March 29, 2025 • 38 mins
What happens when a burnt-out attorney with $200,000 in student loan debt decides to completely transform her life as an empty nester? Join us as Jessica Medina candidly shares her experiences burdened with a staggering average student loan debt of $145,000. She discusses the emotional weight of student loans and why they require special consideration, alongside practical strategies for parents approaching college funding conversations with their children.
The conversation takes a personal turn as Jessica prepares for her own empty nest. After raising twins as a single mom while juggling her legal career, she found love and began plotting her “second chapter” with her husband, which included developing the financial skills necessary to leave law behind and pursue their dream of vineyard ownership in Asheville, North Carolina.
Highlights:
- The emotional burdens associated with student debt and its impact on effective financial planning.
- Strategies for open conversations about college funding expectations with children.
Key Takeaways:
- Addressing student loan debt requires unique strategies and emotional awareness.
- Early discussions about college funding can alleviate future stress and miscommunication.
Join us for this insightful episode as we explore Jessica's journey and her wisdom on navigating the challenges of student debt, redefining personal identity in mid-life, and building a vibrant community as an empty nester.
Jessica Medina's Bio
Jessica Medina is a lawyer turned Accredited Financial Counselor on a mission to help attorneys create the financial freedom they need to do big things. She graduated from Columbia Law School in 2004 as a single mom of twins with over $200,000 in student loans and went straight to work at a Biglaw firm. After eight years she switched roles and became Senior Counsel at the Division of Enforcement at the United States Securities and Exchange Commission. She left the government to work in an area of the financial industry outside of the securities world and now teaches other lawyers how to use their money to finance their dream lives.
You can find Jessica online: LinkedIn, Instagram, Facebook, Website
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
I help people with all of the basic money
management skills that I wish Ihad had when I had started my
professional career.
Learning them gave me what Ineeded to feel comfortable that
I could leave that professionand I could do something else
that maybe wasn't as lucrativebut was much more aligned with
how I wanted to live my life.
Speaker 2 (00:19):
Welcome to this Empty Nest Life.
Join Jay Ramsden as he leadsyou on a transformative journey
through the uncharted seas ofmidlife and empty nesting.
If you're ready to embark onthis new adventure and redefine
your future, you're in the rightplace.
Here's your host, the EmptyNest Coach, Jay Ramsden.
Speaker 3 (00:40):
Jessica Medina.
Welcome to the show.
It's so good to see you, myfriend.
Speaker 1 (00:44):
Thanks for having me, Jay.
I'm excited for ourconversation.
Speaker 3 (00:47):
You know why I'm excited?
It's because, well, you havethis wonderful business who kind
of helps attorneys figure outmoney.
But I would imagine that theystockpile a lot of debt too
going into the law school.
And I think it would be greatfor my folks whose kids are
either in college still or justout of college.
(01:08):
It's like, how do we figurethat stuff out, the money, like
what's in your brain?
Tell me what goes on when youare talking to your people.
I'm sure there's some benefitfor my folks.
Speaker 1 (01:18):
Yeah, a lot of my clients have either recently
graduated law school or maybeare in their first 10 years of
practice, and many of them arestill carrying a mortgage-sized
debt from that law schoolexperience, and so one of the
things that I specialize in ishelping people deal with that
level of student loan debt.
The typical American graduatehas about $35,000 of student
(01:41):
loan debt, whereas the typicallaw school graduate has over
$145,000 of student loan debt,whereas the typical law school
graduate has over $145,000 ofstudent loan debt.
So, as you can imagine, thestrategies for tackling those
different types of debts arevery different, and so I work
with my clients a lot on makingsure that they are putting their
student loan debt in the rightpriority order of all of their
(02:02):
financial goals, and I thinkthis is something that a lot of
you know younger professionalscoming out of school really
struggle with, because so muchof the personal finance world is
really beating them over thehead about making sure that they
pay off those loans as quicklyas possible.
It's a responsibility thatthey've taken on, that that's
what their career is for, and ifthey can't do it, then there's
(02:22):
something wrong with them, andso, to the extent that you know
there are parents that are alsoinvolved in this dynamic.
They also may have brought someideas about debt overall
student loan debt in particularand so I really love helping
people maneuver the emotionaljourney of working on paying off
their student loans and makingsure that it doesn't overshadow
(02:44):
other financial goals they mayhave for their life.
Speaker 3 (02:47):
Oh, so good.
Like I'm curious, what is thelike number one emotional
concern that people have when itcomes to tackling debt?
Speaker 1 (02:57):
So debt, I think, overall has a lot of shame
attached to it, because it'salmost a sign of
irresponsibility.
Right, debt for many peopleappears to mean that you didn't
have the resources when youneeded it and you couldn't wait
right.
So there's all of this mix ofoh, if I had been a better
(03:20):
steward with my money, or if Ihad been a better person, I
wouldn't have had to have takenout the debt in the first place.
You're automatically assumed tobe behind the starting line if
you have to start from anegative.
Now I have a lot of thoughts onhow debt is treated in this
country and we don't have timeon this podcast to get into all
of them.
Speaker 3 (03:40):
It could be another show, that's right.
Speaker 1 (03:42):
But there are different types of debt, and I
think that, sadly, many peoplelump all of the different types
of debt together and put themunder the category of evil,
terrible for your financialhealth, an irresponsible
decision and something that youhave to take care of immediately
and as quickly as possible.
Specifically with respect tostudent loan debt, this is a
(04:03):
particular type of debt withspecial rules that apply,
especially if we're thinkingabout the federal student loan
debt world.
There are just different rulesin terms of when you have to pay
it back, what the terms aregoing to be, what programs are
available in terms of relieffrom this type of debt, and so I
think it's very important tocarve this out from the more
(04:25):
general high-interest debtconversation, or even
low-interest debt conversation,because there are so many twists
and turns to the student loanworld, and anyone who's been
paying attention for the pastfour years knows that the
student loan world is in atumult right now.
We're recording this podcast infall of 2024 and student loans
(04:46):
are on the docket for theSupreme Court.
That's crazy.
Why is the Supreme Courttalking about student loan debt?
But that's the world that we'rein right now, and so I help my
clients maneuver that reallycomplicated environment and be
able to take advantage ofwhatever relief programs may be
out there and also just helpthem understand that whatever
(05:07):
emotions they're having aboutdebt could be separated from
some of the numerical strategiesthat we can use to tackle it
over their financial journey.
Speaker 3 (05:16):
Yeah, I think that's a great point, jessica, because
I think oftentimes the averagehuman in America right takes on
debt for certain reasons.
The average human in Americaright takes on debt for certain
reasons, but what they forget islike wealthy people leverage
debt to make investments rightin property and other things and
businesses to actually getwealthier.
So it's not a bad thing.
(05:37):
It's just like how do youapproach it and I think the
mindset piece is key.
It's like sometimes we have toright, especially student debt
for college.
Speaker 1 (05:46):
Exactly this is for education.
This is to provide moreopportunities, and you know, I
have a very soft spot for peoplewho felt like they were in a
position where they had to takeout a lot of debt in order to
create those opportunities forthemselves.
I do have clients who have nostudent loan debt.
They never did.
Maybe their family was able tohelp out, which is a wonderful,
wonderful privilege to be ableto start your career with a leg
(06:09):
up and start at zero, as opposedto in the negative.
But it's that very education,especially for my clients who
are primarily practicingattorneys it's that education
that opens the doors to the typeof financial life that really
gives them everything thatthey've been looking for Right.
Speaker 3 (06:27):
So if you had some advice for the people out there
it's going to be parents who arelistening who may be trying to
help their kids right, getthrough like, how are you going
to tackle this?
Because it's a conversation, Ithink that needs to be had and
it's an uncomfortable one forsure.
I think that needs to be hadand it's an uncomfortable one,
for sure.
Obviously, attorneys who areout there with student law debt
(06:48):
are like they're working towardsto pay that off.
They're maybe not having thatsame conversation with parents,
but I'm sure you have some tipsor ideas to help folks out there
with that conversation.
Speaker 1 (06:58):
No, absolutely, and, like with many things, we like
these conversations to startearly and to occur often.
I think undergraduate educationis actually one of the most
difficult things to pay for inthis country.
I have the privilege of workingwith a lot of folks who carry a
vast amount of graduate schooldebt.
