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December 19, 2025 28 mins

What happens when life throws multiple pivots at you simultaneously? Jessica Porter found herself facing this exact scenario when she moved from Texas to Portland, transitioned from the automotive industry to financial services, and became a stepmother to an eight-year-old. All at the same time.

Jessica's journey begins with the challenges of relocating to rainy Portland in January, knowing virtually no one except her partner who worked long hours. At 27, she discovered the difficulty of making adult friendships, pushing herself as an introvert to join Meetup groups and networking events. "Making friends as an adult is a lot harder than you think," she shares, describing her evolution from networking novice to confident professional through persistence and authenticity.

Eleven years later, Jessica has transformed these simultaneous pivots into a life she "could never have seen" for herself - a thriving career as a partner and co-founder of the 401k Girls, a strong marriage, and a meaningful relationship with her now 19-year-old stepdaughter. Her story reminds us that sometimes the most rewarding paths forward come when we say yes to multiple changes at once.

Guest Bio:

As one of three children of a plumber and a homemaker, Jessica grew up never knowing what a financial advisor was. Once immersing herself in the industry and learning the incredible ways advisors can help people, she focused her practice on providing the education and planning that helps her clients gain a handle on their finances and not only avoid making mistakes that so many do, but strategically plan for their futures.

In 2025, Jessica and a colleague founded The 401(k) Girls with the goal to make financial education approachable, relatable, and actually fun. Whether you’re a young professional just getting started or a seasoned exec gearing up for retirement, they can help you avoid common pitfalls, plan strategically, and take control of your financial future.

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_01 (00:41):
Hello, everybody.
Welcome to this week's episodeof Step Into the Pivot.
We're so happy to have all ofour amazing listeners here.
And also happy today tointroduce Jessica Porter.
Jessica, thank you so much forbeing here today.
Thank you for having me.
I'm excited for thisconversation.
Um, I love that you are one ofthe founders of the 401k girls,

(01:06):
right?
I think that's such a cool thingand so much fun.
And I love that you callyourselves that.
Um, so I'm really excited.
I know our conversation doesn'treally have anything to do with
that today, but I just wanted tokind of mention it to our
listeners.
So, Evie, uh, I'll let youintroduce Jessica a little more.

SPEAKER_00 (01:27):
Thank you, Teresa, and uh welcome, Jessica.
You are someone that umdefinitely I think talks about
family quite a bit.
It was one of the first thingsthat we bonded over when we met
here in the Portland communityof women in finance.
And I wanted to uh read thestart of your bio.
We normally don't do that uhbecause you know, bios are

(01:50):
something that our listeners cancheck out in the show notes, and
obviously more information aboutyou will be available there too.
However, I want to highlightthis because this is how you
start.
As one of three children of aplumber and a homemaker, Jessica
grew up never knowing what afinancial advisor was.
So, you know, you've chosen toeven lead your little
description of um of you knowwho you are, what you do that

(02:13):
you submitted to us with family.
And then uh blended family inparticular is what you and I
bonded over when we bothrealized that we have, you know,
um personal experience with it.
Without giving anything elseaway about your story and your
pivots, tell us what uh lifeevent or events or series of
circumstances helped shape youthe most?

(02:36):
And uh what was that major pivotthat transformed you?

SPEAKER_02 (02:40):
Yeah, well, thank you again for having me.
I'm excited to be here.
I think for me, the pivot thathappened was kind of a pivot of
a bunch of things at once.
So uh about 11 and a half yearsago, I moved to Portland.
I'm originally from Texas.
I grew up in Houston and livedin Austin for a few years.
And I met my now husband there,and he was moving back to his

(03:03):
hometown of Portland.
And so I moved here.
At the same time I moved here, Iwas giving up my career in the
automotive industry and startingat the time I didn't know this,
but starting somethingcompletely different.
And then, as you alluded to,Evie, I became a part of a
blended family.

(03:23):
I have a stepdaughter who's now19, but the time was eight years
old.
Um, and so sort of becoming aninstant parent, especially as
somebody who had chosen to bechild-free of my own biological
children, and then sort ofnavigating being in a new place
with a new family, what thatlooks like, how everybody gets

(03:44):
along.
And then at the same time, ofcourse, navigating kind of
drinking from a fire hose in acompletely new career as well.

