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April 16, 2025 41 mins
Stop following the rules and be weird, ruthless, and bossy. That’s the message from Jenny Wood, a former Google executive who approached a stranger on a train because she thought he was handsome. That man later became her husband. This former executive says too many people are being held back because they are afraid to be bossy, shameless, and weird. In this podcast and in her book, Wild Courage, she talks about her unconventional fundamentals to finding success. 

https://itsjennywood.com/book



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Speaker 1 (00:00):
Hey, everyone, welcome to ten seconds to air. Before we begin,
please do me a favor and hit the subscribe button
on YouTube.

Speaker 2 (00:06):
It's free. Okay.

Speaker 1 (00:08):
Today we have an energetic and inspirational guest who says
we need to shatter conventional wisdom to get what we
want in life. Jenny Wood is an author, motivational speaker,
and former Google executive who's changing the way we achieve success.
She says be weird, shameless, and bossy. In her new book,
Wild Courage, she tells us to stop following the rules

(00:31):
and go after what we want unapologetically. She joins me
now to talk about what we can do today to
change our story and our future brand.

Speaker 3 (00:41):
Bye, We're going live, go hard.

Speaker 2 (01:01):
Hello Jenny Wood.

Speaker 3 (01:04):
It is a delight to be here, Alida.

Speaker 2 (01:06):
I love the book behind you. I can see it.
Wild Courage.

Speaker 3 (01:10):
Oh, this whole thing, that little.

Speaker 1 (01:13):
Old thing back there, shameless, unapologetic.

Speaker 2 (01:17):
We're gonna dive right into this.

Speaker 3 (01:19):
We are flanked by Wild Courage.

Speaker 1 (01:22):
Before we get to what's inside the book. I want
to know what's inside your mind, what goes through your mind?

Speaker 2 (01:28):
Ten seconds to air?

Speaker 3 (01:31):
Am I prepared enough? Yeah? Am I prepared enough? And
I think that you know, this kind of taps into
the obsessed chapter, which is the courage to set your
own standard, to push, perform, persist, and prepare. And I
think that so much good stuff in life comes from preparation,
So much success comes from preparation.

Speaker 1 (01:50):
Dive into that a little bit more to be to
have wild courage, get into preparation.

Speaker 3 (01:56):
Yeah, so it's almost like the you know, think of
wild curds, like that moment that you just you leap
before you look right. But this is the prep work,
the you know, as I launched this book into the world,
the number of social media posts I've written, the number
of prereaders who've read it and given me feedbacks, like
so I can integrate that feedback, the illustrator that I

(02:19):
hired to illustrate some of the ideas in the books,
so we can really bring this home, you know, with readers.
It's like all of that preparation, all those relationships that
I've built with other authors so that they can help
spread the word as well. Like all of that preparation.
It's three years of preparation that culminates in a book launch.
Now I'm saying, do I feel prepared for this particular
conversation right, whether you know, for someone it might be

(02:41):
an interview, it might be a meeting one on one
with their boss. It might be a meeting with a
mentor or a sponsor or their boss's boss. How have
you prepared for that meeting? Right? Have you written a
couple bullets ahead of time that have specific numbers and
accomplishments from the last week? Have you thought about questions?
Do you want to ask them? So like, preparation looks
really different in this particular moment for our conversation or

(03:02):
for someone else preparing for a promotion or a big
project or a new customer they're trying to acquire. But
you know, I'm both thinking about this moment with us
right now, ten seconds to air what goes through my mind?
Am I prepared? But also am I prepared for this
book launch that's about to, you know, hit the world?
Am I prepared for? What? Is my family ready if
this book takes off? Right?

Speaker 1 (03:23):
So?

Speaker 3 (03:23):
Am I prepared if I have to downsize my house
because the book flops?

Speaker 1 (03:29):
So what brought you to this anyway? Wild Courage, It's unconventional.
What you talk about is unconventional. I assure you I
have read nothing like it. And I have lots of
people on this podcast, but you go out there and
you say, go for it, go for it?

Speaker 3 (03:45):
Wow?

Speaker 2 (03:45):
What got you to that point?

Speaker 3 (03:47):
What got me to this point was a moment on
a dirty, crowded sea train in New York City in
twenty eleven, when I'm riding the subway home from work
and about twenty feet away from me SAMs this really
hot guy, and I want to talk to him, but
you know, I let my fears hold me back. Despite
the gorgeous blue eyes, despite the thick, wavy brown here.

(04:09):
You know, I say, I'm not going to just go
up and talk to some stranger on the subway. What
if he's a convicted felon? What if he's married? What
if a hundred people stare at me while I make
a fool of myself on this train? And I later
came to realize that those three fears were kind of
underpinned by the three fears I've seen hold so many
people back. Fear of failure, what if he's married, Fear

(04:32):
of uncertainty, what if he's a convicted felon. Fear of
judgment by others? What if a hundred people stare at me,
so I yet I still want to talk to him.
So I make a deal with the universe. I say,
if he gets off at my stop, then maybe I'll
try to strike up a conversation with him, and if not,
then that's the universe telling me it wasn't meant to be. Well,
he gets off at the next stop, which is not
my stop, and I say, as I feel this wave

(04:56):
of wild courage washed over me and push me off
of the tra I'm basically prying the doors to the
train opening, and I say, forget the universe, I'm making
my own damn meant to be and I run off
the train. I tap him on the shoulder. I say,
you're wearing gloves, so I can't tell if you're wearing
a wedding ring. But in the event that you're not married,
you were on my subway and I thought you were cute.