That's because federal loanswill pay for your entire
(07:20):
graduate school level education.
They'll pay for the entire costof tuition, including room and
board.
It's not the case that you canget federal loans at the
undergrad level to that extent,and that creates a real bind for
parents who want to send theirchildren to the best school that
they got into, whether or notthat school wants to help pay
for that experience for thechild.
(07:42):
And so, with my parent clients,we often have conversations
about where does college savingssit on your list of priorities?
Are you someone who is carryinga lot of student debt yourself
and you don't want your childrento have that experience?
Are you already doing well onyour own financial goals in
terms of preparing for yourretirement, in terms of if
(08:03):
you're trying to move to alarger house, being ready to
take on those additionalresponsibilities?
And so I think it's importantto have conversations with
children early about what familyresources may be available,
because that's going to be thebulk of where their college gets
paid for, unless the kids areable to seek out merit
scholarships, unless the schoolis a type of school that offers
(08:25):
a lot of aid to families thatmight not otherwise qualify for
it because of their incomes.
And so I think it's reallyimportant to come up with the
matrix of different sources thatyou're going to use for your
children's college education,and some of that can be on the
child's shoulders as well.
Some of that can be on thechild's shoulders as well, but
just making sure that theyunderstand what is the range
(08:46):
that you are willing tocontribute toward their
education, because, especiallyat the undergraduate level,
there aren't a lot of federaloptions to get you know, safe,
cheap money for school.
It's going to come fromsomewhere else, and I know so
many parents that are justheartbroken of the amount of
loans that they may have to takeout if they really want their
(09:07):
kids to be able to attendparticular universities Right.
Speaker 3 (09:10):
Right?
No, I think that's that's greatadvice to for.
To keep them, for folks to keepin the back of their head.
Is that as you are goingthrough the process, and if
you're already through theprocess, it's like all right.
Well, how do you figure out howyou're going to help if you
want to?
I know a lot of parents do Noteverybody does but a lot of
parents do help their kidsoffset the loans that they had
(09:32):
to take, and there's somebenefit of taking loans right.
Speaker 1 (09:35):
It helps build credit for the kids themselves, but
being mindful of how much andwhat does that look like, and
what kind of lifestyle not onlyfor your kids but for yourself
that you want to live in later,yeah, I also see a lot of
families, if they have thebandwidth, the children will
(09:56):
take out loans in their own namewhile they're in school and the
family will pay them off andthen the child will be put on a
payment plan through a familyloan.
I see that with a lot of myclients and when we're doing
transition planning because Iprimarily help attorneys figure
out either another career thatthey might want to explore that
maybe doesn't pay what theircurrent lawyer salary is, or
(10:18):
choosing to practice lawdifferently, which also often
comes with a pay cut when we'retrying to figure out where are
the levers that we can pull interms of adjusting, you know
what income is needed to supportyour lifestyle.
Being able to take a pause on afamily loan is very different
than being able to take a pauseon a loan that's held by a bank
or a loan that's held by thefederal government.
(10:39):
So, to the extent you know,your listeners are of the means
where they are able to alleviatesome of the immediate stress
that their kids might be feelingfrom their student loan debt
load and be able to shoulderthat be getting you know through
their student loan provider andhave that be how they kind of
pay for their education on atimetable that makes more sense
(11:10):
for their career and for theirfinancial growth.
Speaker 3 (11:12):
Yeah, I think that's.
I think that's an importantthing to know and for the folks
listening, like, if you're notin that space or that you don't
have that ability, there's noshame in that.
Right, that is not a commonthing.
It is something that lots ofpeople do do, but also other
folks don't, and that's okay.
But I think the most importantthing to take away from this
(11:33):
first part of the conversationis just to start having
conversations.
Right, have conversations, Ithink you said, frequently, and
start early and don't stop.
In terms of, but you also haveto see I think this is something
like in my own experience, likeas a Gen Xer and having kids
(11:53):
who are, I guess, like the righton the cusp, millennial and Gen
Z is that their thought aboutmoney and the future is
different.
Right, in terms of like economyand inflation and what
long-term life looks like, theyhave a different viewpoint than
we do.
Speaker 1 (12:11):
Yeah, they certainly have a lot less confidence that
things are going to go as well,as many of us always just kind
of assumed that they would,because that is what we had seen
previously Right right.
Speaker 3 (12:24):
How are you taking what you teach and living that
in your life?
Speaker 1 (12:28):
Oh gosh.
So I am naturally an optimist.
I also am of Generation X.
I snuck in there with a 1979birthday.
Well welcome.
I've been here the whole time,Jay.
Speaker 3 (12:43):
The whole time.
Speaker 1 (12:45):
But, you know, I think what I've been seeing,
primarily in my younger clients,is a really much stronger
entrepreneurial spirit and amuch more openness to
non-traditional career paths.
Now, granted, I work primarilywith attorneys, but the
attorneys that I work with areoften interested in pursuing
something outside of the law, orat least outside of the typical
(13:09):
large law firm.
Partner in a law firm workthere for 45 years trajectory,
and so I think what I've seen insome of the younger generations
is that they are much more opento a little bit more risk and
aligning their spending andtheir income generation with the
other lifestyle values thatthey carry right.
(13:29):
It's not worth it to them to gowork somewhere where they're
going to have to kill themselves, you know, burn out, suffer
immense amounts of anxiety andstress and overwhelm in order to
just be able to get a paycheck.
I think some of the priorgenerations saw those careers
and those paychecks as kind ofthe top of the mountain,
(13:49):
regardless of the price that hadto be paid for it, and I just
don't see that with the youngergenerations, which I think is
great.
It does mean that we need to beeven more mindful of how we're
allocating those spendingresources right, if we're not
going to be going after you knowthe top tier salaries you know
in your industry, that meansthat your lifestyle might also
(14:13):
look a little different and weneed to be prepared for that.
Lifestyle might also look alittle different and we need to
be prepared for that.
And so it's always interestingto me to kind of I think there
must be two parts of GenerationZ one that is like on TikTok and
on cruises and all flyingplaces, and the other one that
you know just wants to live offof the land and do homesteading
and, you know, write a blog.
Speaker 3 (14:33):
It's fascinating to me, I agree.
I agree it's interesting, right, but I think every generation
has their own thing that they'reknown for for sure.
But I think I love thisconversation for the folks that
are listening because it's atopic I think that some people
think is taboo to talk about interms of like, how do you fund
things?
(14:53):
How do you pay off student debt?
What does that look like?
And it's just a toughconversation for people to get
into with their kids sometime.
So it's been helpful hearingkind of how you process that
with folks and I love the piecethat is like what do you want
your lifestyle to look like?
That's how you figure out howyou manage the debt.
Speaker 1 (15:13):
Absolutely.
Speaker 3 (15:14):
Yeah, so good.
What's one thing in your ownpersonal life, in your empty
nest journey how long have youbeen an empty nester?
Now it's relatively recent,yeah.
Speaker 1 (15:25):
It is relatively recent.
Our two youngest we have, thetwins are the youngest of our
kids.
They graduated high school in2021.
And I would say we haveofficially been empty nesters
since spring of 2022.
So that was when everyone hadtheir own place, was off on
their own adventures, and myhusband and I decided to begin
(15:49):
our next phase of life as emptynesters and as future vineyard
owners here in Asheville, NorthCarolina.
Speaker 3 (15:57):
Yeah, Entrepreneurial , and that's what I think I love
about your story too.
Like I'm glad we talked aboutwhat you do to help people, but
your story is fascinating aswell because you're kind of
running it in parallel, Likeyour kids are trying to figure
out what they want to do withthe rest of your life and you've
you're doing that right.
Your husband is off learningabout how to become a vineyard
owner and you have pivoted intorunning your own company.
(16:21):
You got out of what you weredoing before, so I'd love to
hear a little bit more aboutthat journey for folks so they
understand like, yeah, you canget to a certain point in life
and pivot and it's okay.
Speaker 1 (16:33):
Yeah, it was, you know.
And Jay, you and I have talkedabout this a little bit.
You know offline because Jayand I are friends in real life,
and you know the empty nestphase.
I had been preparing for itmentally and strategically for
probably a decade leading up tomy twin boys, you know, kind of
getting ready to graduate fromhigh school.
(16:53):
I had the boys when I was inlaw school.
They were a surprise.