SPEAKER_00 (03:52):
Okay, so do we have this right?
Like so the trifecta.
Here you are in a you know,growing a relationship, so
romantic relationship,partnership.
And then that also comes with umexperimental role and uh all the
complexities.
And then uh completely newterrain.

(04:14):
That's interesting, you know,it's not just uh it's not just
oh we moved, it's I moved to atotally different state.
Probably means I don't knowanybody.
I know this guy, and he he hasroots here, but I don't know
anybody.
And then there is the oh, andalso I'm I'm pivoting
career-wise.
I feel like we could go deeperhere, like with any one of
these, you know, how did theylike help us make sense of, you

(04:37):
know, what was going on first,and then where were you, you
know, were you disoriented?
How did you feel when you firststarted like learning about the,
you know, Portland culture isalso quite unique and specific
to this location, very differentfrom what I imagine you were
experiencing in Texas.
So yeah, help us get a littledeeper and a little oriented.

SPEAKER_02 (04:58):
Yep, very much so, all of that.
I uh so I moved here in January,which is a really tough time for
anybody who knows Portlandweather.
It's a difficult time to move tothe area.
I sort of thought, I'll takesome time off of work, I'll
relax, I'll get out and explore.
It was way too cold, it was waytoo dreary.

(05:20):
I didn't know anybody.
I there was, you know, myhusband was working uh 12 hours
a day at the time.
I didn't have anybody to hangout with, and I was really
bored.
I wanted to do something.
I didn't like not working.
Um, and so yeah, it was reallytricky as you mentioned not
having a network, not knowinganybody.

(05:40):
I was 27 when I moved here, andmaking friends as an adult is a
lot harder than you think it is.
It's when you're younger, you'rein school, you know, you're
working at different jobs.
It's really easy to kind ofbuild your community and your
network.
And then you become an adult andeverybody has their own lives,
and it was really tricky.
So for me, I kind of reallynavigated a lot of different

(06:04):
things, some that worked andsome didn't.
I explored a lot of meetup.
Uh, so I actually don't evenknow if meetup is still a thing
anymore.
But back then you could kind ofreach out and connect with
people and you know, I wouldjoin groups and the women would
go and walk together in the parkor we'd go play tennis.
And so I kind of did a littlebit of that, just trying to get
to know the community a littlebit more.

(06:26):
And then once I started working,then I kind of dove into
different networking groups.
And that was really, reallydifficult.
I am naturally an introvert.
And so sort of throwing myselfout there, being a part of these
different groups in this roomof, you know, hundred people

(06:47):
that you don't know and havingto make conversation.
And I was truly, really awful atit in the beginning.
Just uncomfortable, couldn'tmake small talk.
You have the mindset of everytime you go into this, I'm gonna
come away with a client.
And it was just, it was allwrong.
And so over time, I've been ableto really navigate and be a part

(07:07):
of some really amazing groups.
And that's also helped me, youknow, kind of build up a network
here, not just professionally,but also personally as well.

SPEAKER_01 (07:16):
Yeah, I think you brought up a lot of really great
points there.
Um, one is, you know, we do makea lot of our friends, at least
initially, maybe like throughwork or through school or
something like that, right?
And if you're not working andyou're no longer in school and
you're in a student, it it isreally hard to do that.
So, you know, it is, and and Ithink a lot of our listeners,
you know, a lot of us have thatproblem when you're in those big

(07:39):
groups and you know, meetingpeople.
And I've taken the approach now.
Um, I love that you talk aboutthat because, you know, we are a
little bit afraid.
Like I now, I I'm at the pointwhere I just start walking up to
people, but I was not alwayslike that, right?
And and try to bring people whowho may be holding back into
that conversation.

(07:59):
And I think that's something wecould all do more, right?
So it's so it's it's really niceto hear you talk about that.
Can you talk a little bit aboutthe blended family dynamic,
right?
Because I'm sure for you, yousaid you were only 27 when you
moved to Portland.
You were pretty young, you know,to have this now eight-year-old
stepdaughter.

(08:21):
So can you talk a little bitabout that dynamic and how you
navigated that a little bit?