(05:17):
Any chance I could give you my business card? We
go out a week later, we get married three years later,
and we've now been married happily for eleven years, with
two little hooligans, ages seven and nine. So that was
the moment that wild courage changed my life.

Speaker 1 (05:30):
Wait back up just one second, so you say to
him I can't see if you're married. I mean, what
is he saying? You don't know if he has wild courage?
And he says sure, and I'm gonna ask you out
and we're gonna get married and we're gonna have children.
I mean, he's on the recipient end of this woman
that just maybe this happens to him all the time.

Speaker 2 (05:50):
Maybe it's never happened to Okay more right, Like.

Speaker 3 (05:52):
So this is you're not gonna believe what I'm about
to say. But John, my husband, had just come from
a networking event where two of their women gave him
their numbers.

Speaker 2 (06:03):
Wow, So apparently, yes, this.

Speaker 3 (06:04):
Does happen to John all the time, or at least
it did that day. I mean, he's really attractive.

Speaker 2 (06:08):
So he's feeling good. He's like, this is my lucky
night number three. I don't know what's gonna happen from
the train to my walk home exactly.

Speaker 3 (06:16):
He's feeling great, so he I mean, John loves attention.
Also he's the first to admit it. But so he's
feeling great. And you know it's interesting, like you're asking
what was his perspective when I come off so bold,
and I'm like owning my weird right. Weird as chapter
one of Wild Courage, and it's about the courage to
stand out right, And that's what I did. Like, I
had just been dating this guy, Brian, when I was

(06:37):
working at Harvard Business School, and he did not like
my fit flavor of weird. He wanted someone blonde and
petite and a wallflower and his words, I want someone
who's really pretty, but she doesn't think that she is.

Speaker 2 (06:50):
Oh oh wow, yeah.

Speaker 3 (06:52):
And I and I was just, you know, like never
going to be that person. I'm the kind of person
who rocks down the sidewalk dancing to akape show tunes
on my on my headphone. Right, And so I figure,
you know, better to start this relationship off with John
on honest footing. And if I'm not his cup of tea,
then se la vie because clearly I can't fit a
square peg into a round hole.

Speaker 2 (07:13):
So what was he thinking? What what he thought I was?

Speaker 3 (07:17):
Actually he's literally thinking I was carrying a bouquet of
flowers from a cappella rehearsal at work, because Google has
all sorts of fun things like acapella, you know, groups,
and he thought I was trying to sell him flowers
that's what he was thinking. Because I was taking home
these leftover flowers. So I had this like big bunch
of yellow gerber daisies.

Speaker 2 (07:33):
So what happens. He calls you, you call him.

Speaker 3 (07:36):
He calls me the no, he doesn't actually he And
there's this is interesting because he said, when he took
my business card, I'll email you, so you're not caught
off guard by a phone call at work. We're still
talking like landlines at the desk, on the desk at work.
And he and when he said that, I knew that
he was going to contact me because of this study

(07:58):
around implementation intentions, this well known study that says if
you identify how and when you're going to do something,
in this case, it was how, you're much more likely
to do it to take the action. And so I
was like, ooh, he's already thinking about how he's going
to get in touch with me email versus phone, So
he's probably going to do it. And he did the
next day eleven PM. Who's counting.

Speaker 2 (08:18):
Wow?

Speaker 1 (08:18):
Okay, So you get together, you go out, you start
to date, you end up getting married.

Speaker 2 (08:25):
All fast forward.

Speaker 1 (08:26):
Now, when does the wild courage dawn on you and
say I need to put this in print.

Speaker 3 (08:31):
Well, this is the thing is that day was the
moment that I started leveraging wild courage as a habit,
and I started setting goals and writing them down and
saying them out loud to people, and started achieving them,
like getting my pilot's license. I started asking for what
I wanted at work at Google, and I grew from
entry level to executive over eighteen years. I ended up

(08:52):
being the COO of several different divisions of Google and
brand new experimental teams that sat between sales and engineering,
helping drive billions of dollars of revenue. And then I
got to this moment where, you know, I'd achieved enough
success at Google that people would come to me for
mentorship and they'd say, hey, can you tell us your secrets?
Like what do you recommend? And so I thought, all right,
let me jot down a couple of ideas of how

(09:14):
I grew within Google. Because eighty percent of people work
at companies, they're not entrepreneurs, you know, or even maybe
closer to ninety percent, and so people wanted to rise
themselves within their company. And I was like, okay, I'll
jot down a couple of notes and I'll lead a training.
I'm sure a dozen people will come. Alida. Two thousand
people came to the first training I led.