It was a surprise that they weretwins, and I basically spent
the first part of my career justtrying to keep my head above
water as a single mom.
I had not met my husband yet,and so there was just a lot of
stress for me and overwhelm as apracticing attorney in
(17:13):
Washington DC running a family,trying to just be a good lawyer
at my firm and then at thegovernment.
And then I did meet my husbandwhen my kids were in their teen
years.
My husband's children werealready, you know, off, were
already grown and flown, as yousay, and so you know, we were a
bit of a mixed family for alittle while, but we always knew
(17:35):
that when the boys kind of wentoff and started on their own
lives, that we wanted to have asecond chapter.
My husband is a 30-year nowretired Army veteran.
So he put in a lot of time andenergy and effort and heart into
serving this country part intoserving this country and he
(18:01):
wanted to do something forhimself but also just something
completely different in thatnext phase of life and I knew I
didn't want to be a lawyer.
So I said I got to get out ofhere and I got to fix this money
stuff, because being a lawyerand living a lawyer lifestyle is
expensive.
I graduated with over $200,000of student loans myself and so,
you know, kind of digging myselfout of that hole, creating
(18:21):
enough prosperity between me andmy husband that we would feel
comfortable on taking this nextleap together.
I think that was, you know,partly about his appreciation
that risk is important for life,mixed with my pessimism as a
lawyer of what, all the thingsthat could go wrong and we make
a great team.
(18:42):
We never agree on anything butwe come out with a good
compromise somewhere in themiddle between you know just
completely.
You know never doing anythingand doing all the things.
But so part of my journey wasalso figuring out what I wanted
to do if I didn't want to be alawyer anymore and that was a
bit of an existential crisis.
I think lawyering is kind ofone of those careers that you go
(19:05):
to law school, you become anattorney and it's kind of what
you're supposed to do for therest of your life.
It is a profession, it is apractice, it is meant to be done
for decades and I just didn'tlove it after a while and that
terrified me because I wasn'tsure what else I would do.
I thought I only had to makeone decision when I was in
college of what I wanted to dowith the rest of my life.
Speaker 3 (19:25):
Be done with it.
Yeah, done, check that off thelist.
Speaker 1 (19:27):
Right, never have to make that decision again.
And then it reared its uglyhead about 10 years into my
practice, and so I did end upfinding this niche in the
financial industry as anaccredited financial counselor.
I love what I do because I usedto work at the Securities and
Exchange Commission and I nolonger do anything with respect
to investments.
(19:48):
I don't advise on anysecurities products.
I'm not allowed to touch them.
It's great.
I don't do anything with taxplanning, insurance, estate
planning.
I help people with all of thebasic money management skills
that I wish I had had when I hadstarted my professional career.
We won't talk about what myfinancial position would have
been had.
(20:08):
I had these skills earlier on,when I was really making money,
but learning them gave me what Ineeded to feel comfortable that
I could leave that professionand I could do something else
that maybe wasn't as lucrativebut was much more aligned with
how I wanted to live my life,and so becoming an entrepreneur
running a business that is 100%remote, that I can do from
(20:29):
anywhere in the world, was partof my value system.
Speaker 3 (20:34):
It was part of my value system no-transcript with
(21:09):
both of you, because obviouslyyou're doing it together but
separately, like together butseparate, kind of like.
What's one thing that you'velearned about yourself this past
year?
Speaker 1 (21:21):
Well, one thing that I've learned is, as much as I
love variety and adventure andexcitement, I do enjoy having a
community, and when we firstwent off on our emptiness
journey, we had been living inthe DC area, in the Washington
DC metro area, for I had beenthere for nearly 20 years and I
(21:44):
had a strong community offriends.
You know I had worked atmultiple places in the area.
I knew all the restaurants.
You know I knew all theneighborhoods.
I knew how to avoid traffic.
You know, I knew all theneighborhoods, I knew how to
(22:12):
avoid traffic.
And after the boys went off tohigh school, my husband and
every morning, or at least everyweek, in a different city.
It was very exciting to be ableto travel around when we hadn't
been able to travel for so long,see people we hadn't seen, see
places I had never imagined thatI would get a chance to see.
But I also craved being able tosee the same faces over and
(22:33):
over again and I didn't thinkthat I would miss that as much
as I did.
And so this year we officiallyrelocated to Asheville, north
Carolina, which is the mostlovely mountain town in Western
North Carolina, and it reallyhas been nice starting to meet
(22:53):
people and see them a coupletimes a month and be able to
continue conversations that westarted earlier and I think I
had taken that for granted.
You know, kind of just livinglife the way that it is.
And then I loved the travelingaspect so much, but I also like
being able to come home and Ireally like being able to come
(23:15):
home here able to come home andI really like being able to come
home here.
Speaker 3 (23:21):
Yeah, yeah, how do you meet people?
That's like I think some emptynesters struggle with.
Like, yeah, this, what I hear alot is like their friends were
friends from the kids schoolright and with sports teams or
or the drama club or the band orwhatever.
Like that's how their friendgroups were formed over time and
then, as the kids go on tocollege, those friend groups
just naturally kind of justdissipate and so you're left
(23:42):
trying to figure out how do Imeet new people?
What does that look like?
So what's the strategy that youdo to make that happen?
Speaker 1 (23:49):
I've had this exact conversation with at least three
people over the past two weeks.
I think it's fascinating.
So now you're an expert Perfect, basically, because I've done
the research.
Also, I've been experimentingon how to meet people because I
loved moving to Asheville, butalso we didn't know anyone here.
This was a completely new cityfor us and my husband is kind of
(24:11):
busy with his stuff and hisworld is a little separate from
mine in terms of, you know heneeds to be in, you know,
immersed in the vineyard world.
So he wants to be connected tovineyard owners and people in
you know, the farming industryand otherwise, whereas you know
I have a strong connection tolawyers, I have a strong
(24:32):
connection to the financialindustry, but none of those
things are particularly strongin Asheville.
Speaker 3 (24:40):
That is not what Asheville is known for.
Speaker 1 (24:42):
No that's right.
That is not the, that is notthe city industry here in
Asheville.
And so I, you know it.
It reminded me I was actuallyvisiting my.
I was visiting my father, youknow, just for a weekend up in
New Jersey and we went to achurch picnic because he was
playing.
My father is a keyboardist.
He has been my entire life, sohis band goes around and plays,
(25:04):
you know, at different venues.
So good, and it was a strawberryfestival and everyone there had
kids.
It was all.
The entire event was basicallyan excuse for people to do
something with their children,and it made me realize that so
much of our society is based onpeople being able to share the
(25:24):
experience of their childrenwith other people who have
children.
Right, all of our socialactivities are surrounded by
that.
The school structure surroundsthat.
That's how you meet people,right?
They're people who havechildren around the same age as
yours and when that is no longerthe cornerstone of your
existence.
There aren't a lot of pre-madestructures to help you have
(25:44):
those interactions with peoplethat really build bonds.
And so you know I was thinkingabout, even when I was in DC, I
was too busy to hang out withthe other parents because they
had different schedules than Idid.
It worked a lot, but I was on acompetitive karaoke team
because that is a.
Speaker 2 (26:02):
Thing.
Speaker 1 (26:03):
It exists, and DC is famous for having intramural
leagues for everything Bocceball, oh, absolutely, you know,
whatever Competitive karaoke andit was how I made so many
friends in the DC area.
Some had kids, some didn't.
You know some I have no ideawhat they even did for work,
which is a wonderful sign comingfrom that, from that
(26:25):
environment.
But so I told myself I need tofind places where adults want to
hang out together doingsomething, you know, where we
share an interest, andpreferably in person.
Because I do a lot on Zoom.
I could.
My whole business is on Zoom,I'm on Zoom all day.
I need that in-person energy and, if you can't tell from this
(26:46):
podcast, I'm fairly extroverted,naturally.
So I like to host, I like to bearound people.
I think I run a pretty goodparty, and so I started looking
around for groups where peoplewould just kind the staff and
the owners about.
You know what kind of maybefoodie groups that are around,
(27:07):
or wine groups, what kind ofvineyards people like to go
visit, and so we started doingthat.
And most recently, as Imentioned, I'm kind of a finance
nerd.
(27:27):
I hosted a local meetup for myChoose FI group here in
Asheville.
Local meetup for my Choose FIgroup here in Asheville.