SPEAKER_02 (08:27):
Yeah, absolutely.
So it's very interesting becauseI'm a stepparent, but I'm also a
stepchild.
Um, and now it was a little bitdifferent in my family dynamic
because for me, my stepfatherwas my father.
My biological father was notreally involved.
And so I had two parents, andthese were, you know, the two
parents that raised me.

(08:49):
In this situation, it was alittle bit different because I'm
now the third parent.
And there's a father and amother that are both very
involved.
And it's really tricky tonavigate what your place is,
what your boundaries are, whatyou are and aren't allowed to
do.
Navigating sort of my influence.

(09:10):
And does that conflict withtheir feelings and what they
want to do?
Especially, you know, we're intwo different households and
sort of influence coming fromboth.
And and, you know, just again,sort of navigating what am I
allowed to do?
What am I not allowed to do?
Can I, am I allowed todiscipline?
Is that uncomfortable?

(09:31):
Like, how does she feel aboutthat?
And so it's just, it's wonderfulfor somebody to have ultimately
at the end of the day, all thesepeople that love them, right?
We're just all these people thatcome into her life and love her
and care about her.
But also for us and for her,navigating like, who is this
person in my life?
Am I the older sister type?
Am I the parent type?

(09:52):
And, you know, kind ofnavigating that relationship and
sort of defining that together.
So that that was definitelydifficult.
And she was young, you know,eight years old is tough for,
you know, she was a couple ofyears younger when her parents
got divorced, but that'sdifficult for your dad now to
have somebody new who's livingwith him.
And I don't have anybody else.
He's my person in this place,you know?

(10:14):
And so yeah, it was it wasdefinitely difficult in the
beginning for, I think, for allthree of us really to kind of
figure out our place and ourdynamic in this relationship.

SPEAKER_01 (10:24):
And I'm sorry, can I ask you one more question?
Did they have a goodco-parenting relationship?
Because sometimes we hear, like,you know, uh, if sometimes
that's good and sometimes that'snot so good.
Can you I I I don't need you toget really deep into it.
It's just more of a curiosityfrom my standpoint.

SPEAKER_02 (10:39):
So no, and that's a great question because it it
makes a difference.
It makes a huge difference forour relationship, for our lives,
for my dynamic in this wholesituation.
And the answer is very luckilyyes.
And it was a little bit trickyin the beginning just because
sort of the dynamic between us,there was, I think, maybe some

(11:02):
skepticism, maybe a little bitof distrust.
Totally fair.
I'm a new person coming into thesituation.
And so that was a little bittricky in the beginning.
Um, but their relationship,their co-parenting was very,
very comfortable, very kind,very flexible.
Um, I've certainly witnessedsituations where it is not like

(11:24):
that, especially when there is anew relationship involved.
Um, and so it was a little bittricky to navigate in the
beginning.
They've always had a reallygreat dynamic.
And, you know, sort of as wewent through the years, we
realized ultimately the bestthing for her is for all three
of us to be able to be presentand for none of us to have to

(11:45):
miss out on these excitingthings that are happening in our
life.
And so we're we have a wonderfulrelationship now.
Uh, she graduated high schoollast year, and all uh four of us
went on her graduation triptogether.
We've traveled together multipletimes.
We go to all kinds of events andthings with her.
So we've got a really wonderfulrelationship now.
And we're very, very luckybecause that takes work on

(12:07):
everybody's part and is not thenorm.
I know.

SPEAKER_00 (12:10):
This is so great to hear, and I would love to see if
I if we can connect a few uhpoints here.
When I first met you, you were apro at networking.
So hearing you talk about these,you know, complexities and the
you know rougher start, uh, itmakes sense to me because I've

(12:30):
personally experienced that too.
It's not easy in the beginning,uh especially if you are in an
environment that is totally new.
And uh I think that you know,one of the one of the things you
were speaking about withnetworking, that then we find
the similarity here with youknow what you're talking about
with your blended familydynamic, is that it um it took

(12:53):
some time, it took some it tookshowing up, and it's that it
took a set of skills that getdeveloped over time, like you
know, same thing as flexing amuscle, and also, you know, some
like targeted exercises for thatskill.
So I know that when it comes tonetworking, when I was first