Speaker 2 (09:33):
Wow Wait at work at Google.

Speaker 3 (09:37):
Yeah, So I started this large career development program within
Google that grew to be used by tens of thousands
of people in almost one hundred countries. And I was surprised,
as anyone. I've never worked a day in HR or
people operations in my life, so I was like, why
are people coming to me for this? But I think
that they wanted that permission to have wild courage, that
permission to ask for what they wanted, unapologetically, that permission

(10:00):
to build deep relationships with people and wield their power
and their influence. And then I got to the point
where I was like, Okay, I like my operations job
and working on bugs, you know, to help engineering and
help our customers be more successful. But holy crap, do
I love helping people to be better than they think
they can be. And that's what I'm able to do
through this program. So I found a top literary agent

(10:23):
in New York, wrote a killer book proposal with a
lot of help, got a great book deal with pangin
Random House, and here we are talking to each other.
As this book launches into the world and I can
hopefully help millions of people launch insane amounts of wild
courage on their own.

Speaker 1 (10:35):
Well, let's talk about the nine traits of what's to courage.
I weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, bossy.

Speaker 2 (10:49):
Those nine? Did I miss anything?

Speaker 3 (10:50):
Those are the nine?

Speaker 2 (10:51):
Those are the nine.

Speaker 3 (10:52):
Okay, easy, breezy, casual language that we all want to
be called.

Speaker 2 (10:57):
Let's begin with weird. What do you mean by be weird?

Speaker 3 (11:01):
Yeah? So you know, again like it was me that
day on the subway, just kind of deciding I was
gonna let my freak flag fly and be the person
who I was to John and start the relationship off
on honest footing. So you know, weird is the courage
to stand out to really, you know, win as you
or lose as who right, because within your so called

(11:24):
weirdness lie your greatest strength. So hone every ounce of
weird you've got. And this could be something as simple
as saying something like someone once wrote on a resume
who was applying to a role under me at Google,
rather than writing foodie, which is boring and forgettable, she
wrote in constant pursuit of the perfect oatmeal raisin cookie recipe,
like that's weird. That's an anecdote that's not strictly necessary,

(11:47):
but it really stood out. So it's about standing out
if you're the intern, not just nodding along in the
meeting and never raising your hand to share something. It's
about taking the risk to say something about a project
or an idea or a process that might simultaneously piss
off three people and impress three people in the same
three minute span. But if you are forgettable, great, maybe

(12:10):
you'll get that company's name on your resume for the
three month stint, but you're not going to stand out
among twenty competitive interns. If you want that full time
gig in the fall.

Speaker 1 (12:19):
Well, there's also a risk, though I'm just going to
play the other side here. There's a risk though you
stand out for the wrong reason.

Speaker 3 (12:26):
There sure is. And with all of these nine traits
I talk about trade traps, and trade traps are when
you take this too far, And I did that when
I was eleven years old in seventh grade. It was
the first day of seventh grade. We get into language
arts class. Missus Howard our teacher gives her spiel and
her background, and then she opens it up for questions
and says, does anybody have any questions? And I, brand

(12:47):
new to the school, doesn't know a soul, ask I've
got a question, Miss Howard. Are you a virgin?

Speaker 2 (12:53):
No? Yes? Yes? And so you've been practicing wild car
for a long time.

Speaker 3 (13:01):
Yeah, And you know what, it's a good thing I
have because I've made tremendous number of mistakes while i've
done it. And that was a big one. That was
a doozy, and that was a gaff and that was insecurity,
and that was me trying to say something obnoxious or
outlandish for attention. And that is not the kind of
weird we're talking about. I want you to be your
best self. I want you to let your strengths and
your authenticity and your superpowers shine. I don't want you

(13:24):
to just seek attention because you're insecure or you have
imposter syndrome. So oopsie is that day?

Speaker 2 (13:30):
Yeah?

Speaker 3 (13:30):
And I learned from it. I don't do that anymore
in that way. I've learned other lessons, the adult version
of that, you know, as I've taken risks with things
I've said at work, but you know that was a
bad moment.

Speaker 1 (13:41):
So number two is selfish? What do you mean by selfish?

Speaker 3 (13:44):
So selfish is the courage to, you know, set your
own standard into stand up for yourself. Really, so give
everyone a leg up at your expense and you'll end
up getting trampled. I really want people to be their
own champion, so starting up for yourself. And people sometimes say, but, like,
isn't selfishness the big problem in this world? But I

(14:06):
would argue that if you think of ten people, just
like ten people you've worked with today, Alita or this week,
chances are you probably want to encourage more of them
to be selfish, and you probably think that some of
them are overly self less. So what do I mean
by this? This could be five of you worked on
a project, but you decide to be the one to

(14:27):
send the update to the boss and all the leadership
so that they know that you've worked on it and
you've signed all the names that participated in the project.
But you take the initiative because the person who sends
the comms oftentimes gets the line's share of the credit.
So you worked on it, show up right, like, say
what happened? And take some credit, or it could be
as simple as the other day. I have a lot

(14:48):
going on with this book launch, and I asked my
husband to sit with both kids on the flight four
hour flight back from New York to Boulder. Well, I
could prep for a keynote that I was doing the
next day, and so you know, I could be selfless
to a fault, and I could be a murtyr and
say oh no, no, no, no, like, well we'll split
halfway through the flight. But no, I needed to be
selfish that day. And sometimes I need to be selfish

(15:08):
and go to that much needed yoga class instead of
being there for the twelfth bedtime in a row at night.
Or when my husband went fully remote and I was
still in the office three days a week, I had
to be selfish and say, I need you to do
more laundry because the circumstances have changed and I need
to be selfish about what I need in terms of
my work schedule.