Choose FI is a great resourcefor anyone who's interested in
the financial independenceretire early movement and they
have local groups in most majorcities of people who are
interested in financialindependence.
And so I said, hey, can we havea meetup?
(27:48):
I see that there's a Facebookgroup and it looks like there
hasn't been much activity overthe summer.
I would be happy to host, andso I did, and I made some new
friends and I could tell thatthey're my people because one of
them had spent last summerrenovating a camper van to take
a camping van, a camper vanadventure around the US.
I said that's it.
(28:08):
This is amazing, we can talkall about it.
We just put our RV in storageafter having traveled the US for
the past two years.
Let's chat, so you know.
I think that finding one of thethings that I love about social
media is it makes it easier forus to find people who have
similar interests and findingthose groups.
(28:29):
You just need someone who'swilling to be a host of some
sort.
I am often willing to stand inthat position, and so it gets
easier for me to kind of makefriends, meet people, because
I'm willing to create the spacefor people to come and, you know
, kind of enjoy each other'scompany and then do it all again
(28:51):
the next month.
Speaker 3 (28:53):
So good and like, I know there's folks listening who
are introverts, who may nothave the same energy or desire
to do it, and it's alsoimportant for them to do it.
I often talk about how canempty nesters who are
introverted find other people,and I think it's just a matter
(29:16):
of like looking at groups, likefinding something that works for
you.
Like tonight, uh, I amextroverted but I have an
introverted tinge to me.
But I'm going to a men'swellness barbecue kickoff for an
organization that's starting amen's wellness program and if
you didn't know, like, obviouslyI believe in men's wellness, so
(29:36):
, but I'm like I don't knowanybody who's going, uh, and it
takes me a little bit to buildup my extrovertedness, and so it
is a challenge for me to dothat.
So that's why I'm going andthat maybe, for the folks who
are like super introverted, islike, take that away as like a
little bit of like, you can doit.
Right, you just have to takethe first step and decide that
(29:58):
that's something you want to do.
Speaker 1 (29:59):
Yes, and I often find if you are particularly
introverted, always start with aconversation with whoever is
hosting.
They're very interested inmaking sure and invested in
people having a good time atwhatever the event is Such a
great tip.
So start there.
That's going to be an easytarget.
They're going to make it easyfor you to have a conversation
(30:22):
and they might introduce you tosomeone nice or someone who can
then, you know, kind of serve asthe next conversation that you
have.
And so you know, that's always.
You know, I am, I am veryextroverted, but I can also be a
little nervous and shy when I'm, you know, first warming up to
a space, and I always used tochat up bartenders when I would
(30:42):
be at an event, I would always,you know, chat up whoever had,
whoever was responsible for theinvitation, because they have to
be nice to you.
It's literally their job.
Speaker 3 (30:50):
As the host.
As the host that's a greatpoint, right the host is the
person that you can actuallyhave your first conversation
with.
I love that as you continueyour emptiness journey.
What's one thing you haven'tdone yet that you've always
wanted to do?
Speaker 1 (31:07):
So I have the typical you know kind of travel
destinations that I haven'tgotten to yet and, sadly,
because my husband was in thearmy for 30 years, he's pretty
much been everywhere, so it'sreally hard for me to get him as
excited about, you know, goingto Japan.
He's like, yeah, it's reallynice there.
(31:30):
I'm like that is not theresponse I was looking for.
I was looking for a yes.
Oh my gosh, we should totallygo and then tell me later that
you know all the places to go.
But I think I'm actually rightnow on a journey to figure out
what is the next big thing thatI want to get done.
A lot of the things that I hadanticipated I would do in my
(31:56):
life, some things that I wassurprised by, but I think for me
right now it really is aboutbuilding community and creating
a space here in a new area ofthe country where I can feel as
comfortable and as loved and asloving toward this community as
I have been in my priorcommunities, and that's going to
take some work to build andsome time, and so I'm giving
(32:24):
myself a little bit of grace tobegin building that and to
hopefully be able to enjoy itfor the rest of this phase.
Speaker 3 (32:27):
Oh, so good.
Building community I thinkthat's an underrated skill too
is like how do you build acommunity, especially if you go
someplace new, because that is afear of empty nesters.
Is like I want to move, I wantto move closer to the kids, or I
want to move someplace totallydifferent, but they're not quite
sure how to go about buildingcommunity.
Speaker 1 (32:47):
I'm not either, so if your listeners have tips,
please send them in.
I'm accepting suggestions.
Speaker 3 (32:54):
Well, yes, so you had mentioned a couple of things
that you've done so far.
Right, reaching out to groups,figuring out what it is, but
that's it.
I think it's just taking thetime to figure out, like, what
is happening in my community andmeet up works and Eventbrite
works.
Those are some places you cango and see what's going on.
No-transcript, take that as achallenge.
(33:37):
What are you not saying yes toright now, jessica?
Speaker 1 (33:41):
Well, right now I actually I just went through
this is a little bit like deepin my business I just went
through a quarterly planningsession with one of my business
coaches and I had to take someof my anticipated projects off
of my Q4 list of things to dowhich was very underwhelming for
(34:02):
me.
As you know, Jay, I have aproblem with being underwhelmed
and I'm super achievementoriented.
It's one of the things thatreally gets me up and going.
I think it's why I've done alot of things that I have set
out to do in my life.
That being said, my newer goalsare less about specific
achievements and more about, youknow, what our coach describes
(34:23):
as the infinite game.
And so working on my infinitegames, I think, is the skill
that I need to work on for therest of my life.
But so part of what I'm sayingno to is being overwhelmed for
this next kind of holiday season.
Whereas I would normally try topile a lot of stuff on I am.
I am not saying yes to a lot ofextra things that I would be
(34:46):
excited to tackle but wouldprobably ruin this season for me
.
Speaker 3 (34:51):
All right, so you went the opposite way.
It's not not what you're sayingyes to, not saying yes to, but
you're like I got to put thebrakes on here, which is fine
too, for sure Interesting,You're slowing down.
Speaker 1 (35:03):
I am.
You know I've done.
I may possibly be in adifferent mode than I think some
people find themselves.
I am not necessarily someonewho needs to be pushed to do
more.
I am someone who needs to bepulled back from doing too much,
(35:24):
and I think a lot of that justcomes from the world that I was
in for a number of years.
A lot of attorneys are likethis.
They are overly achievementfocused.
They will burn themselves outbefore giving up, regardless of
whether the goal is actuallysomething that they want at the
end of the day, and that hasbeen something that I have been
(35:46):
working on now as anentrepreneur, where those same
tendencies get carried alongright Wherever.
What do they say?
Wherever?
Wherever you go, there you are.
That's right, regardless ofwhat career I'm in.
Hey, there I am.
Look at me.
I am, like you know, nose tothe grindstone, going really
(36:06):
hard all the time.
I've had a very good year sofar and starting to think
through where can I take my footoff of the gas?
To not recreate the very stress, overwhelm and burnout that I
created in the last phase of mylife.
I'm trying to let this emptynest phase feel different than
(36:32):
the earlier phases be feeldifferent than the earlier
phases, and that's a skill forme in terms of, you know, kind
of not treating it like theearlier parts of my life where I
just had to get everything doneand get through it so that I
could be at the end.
I don't actually want to be atthe end of this phase, Jay.
That's a little scary.
Speaker 3 (36:47):
Though we know it's coming right.
That was a conversation I hadthe other day with someone
interviewing a guest.
Like you know it's coming, justlike you know empty nesting
coming.
You know the end is coming, buthow do you want to live your
life between now and then?
And I think that's one of thethings I try and impress upon
people is that every day is achance to live your life the way
(37:10):
you want to live it.
You just have to say yes to it.
Just have to say yes to it.
Just have to say yes to it.
Before I let you go finish thissentence for me, empty nest
happiness is.
Speaker 1 (37:24):
Ooh, empty nest happiness, it is community.
Speaker 3 (37:31):
It's community circling back to community.
Yeah, I love that.
Emptiness happiness iscommunity.
It's community Circling back tocommunity.
Yeah, I love that.
Emptiness happiness iscommunity.
So good.
Speaker 1 (37:37):
Sometimes that community is just my husband and
sometimes that community is alittle bit larger.
Speaker 3 (37:44):
So good, so good.
All right, before you leave,where can people find you, in
case they know an attorney whomay need your services?
Speaker 1 (37:53):
Absolutely.