(13:14):
starting to network, I really umfirst I was not overwhelmed.
I think that's a really good wayto describe it.
And then I sought out help.
And there were really someexcellent pieces of advice that
other women gave me, breaking itdown, you know, saying, like,
okay, so here's a goal, um, dothis, try to try to connect with

(13:37):
this person.
And then there were a lot ofintroductions, people opening
doors.
So there was uh what I'm gettingto is that there was an approach
that I was suggested that Itake.
And uh it wasn't artificial, itcame from people's authentic
experiences, which is why Iresponded well to it, and then I
did it.
When it comes to the blendedfamily experience, especially

(13:58):
10, 15 years ago, I feel like wehave much better resources now.
There really wasn't much.
When we were trying to do thisfor the first time 15 years ago,
blending our family, I didn'thave anything even remotely
close to this.
Like, look, you guys, if you dothis and this and this and try
it like this and this, thismight go better than this other

(14:19):
thing you're trying to do.
You know, and in and in manyways, you know, we get to that
point about presence.
It all ends up being about like,well, just you know, whatever it
takes to show up for whatever isin front of you and be as
present as you possibly can.
You know, it worked in thisvery, you know, let's say
low-stakes situation withnetworking and much higher
stakes situation with blendedfamily, end result being the

(14:42):
same.
Like both of these experiencesfor me are so much deeper
because I found a way to bepresent.
But boy, was it harder to findsome good advice on how the
frick to do it for the blendedfamily piece than it was for
networking.
So that's my little like pivotvent over here.

(15:03):
I'd love to hear your experiencewith any and all of this.

SPEAKER_02 (15:08):
A hundred percent I would agree.
And I think to me, thedifference is because networking
feels a bit more generic, it'sthe the principles are sort of
the same.
Everybody's gonna be a littlebit different.
The best advice that I got fornetworking was go in and listen,
right?
Just ask questions and letpeople talk about themselves.

(15:31):
And that's what people love totalk about themselves, right?
And that I mean, myself includedin that.
And so when people are verycurious and they ask questions,
then you find that you like thatperson because you get to talk
about yourself and you get toshare more.
And so that's easy, right?
It's easy for me to walk into aroom and ask questions.
It is not easy to, you know,every family's different.

(15:54):
Your blended family looksdifferent than my blended family
and what the dynamics are andthe ages of the children when
that happened and therelationships between everybody
that's involved.
And I think that's why it's somuch harder because it is such a
personalized thing.
And you're right, there aregoing to be some sort of general
ideas of how to navigate, howto, you know, figure out certain

(16:16):
things and work together andcommunicate.
But in general, the relationshipof those two parents and how
that affects the child.
And if there's more than onechildren, it could be different
between both of them, dependingon their ages when this
happened.
And so it it is just such acomplex thing.

(16:36):
It it takes, I think, a lot moretime and effort and energy, not
in a bad way, but just in a waythat you have to really sort of
like pay attention to all ofthese things to make it work.
Whereas networking can, like yousaid, it's also lower stakes.
So it doesn't feel like such abig deal, you know?

SPEAKER_00 (16:55):
Yeah.
And I just want to like put onefinal point on this, Teresa,
before um I let you uh continue.
Being members of blended familyis what, as I was saying in the
beginning, allowed you and I tostart connecting in a networking
setting.
Because this was, you know,authentically, we were asking

(17:16):
each other questions about so,oh, you too, right?
Tell me about your experience.
Here is my experience.
And that was really that was wedidn't talk about a financial
advice, we didn't talk aboutyour firm, and we had some
people in common, but reallythat was the first thing we
talked about.
And then that, you know, led toother conversations and more
professional conversations andconnections, also.

(17:38):
So just you know, um, one of thethings we like to highlight on
the show is that you know, whileit's important to be aware of,
you know, now I'm at work andworking, and now I'm at home and
I'm at homing, we are you knowone container of energy, and
you'll be a mom at work and uhyou know, a professional in mom

(17:59):
world, we don't compartmentalizereally, like, you know,
emotionally.

