Will AI Replace HR While Bosses Keep Plans Vague on Purpose?
Jerremy Alexander Newsome and Dave Conley discuss how AI is reshaping hiring, arguing that blasting resumes into automated systems misses the human connection and that networking and informational interviews still matter. Kathryn, who works in HR ops, says much of her job (emails and core systems) could be replaced by AI, while many HR ops peers feel resilient because they’ll manage and direct AI; she adds company messaging about AI is vague and five-year plans are unclear, possibly intentionally. She cites legal risk from AI misuse, calls today’s interview process “tragic” with extreme multi-round demands even for junior roles, and says internal mobility is limited. Kathryn describes a murky career landscape, the difficulty of job-hopping or switching industries, and her boyfriend’s year-plus search that ended via family connections. She notes peers seeking housing and financial stability, often staying put, and daydreams about a land-and-coffee-shop life while weighing it against traditional career paths.
Timestamps:
- (00:00) AI is already changing the hiring room – blasting resumes misses human connection that still decides offers
- (01:10) Large parts of HR ops emails and systems are replaceable by AI – peers think they’ll just manage the AI instead
- (03:42) Today’s interview process is tragic – extreme multi-round demands for even junior roles
- (05:36) The career social contract is being rewritten in real time – job-hopping and industry switches feel impossible
- (15:05) Many daydream about buying land and opening a coffee shop – stability and community now compete with traditional paths
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Transcript
The company messaging is vague, the timeline is unclear,
2
:and HR tells itself it's STEERING
the AI—not being replaced by it.
3
:Jerremy and Dave push past
the spin to what's actually
4
:changing inside the hiring room.
5
:Dave: So we were, we were talking to,
somebody, who's in, beginning, really
6
:middle management and building his career.
7
:And we've talked a lot
about AI across this series.
8
:And he, he works particularly with,
corporations that are doing that.
9
:And like one thing he's seeing is
AI and the work that he does and
10
:what's not being replaced are the
things that only humans can do.
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:And that there's such a value
with the human connection.
12
:And what occurs to me is,
is just firing off resumes.
13
:You're just firing it into a machine and
the machines are deciding, and that's.
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:Not the human thing.
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:I know every young person I've talked
to who's been like, man, I need a job.
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:It's like, well, pick up the phone
and start, people will, will, will
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:be surprised that their phone even
rings, to, to do the informational
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:interviews, to make the connections.
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:like every job I ever had
was by the people I knew it
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:wasn't by sending out a resume.
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:So Kathryn you tell me, like, I think.
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:AI is already handling a lot of
functions, particularly in your field.
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:how much of your current job even exists
in five years, and does anyone in HR
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:leadership talk about that out loud?
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:Kathryn: Yeah, I think a lot of
my job could be replaced with ai.
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:I mean, I do, I mean, the
emails that I write, the, the
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:like systems that I use to.
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:Operate and that are like
a core function of my job.
29
:I think every, every place is different.
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:Every, every company, every firm is
at a different stage in the way that
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:they've obviously like adopted AI
and the way that they plan to use ai.
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:and I feel like, I don't know.
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:I, I feel like the, the challenging.
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:Part is like, I dunno, like
the challenging part is, is
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:the, is the messaging, right?
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:Like everyone is super concerned.
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:and I think a lot of people
in my field are concerned with
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:the exception of some folks.
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:I think generally in the HR ops
space, it's actually interesting.
40
:I feel like, a lot of people
in my network who are working
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:in HR ops are feeling like.
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:Pretty resilient to the AI boom.
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:in the sense that they're kind of the
people who can tell the, they're the
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:people who will tell the AI what to do.
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:Like they, they will be in
charge of like, managing that.
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:And so Cool.
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:what does that leave for us?
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:but yeah, communications and messaging,
I mean, depends on the industry.
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:Just like in general for my industry,
the concern at large is, is you.
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:For any attorney out there,
like there have been lawsuits
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:because of AI used incorrectly.
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:Like that is absolutely awful.
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:So, and I don't know, I,
I think that my, I think.
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:Just speaking kind of generally about
the, the way that it's being communicated
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:is, is it's pretty vague, it's pretty,
it can be more communicative in like
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:a, a micro way about like something
specifically that you're working on.
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:But in terms of like where we're
going in five years, no clue.
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:Like I think that they're
probably purposely keeping
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:that, pretty vague to, to,
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:Maybe keep us all at ease or keep
us all anxious and working harder.
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:I don't know.
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:Jerremy: Yeah, yeah, yeah, yeah.