You can find me on LinkedIn.
I'm prolific on there,jessicamedinallc, and my website
is wwwJessicaMedinaLLCcom.
There are lots of resources andblog articles for how to
approach any type of careertransition that folks may be
interested in.
If you feel like you might betaking a pay cut, then there's
(38:15):
some strategies to help youthink through what that could
look like, whether you're anattorney or not.
Speaker 3 (38:19):
Oh, so good.
Thanks so much for being here.
Totally enjoyed theconversation and I will see you
around, I'm sure.
Speaker 1 (38:25):
Yeah, thanks, jay.
Speaker 2 (38:29):
Are you ready to start living and enjoying your
empty nest years?
If so, head over tojasonramsdencom and click work
with me to get the conversationstarted.
This Empty Nest Life is aproduction of Impact.
One Media LLC.
All rights reserved.
I help people with all of the basic money
management skills that I wish Ihad had when I had started my
professional career.
Learning them gave me what Ineeded to feel comfortable that
I could leave that professionand I could do something else
that maybe wasn't as lucrativebut was much more aligned with
how I wanted to live my life.
Speaker 2 (00:19):
Welcome to this Empty Nest Life.
Join Jay Ramsden as he leadsyou on a transformative journey
through the uncharted seas ofmidlife and empty nesting.
If you're ready to embark onthis new adventure and redefine
your future, you're in the rightplace.
Here's your host, the EmptyNest Coach, Jay Ramsden.
Speaker 3 (00:40):
Jessica Medina.
Welcome to the show.
It's so good to see you, myfriend.
Speaker 1 (00:44):
Thanks for having me, Jay.
I'm excited for ourconversation.
Speaker 3 (00:47):
You know why I'm excited?
It's because, well, you havethis wonderful business who kind
of helps attorneys figure outmoney.
But I would imagine that theystockpile a lot of debt too
going into the law school.
And I think it would be greatfor my folks whose kids are
either in college still or justout of college.
(01:08):
It's like, how do we figurethat stuff out, the money, like
what's in your brain?
Tell me what goes on when youare talking to your people.
I'm sure there's some benefitfor my folks.
Speaker 1 (01:18):
Yeah, a lot of my clients have either recently
graduated law school or maybeare in their first 10 years of
practice, and many of them arestill carrying a mortgage-sized
debt from that law schoolexperience, and so one of the
things that I specialize in ishelping people deal with that
level of student loan debt.
The typical American graduatehas about $35,000 of student
(01:41):
loan debt, whereas the typicallaw school graduate has over
$145,000 of student loan debt,whereas the typical law school
graduate has over $145,000 ofstudent loan debt.
So, as you can imagine, thestrategies for tackling those
different types of debts arevery different, and so I work
with my clients a lot on makingsure that they are putting their
student loan debt in the rightpriority order of all of their
(02:02):
financial goals, and I thinkthis is something that a lot of
you know younger professionalscoming out of school really
struggle with, because so muchof the personal finance world is
really beating them over thehead about making sure that they
pay off those loans as quicklyas possible.
It's a responsibility thatthey've taken on, that that's
what their career is for, and ifthey can't do it, then there's
(02:22):
something wrong with them, andso, to the extent that you know
there are parents that are alsoinvolved in this dynamic.
They also may have brought someideas about debt overall
student loan debt in particularand so I really love helping
people maneuver the emotionaljourney of working on paying off
their student loans and makingsure that it doesn't overshadow
(02:44):
other financial goals they mayhave for their life.
Speaker 3 (02:47):
Oh, so good.
Like I'm curious, what is thelike number one emotional
concern that people have when itcomes to tackling debt?
Speaker 1 (02:57):
So debt, I think, overall has a lot of shame
attached to it, because it'salmost a sign of
irresponsibility.
Right, debt for many peopleappears to mean that you didn't
have the resources when youneeded it and you couldn't wait
right.
So there's all of this mix ofoh, if I had been a better
(03:20):
steward with my money, or if Ihad been a better person, I
wouldn't have had to have takenout the debt in the first place.
You're automatically assumed tobe behind the starting line if
you have to start from anegative.
Now I have a lot of thoughts onhow debt is treated in this
country and we don't have timeon this podcast to get into all
of them.
Speaker 3 (03:40):
It could be another show, that's right.
Speaker 1 (03:42):
But there are different types of debt, and I
think that, sadly, many peoplelump all of the different types
of debt together and put themunder the category of evil,
terrible for your financialhealth, an irresponsible
decision and something that youhave to take care of immediately
and as quickly as possible.
Specifically with respect tostudent loan debt, this is a
(04:03):
particular type of debt withspecial rules that apply,
especially if we're thinkingabout the federal student loan
debt world.
There are just different rulesin terms of when you have to pay
it back, what the terms aregoing to be, what programs are
available in terms of relieffrom this type of debt, and so I
think it's very important tocarve this out from the more
(04:25):
general high-interest debtconversation, or even
low-interest debt conversation,because there are so many twists
and turns to the student loanworld, and anyone who's been
paying attention for the pastfour years knows that the
student loan world is in atumult right now.
We're recording this podcast infall of 2024 and student loans
(04:46):
are on the docket for theSupreme Court.
That's crazy.
Why is the Supreme Courttalking about student loan debt?
But that's the world that we'rein right now, and so I help my
clients maneuver that reallycomplicated environment and be
able to take advantage ofwhatever relief programs may be
out there and also just helpthem understand that whatever
(05:07):
emotions they're having aboutdebt could be separated from
some of the numerical strategiesthat we can use to tackle it
over their financial journey.
Speaker 3 (05:16):
Yeah, I think that's a great point, jessica, because
I think oftentimes the averagehuman in America right takes on
debt for certain reasons.
The average human in Americaright takes on debt for certain
reasons, but what they forget islike wealthy people leverage
debt to make investments rightin property and other things and
businesses to actually getwealthier.
So it's not a bad thing.
(05:37):
It's just like how do youapproach it and I think the
mindset piece is key.
It's like sometimes we have toright, especially student debt
for college.
Speaker 1 (05:46):
Exactly this is for education.
This is to provide moreopportunities, and you know, I
have a very soft spot for peoplewho felt like they were in a
position where they had to takeout a lot of debt in order to
create those opportunities forthemselves.
I do have clients who have nostudent loan debt.
They never did.
Maybe their family was able tohelp out, which is a wonderful,
wonderful privilege to be ableto start your career with a leg
(06:09):
up and start at zero, as opposedto in the negative.
But it's that very education,especially for my clients who
are primarily practicingattorneys it's that education
that opens the doors to the typeof financial life that really
gives them everything thatthey've been looking for Right.
Speaker 3 (06:27):
So if you had some advice for the people out there
it's going to be parents who arelistening who may be trying to
help their kids right, getthrough like, how are you going
to tackle this?
Because it's a conversation, Ithink that needs to be had and
it's an uncomfortable one forsure.
I think that needs to be hadand it's an uncomfortable one,
for sure.
Obviously, attorneys who areout there with student law debt
(06:48):
are like they're working towardsto pay that off.
They're maybe not having thatsame conversation with parents,
but I'm sure you have some tipsor ideas to help folks out there
with that conversation.
Speaker 1 (06:58):
No, absolutely, and, like with many things, we like
these conversations to startearly and to occur often.
I think undergraduate educationis actually one of the most
difficult things to pay for inthis country.
I have the privilege of workingwith a lot of folks who carry a
vast amount of graduate schooldebt.
That's because federal loanswill pay for your entire
(07:20):
graduate school level education.
They'll pay for the entire costof tuition, including room and
board.
It's not the case that you canget federal loans at the
undergrad level to that extent,and that creates a real bind for
parents who want to send theirchildren to the best school that
they got into, whether or notthat school wants to help pay
for that experience for thechild.
(07:42):
And so, with my parent clients,we often have conversations
about where does college savingssit on your list of priorities?
Are you someone who is carryinga lot of student debt yourself
and you don't want your childrento have that experience?
Are you already doing well onyour own financial goals in
terms of preparing for yourretirement, in terms of if
(08:03):
you're trying to move to alarger house, being ready to
take on those additionalresponsibilities?
And so I think it's importantto have conversations with
children early about what familyresources may be available,
because that's going to be thebulk of where their college gets
paid for, unless the kids areable to seek out merit
scholarships, unless the schoolis a type of school that offers
(08:25):
a lot of aid to families thatmight not otherwise qualify for
it because of their incomes.
