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January 17, 2025 • 26 mins

Jessica's journey is nothing short of inspiring, as she shares her remarkable story of resilience and leadership. From facing bullying as the only Black person in her family, to discovering the circumstances of her conception, and stepping into her own unwavering strength as a mother, Jessica's life has been a testament to overcoming adversity. Her unique experiences have fueled her commitment to equitable leadership, and she passionately works to create inclusive spaces where everyone feels they belong. Jessica's narrative highlights the profound impact of empathy and the importance of recognizing our personal growth, making her a powerful voice for change.

Parenting and leadership are intertwined in Jessica's philosophy, where authenticity and humor play crucial roles. She emphasizes the need to nurture children's unique gifts, encouraging them to grow beyond imposed labels or expectations. By sharing touching stories, Jessica illustrates how humor can bridge connections, even in challenging times, and how life events shape our resilience and empathy. Her insights remind us that true leadership is about fostering environments that promote growth and healing, embracing vulnerability, and using challenges as stepping stones to a more meaningful life. Join us as we unpack the profound lessons from Jessica's incredible journey.

Guest Bio:
Dr. Jessica Taylor is passionate about equitable leadership and empowering others to transform their organizations and leadership legacy. Known for her empathy, pragmatism, and humor, Jessica empowers and builds organizations where everyone can courageously be themselves without bias, discrimination, or barriers determining their success. With a lifetime of perspective as a biracial, woman of color, years of executive experience, and a background in human development, Jessica coaches executive leaders and guides organizations through equitable leadership strategies through nuanced and comprehensive methods. (she/her)

Connect with Jessica:
LinkedIn

Connect with Theresa and Ivana:

Theresa, True Strategy Consultants: tsc-consultants.com
LinkedIn @treeconti, Insta @tscconsultants

Ivana, Courageous Being: courageousbeing.com
LinkedIn @ivipol, Insta @courbeing

SITP team, Step Into The Pivot: stepintothepivot.com
LinkedIn @step-into-the-pivot, YouTube @StepIntoThePivot


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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hello everybody, Welcome to this week's episode
of Step Into the Pivot.
I am super excited to havewoman of color, years of
executive experience and abackground in human development.

(00:27):
Jessica coaches executiveleaders and guides organizations
through equitable leadershipstrategies, through nuanced and
comprehensive methods.
So that just really spoke to meand, Jessica, we're so happy to
have you here with us today.

Speaker 2 (00:42):
It's my privilege, thank you.

Speaker 3 (00:44):
Welcome to the show.
Jessica and Teresa said nuancedand comprehensive from your bio
.
This is what my experience withyou so far has been.
Every time we talk, there issuch depth to what you share and
such nuance and it'scomprehensive and you can also
back a punch right In this likepunch of love.

(01:07):
So you, in a few sentences, canreally help a person completely
shift perspective and connectthe dots and really bridge.
You know different realms and Iso appreciate that about you.
Oftentimes we play with thismetaphor here on the show of you
know bag of lemons, because youknow the metaphor of like, oh,

(01:28):
when life gives you lemons, youmake lemonade or you make a
margarita is sometimes a joke,right.
But we say what happens whenlife, you know, throws you a
massive 40 pound bag of lemonsand straight into, like a you
know, your head or your solarplexus and it buckles you over.
And it seems to me the way youstarted, the way this life
started for you, was like youwere thrown into the bag of

(01:48):
lemons and then the bag oflemons was thrown around and
it's just, you know, let's getin there.
Please tell us about your earlylife and the resilience that
you know was required of youright from the get-go.

Speaker 2 (02:05):
Thank you for the question.
So I've been thinking about youknow was required of you right
from the get-go.
Thank you for the question.
So I've been thinking about youknow where it doesn't just
start, where it starts.
There's kind of a space in yourstory where you realize that it
starts.
And so, as I reflect on my story, there was this really powerful
memory that I have of being onthe bus and I was about six
years old and there was justrelentless bullying that
happened on the bus.
And I was about six years oldand there was just relentless

(02:26):
bullying that happened on thebus.
At all times.
It was just unsupervisedchildren, not always a great
idea, and one day one of theparticular bullies who just
really wanted to get a rise outof me, he yells at me the N word
, and I am six.
I don't know what that wordmeans, and I can tell from the

(02:47):
intonation, from his body, fromthe reaction, that this word is
really bad, that this word isreally charged, and it basically
means you are disgusting, youdon't belong, and so I feel like
I know what it means, but I'venever heard it.
And so from that sense ofseparation, even just from my
peers, I come home and I end uptelling my parents and I have