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:So, Kathryn, it'd be, this would be fun
to, to, to plan on or think about if you
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:could change one thing about how companies
actually hire, not like a press release
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:version, but one real structural change.
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:What is it and why isn't
it already happening?
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:Kathryn: That's a really good question.
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:I feel like we could definitely.
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:I don't know.
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:There were like so many things that like
nothing is coming to mind immediately.
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:I gotta think.
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:I feel like the interview
process is tragic and awful.
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:That needs to be overhauled majorly.
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:Obviously it's very different depending
on the role that you're applying
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:to, and all of that good stuff.
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:But, it is shocking to
me to think that like.
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:other generations of people that I
know, my parents, et cetera, maybe
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:they went through like one interview
and then they got the job or like
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:a few interviews they got the job.
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:and I feel like now the interview
length, like the process,
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:the commitment is so extreme.
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:It is like.
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:10 interviews for like an assistant
role, 10 interviews for like,
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:like a Yeah, it's, it's, you're
coming in person multiple times.
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:You're like trying to
figure out all of that.
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:And depending on where you work, like it
can be challenging to get that time away.
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:so.
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:Yeah, I think that's part of it.
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:I also think that like when
you're through the door, certain
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:firms do it better than others.
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:Certain companies do it better
than others, but, there is not
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:a lot of internal mobility.
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:And I think people from my people
in my generation, I know myself like
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:that is something that I really value.
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:Like being able to know, okay, if
this path isn't the right one for me.
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:Dave: Yeah.
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:Kathryn: another path.
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:There's another path.
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:There's some other people
we can connect you with.
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:Dave: Well, let me ask you about that,
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:Kathryn: Mm-hmm.
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:Dave: like you're, you're in a, what I,
what I would say is the contract that
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:we're talking about, and that contract
is the one that needs to be rewritten,
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:which is go to school, get a job, have
a happy life, and it's, it's something
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:that, tens of millions, hundreds of
millions of us, we've done it and also
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:been talking to people who started
that path and then they opted out.
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:They started their own businesses
or they went and did something else.
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:We also, there's also, have
been quite successful, I.
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:And there's, there's other avenues
not only just starting your
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:own job, but just opting to do
something completely different.
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:Or there's also the trades.
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:When you think about like what
you're doing today and what ideally
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:you would like to do, knowing that.
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:like some co some countries like totally
support people careering and paying
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:them while they're figuring it out.
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:Like there's unemployment
insurance that actually works.
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:And, knowing what you know today, would
you be choosing different paths or do
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:you want to choose different paths?
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:Kathryn: Yeah, absolutely.
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:I think, I mean, my Dr my dream and
my future doesn't even really central
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:center around work, like at all.
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:It's, it's kind of, where
am I, where am I gonna live?
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:Dave: Yeah.
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:Kathryn: am I gonna be spending
a majority of my time doing?
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:If I could be on a large plot of
land, like with a large garden, close
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:to a body of water, to any extent,
and like, you know, running a little
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:coffee shop, that would be awesome.
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:Like, that would be great to me.
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:but also I think.
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:The question in my head of where I am
going professionally and in, in a work
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:capacity is so unclear to me still.
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:I mean, I, I feel like, when you, when
you enter the workforce, there are so
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:many people around you, at least so many
people around me that told me, you're
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:just figuring out what you don't like,
and then you'll figure out what you like.
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:But I feel like the
reality is much different.
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:we have, I mean, yes, you
can job hop and that's huge.
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:Now, yes, you can do that, but especially
in this current state of job affairs,
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:job hopping is more challenging.
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:People are catching onto it.
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:and also job hopping industries
involves, a dramatic pay cut potentially,
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:or, work life balance, changing
all of that stuff, like you have
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:to kind of make those compromises.
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:So it's a little bit harder to
do that and harder to kind of.
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:Determine, alright, do I wanna go, do
I wanna switch up my life completely
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:and do something that maybe I'll be
interested in, but also could just be a
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:part of me figuring out what I don't want?
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:Or do I continue on this path, kind of
like my parents' generation of, of working
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:a very similar job for the entirety of
your career, just to ensure kind of like.
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:Job security to an extent, I don't
know, job, consistency, all of that.
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:So I think it's like a really murky
environment to be in and kind of makes
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:it hard to, to make that, that change.
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:And like my boyfriend Charlie, for
an example, he went from being a
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:high school teacher to, working
at a bank that was the craziest.
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:Job search journey I have ever
witnessed in my entire life.
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:Jerremy: Yeah.
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:Kathryn: was unemployed,
searching for a year.