And so I think it's reallyimportant to come up with the
matrix of different sources thatyou're going to use for your
children's college education,and some of that can be on the
child's shoulders as well.
Some of that can be on thechild's shoulders as well, but
just making sure that theyunderstand what is the range
(08:46):
that you are willing tocontribute toward their
education, because, especiallyat the undergraduate level,
there aren't a lot of federaloptions to get you know, safe,
cheap money for school.
It's going to come fromsomewhere else, and I know so
many parents that are justheartbroken of the amount of
loans that they may have to takeout if they really want their
(09:07):
kids to be able to attendparticular universities Right.
Speaker 3 (09:10):
Right?
No, I think that's that's greatadvice to for.
To keep them, for folks to keepin the back of their head.
Is that as you are goingthrough the process, and if
you're already through theprocess, it's like all right.
Well, how do you figure out howyou're going to help if you
want to?
I know a lot of parents do Noteverybody does but a lot of
parents do help their kidsoffset the loans that they had
(09:32):
to take, and there's somebenefit of taking loans right.
Speaker 1 (09:35):
It helps build credit for the kids themselves, but
being mindful of how much andwhat does that look like, and
what kind of lifestyle not onlyfor your kids but for yourself
that you want to live in later,yeah, I also see a lot of
families, if they have thebandwidth, the children will
(09:56):
take out loans in their own namewhile they're in school and the
family will pay them off andthen the child will be put on a
payment plan through a familyloan.
I see that with a lot of myclients and when we're doing
transition planning because Iprimarily help attorneys figure
out either another career thatthey might want to explore that
maybe doesn't pay what theircurrent lawyer salary is, or
(10:18):
choosing to practice lawdifferently, which also often
comes with a pay cut when we'retrying to figure out where are
the levers that we can pull interms of adjusting, you know
what income is needed to supportyour lifestyle.
Being able to take a pause on afamily loan is very different
than being able to take a pauseon a loan that's held by a bank
or a loan that's held by thefederal government.
(10:39):
So, to the extent you know,your listeners are of the means
where they are able to alleviatesome of the immediate stress
that their kids might be feelingfrom their student loan debt
load and be able to shoulderthat be getting you know through
their student loan provider andhave that be how they kind of
pay for their education on atimetable that makes more sense
(11:10):
for their career and for theirfinancial growth.
Speaker 3 (11:12):
Yeah, I think that's.
I think that's an importantthing to know and for the folks
listening, like, if you're notin that space or that you don't
have that ability, there's noshame in that.
Right, that is not a commonthing.
It is something that lots ofpeople do do, but also other
folks don't, and that's okay.
But I think the most importantthing to take away from this
(11:33):
first part of the conversationis just to start having
conversations.
Right, have conversations, Ithink you said, frequently, and
start early and don't stop.
In terms of, but you also haveto see I think this is something
like in my own experience, likeas a Gen Xer and having kids
(11:53):
who are, I guess, like the righton the cusp, millennial and Gen
Z is that their thought aboutmoney and the future is
different.
Right, in terms of like economyand inflation and what
long-term life looks like, theyhave a different viewpoint than
we do.
Speaker 1 (12:11):
Yeah, they certainly have a lot less confidence that
things are going to go as well,as many of us always just kind
of assumed that they would,because that is what we had seen
previously Right right.
Speaker 3 (12:24):
How are you taking what you teach and living that
in your life?
Speaker 1 (12:28):
Oh gosh.
So I am naturally an optimist.
I also am of Generation X.
I snuck in there with a 1979birthday.
Well welcome.
I've been here the whole time,Jay.
Speaker 3 (12:43):
The whole time.
Speaker 1 (12:45):
But, you know, I think what I've been seeing,
primarily in my younger clients,is a really much stronger
entrepreneurial spirit and amuch more openness to
non-traditional career paths.
Now, granted, I work primarilywith attorneys, but the
attorneys that I work with areoften interested in pursuing
something outside of the law, orat least outside of the typical
(13:09):
large law firm.
Partner in a law firm workthere for 45 years trajectory,
and so I think what I've seen insome of the younger generations
is that they are much more opento a little bit more risk and
aligning their spending andtheir income generation with the
other lifestyle values thatthey carry right.
(13:29):
It's not worth it to them to gowork somewhere where they're
going to have to kill themselves, you know, burn out, suffer
immense amounts of anxiety andstress and overwhelm in order to
just be able to get a paycheck.
I think some of the priorgenerations saw those careers
and those paychecks as kind ofthe top of the mountain,
(13:49):
regardless of the price that hadto be paid for it, and I just
don't see that with the youngergenerations, which I think is
great.
It does mean that we need to beeven more mindful of how we're
allocating those spendingresources right, if we're not
going to be going after you knowthe top tier salaries you know
in your industry, that meansthat your lifestyle might also
(14:13):
look a little different and weneed to be prepared for that.
Lifestyle might also look alittle different and we need to
be prepared for that.
And so it's always interestingto me to kind of I think there
must be two parts of GenerationZ one that is like on TikTok and
on cruises and all flyingplaces, and the other one that
you know just wants to live offof the land and do homesteading
and, you know, write a blog.
Speaker 3 (14:33):
It's fascinating to me, I agree.
I agree it's interesting, right, but I think every generation
has their own thing that they'reknown for for sure.
But I think I love thisconversation for the folks that
are listening because it's atopic I think that some people
think is taboo to talk about interms of like, how do you fund
things?
(14:53):
How do you pay off student debt?
What does that look like?
And it's just a toughconversation for people to get
into with their kids sometime.
So it's been helpful hearingkind of how you process that
with folks and I love the piecethat is like what do you want
your lifestyle to look like?
That's how you figure out howyou manage the debt.
Speaker 1 (15:13):
Absolutely.
Speaker 3 (15:14):
Yeah, so good.
What's one thing in your ownpersonal life, in your empty
nest journey how long have youbeen an empty nester?
Now it's relatively recent,yeah.
Speaker 1 (15:25):
It is relatively recent.
Our two youngest we have, thetwins are the youngest of our
kids.
They graduated high school in2021.
And I would say we haveofficially been empty nesters
since spring of 2022.
So that was when everyone hadtheir own place, was off on
their own adventures, and myhusband and I decided to begin
(15:49):
our next phase of life as emptynesters and as future vineyard
owners here in Asheville, NorthCarolina.
Speaker 3 (15:57):
Yeah, Entrepreneurial , and that's what I think I love
about your story too.
Like I'm glad we talked aboutwhat you do to help people, but
your story is fascinating aswell because you're kind of
running it in parallel, Likeyour kids are trying to figure
out what they want to do withthe rest of your life and you've
you're doing that right.
Your husband is off learningabout how to become a vineyard
owner and you have pivoted intorunning your own company.
(16:21):
You got out of what you weredoing before, so I'd love to
hear a little bit more aboutthat journey for folks so they
understand like, yeah, you canget to a certain point in life
and pivot and it's okay.
Speaker 1 (16:33):
Yeah, it was, you know.
And Jay, you and I have talkedabout this a little bit.
You know offline because Jayand I are friends in real life,
and you know the empty nestphase.
I had been preparing for itmentally and strategically for
probably a decade leading up tomy twin boys, you know, kind of
getting ready to graduate fromhigh school.
(16:53):
I had the boys when I was inlaw school.
They were a surprise.
It was a surprise that they weretwins, and I basically spent
the first part of my career justtrying to keep my head above
water as a single mom.
I had not met my husband yet,and so there was just a lot of
stress for me and overwhelm as apracticing attorney in
(17:13):
Washington DC running a family,trying to just be a good lawyer
at my firm and then at thegovernment.
And then I did meet my husbandwhen my kids were in their teen
years.
My husband's children werealready, you know, off, were
already grown and flown, as yousay, and so you know, we were a
bit of a mixed family for alittle while, but we always knew
(17:35):
that when the boys kind of wentoff and started on their own
lives, that we wanted to have asecond chapter.
My husband is a 30-year nowretired Army veteran.
So he put in a lot of time andenergy and effort and heart into
serving this country part intoserving this country and he
(18:01):
wanted to do something forhimself but also just something
completely different in thatnext phase of life and I knew I
didn't want to be a lawyer.