Speaker 2 (15:27):
You say, shameless, that's the next one.

Speaker 3 (15:30):
Yeah, So shameless is about finding your swagger. It's the
fact that audacity or shamelessness is a survival skill, because
how will you learn whether you've got the goods if
you don't start acting like it. And this is really
the one that people struggle with, right impose, This is
solving for what people struggle with, imposter syndrome, lack of confidence.

(15:52):
I know, I've got this wonderful story about my grandmother.
When John unfortunately got laid off from his job. We
were just newly weds. We were living with her in
her New York City apartment on her pull out couch.
We sit down to dinner one night and John shares
this unfortunate news that he's been part of this company
restructure and he's been laid off. And I'm crushed, right,

(16:14):
But I look across the table at Grandma, who was
four foot ten and ninety pounds in CEO of her
own financial services company until the age of ninety two,
and not just shameless, but unstoppable. And I look across
the table and Grandma has this gleam in her eye
and she shares one of her all time favorite lines.
No is just an opening offer. Don't sign the paperwork.

Speaker 2 (16:36):
John.

Speaker 3 (16:37):
He's like, Grandma, what do you mean? And He's like,
a layoff is like a one sided thing. They say,
you don't work here anymore. And I say okay, and
she's like, sure, it would be more comfortable to take
Noah as an answer, but that discomfort will pass, you know,
get your ego out of the way and find a solution.
You both want something. They want to get stuff done

(16:58):
even though they can't afford to pay you, and you
want a job because it's easier to get a job
when you have a job. So go find a compromise.
And so the next day, like relentlessly or you know,
not relentlessly, reluctantly, reluctantly, he calls up his VP and
offers to stay on for ten percent time and pay
while he job searches, and surprisingly they say yes. And

(17:21):
the point is Grandma Lilah's lesson, don't let shame shame
your decisions. And to me, that is what shameless is.
Obsessed Yeah, obsessed, okay, So obsessed is the courage to
you know, to set your own standard. Really it's to
push perform persists. We talked about this with my what

(17:42):
goes through my head? Because none of these traits will
serve you if you don't learn to deliver, not for
some company, but to achieve your greatest ambitions. So one
of my favorite obsessed tools is the Monday manifesto, and
this is an email that I want you to send
to your boss every single Monday. It's a minifesto, not
a manifesto, because it should take no more than fifteen

(18:03):
minutes to write, and it's four bullets. Two things you're
proud of from last week. That's kind of shameless as well, right,
two things you accomplished and two things you're excited to
do this next week. Because fifty percent of your job
is doing your job and the other fifty percent is
communicating up, down and across. And when you're obsessed, you
take the time to proactively share with your boss what

(18:25):
you're working on. So the two from last week could be,
you know, I completed seventy percent of this ath leisure
marketing campaign you know document, and I met with these
three stakeholders to get everyone on board. The two things
I'm excited for this week are that I'm going to
compare three competitors and do an analysis on that across
five metrics. I love when you add numbers to that
mini Monday manifesto that's also obsessed, and then another one,

(18:48):
you know, might be something else. So the Monday manifesto
is an obsessed way you can show your boss how
awesome you are at doing your job, which is what
ultimately gets you promoted. Because what moves the business is
what moves your career. So show them that you're moving
the business.

Speaker 2 (19:03):
Nosy.

Speaker 3 (19:05):
Nosy is getting insatiably curious, and this is the courage
to dig deeper. This is a wild story that I
share on this one, and it's where so my family is,
we're survivor. My grandparents survived the Holocaust, so I'm a
third generation Holocaust survivor, and my grandmother, my Bubby, my
paternal grandmother. This is a different one. Was in Hungary

(19:27):
when the Nazis had invaded or it was really the
Arrow Cross ruling party, and she was in a hideout.
She's marched, she goes out to find a bucket of water.
She's marched at gunpoint, rounded up with a bunch of
other Jews that were on the street. She's literally walking
over dead bodies as this is happening, and she's lined
up either for you know, a summary execution, to be
shot right there or to be rounded up and taken

(19:50):
to Auschwitz. And she gets nosy, and her nosiness is
what is what ended up causing her survival. She says
to the also young, scared soldier, this Hungarian idiom that
translates to, you know, when he's standing there with his
gun cocked, she says to him, what would happen if