(03:10):
this really definingconversation with my mother
because I am the only Blackperson in my family, and it
wasn't until that moment that Irealized that maybe there was
something wrong with that.
And so, in that definingconversation with my mother, she
talked to me about myconception, how she was in this
unhealthy marriage and that wasreally marked by substance abuse

(03:32):
, and she had already chosen toterminate two pregnancies and
said you know, I'm really notready to be a mother.
And then, after all of that,she had this non-consensual
encounter with a man that wasn'ther husband and then realized
that she was pregnant and shewas pregnant with me.
And so, despite these obviouschallenges that she was going to
face in that space, she feltcompelled to bring me into the

(03:54):
world and to raise me herself.
And so, even though I didn'tfeel it then, now beyond a
shadow of a doubt, I believethat I've always been divinely
protected and set apart for ahigher purpose.
But growing up as the only Blackperson in my family, I was just
keenly aware of the contrastaround me.
Right, I was placed in thisfamily, where you're supposed to

(04:16):
feel belonging, and then thiscontrast made me feel like I'm
part of something, but I'm apartfrom it.
Right, I'm an outsider whohappened to be inside.
And then that experience gaveme this deep empathy for other
people who felt disconnected orout of place.
And it's still in me a realpassion, I think, for creating a

(04:37):
space where people could feelseen and to have those
conversations, but also to feelvalued in all of their
complexity.

Speaker 3 (04:51):
What a massive experience, just right from the
get-go, from the microexperience of the bus story, to
then the conversation with yourmom, to then what you're talking
about already you know, kind oflike raising the vibe and
taking us into a place of youknow where you really operate
today, which is equitableleadership not only living it
but thinking it and becoming avoice for inclusivity.
You're also alreadydemonstrating, I'm curious, some

(05:14):
things.
Just came up with a side notequestion who would you say was
out there when you were?
Or in there in the, in thefamily space or maybe somewhere
adjacent to it that as you weregrowing up, you did have some
kind of role modeling of whereyou're, where you are today?
Was there anybody where youwere?

(05:35):
Like, interesting, I like thisor this is helpful.

Speaker 2 (05:40):
Yeah, so around 11 years old I met a basketball
coach.
I did not want to playbasketball, but I was forced to
play basketball, and so she wasa tough Black woman, but she
also had a compassionatesoftness to her as well that I
knew she wanted us to succeed asa team, and so I really.

(06:02):
She was one of my very firstBlack role models, where she
didn't say a whole lot but sheshowed with her action that she
saw potential in me.
And so I was not a naturalathlete.
I was naturally verycompetitive, but not very good,
and actually at the end of everyyear she would give me the most
improved award, and thatactually was a beautiful gift,

(06:23):
because it was recognizing mygrowth over my performance,
which was something I deeplyneeded to know.
Her belief in me kind ofplanted a seed, helping me
understand that my worth wasn'tjust about what I did but about
my growth and resilience, and soI knew, hey, I'm not going to
be the MVP, but if I can be themost improved player, that

(06:45):
that's still winning, butwinning at growth, not just
being the best or the mostcompetitive.
And so I think that thatinstilled something in me seeing
her leadership with strengthand competitiveness, but also
with that softness to recognizethe growth.

Speaker 1 (07:00):
Yeah, I love that.
That really spoke to me, right,because we're not always the
top player or the top person,but it's about trying and doing
your best and all that.
So I really love that.
Your conversations I know thatyou know everything that was

(07:26):
wrong about you ended up beingyour, your kind of redemption,
right?
Um, embracing those kind ofaspects of yourself that others
viewed as flaws really shapedwho you are today.
So can you talk a little bitabout that, because I think we
don't all recognize that enough,right?
I said it to a friend the otherday who I know is struggling
and he's like you know, he'slike I feel like I've been
through 15 lifetimes.

(07:46):
I'm like, yes, but they madeyou who you are today and we
learn from them, we grow fromthem.
So can you talk a little aboutthat, because I think you have
some some story there too.

Speaker 2 (07:56):
Yeah, 15 lifetimes sounds familiar.
I think people would alwaystell me growing up that I was an
old soul, and I think that whenyou cram a lot of those
experiences or complex traumainto early childhood, then you
do develop, yes, a maturity.
But looking back then yourealize, hey, I was just a kid
and that weight was too heavy,and so I think that often we

(08:17):
don't get enough time to sitwith that weight or to have
someone unpack it with us later,which just has been a beautiful
journey of healing for me.
So growing up I felt likeliterally everything about me
was wrong.
My blackness didn't match, Iwas a woman.
I used to just wish that I wasa boy.
I saw them gettingopportunities that I just