SPEAKER_01 (18:04):
Well, I was gonna add too that you know, like what
I when I heard Jessica talking,like I think a lot of the things
you were doing were veryintentional, right?
You were very intentional about,you know, what's my role now?
How is that gonna work?
How's that, what's the dynamic?
You know, am I like I thinkthere's I think having that
intentional mindset, wanting todo in my mind what's right for

(18:28):
her and not what's necessarilyright for all the adults in the
room, it it makes the differencea lot of times, right?
So that's what I was thinking asyou were both talking about
that, right?
Us being intentional sometimeshelps the situation and helps us
to understand, right?
Not just walking there and say,well, I'm a parent now and this
is what you know, does no, itwas very intentional about how

(18:50):
you were gonna work throughthat.
So that's what I got from it.
But you know, um, so Jessica,um, can you talk a little about
when you when you look back now?
Um, especially at moving to anew town, not knowing anybody,
now being this parent, you know,uh, all those things.
What what advice would you givesomebody?

(19:11):
What what would you, you know,not change, but what advice
would you give somebody who whomay be going through something
like that?
Because I think sometimes we'reforced to do that, or people did
it, you know, after the pandemicbecause something worked better
for them, or, you know, anynumber of things can happen.
Can you talk a little about, youknow, looking back at that?
What what might have changed foryou?

SPEAKER_02 (19:33):
Yeah.
So, you know, for me, when I waskind of going through all of
these things, at the same time,I was also starting a brand new
career.
And so kind of figuring out howto live in this new place, build
a network, blend this family,um, be a partner at this point.
My, you know, my now husband,we'd only been together for two

(19:53):
years at this point.
So Evie, as you said, it wasstill a newer relationship and
kind of navigating that togetherand all these changes, and then
diving into a brand new careerthat I knew nothing about.
I had no background, and I'mjust sort of like, you know,
right here in the water.
I think I would look back.

(20:14):
I I always sort of jokinglydescribe myself as a recovering
perfectionist.
And I would look back and say,it's okay to fail.
Like it's okay to mess up.
It's, you know, Teresa, as yousaid, it's important to go into
something with intention, butalso sometimes it doesn't go the
way you want it to.
And sometimes things don't workout.

(20:35):
And sometimes, you know, you'rekind of a jerk stepmom and you
have to go, oops, I'm sorry.
Like, let's rewind this.
Let me figure out how to do thisbetter.
Or sometimes you fail in yourjob and you have to like not
beat yourself up.
We're all humans.
We make mistakes, you know?
And so I think for me, again, asa recovering perfectionist, I
would say it's okay to like takesome chances and to take the

(20:58):
leap and not be too worriedabout failing.
You don't have to be 100% readyhere.
If it doesn't work out, great.
Now you know what not to do.
Let's move on to the next thing.

SPEAKER_00 (21:08):
Yeah, totally.
You know, this like an imagecomes to mind um sometimes in
the work that I do um with womenone-on-one when we're spending
time like preparing for thingswhere they're worried about not
doing a good job, and they'reperfectionists who are on their
that path of recovery will talkabout falling on my face.
Like I am like preparingemotionally um to fall on my

(21:31):
face, and that not reallydefining who I am if that
happens.
Like, I'm gonna go out there,take a risk, and um and
literally, you know, maybe evenfall on my face.
I've had that physicalexperience.
I fell on my face in front ofsomebody that I was uh I really
wanted them to think very highlyof me and think that I was

(21:52):
awesome.
And I was I was still living inCrusha.
This was before I moved.
And in my, I think, um,nervousness around, you know,
literally walking around them, Itripped and and fell on my face.
And I remember um that being apivotal moment in essentially
deciding what am I doing?
Why am I so worried about, youknow, how they're gonna see me,

(22:14):
how they're gonna perceive me,the and the perfectionist of the
image, where look, I am justgonna stand up and brush all
this like literal dust off.
And it's okay.
And I was like, it's okay, I'mokay.
And uh it was, you know, such anit was such a visceral
experience of this like failurethat I think it helped me learn

(22:37):
that lesson of like just failfaster.
You know, sometimes you know,take the risk, fail faster, get
up, and it doesn't, you know.
Um, it's it's okay to make thatmistake, and sometimes it's
totally beyond your control,also, you know.
So I I felt that like buildingthe blended family and also
networking and also you know,growing uh my career included a

(22:59):
lot of these.
Like, I'm just gonna, I'm gonnatry it and I might stumble.
And if that happens, I'll dealwith it.
Yeah.
So yeah.
Thank you for sharing yourwisdom on that note.