(20:10):
I stepped out of line the line that she's done,
to either be you know, carted off to Auschwitz or
to be shot And he says this, sorry, she asked
the question. It was him who responded with the Hungarian idiom.
The idiom was, is the mademoiselle so stupid or just
pretending to be? And he kind of chuckled, and with
that chuckle, with that lightness in his voice, my bubby

(20:31):
decided to step out of line and just walk home.
And she just kept walking, and she could hear the
click of her heels on the cobblestone sidewalk, and with
her heart thumping as she described it to me and
her Fort Lauderdelle apartment years years later, and her beige recliner,
she said, the only reason I survived was because I
had the courage to ask a question. So think about

(20:54):
what questions you're afraid to ask. Maybe it's you know,
something obviously not life or death. That was an un
believable story, But think about how much we're scared to
ask questions. You might be scared to ask to your
boss what might it look like to get assigned to
a project that would help lead to a promotion, Or
if you're in an interview, you know, what are the
three things that I could bring to the table that

(21:15):
could set me apart from other candidates? Right? So, always
what are how questions? Never yes or no questions? Because
what are how? Questions open up the expansive opportunities for
forward thinking and more collaboration. So that's nosy. What questions
are you still yearning to ask?

Speaker 1 (21:32):
Did you feel as you were moving up the ranks
that people would ask less questions?

Speaker 3 (21:37):
Or absolutely?

Speaker 1 (21:38):
Yeah?

Speaker 2 (21:39):
Yeah, why does that happen? Well?

Speaker 3 (21:41):
I mean even I would ask fewer questions at some
points in my career, and those are mistakes I made
because you think that when you're at the top, you
need to have all the answers. Do you think that
as you grow in leadership you need to be the
answer giver, not the question asker? But the most brilliant
questions are the basics? Like the leaders that I admired
would be the ones who just boldly in a meeting

(22:02):
with two hundred people would say, hey, what does TPR
stand for? On that slide, like they know that there
are thirty people in the room that like, don't know
one of the company's latest seven hundred acronyms, right, And
it's the ones who kind of have the boldness to
ask that are the most regarded, the most admired, and
some of the I call this the humble too. Two

(22:24):
of the best things a leader can say are I
don't know and I was wrong. It's that humility of yes,
I try to be right. I try to have answers.
That's my job as a leader. We want that out
of our leaders. But when you can have that humility
to also acknowledge when you're wrong or when you don't know,
and that you have to go ask your own questions
and get the answer and get back to your team,

(22:45):
that to me is the leader I want to work for.

Speaker 1 (22:49):
One of the other traits is manipulative. Yeah, that doesn't
sound good.

Speaker 3 (22:54):
That doesn't sound good. This one is spicy. And remember,
let's just like back up on the framing here for moment.
Because I acknowledge that these are nine eyebrow raising traits, right,
And that's why this book I would say is a
bit risky. You said, it's like nothing else you've ever read,
Like that's music to my ears. And it also tells
me I'm taking a massive risk because if I'd written

(23:17):
this safe book, it would have been something that would
have felt quite familiar to you. Manipulative is the spiciest
of all of these. And again, these are traits that
create the bars of an invisible cage that keep you small.
So when you're scared to be called manipulative, you are
limiting your ability to build influence through empathy. Because whether

(23:37):
you're selling a product or an idea or yourself, the
ability to win friends and allies and supporters is all
about mutual benefit. And that's really what I'm talking about here.
So go figure out what people want and get it
for them. And it's like we're scared to acknowledge that
relationships take effort. They take effort, they take investment of

(23:59):
friendship if you're not quote unquote manipulating the friendship texting
them to check in how they're doing when a parent
is sick, or asking, hey, does anybody want to go
grab coffee after we drop the kids off? For you know,
a drop off in fourth grade if we're not manipulating,
putting intentional effort, energy and investment into relationships, then we're

(24:23):
limiting our full potential. And I did this one time
really obviously. I wanted to meet this author, famous author
named Vanessa van Edwards, best selling author of Captivate and Cues,
and I was going to be in Austin where she lives.
I sent her an email. We've just been introduced over
email and I said, Hey, Vanessa, I'm going to be here,
you know, Tuesday through Thursday. Could we meet for coffee?
And she says, ah, as luck would have it, I'm

(24:44):
going to be out of town those same days. I
leave on Tuesday, just when you know the day you're arriving.
And I said, well, what time does your flight depart?
And she said four pm? And I said that's perfect.
I get in just before that so I could meet
you at your gate. Now, Alita, I was being manipulated.
I straight up lied. My flight did not get in
just before four pm. My flight got in after she

(25:06):
already took off. But with a sixty dollars change fee
and a quick little adjustment on Delta dot com boom,
I've manipulated the situation made it easy, breezy for her.
She never knew the difference, and we had this amazing
sixty minute meeting. She's now a friend, a mentor, a
wonderful confidant. Of course I fessed up to her afterwards.
She found it hilarious as the question did you tell her? Yeah,

(25:27):
but That's what I'm talking about, right, It's like putting
the effort in, even if it feels like weird or
unusual or like while who would change a flight?

