30

major company restructure and unfortunately he

52:32

tells us he's been laid off.

52:34

So I am crushed as a

52:36

newlywed and feel so bad for

52:38

him. But I look across the

52:40

table and Grandma Lila says one

52:42

of her classic lines, which was

52:44

no is just an opening offer.

52:46

And John and I look at

52:48

each other trying to silently communicate

52:50

what we're thinking. And then John

52:52

says, grandma, I don't think it

52:54

works that way. A layoff? It's

52:56

like a one-sided thing. They say,

52:58

you don't work here anymore. And

53:00

I say. Okay, and then grandma

53:02

Lila's size, and she says, well,

53:04

sure, it might be more comfortable

53:06

to take no for an answer,

53:08

but that discomfort will pass. Get

53:10

your ego out of the way

53:12

and find a compromise. You both

53:14

want something. You want a job

53:16

because it's easier to get a

53:18

job when you have a job,

53:20

and they want to get stuff

53:22

done, even though they can't afford

53:24

to pay you. And so then

53:26

finally, genre lens and half-heartedly the

53:28

next day goes to his VP

53:30

and offers to stay on for

53:32

10% time and pay while he

53:34

job hunts. And surprisingly, Chase, they

53:36

accept. And so, and by the

53:38

way, then they moved him back

53:40

to 50%, then back to 100%

53:42

time when the financial crisis passed.

53:44

Like, it's a banana story. So

53:46

I'm not telling the story as

53:48

some influenced tactic per se. The

53:51

point is Grandma Lila's lesson. Don't

53:53

let fear shape your decisions. And

53:55

how often do we do that?

53:57

How often do we not ask

53:59

a partner for what we want

54:01

or a client for what we

54:03

need or that cute person on

54:05

the subway for their business card?

54:07

When we don't do it, it's

54:09

oftentimes because of fear of failure,

54:11

fear of uncertainty, fear of judgment

54:13

of others, or fear that we

54:15

might be called shameless or selfish

54:17

or reckless or weird. But when

54:19

fear is the root of the

54:21

blocker, it's actually such good news,

54:23

because fear... you can work with

54:25

and muster the wild courage to

54:27

chase after what you want in

54:29

life and you will discover a

54:31

vital truth no matter whether you

54:33

succeed or fail in any one

54:35

given thing and we talked about

54:37

some of those on this podcast

54:39

where I failed like blatantly the

54:41

three a.m. meeting the email from

54:43

this famous author no matter whether

54:45

you would succeed or fail in

54:47

any one given thing you will

54:49

never feel as purposeful. powerful and

54:51

alive as when you're pushing past

54:53

that fear to the joy and

54:55

success on the other side, because

54:57

everything you've ever wanted is right

54:59

there waiting for you on the

55:01

other side of fear. So reach

55:03

for it. with wild courage. That

55:05

is the reason that I wrote

55:07

the book Never Play it Safe

55:09

is the same punchline. We're so

55:11

cut from the same cloth, right?

55:13

It's bananas to me. All the

55:15

best stuff is right over there.

55:17

Yeah. Here's the ticket price. Are

55:19

you willing? Yeah. And sometimes you

55:21

do have to be the price.

55:23

I have many times, right? And

55:25

sometimes it stings and sometimes it

55:27

costs you money or time or

55:29

energy or ego. But... You got

55:31

to do it. You got to

55:33

do it. It's not an accident

55:35

that your book is number one

55:37

bestseller in professional development on Amazon

55:39

right now. Please folks, Wild Courage

55:41

is the title, Go After What

55:43

You Want and Get It. Jenny,

55:46

thank you so much for being

55:48

a guest on the show. You're

55:50

welcome any time here. Keep putting

55:52

this great workout into the world

55:54

and grateful to have had you

55:56

on the show. Thank you so

55:58

much. What a joy. to be

56:00

here and have this conversation. Until

56:02

next time from Jenny, and yours

56:04

truly, we're signing off, have an

56:06

amazing day. Thanks for listening. All

56:08

right, hey, before you go, thanks

56:10

so much for listening. And if

56:12

you got value from this show,

56:14

chances are your community will too,

56:16

right in the particular, Lies the

56:18

Universal. Please share this link to

56:20

the show with a friend or

56:22

mention the show on social. That

56:24

is a huge benefit for us

56:26

in hopefully an exchange for providing

56:28

value to you. I want you

56:30

to know that I really appreciate

56:32

your time, the attention, anything that

56:34

you give to the show, and

56:36

the questions that you ask our

56:38

guests here on social media or

56:40

through my text community, all that

56:42

is pure gold. This community, like

56:44

any community, is a testament to

56:46

that old phrase, a rising tide

56:48

floats all boats. and by elevating

56:50

one another, by sharing and resharing

56:52

this show, the tidbits that you

56:54

learn and the experiences you take

56:56

away, all of that has a

56:58

collective, massive, positive impact on the

57:00

world. So, just a quick thank

57:02

you. I appreciate all the effort

57:04

you put into sharing for the

57:06

show. All right, that's a wrap.

57:08

Let's put today's episode into practice

57:10

and get back to growing together.

Unlock more with Podchaser Pro

  • Audience Insights
  • Contact Information
  • Demographics
  • Charts
  • Sponsor History
  • and More!
Pro Features