So I said I got to get out ofhere and I got to fix this money
stuff, because being a lawyerand living a lawyer lifestyle is
expensive.
I graduated with over $200,000of student loans myself and so,
you know, kind of digging myselfout of that hole, creating
(18:21):
enough prosperity between me andmy husband that we would feel
comfortable on taking this nextleap together.
I think that was, you know,partly about his appreciation
that risk is important for life,mixed with my pessimism as a
lawyer of what, all the thingsthat could go wrong and we make
a great team.
(18:42):
We never agree on anything butwe come out with a good
compromise somewhere in themiddle between you know just
completely.
You know never doing anythingand doing all the things.
But so part of my journey wasalso figuring out what I wanted
to do if I didn't want to be alawyer anymore and that was a
bit of an existential crisis.
I think lawyering is kind ofone of those careers that you go
(19:05):
to law school, you become anattorney and it's kind of what
you're supposed to do for therest of your life.
It is a profession, it is apractice, it is meant to be done
for decades and I just didn'tlove it after a while and that
terrified me because I wasn'tsure what else I would do.
I thought I only had to makeone decision when I was in
college of what I wanted to dowith the rest of my life.
Speaker 3 (19:25):
Be done with it.
Yeah, done, check that off thelist.
Speaker 1 (19:27):
Right, never have to make that decision again.
And then it reared its uglyhead about 10 years into my
practice, and so I did end upfinding this niche in the
financial industry as anaccredited financial counselor.
I love what I do because I usedto work at the Securities and
Exchange Commission and I nolonger do anything with respect
to investments.
(19:48):
I don't advise on anysecurities products.
I'm not allowed to touch them.
It's great.
I don't do anything with taxplanning, insurance, estate
planning.
I help people with all of thebasic money management skills
that I wish I had had when I hadstarted my professional career.
We won't talk about what myfinancial position would have
been had.
(20:08):
I had these skills earlier on,when I was really making money,
but learning them gave me what Ineeded to feel comfortable that
I could leave that professionand I could do something else
that maybe wasn't as lucrativebut was much more aligned with
how I wanted to live my life,and so becoming an entrepreneur
running a business that is 100%remote, that I can do from
(20:29):
anywhere in the world, was partof my value system.
Speaker 3 (20:34):
It was part of my value system no-transcript with
(21:09):
both of you, because obviouslyyou're doing it together but
separately, like together butseparate, kind of like.
What's one thing that you'velearned about yourself this past
year?
Speaker 1 (21:21):
Well, one thing that I've learned is, as much as I
love variety and adventure andexcitement, I do enjoy having a
community, and when we firstwent off on our emptiness
journey, we had been living inthe DC area, in the Washington
DC metro area, for I had beenthere for nearly 20 years and I
(21:44):
had a strong community offriends.
You know I had worked atmultiple places in the area.
I knew all the restaurants.
You know I knew all theneighborhoods.
I knew how to avoid traffic.
You know, I knew all theneighborhoods, I knew how to
(22:12):
avoid traffic.
And after the boys went off tohigh school, my husband and
every morning, or at least everyweek, in a different city.
It was very exciting to be ableto travel around when we hadn't
been able to travel for so long,see people we hadn't seen, see
places I had never imagined thatI would get a chance to see.
But I also craved being able tosee the same faces over and
(22:33):
over again and I didn't thinkthat I would miss that as much
as I did.
And so this year we officiallyrelocated to Asheville, north
Carolina, which is the mostlovely mountain town in Western
North Carolina, and it reallyhas been nice starting to meet
(22:53):
people and see them a coupletimes a month and be able to
continue conversations that westarted earlier and I think I
had taken that for granted.
You know, kind of just livinglife the way that it is.
And then I loved the travelingaspect so much, but I also like
being able to come home and Ireally like being able to come
(23:15):
home here able to come home andI really like being able to come
home here.
Speaker 3 (23:21):
Yeah, yeah, how do you meet people?
That's like I think some emptynesters struggle with.
Like, yeah, this, what I hear alot is like their friends were
friends from the kids schoolright and with sports teams or
or the drama club or the band orwhatever.
Like that's how their friendgroups were formed over time and
then, as the kids go on tocollege, those friend groups
just naturally kind of justdissipate and so you're left
(23:42):
trying to figure out how do Imeet new people?
What does that look like?
So what's the strategy that youdo to make that happen?
Speaker 1 (23:49):
I've had this exact conversation with at least three
people over the past two weeks.
I think it's fascinating.
So now you're an expert Perfect, basically, because I've done
the research.
Also, I've been experimentingon how to meet people because I
loved moving to Asheville, butalso we didn't know anyone here.
This was a completely new cityfor us and my husband is kind of
(24:11):
busy with his stuff and hisworld is a little separate from
mine in terms of, you know heneeds to be in, you know,
immersed in the vineyard world.
So he wants to be connected tovineyard owners and people in
you know, the farming industryand otherwise, whereas you know
I have a strong connection tolawyers, I have a strong
(24:32):
connection to the financialindustry, but none of those
things are particularly strongin Asheville.
Speaker 3 (24:40):
That is not what Asheville is known for.
Speaker 1 (24:42):
No that's right.
That is not the, that is notthe city industry here in
Asheville.
And so I, you know it.
It reminded me I was actuallyvisiting my.
I was visiting my father, youknow, just for a weekend up in
New Jersey and we went to achurch picnic because he was
playing.
My father is a keyboardist.
He has been my entire life, sohis band goes around and plays,
(25:04):
you know, at different venues.
So good, and it was a strawberryfestival and everyone there had
kids.
It was all.
The entire event was basicallyan excuse for people to do
something with their children,and it made me realize that so
much of our society is based onpeople being able to share the
(25:24):
experience of their childrenwith other people who have
children.
Right, all of our socialactivities are surrounded by
that.
The school structure surroundsthat.
That's how you meet people,right?
They're people who havechildren around the same age as
yours and when that is no longerthe cornerstone of your
existence.
There aren't a lot of pre-madestructures to help you have
(25:44):
those interactions with peoplethat really build bonds.
And so you know I was thinkingabout, even when I was in DC, I
was too busy to hang out withthe other parents because they
had different schedules than Idid.
It worked a lot, but I was on acompetitive karaoke team
because that is a.
Speaker 2 (26:02):
Thing.
Speaker 1 (26:03):
It exists, and DC is famous for having intramural
leagues for everything Bocceball, oh, absolutely, you know,
whatever Competitive karaoke andit was how I made so many
friends in the DC area.
Some had kids, some didn't.
You know some I have no ideawhat they even did for work,
which is a wonderful sign comingfrom that, from that
(26:25):
environment.
But so I told myself I need tofind places where adults want to
hang out together doingsomething, you know, where we
share an interest, andpreferably in person.
Because I do a lot on Zoom.
I could.
My whole business is on Zoom,I'm on Zoom all day.
I need that in-person energy and, if you can't tell from this
(26:46):
podcast, I'm fairly extroverted,naturally.
So I like to host, I like to bearound people.
I think I run a pretty goodparty, and so I started looking
around for groups where peoplewould just kind the staff and
the owners about.
You know what kind of maybefoodie groups that are around,
(27:07):
or wine groups, what kind ofvineyards people like to go
visit, and so we started doingthat.
And most recently, as Imentioned, I'm kind of a finance
nerd.
(27:27):
I hosted a local meetup for myChoose FI group here in
Asheville.
Local meetup for my Choose FIgroup here in Asheville.
Choose FI is a great resourcefor anyone who's interested in
the financial independenceretire early movement and they
have local groups in most majorcities of people who are
interested in financialindependence.
And so I said, hey, can we havea meetup?
(27:48):
I see that there's a Facebookgroup and it looks like there
hasn't been much activity overthe summer.
I would be happy to host, andso I did, and I made some new
friends and I could tell thatthey're my people because one of
them had spent last summerrenovating a camper van to take
a camping van, a camper vanadventure around the US.
I said that's it.
(28:08):
This is amazing, we can talkall about it.
We just put our RV in storageafter having traveled the US for
the past two years.
Let's chat, so you know.
I think that finding one of thethings that I love about social
media is it makes it easier forus to find people who have
similar interests and findingthose groups.
(28:29):
You just need someone who'swilling to be a host of some
sort.