Speaker 1 (25:35):
Right? Right?

Speaker 2 (25:36):
A lot of people are afraid to do things like that. Right.

Speaker 1 (25:38):
They don't think about it, or they they think that's
too direct, or that's too manipulative.

Speaker 3 (25:44):
It's or it. Oh, I would look too eager. I
would look too I'd look too hungry. Well, guess what
being opportunistic, being hungry, being eager, those are great leadership qualities.
Those are great qualities of anybody in the working world.
A lot of people at Google massive amount huge teams,
and guess what got me excited about working with them

(26:06):
when they were eager and hungry and wanted opportunities.

Speaker 2 (26:09):
Yeah. Right, So you also say to be brutal.

Speaker 3 (26:13):
Well, this is an important balance to some of the
other ones, because this is the courage to set your
own boundaries. This is the power of no and we
all know how hard it is to use that word,
but really people pleasing pleases no one, and it also
keeps you small. Brutality is far cleaner, it's more effective,

(26:34):
and frankly, it's a lot kinder. So cut through the
bull and spare everyone's time, energy and attention. Now, this
could be something that my friend Kim did when she
was brutal quote unquote to her fiance and called off
the wedding three days before the big day. Okay, feels brutal,
but think about it. Would it have been better to just,
you know, acquiesce to the fact that people had already

(26:57):
sent gifts and booked their flights and the caterer had
been paid To me, it was the far kinder decision
to spare her and her future husband and any children
three months, three years, three decades of discomfort and unhappiness
and potentially misery, and so she made the brutal call
to call that wedding off. It could also be as
simple as when you communicate and like, go, Kim, She's

(27:19):
now married to the love of her life and her
husband's awesome, and you know she's so happy. It could
also be the brutal call if you are sharing constructive
feedback with a colleague rather than a big bowl of
words salad and kind of softening and backpedaling and not
being direct with what you think they could improve or
to a direct report. It's actually just like tearing off
the band aid and saying the hardest thing that needs

(27:41):
to be said within the first ninety seconds of the conversation,
not you know, I think there's some things we need
to talk through on this project, but I don't feel
like you're pulling your weight. Could we think about rebalancing
the work distribution so it feels more even.

Speaker 1 (27:56):
Do you think that people when you mentor that they
have a hard time with this one.

Speaker 2 (28:00):
In particular, it's among the hardest. Yeah, I think so.

Speaker 1 (28:04):
Yeah, yeah, because you don't want to leave, you know,
we also don't want to be brutal.

Speaker 2 (28:08):
Sounds like it has a lot of other things in it.

Speaker 1 (28:10):
It's selfish, it's you know, there are a lot of
other names that you could be called other than brutal
that aren't very kind.

Speaker 3 (28:17):
Right, But it's to me, it's also about your calendar.
It's about like, you know, I had a boss once.
I think maybe what inspired me calling this chapter brutal
is this boss who said, you know, he was going
through a ton of huge restructure and he was moving
his family across the country, like just a ton of
stuff in the business and personally, and I was like,
how are you navigating all of this? He's like, Jenny,
two words, ruthless, prioritization, And to me, it's the same

(28:39):
kind of idea. It's also about being brutal with your calendar, right,
so it's like, you know, blocking time for lunch, blocking
time for a hike, like I do every day at
four thirty pm.

Speaker 1 (28:47):
Yeah, reckless, We just have two more reckless he's number eight.

Speaker 3 (28:51):
Yeah, yeah, Reckless is eight. And reckless is the courage
to take calculated risks and to air on the side
of action, because to learn from your mistakes then waste
a bunch of time predicting the consequences of every decision
in life. Right, So think fast and fearless, and if
you're on the fence, do it. And I oftentimes get

(29:12):
asked like, which is the hardest trait for you, Jenny,
And it depends on the day, But I would say
this one, this one plagues me a decent amount. I
was hiking in Montana with my good friend Taylor, and
we were in this beautiful forest, and and I'm always
trying to optimize. I'm always trying to like analyze right
the pros and the cons of everything, the spreadsheets and
thinking on the with the left side of my brain
and with my head and not always my heart. Reckless

(29:33):
is about thinking with your heart. So on this hike,
I found that park ranger at this fork in the road,
and I asked all these these things, like you know,
which which of the trails is has the better view,
which one is a loop, which one's out and back,
which one has trail work being done on it, which
one is muddy? And from like you know, thirty feet
ahead of made tailors.

Speaker 2 (29:50):
Like Jenny, It's all beautiful.

Speaker 3 (29:52):
Let's go, Like reckless is about, let's go take the
make the decision. You know, few things in life are are,
you know, detrimental no matter what you choose, And so
make that decision and just go for it. So, if
you want to be an entrepreneur, don't perfect your website
and perfect your business name and your business cards. It's

(30:14):
about just asking for a customer like take the reckless
move to ask for one customer, then build the website,
then get the business cards.

Speaker 1 (30:23):
So the ninth one of wild courage is bossy. Not
a lot of people want to be called bossy.