(08:38):
thought, oh, I'll never havethose.
I was very, very poor.
Later understood, okay, I wasundiagnosed neurodivergent, I
was chronically ill, I wasoverweight and shy and
introverted, deeply sensitive,and I was anxious, all these
things, and I felt reallysilenced and unprotected in all
of those places.
And so early on I learned tohustle for my worthiness and

(09:04):
then I carried, like, this deepsense of obligation to prove
that I even deserve to be alive.
And I lived with that constantpressure, not from my mother but
from myself, that I needed tomake up for the pain that I came
from.
And that is a really horribleweight to carry, to feel like
you have to apologize for yourexistence and then to make up

(09:26):
for pain that you didn't causeor to make things right as a
child, in a way that you justcan't make them right.
And so all those experiences, Ithink, came together to inform
my work now that, because I'm awoman, because I'm a person of
color, because I understandability and disability and
illness and fat phobia and allthese different things that I've

(09:47):
experienced in my life, then Iwas able to help others embrace
those parts of themselves thatthey felt like, hey, those
things don't fit, or we don'ttalk about those things in
polite company and encouragethem to see their experiences as
a foundation.
That provided for me empathyand strength and authenticity.
And then I've used that purposeto help me and to help me heal

(10:09):
and then also to help guideothers to recognize that there
is power within our stories,especially the things that we
think are the throwaway things,and we can lead from a place of
acceptance and a place ofconfidence that we were given
that story with a purpose.

Speaker 3 (10:25):
That's so, so important to pay attention to,
and a place of confidence thatwe were given that story with a
purpose.
That's so, so important to payattention to.
And I'm, you know, when I'mlooking down for those of you
seeing us on video it's becauseI'm taking notes, because this
is so.
This is so wonderful, soinspiring, so motivating.
Now, Can you drop us into anexample of what you're sharing,
and particularly aroundinternalizing maybe some of

(10:47):
those messages?
Going back to the conversationaround your coach, your
basketball coach, who is givingyou the most improved award and
teaching you something, soteaching you to pay attention to
growth over performanceexternal validation measurements
, both over performance externalvalidation measurements.
Second, to what it means to befeeling a sense of you know,

(11:09):
evolution and awakening to whoyou really are.
Okay, so that all sounds reallycool, right, but can you help
us with some personal examplesof what was it like to start
shifting from seeking thatexternal validation to
experiencing more of internalconfidence, but through
something that was, you know,specific moment, that is, you

(11:31):
know, just yours.

Speaker 2 (11:32):
Yeah, I think I have a lot of experience of proving
myself wrong, like proving myown narrative wrong and then
kind of sitting there with whatdo I do with that?
If I'm a very logical personthat's looking at the evidence,
I've kind of proven my negativethinking wrong or I've proven
the limits I thought I had wrong.
And so I found the industry ofcoaching and thought, oh, this

(11:57):
is what I was made to do, wascome alongside people but ask
these powerful questions.
And there was a reallytransformative season where I
actually ended up working forthe coaching school that I went
to and I remember supporting theleaders there and getting to be
around these dynamic, confidentpeople and just thinking I
could never be like them.

(12:18):
And I was aspiring topotentially one day be an
executive assistant and Ithought I could help someone
else be so great in theirpassion and in their calling and
really thought that that wasthe limit.
And so I thought of myself asan executive assistant.
But I never imagined that oneday I would be an executive or
that I would lead executives,that executives would come to me

(12:40):
and so really recognizing inthem what I saw in me, I
actually can ask powerfulquestions, or they shared pieces
of their story and I have astory.
I just haven't shared it.
And then recognizing anddiscovering I had a talent for
helping people get that clarityor lasering in on what it is
that they needed, and that was areally pivotal shift where I

(13:03):
realized I could not just be asupport, but I could also lead
and that my leadership couldlook like support.
So, again, I had proven myselfwrong and then had to wrestle
with that understanding of Ithought I would always be the
neck that turns the head.
I always thought I would stayin the background as an
introvert and never thought thatI might go out front with my

(13:25):
story and my experiences toguide others.
And I learned later.
I felt drawn to leadershiproles where I was providing
spaces for the hardconversations that weren't
happening in the status quo.
The meeting after the meetingwhere I could sense some people
are not settled or some peopleare needing more.

(13:45):
That was the role I was playing,especially during crisis and a
lack of surety that I was ableto come in and provide really a
steadiness and a non-anxiouspresence.
And so that experience shiftedmy focus from seeking the
validation outside of what otherpeople told me I could do, from
seeking the validation outsideof what other people told me I

(14:06):
could do.
Often I was limited, actually,by my own imagination and the
imagination of the leadersaround me who loved my support
but who didn't necessarily seethat I could be more, and I
didn't see it in myself.
And so now I recognize if I seeit in other people to stay and
be an integrity, I have to seeit in myself.
I can't tell you that I seethat potential in you and then
not access it in me.