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:He was doing all the things in the
book that you recommend, like Dave,
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:like you mentioned, like building
a network, talking to a bunch of
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:people, going to networking events,
calling up random people and just like
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:setting up time to chat this through.
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:He did all of that.
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:Dave: Mm-hmm.
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:Kathryn: It was still a year and a
half before he got a job, and he got
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:that through, familial connections
and it's like super entry level.
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:It's, it's, it requires so much work.
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:And also he thankfully had like a
cushion that he had built, to your
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:point about like unemployment, insurance
of other, another countries at work.
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:Like he didn't have any of that.
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:So it's like, okay.
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:Does, he was reaching a point where he
was like, okay, do I, do I just get a
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:random job somewhere in the meantime?
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:Dave: Mm-hmm.
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:Kathryn: Do I like,
like when is that point?
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:When I like absolutely have to
do that and when my, my savings
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:is gonna be depleted essentially.
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:and, and that was a, that was a
challenging additional thing that
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:you have to navigate when you
kind of decide to make that shift.
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:Dave: What's.
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:What's different for your generation?
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:I know certainly talking to, to to older,
folks and being older folks, like they,
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:they would've done exactly what you're
doing and worked like really, really hard.
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:And then, they also look back
at that time we just got off an
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:interview with someone who back.
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:their career with some regret,
like their, their adult daughter
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:still talks about times when he
wasn't available, as an adult.
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:She's still talking about this and
like I've heard, a lot of stories
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:from, younger folks that are like
delaying a lot in their lives, whether
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:it's through because of debt or.
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:indecision or, not knowing
or, just like the not knowing.
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:And I think you even mentioned to me
that, like also people are accelerating
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:things that maybe they shouldn't be.
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:So like, what's, the, I mean, what's the
world like for you and your generation?
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:Kathryn: Yeah.
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:Yeah, it's interesting.
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:I mean, well, what you were
saying too about the, the, like,
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:people jumping into things.
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:I mean, yeah, people are moving in
together, very soon in New York.
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:partners are, maybe, I think I've said
two weeks, but facetious, a a few months
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:they're moving in together, just to kind
of create that stability in their life of.
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:Housing stability of,
financial stability and.
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:that leads to complications.
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:I, I know other people who have been,
who are just totally unmarried and
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:just bought a house with their partner.
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:And that's like fascinating
to me to, to split a house.
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:Like, I don't know if, maybe I'm
old school, but I'm like, what is
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:gonna happen if you guys break up?
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:Like, who gets it?
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:Like what, what is the agreement there?
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:Jerremy: Right.
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:Kathryn: I dunno.
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:Dave: are
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:Kathryn: So.
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:Dave: having, are people having babies?
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:are they moving, are they, are
they, moving back towards their
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:parents or where they grew up?
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:Like what, what's the mobility
and what's the family situations?
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:Kathryn: Yeah, I would say, I have
kind of a mixed bag of friend groups.
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:So I have like some people who
I met in Chicago who are like,
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:obsessed with big cities or Chicago
in particular, and, they're kind
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:of living a more urban lifestyle.
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:So.
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:The extent of like, kids,
not, not in the picture yet.
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:but people are definitely
looking for that.
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:Housing security.
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:I'm seeing a lot more people like buying
a, apartments or condos in, the Chicago
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:area to kind of like secure that.
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:Then my other friends who are from
the DC area, I mean like marriage,
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:kids, they're on that track.
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:they are.
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:And they've been on that
track for a really long time.
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:I think I'm kind of like in an interesting
age where, I'm 27, so we're kind of like
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:on the precipice of everyone starting to
have kids, but I haven't really met anyone
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:who's like, not married, that has kids.
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:and the mobility portion, I'm
definitely seeing a lot of people in.
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:From my friend group who, who is based
in the Midwest, stay in the Midwest.
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:They're not interested
in leaving anytime soon.
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:They're not interested in the
coasts, they're not interested in
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:the expenses of living over here.
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:They like kind of the, the
nature of, of the Midwest.
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:And I think also my friends are, mm-hmm.
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:Concerned about the climate crisis,
and they're like, all right, I wanna
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:live near a body of fresh water.
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:I'm gonna live near the lake.
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:Like they're thinking about that.
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:and also their family lives in that area.
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:Yeah.
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:And that's why I moved to New
York was because I wanted.
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:I, because I, I grew up outside of
DC East Coast, went to the Midwest.
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:I felt like I was trapped in a bubble.
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:I felt like I had nowhere else to go.
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:I felt like I was landlocked.
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:I know my mom felt pretty similar
when she was out in the Midwest.
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:and I think a big portion of it for me
too was being so far away from family.