Speaker 3 (30:29):
Yeah, but when you reclaim it, maybe you do. Because
bossy is the courage to listen and lead and to
steer others to success. Because all of these nine traits
come together and essentially create a leader. So cultivate partners
and allies and you know, mentors and collaborators and help

(30:50):
them aggressively, push them mercilessly, win their gratitude and ultimately
achieve amazing things together. Michael Jordan pushed his team mercilessly,
and at the end of the day, even though he
needled them and made them work hard and work out
and train, at the end of the day they were
grateful he made them champions. And I've made lots of mistakes,

(31:14):
as you know in this as a boss, right and
I've had to learn my own flavor of Bossingess the
most important tool here, I would say, is shadowing your team,
giving clear feedback, knowing that people need to weigh in
to buy. And I was once on this flight back
from Chicago, and we were restructuring this team. Actually, we
were shutting down a business division in one part of
the world and building it back up in another part

(31:36):
of the world. And I was new to the team,
new to the products, new to the regions. All the
managers who reported to me knew more than I did.
And I felt so insecure that, like, as boss, I
had to put together this thirty slide deck and cram
all of my leadership and you know, decisions into this
deck that I would present to them and this off
site that we were having together the next day, because
I just wanted to prove myself. And we got there

(31:58):
the next day, Alita and I presented this and you
could have heard a rasable marker drop on the floor.
They were They looked at me with such scorn, and
I was like, what's going on? And They're like, Jenny,
why would you come in here and think that you
have all the answers. We have so much more combined
experience than you do on this team, these products, et cetera.
Like we're here today to build this together. And so

(32:21):
what I failed to do in that moment was I
failed to listen. I failed to listen in order to
lead and to collect the wisdom of the crowds to
make the the decisions together. And to me, that's why
bossy is the courage to listen and lead, and that
is ultimately what makes you an awesome boss.

Speaker 2 (32:37):
Listening and leading.

Speaker 3 (32:38):
Listening, Yeah, in order to lead.

Speaker 2 (32:40):
Do you have you.

Speaker 1 (32:41):
Found in your experience that it's hard to have all
of these You do find people who do have all
of these qualities.

Speaker 3 (32:48):
Well, I think that we all have elements of them.
I think what is hard is that we get in
our own way right. So, like, whatever it is that like,
think of something you want right now. It could be
a job, it could be a goal, it could be
you know, a partnership, and think about what's sitting between
you and achieving that thing. It's oftentimes fear, And we

(33:10):
talked about these fears. Fear of failure, fear of fear
of uncertainty, fear of the judgment of others. And so
when people have all of these things to me, it
shows that they have an outsized ability to push past
that fear because these are all rooted in fear. We
are scared that we're going to be called shameless. We're
scared we're going to be called bossy. Even when we

(33:32):
have a good idea and we want to share it,
we're scared we're going to be called brutal when we
want to say no to that meeting on our calendar.
That you know where we neither add value nor derive value.
We don't take these actions, we don't live these values
of shameless, brutal or manipulative out of fear of what
someone else might think. Right, But that means that we
are our own worst enemy, that we are the blocker.

(33:53):
And if that's the case, then that's actually such great news.
If you are the problem, then you can also be
the solution because when you muster the wild courage to
push past the fear, which we all can do no
matter whether you succeed or fail in any one given thing,
you recognize that you will never feel as powerful or

(34:14):
as purposeful as when you're pushing past that fear to
the joy and success on the other side, because everything
you've ever wanted is waiting for you on the other
side of fear.

Speaker 1 (34:25):
Do you find that men versus women it's different. Where
what's your experience with that?

Speaker 3 (34:32):
Yeah, So a lot of these traits have like a
little bit of an extra oomph when they're referred to,
you know, when they're talked about for women, right, And
it'll be really interesting to see how this book lands
in the marketplace because I wrote it very intentionally to
be gender agnostic. There's no pink on the cover, right,
there's no like we're really I've really tried to make

(34:54):
it even with the examples of men and women in
the book. But I do think that because women are
more scared to be called bossy, shameless, selfish, manipulative in particular,
I do think it'll be really interesting. It's more like
a curiosity I have. I want to get nosey a
lead it and see, like, well, what does the market say,
what do the readers say? I have had a lot

(35:15):
of men who've read the book and who have just
found tremendous, tremendous value in it. Because even though these
words themselves can have a little bit of an extra
feminine twist, the underlying tools and stories and frameworks and
tactical practical you know, things that help people succeed in
their career and in life are just as applicable for

(35:37):
women as they are for men.

Speaker 2 (35:39):
What are you doing when you're not writing this.

Speaker 3 (35:40):
Book, I'm doing keynotes at companies, I'm doing consulting at
you know, Fortune five hundred partners, leading facilitation. And then
just like I'm out razzle dazzling the book. I left
Google with a ton of my own fear, left this
big paycheck right executive Google breadwinter for my family. I

(36:01):
had to get over my truths and tales of like
what this meant to leave Truth, I will make less
money in my first year. Truth, I will be a writer,
you know, Truth, I will not be getting a paycheck
every two weeks. But the tales I told myself were
I'm going to be a starving artist. We're going to
have to downsize from our beautiful home and boulder on
the base of these hiking trails. My parents are going

(36:22):
to be disappointed in me. What if my husband leaves me?