Speaker 1 (14:28):
I love so many things that you said I'm really going
to have to go back and listen tothis, but I, um, I love that
because, you know, I think, evenas women, right, you're, you're
, you're a woman of color, but Ithink all women you're, you're
a woman of color, but I thinkall women really struggle with

(14:49):
that a lot, like I know, I didearly in my career.
But you know that, thatconfidence that you get um from
others and you know, seeing itand being your authentic self
you said you use the wordauthentic a little while ago,
and that is honestly one of myabsolutely favorite words.
Right, I feel that we need tobe who we are.
That may not always fit themold of what people think we

(15:12):
should be, maybe, but, right,being being ourselves is really
showing who we are, what we cando, what our capabilities are.
You know how that works.
I mean, is there something thatstands out for you there?
And I?
You have two daughters, I think, right, I mean, are you
teaching them those kinds ofthings and teaching them to, you

(15:34):
know, be themselves?
Because I think that's reallyhard in a lot of ways,
especially in today's world.
I think it was hard enough, youknow I mean I'm older than you
but I know it was hard when Iwas growing up.
I know you had challenges whenyou were growing up and now we
teach that other generation howto do that.

Speaker 2 (15:50):
My daughters absolutely inspire me again to
stay in integrity, that I can'tteach them what I don't actually
believe, and so it's.
It's been a huge moment for meto just walk in my motherhood
and say how do I want to do thisreally intentionally?
And so I remember reading abook by an author.

(16:12):
She was in a faith-basedcommunity, I think, that often
threw away a lot of gifts ifthey weren't the typical gifts
you wanted to see, and one ofthe gifts that she named was
humor.
And she said I realized thatthis is not a throwaway gift and
I recognized I was hiding andthrowing away parts of me in my

(16:34):
authenticity because they didn'tfit within a corporate
structure.
Right, it was very serious andI am often finding the humor in
things.
Right, it was very serious andI am often finding the humor in
things.
It is very direct and I'm oftenfinding the way to influence
versus command.
And so I recognize I have a lotof gifts that I've been told or
internalized or throw away,gifts that should not be thrown

(16:58):
away.
That is what makes up myauthenticity, what makes me
different, and so I try to pullthat out of my children, not by
naming it for them, but bygiving it as a gift or as a
question to them.
So instead of saying you're sotheatrical, to say you seem to
really love to act things out.

(17:19):
What are you interested in?
Drama, or you know, you justmade that story come alive and
so I try to not again name itfor someone so that it becomes a
place where they can my girlscan hustle for my attention or
approval, but to say what do youthink?
So anytime they bring mesomething, I say how do you feel
about what you did here?

(17:39):
Tell me about it.
Not good job.
And I think that thatexploration has actually allowed
me to be really empathetic to.
I worked really hard on thispart, mom, or I tried really
hard at this.
And then again back to thatstory of that coach that I had
being able to talk about theirimprovement and their growth,
not just their achievement.
So absolutely that intersectswith my motherhood, with my

(18:01):
womanhood, but also with how Ido my work, is that I'm often
looking at whatever happens andsaying we're telling ourselves a
story about that.
Tell me the story you're tellingabout that.
Does that story fit thenarrative that you want to have
for the rest of your life?
Is there a place.
Maybe you're being invited toprove yourself wrong with that
story and the facts that wethink that we have when we're

(18:22):
looking at what just happenedand I love getting to explore
that because there's so muchgrowth that happens there and
there's so much transformationthat happens there when someone
can gently push and challenge,to say I see something in you,
but I can't just speak it overyou.
I want to actually bring it outof you and provide safety for
that to happen.

Speaker 1 (18:43):
Yeah, we have to explore our own.
You know like we all have ourown thing, but we have to
sometimes figure that out forourselves, right?
And so I love how you do thatwith your daughters, so even I'm
sure you have something to saybefore we ask her our final,
before we ask Jessica our finalquestion, but this has been an
amazing conversation for me.

Speaker 3 (19:04):
So amazing.
I am reminiscing about a timewhen I would watch my son, when
he was little, well, entertainthe room, right, and he would.
I'm thinking back on thebeautiful and poignant comments
you made about humor.
I saw him as a little kid.
He wasn't necessarilyconsciously choosing to use

(19:25):
humor and goof off to bring inlevity into a room full of
density.
So that would be what thatmeans.
It's like some kind of a familygathering.
Everybody has their happy faceon.
Let's say it's the holidays andthey're like haha, I love you,
I love you too.
But that's not really the energyin the room.
The energy in the room is thatthere's some unresolved tension.