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:Like to not be able to get in the
car and just drive and be there.
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:So it was really important to me to
move back to the East coast, but also
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:get some access to, food scene culture,
music arts, all of that good stuff.
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:And, and New York was, was
just the perfect place.
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:So, I have that and then I have the
benefit of being, close to, to my mom,
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:not my brother anymore, but, close
to her by being, four hours away.
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:So yeah, I think everyone's kind of.
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:Sticking where they're
at for the most part.
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:And if they're going anywhere, they
might be going like a couple cities
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:away, like maybe one state away,
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:Jerremy: Well, let's, let's
daydream for a second.
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:'cause you, you, you got me all fired
up about this coffee shop vision.
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:Walk me through that for a second.
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:What, what does that look like and
what's keeping you from doing it?
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:Kathryn: Yeah.
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:I mean, I.
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:Feel like I'm torn with my life.
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:I, I really would love
that dream of, of, quaint
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:Jerremy: But here's the second.
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:Kathryn: small town lifestyle, where I am.
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:walking to the farmer's market and
I'm growing things on my own and, and
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:I'm, I feel like I'm living in this
sustaining ecosystem and I have a
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:community that's around me that kind
of, we all support each other and, and.
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:Like each other, that sounds wonderful and
great, and that's something that I want
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:to experience at some point in my life.
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:But I do feel right now this
kind of pull to use my brain to
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:whatever capacity I can use it in.
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:which is interesting because at the
beginning of this conversation I was
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:talking about entering the workforce
and not wanting to compromise, like or
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:feeling suspicious of it all and, and
not wanting to kind of engage in it all.
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:But now I'm kind of like.
285
:At this point where maybe it feels
like a crossroads of like, do I
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:work a career that gives me balance
to do things that can help me work
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:towards that quaint lifestyle, on
the coast with the farmer's market?
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:Or do I do things that really
involve working so hard and involve.
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:Like a lot of brain power, like
going to law school, getting my MBA,
290
:like doing things that feel quote
unquote successful in that way.
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:Like which path do I go down?
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:It feels like now I have to
decide, even though I don't.
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:But, it's,
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:Jerremy: I, I
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:Kathryn: yeah.
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:Jerremy: it's almost, it's
almost, you can have both, right?
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:So for example, if you go and live on
the coast, how, the question really
298
:could be like, well, how can I live
on the coast and use my brain power
299
:to create a job or an economy There?
300
:Where I'm getting paid more than
I'm getting paid now, and I'm
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:living the life that I want.
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:Because that world exists, right?
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:There's people that, that
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:Kathryn: Yeah.
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:Jerremy: and live there that
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:Kathryn: Yeah.
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:Jerremy: that, generate enough to live
there, So it's like how are they doing it?
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:Kathryn: How.
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:Jerremy: the cool part is like
if you're there and you're going,
310
:okay, 'cause really brain power is
thinking power and thinking power is
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:answering questions that we ask it.
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:if we ask it enough,
we will start getting.
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:Answers and, uh, of your
questions determines the
314
:quality of your life, right?
315
:So if you say, Hey, how
do I make more money?
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:If you get a dollar that's more
money, so now you have more money.
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:You're like, well,
that's not what I wanted.
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:A dollar doesn't do anything.
319
:It's like, well, you ask for more.
320
:How much more?
321
:Kathryn: Yeah.
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:Jerremy: then you get extremely
specific and get extremely detailed,
323
:because I, I really like that
coffee shop version of you where.
324
:imagine if you're like, Hey,
we are gonna create this coffee
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:shop with your specialty and
your and your brain power, right?
326
:And your skills and your knowledge
that we are a hiring funnel
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:for every other coffee shop.
328
:In the Northeast.
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:So if a coffee shop needs an employee
of some kind, they can message me here
330
:because we train and we facilitate, and
we hire, and we teach and we educate
331
:the community on coffee, coffee,
beans, the whole thing from start
332
:to finish from, you know, buying and
planting and harvesting to making the
333
:actual physical coffee, and it becomes
a vertically integrated ecosystem.
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:Kathryn: I love it.
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:Didn't even think about it that way.
336
:Jerremy: Yeah.
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:Kathryn: I'm wondering, like it's one
of those things where I wonder if that's
338
:kind of, if that's a generational thing
or if that's like a me thing or what, but
339
:like I feel like I get stuck into these
two kind of spaces is like, all right,
340
:is it I do X, like I do X or I do y.
341
:Not like, do I do both?
342
:And if I'm doing X, like
X in this situation can.