Speaker 1 (36:25):
Right?

Speaker 3 (36:25):
What if my kids are mad because they can't get
the Google free snacks and ride the fun slides of
the office. And so, you know, when I'm not writing
this book and not working on this, I'm out there,
you know, doing business development, so that I can recognize
that like those tales are just tails, stories that have
created in my head to make sense of the truth.
Or the facts that are verifiable and that I can

(36:47):
go out and make my own luck and apply my
own wild courage to being successful in this new entrepreneurial capacity.

Speaker 2 (36:53):
So, for those of us that.

Speaker 1 (36:54):
Are are wanting to implement some new things, how do
you suggest we get started to have some wild Where
do we begin today?

Speaker 2 (37:02):
Yeah?

Speaker 3 (37:02):
Okay, So let's talk about a couple of things you
can do right now. You can set up a meeting
with your boss's boss. If you're at a company that's
more than three and a half people, your boss's boss
is somebody you should know. So keep your boss in
the loop, let them know you're doing it, and then
twice a year have a conversation with your boss's boss.
Let him or her know the awesome stuff you're working on.

(37:23):
Number two is think about what are your three power assets.
These are the things that make you who you are,
what makes you weird and get shameless about it. So
mine are people leadership, influencing stakeholders, and building things from
startup to scale. So think about your three power assets
that make up your power portfolio. And if you're an introvert,

(37:44):
no problem. You do not need to be a subway
chaser and you know, chase strangers off public transportation. To
sit down for five minutes right now when this episode
is over, and write down your three strengths and then
share them with your boss in your next meeting. And
then the final thing that I want people to start
doing is asking for asking in some capacity for something

(38:05):
that they want. Right. Maybe you're at a restaurant and
they serve you lukewarm mashed potatoes. Send those potatoes back.
I have a goal achieving assessment where people get designated
zealous zebra, a deliberate dolphin, or a cautious chameleon. You
can take it at it's jennywood dot com slash quiz,
and fifty seven percent of people say I ask for

(38:26):
what I want. They say they strongly agree or they
agree with that statement. But then when I ask the question,
do you send back the cold mashed potatoes at a restaurant,
only thirty seven percent of people agree, right, you know,
twenty percentage point ish differential there. So you know, whatever
it is, whether it's at work or in life or
with a friend, ask for something that you want this

(38:48):
week for you get a little bit selfish, be your
own champion.

Speaker 1 (38:53):
Okay, Okay, So those are the three set up, the
meeting with the boss's boss, three power assets, and be
your own jam In.

Speaker 3 (39:00):
Yeah, ask for something that you will cold mashed potatoes
or a promotion you choose.

Speaker 2 (39:04):
I like it. When does the book come out?

Speaker 3 (39:06):
The book is out March twenty fifth, and it is
available in all formats paperback, audio, ebook. If you want
to help the success of this book, I would be
delighted if you bought the paperback. If you're indifferent to
the format, the paperback, especially when you buy a week
one of the launch, helps the book's success the most.
It's like opening weekends.

Speaker 2 (39:26):
Of The New Kiss.

Speaker 3 (39:27):
Okay, Yeah, the paperback is what counts for the best
seller lists.

Speaker 2 (39:30):
All right, okay, well this should be out.

Speaker 1 (39:32):
We're recording before the twenty fifth for anyone's listening, so
but we'll we'll release it so that people can hear it,
you know, by then.

Speaker 2 (39:39):
Well, Jenny, this has been terrific.

Speaker 1 (39:41):
Anything I didn't ask you about or that you wanted
to mention you get a lot in.

Speaker 2 (39:46):
You're very efficient.

Speaker 3 (39:47):
Well, I love I love how we how we got
through so much of it. Yeah. I would just encourage
people to be like Grandmaalilah, Right, don't let fear shape
your decisions.

Speaker 2 (39:57):
I love Grandma Aliah.

Speaker 3 (39:59):
No is just an opening.

Speaker 2 (40:00):
It was a badass in her own day.

Speaker 3 (40:02):
She was a badass in her own day. She was
a bridesmaid in my wedding at eighty eight. How fun
is that?

Speaker 2 (40:07):
Oh? I love it.

Speaker 3 (40:08):
I love it super fun. And I do have a
free gift for everybody listening or watching. If you go
to It's Jennywood dot com slash get Promoted. I T
S J E n N y w o O D
dot com slash get Promoted, you'll get my free guide
eight tips, tricks, strategies, script to uh to land a promotion.

Speaker 2 (40:28):
Nice.

Speaker 1 (40:28):
Okay, we'll have that all the link, all in the notes,
jas Wood Wild Courage. Thank you so much, such a
pleasure to talk to you, you too, such.

Speaker 3 (40:38):
A fun, fun, fun conversation. Thank you,
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