(19:47):
There's something going onwhere there is a lot of stress
in the space.
And then I watched him justnaturally tried to intervene and
you know, with his toddlerenergy or his little boy energy
and just monkey around, goof offand essentially attempts to
raise everybody's you knowexperience and there were two or

(20:10):
three different ways in which Iwitnessed him do that.
One was where he wasessentially giving himself up in
the process.
He was basically coming in andkind of I could see already
taking on.
There must be something thatI'm doing or not doing that is
causing these grownups to be sodressed out and that couldn't

(20:32):
have been further from the truth.
But you can just see that youknow false belief, thinking that
kids start to absorb from theenvironment until and unless
someone shows up and startsinterrupting that you know, and
helping them learn that that'snot the case.
So I saw the expression of thatlike humor, from a place of him
basically caretaking everybodyin the room, trying to like come
on, you all Now simultaneously.

(20:54):
That's really his true nature.
He's got in him this likeleadership, quality of like you
can do it, that leader who canserve and support, you know,
like what you were talking about, and he does that with humor
and levity and it is a tool thatcomes through him naturally.
So you just, you know, you justspoke about something that is,
you know, for me so personal,but I think you're also bringing

(21:17):
up something so important topay attention to, generally
speaking, because you knowyou're not talking about
self-deprecating humor You'renot talking about, you know,
sarcasm, but you are talkingabout levity and you know what a
joy to have you on the show andyou know, demo, that You've
brought up so many difficultsubjects with levity.

(21:37):
Thank you.

Speaker 2 (21:39):
Thank you for sharing about your son as well, and I
think every one of our gifts canhave that shadow side, and I
definitely think that that waswhat I thought was authenticity
making fun of myself only, orthe deprecation and then
realizing I actually don't needto do that I can.
I can make fun of the situationor these different things in a
way that brings a light.

Speaker 1 (21:59):
Yeah, absolutely, yeah, for sure.
Okay.
So, in summary, all these life,big life events that you, that
we've talked about these pivotsright.
How are they a step forward?
Can you talk just a littleabout that before we end?

Speaker 2 (22:16):
So every experience I shared, from my conception or
the bus incident or the coach Ithink that we all can kind of
have those touch pointsthroughout our lives and I think
that now I realize that theyare all experiences that have
shaped me and taught meresilience and, again, empathy
for other people and just havecreated in me a deep commitment

(22:38):
to creating space that otherpeople can grow and have
reactions and responses thatallow us, even from our trauma,
to grow from that, versus bestunted by those experiences.
And so, through my work inhigher education and with
nonprofits and with my business,I feel like the calling to work
with executives, with CEOs,with the leaders who are in

(22:59):
charge really of theirorganization's experience in so
many ways they're all chiefculture officers that they're
setting the culture that, when Ican help them safely explore
their own self-awareness inwhat's happening, implement
practices that work for everyone, support genuine growth and
healing in them and theirorganization so that everyone

(23:19):
gets the experience and thebenefit of that resilience, push
into difficult conversations,then that's where I really feel
people who feel supported inthese real, lasting ways produce
the best outcomes for theirmissions and for their companies
, and so I really do think thatthat is a way that we can be
wildly competitive andsuccessful but also go home and

(23:43):
sleep at night and be full wholehuman people.
And so my journey has taught methat that healing is possible,
even from some of the darkest,deepest pains, and that growth
is possible.
And I've dedicated my life towalking with leaders as they
want to do that growth andhealing.
And I think that as we togetherbecause I'm still in process on

(24:03):
that find our resilience, wealso find our sense of purpose.

Speaker 1 (24:08):
Yeah, no, I love that and you know, I always say, as
a leader, if you're a goodleader, those difficult
conversations are the hardest,but they're the most important,
right Us having thoseconversations and having open,
honest conversation is so hard,you know, sometimes, but it's
really important.
So thank you so much, Jessica,for being here today.

(24:30):
It was a wonderful conversation.
We really appreciate you beingon this episode of Step Into the
Pivot.

Speaker 3 (24:37):
Thank you so much, so much gratitude for you, jessica
, and sorry to be in stereo withthat gratitude for you and
talking over.
It's just that my heart isreally overflowing with feeling
so good and so light, inspiredby this conversation.

Speaker 2 (24:55):
Thank you for giving me space to share my story,
absolutely.

Speaker 1 (24:59):
All right, everybody.
This ends this week's episode,and remember if you have a pivot
step into it.
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