SPEAKER_02 (23:11):
Absolutely.
And I will add too, I think, atleast for me, getting older, I
think helps with that too.
You just you get a little bitolder, you have a little bit
more life experience where youstop worrying so much about the
perception.
I look back at myself, you know,11 years ago early on in my
career, and you are trying toprove something, right?

(23:34):
Absolutely you are.
And but then once you get olderand you've got a little bit more
experience under your belt, butyou just stop caring as much,
right?
And I luckily am just a veryclumsy person in general.
So if I trip and fall on my facein front of somebody, I'm just
gonna laugh at myself and go onbecause it happens.
Um, but I do think that luckilycomes with age and being just

(23:54):
more comfortable in your ownskin and saying, you know what,
this is fine.
I can't please everybody.

SPEAKER_01 (23:59):
You're you're so right, right?
Like because I'm, you know, mucholder than you are.
And I totally agree.
My my perception of that hascompletely done a 360, right?
It's, you know, I do the thingsthat make me happy, right?
I give myself grace when I messup, right?
And that's still hard to do.
Don't get me wrong, right?

(24:20):
There's still days I'm like, whydid I do that?
But, you know, it's just thatdifferent kind of feeling.
Um, okay, we're ready to wrap.
So, how are our question that wealways ask is, how was this
pivot a step forward?
Can you just summarize that forus?

SPEAKER_02 (24:37):
This pivot as a whole literally has changed my
entire life, the entiretrajectory of my life.
I mean, I now call a brand newplace home.
I have a family that I didn'tthink I would have.
You know, my husband and I havebeen together for 13 years, and
we actually just got marriedthree years ago.

(24:58):
Um, and so that's, you know,building this life together,
having this child that I now,you know, as we all know, and
having children or somebody inyour life that you, you know, in
some dynamic, you just the lovethat you feel, the sort of
responsibility and care that youfeel for their future and to be
able to be a part of that ishuge.

(25:19):
And then, you know, my careerkind of just accidentally
landing in financial servicesand now being 11 years in, being
a partner, starting my own brandwith the 401k girls, being able
to help support my family.
It, I mean, all of this in a waythat I could have never ever
seen at the time has completelychanged who I am and the future

(25:41):
of my life.

SPEAKER_01 (25:42):
Awesome.
Great summary, honestly,Jessica.
Thank you so much.
Evie, you have some fun.

SPEAKER_00 (25:48):
So grand, Jessica.
It's wonderful to hear, youknow, examples of pivots where
there is this like mixture ofchoice and life happening to us.
You know, sometimes we talk toguests where it's like, okay, so
this I had absolutely no choice.
Here's a pivot that occurred.
You know, lemons were thrown atme from all directions, and I
didn't know what to do withthem.

(26:09):
And then I figured out, youknow, let's let's make some
lemon pie.
But in your case, you know,you're also um you're also
playing with some of theseexperiences where along the way
you had many choices.
In many of these cases, youcould have said no.
I'm not gonna date someone whohas a child, I'm not going to
move to a different state, I'mnot going to change careers,

(26:33):
right?
There were a lot of these likechoices to say, yes, let's see
what happens.
Like, yes to the growth.
So, you know, some of thesepivots I think are, you know,
they're just occurring.
And then some of them you areessentially, you know, you're
being like, Would you like apivot?
And you're like, Yes, sign me upfor the pivot.
Yeah.
So I just I love that as a asone of the examples of how how

(26:56):
pivoting works.
Uh thank you so much for showingthat to us.

SPEAKER_02 (27:01):
Yeah, absolutely.
Thank you both for having me.
This was so fun.

SPEAKER_01 (27:04):
Yeah, awesome.
Well, thank you.
Thank you, Evie, as always.
And thank you, of course, to ourguest, Jessica the Porter, for
being on today.
Uh, we will be back in a coupleof weeks with another episode.
And uh, in the meantime,remember if you have a pivot,
step into it.
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