343
:And I think for some, like a lot of people
I know is kind of like just throwing your
344
:hands up and just being like, alright, I'm
gonna do the bare minimum and that's it.
345
:And then Y is like going so hard into it.
346
:There's no like in-between
347
:Jerremy: Yeah,
348
:Kathryn: or both.
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:Jerremy: What?
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:What's cool is I think, I think
that's really is maybe not, maybe
351
:not even a generation thing.
352
:I think that's a human thing.
353
:It's just like life is lifeing and
we're over here like, oh, I'm doing it.
354
:I'm living life.
355
:And you kinda get kicked in the
face and you have to make these like
356
:existential decisions that create
anxiety and fear and frustration.
357
:'cause we're also told from the
top down and from early in our
358
:life that one plus one equals two.
359
:Any other answer than that is incorrect.
360
:Even though if you have a one
and a one you put together,
361
:it looks a lot like an 11.
362
:To me, like when I was in school and they
taught me one plus one equals two, I'm
363
:like, y like the, the number changed.
364
:We, I'm, I'm so confused.
365
:Like you put these two together, it's
so, it is also a different number.
366
:You know, it's like, you're going
through school, there's only
367
:one answer and there's only one.
368
:This is the correct.
369
:This is it.
370
:There's no other versions.
371
:That's where it comes from.
372
:the stemming of like, you have X or
you have Y you can't have XY can't.
373
:Right.
374
:The belief is you can't have
everything that you want.
375
:Right.
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:The the popular saying, you can't
have your cake and eat it too.
377
:I go on stage Kathryn all the time and
tell people not only can you have your
378
:own cake, it can be served to you on
a beach by a Michelin star chef, and
379
:it can be gluten free and sugar free
and taste delicious and give you abs.
380
:You know, it's like you can
have it, have, but you gotta
381
:Kathryn: Yeah.
382
:Jerremy: the cake.
383
:You gotta think about
384
:Kathryn: Yeah.
385
:Jerremy: You gotta think about
where you want to eat it.
386
:Do you even like cake?
387
:Do you want cake?
388
:Maybe you want a cupcake.
389
:Maybe you want, maybe you want ice cream.
390
:is it that you want?
391
:And when you get extremely
clear, you start working on the.
392
:the backward answer of like, all right,
well, let me figure out how I get it,
393
:because it, it all stems from a choice.
394
:And, uh, I think that that's the
ultimate failure of our education system.
395
:Like can we, as we addressed on earlier,
is we just do not help people understand
396
:how to critically think and go down
the paths of, of choices that, Hey
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:man, you got so many opportunities.
398
:There's so much that you can do.
399
:You have.
400
:whole alphabet, right?
401
:It ain't just X and y man.
402
:It goes A to Z.
403
:There's so many things that you can
do and you can combine them and you
404
:can play with 'em, but we have to
think, we have to figure out how to
405
:do so, and I'm so happy that you even
know, 'cause a lot of people don't.
406
:A lot of people don't even
have that belief and that
407
:ideal of like, what could I do?
408
:Because it can pull you and it can
excite you, and that that's always
409
:a version of your life that feels
extremely compelling and exciting.
410
:Kathryn: Yeah, absolutely.
411
:Absolutely.
412
:It's interesting, it's like,
it feels like the kind of, I
413
:don't know what you were saying.
414
:It reminded me of just high school and
the whole college app process and talk
415
:about feeling like I gotta figure out what
I wanna do and it's gonna be right now.
416
:And what I figure out to do right
now determines the rest of my life.
417
:And.
418
:It's so funny because it's like, to
your point earlier, Dave, I mean like,
419
:like trade school isn't even brought
up in certain school environments.
420
:Like no one even touches on it.
421
:I'm like, if I did it a trade,
I'd be so happy right now.
422
:Like, maybe I should have done that.
423
:Maybe I should be a plumber.
424
:Oh my God.
425
:Like, but that was never
discussed, I, I, I remember.
426
:The kind of elitism of people when it
comes to which colleges you get into,
427
:how none of that ended up mattering.
428
:And you have all these adults who
are telling you, it doesn't matter,
429
:but it's not really permeated into,
into the class, like everyone's very
430
:obsessed with, with status and, and
how that determines your future.
431
:so, and how, and the opportunity
to change your mind is like.
432
:Is there, and even though it can
be really challenging to do, it is
433
:there and I feel like I know I need
a reminder of that like once a week
434
:Alex: Kathryn's coffee shop dream
isn't nostalgia—it's a generation
435
:quietly engineering an EXIT from
a system that never wrote them in.
436
:But when Dave asks her to look back from
45, what she fears most starts to surface.