I am often willing to stand inthat position, and so it gets
easier for me to kind of makefriends, meet people, because
I'm willing to create the spacefor people to come and, you know
, kind of enjoy each other'scompany and then do it all again
(28:51):
the next month.
Speaker 3 (28:53):
So good and like, I know there's folks listening who
are introverts, who may nothave the same energy or desire
to do it, and it's alsoimportant for them to do it.
I often talk about how canempty nesters who are
introverted find other people,and I think it's just a matter
(29:16):
of like looking at groups, likefinding something that works for
you.
Like tonight, uh, I amextroverted but I have an
introverted tinge to me.
But I'm going to a men'swellness barbecue kickoff for an
organization that's starting amen's wellness program and if
you didn't know, like, obviouslyI believe in men's wellness, so
(29:36):
, but I'm like I don't knowanybody who's going, uh, and it
takes me a little bit to buildup my extrovertedness, and so it
is a challenge for me to dothat.
So that's why I'm going andthat maybe, for the folks who
are like super introverted, islike, take that away as like a
little bit of like, you can doit.
Right, you just have to takethe first step and decide that
(29:58):
that's something you want to do.
Speaker 1 (29:59):
Yes, and I often find if you are particularly
introverted, always start with aconversation with whoever is
hosting.
They're very interested inmaking sure and invested in
people having a good time atwhatever the event is Such a
great tip.
So start there.
That's going to be an easytarget.
They're going to make it easyfor you to have a conversation
(30:22):
and they might introduce you tosomeone nice or someone who can
then, you know, kind of serve asthe next conversation that you
have.
And so you know, that's always.
You know, I am, I am veryextroverted, but I can also be a
little nervous and shy when I'm, you know, first warming up to
a space, and I always used tochat up bartenders when I would
(30:42):
be at an event, I would always,you know, chat up whoever had,
whoever was responsible for theinvitation, because they have to
be nice to you.
It's literally their job.
Speaker 3 (30:50):
As the host.
As the host that's a greatpoint, right the host is the
person that you can actuallyhave your first conversation
with.
I love that as you continueyour emptiness journey.
What's one thing you haven'tdone yet that you've always
wanted to do?
Speaker 1 (31:07):
So I have the typical you know kind of travel
destinations that I haven'tgotten to yet and, sadly,
because my husband was in thearmy for 30 years, he's pretty
much been everywhere, so it'sreally hard for me to get him as
excited about, you know, goingto Japan.
He's like, yeah, it's reallynice there.
(31:30):
I'm like that is not theresponse I was looking for.
I was looking for a yes.
Oh my gosh, we should totallygo and then tell me later that
you know all the places to go.
But I think I'm actually rightnow on a journey to figure out
what is the next big thing thatI want to get done.
A lot of the things that I hadanticipated I would do in my
(31:56):
life, some things that I wassurprised by, but I think for me
right now it really is aboutbuilding community and creating
a space here in a new area ofthe country where I can feel as
comfortable and as loved and asloving toward this community as
I have been in my priorcommunities, and that's going to
take some work to build andsome time, and so I'm giving
(32:24):
myself a little bit of grace tobegin building that and to
hopefully be able to enjoy itfor the rest of this phase.
Speaker 3 (32:27):
Oh, so good.
Building community I thinkthat's an underrated skill too
is like how do you build acommunity, especially if you go
someplace new, because that is afear of empty nesters.
Is like I want to move, I wantto move closer to the kids, or I
want to move someplace totallydifferent, but they're not quite
sure how to go about buildingcommunity.
Speaker 1 (32:47):
I'm not either, so if your listeners have tips,
please send them in.
I'm accepting suggestions.
Speaker 3 (32:54):
Well, yes, so you had mentioned a couple of things
that you've done so far.
Right, reaching out to groups,figuring out what it is, but
that's it.
I think it's just taking thetime to figure out, like, what
is happening in my community andmeet up works and Eventbrite
works.
Those are some places you cango and see what's going on.
No-transcript, take that as achallenge.
(33:37):
What are you not saying yes toright now, jessica?
Speaker 1 (33:41):
Well, right now I actually I just went through
this is a little bit like deepin my business I just went
through a quarterly planningsession with one of my business
coaches and I had to take someof my anticipated projects off
of my Q4 list of things to dowhich was very underwhelming for
(34:02):
me.
As you know, Jay, I have aproblem with being underwhelmed
and I'm super achievementoriented.
It's one of the things thatreally gets me up and going.
I think it's why I've done alot of things that I have set
out to do in my life.
That being said, my newer goalsare less about specific
achievements and more about, youknow, what our coach describes
(34:23):
as the infinite game.
And so working on my infinitegames, I think, is the skill
that I need to work on for therest of my life.
But so part of what I'm sayingno to is being overwhelmed for
this next kind of holiday season.
Whereas I would normally try topile a lot of stuff on I am.
I am not saying yes to a lot ofextra things that I would be
(34:46):
excited to tackle but wouldprobably ruin this season for me
.
Speaker 3 (34:51):
All right, so you went the opposite way.
It's not not what you're sayingyes to, not saying yes to, but
you're like I got to put thebrakes on here, which is fine
too, for sure Interesting,You're slowing down.
Speaker 1 (35:03):
I am.
You know I've done.
I may possibly be in adifferent mode than I think some
people find themselves.
I am not necessarily someonewho needs to be pushed to do
more.
I am someone who needs to bepulled back from doing too much,
(35:24):
and I think a lot of that justcomes from the world that I was
in for a number of years.
A lot of attorneys are likethis.
They are overly achievementfocused.
They will burn themselves outbefore giving up, regardless of
whether the goal is actuallysomething that they want at the
end of the day, and that hasbeen something that I have been
(35:46):
working on now as anentrepreneur, where those same
tendencies get carried alongright Wherever.
What do they say?
Wherever?
Wherever you go, there you are.
That's right, regardless ofwhat career I'm in.
Hey, there I am.
Look at me.
I am, like you know, nose tothe grindstone, going really
(36:06):
hard all the time.
I've had a very good year sofar and starting to think
through where can I take my footoff of the gas?
To not recreate the very stress, overwhelm and burnout that I
created in the last phase of mylife.
I'm trying to let this emptynest phase feel different than
(36:32):
the earlier phases be feeldifferent than the earlier
phases, and that's a skill forme in terms of, you know, kind
of not treating it like theearlier parts of my life where I
just had to get everything doneand get through it so that I
could be at the end.
I don't actually want to be atthe end of this phase, Jay.
That's a little scary.
Speaker 3 (36:47):
Though we know it's coming right.
That was a conversation I hadthe other day with someone
interviewing a guest.
Like you know it's coming, justlike you know empty nesting
coming.
You know the end is coming, buthow do you want to live your
life between now and then?
And I think that's one of thethings I try and impress upon
people is that every day is achance to live your life the way
(37:10):
you want to live it.
You just have to say yes to it.
Just have to say yes to it.
Just have to say yes to it.
Before I let you go finish thissentence for me, empty nest
happiness is.
Speaker 1 (37:24):
Ooh, empty nest happiness, it is community.
Speaker 3 (37:31):
It's community circling back to community.
Yeah, I love that.
Emptiness happiness iscommunity.
It's community Circling back tocommunity.
Yeah, I love that.
Emptiness happiness iscommunity.
So good.
Speaker 1 (37:37):
Sometimes that community is just my husband and
sometimes that community is alittle bit larger.
Speaker 3 (37:44):
So good, so good.
All right, before you leave,where can people find you, in
case they know an attorney whomay need your services?
Speaker 1 (37:53):
Absolutely.
You can find me on LinkedIn.
I'm prolific on there,jessicamedinallc, and my website
is wwwJessicaMedinaLLCcom.
There are lots of resources andblog articles for how to
approach any type of careertransition that folks may be
interested in.
If you feel like you might betaking a pay cut, then there's
(38:15):
some strategies to help youthink through what that could
look like, whether you're anattorney or not.
Speaker 3 (38:19):
Oh, so good.
Thanks so much for being here.
Totally enjoyed theconversation and I will see you
around, I'm sure.
Speaker 1 (38:25):
Yeah, thanks, jay.
Speaker 2 (38:29):
Are you ready to start living and enjoying your
empty nest years?
If so, head over tojasonramsdencom and click work
with me to get the conversationstarted.
This Empty Nest Life is aproduction of Impact.
One Media LLC.
All rights reserved.
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