May 29, 2025 • 24 mins
In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career.
Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family, your dreams.
Hear more stories from the Root Community here: https://www.skool.com/rootcollective/what-was-your-experience-when-you-told-your-employer-you-were-retiring
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The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
The Root Collective is our free community where you
can go and learn from otherpeople in a similar stage of
life to you.
It's one thing to hear fromJames or myself hey, you should
go retire early.
Hey, you should consider thisstrategy.
It's different when someoneelse is saying, hey, I'm 54.
I want to retire early.
It's healthcare that'sbothering me.
It's oh my gosh, how am I goingto fulfill my time?
But today's episode is aspecial one.
(00:22):
I alluded to it two weeks ago,but it's about actually how do
you quit.
We're talking aboutlogistically how do I tell my
boss or myself if you're runningyour own business, hey, I'm
going to walk away.
And this was prompted by a postin the Root Collective.
And that is how we select whatwe're going to talk about.
And this comes from Eric, whosays what was your experience
(00:44):
when you told your employer youwere retiring?
He writes a lot of awesomestuff.
Here I'm going to summarize it.
And he says here I'm going togive my employer two months
notice so they can find areplacement.
I know they're going to try totalk me out of it.
They're going to make promises,they're going to throw more
money.
I will certainly beprofessional and thank them for
the opportunity, but more moneyis not what I'm looking for.
(01:05):
I need to start valuing my timeover money.
So start valuing time overmoney.
I don't know how old Eric is,but the first thing I'm seeing
is was that not happening before?
Why now?
These are thoughts that go intoour heads.
He further goes on to say I wascurious if others here, who may
have retired, experienced thesethings, and how did you deal
(01:25):
with it?
So that's what we're going tobe talking about today.
Speaker 2 (01:29):
Let's do it and I there's.
There's kind of three maincategories that I think through.
The first is obviously thefinancial side.
Like, don't go say you're goingto retire if you don't have
that dialed in.
The big things I look at is doyou have income to replace your
paycheck Obviously thepaycheck's going away Do you
have insurance coverage thatwill see you through and that
you'll maintain the right healthinsurance coverage?
Have you made the appropriatechanges to your investments?
(01:49):
And do you have a tax strategyto minimize whatever your tax
liability might be when youstart lifting off your
investment?
So that's obviously step one.
But I think Eric I've got toassume has gone through those
steps.
It's more of the call it, theemotional side or the fear side,
or what do you do when you feellike you're letting people down
side of this I got so manythoughts.
If people I was fired from mylast job, I was asked to resign
(02:12):
and I think that one thing thatpeople don't realize or maybe we
fail to think of we are soreplaceable as employees we feel
like I mean I had a goodrelationship with my last firm.
I had a great relationship withmy boss and with the owner.
I employees, we feel like Imean, I had a good relationship
with my last firm.
I had a great relationship withmy boss and with the owner.
I thought I was going to bethere forever and then,
literally in a span of 24 hours,that was gone, and so it kind
(02:34):
of got me to think of I feellike I've given so much to this
organization and I'm justeffectively forced out on a dime
like that.
And I think that a lot ofpeople have that experience of
this extreme loyalty to acompany, which is great.
I think you should have loyaltyto your company.
I think that you should dogreat work, but you should never
.
You know, people talk about workbeing like family.
Hopefully, it feels like thatin some ways, but work is never
(02:56):
going to be family.
Family is going to be thisgroup that, for better or worse,
they're with you through it.
Work's not that Like you hope.
That work is a place where youcan have an amazing life, you
can have amazing friendships,you can do incredible work for
people.
It's not a family.
There are some standards thatyou have to hit to continue to
be part of that, and I thinkthat that goes both ways.
(03:20):
We feel this extreme loyalty towork.
But sometimes, especially inthe corporate world, you see
this all the time.
How many times do you go onLinkedIn and you see all these
people from a certain company.
I gave my all to this company.
I worked weekends for thiscompany, I sacrificed everything
for this company.
Then layoffs and I was asked tojoin a Zoom meeting with 300
other people and we were toldour positions are gone.
(03:42):
And it's that sense of of coursewe don't properly, I think,
view our relationship with workin the right context.
Have that loyalty, have thatduty of care, have those things
that you do, but let's neverforget that we're replaceable
and so we have to have that samemindset of is work still giving
us what we need?
But I think the biggest thingfor Eric here is anything you
(04:03):
say yes to by default, you aresaying no to something else.
So by you not retiring, by yousaying yes to the money, by you
saying yes to it doesn't soundlike it's about that.
Maybe it's yes because youdon't want to let them down.
Just keep in mind that everysingle time you do that, you are
saying no to your freedom.
You are saying what did you sayTime?
You are saying no to your fillin the blank that you want to do
(04:27):
.
Are you okay with that?
And then be honest withyourself, because I think we
would say, no, I'm not okay withthat.
But then we would justify sixmore months, then we would
justify one more year, then wewould justify I'll stay on until
they find my replacement.
And this isn't to say you shouldjust drop out cold turkey.
Yes, if your company has beengood to you, if you've got a
great relationship, don't justleave them high and dry, but set
(04:51):
a very real end point for this.
I am going to do this.
Here's a time I can commit,here's what I'm going to do.
And then do it and recognizethat these conversations are not
always.
It's a breakup.
We're growing fast here at Rootand we are onboarding great
advisors.
They're very excited to joinRoot.
(05:11):
They're also nervous to telltheir current firm, hey, we're
leaving.
They've got great relationships.
They're not trying to leavesomewhere, they're trying to
come to Root.
And that's hard.
And so I think that it's what'son the other side of that hard
conversation is what you have tokeep in mind and what's on the
other side of that conversationwhether it's joining a great
firm that you're really excitedto join, whether it's retirement
and being able to do what youwant to do.
(05:32):
That hard conversation doesn'tget easier because you push it
off, and so just recognizing thefact that you continuing to say
yes to more work is you say noto whatever you could have been
doing with that time instead.
Speaker 1 (05:46):
I'm going to read some of these responses in just
a moment, because the questionwas what was your experience
when you told your employer youwere retiring?
And the amazing thing aboutthis community is you guys went
and told them and there's over.
It looks like 30 to 40responses in here and there are
people just like you going andI'm reading a few of them.
Now I plan to retire in 10years.
(06:06):
I've already begun to imaginethe conversation might be like
10 years out.
He says, like you, I expectpushback, more money thrown,
even a possibly moreadvantageous work schedule.
Very curious for an update inyour story as it will help me.
So this is someone who's 10years out thinking about that
conversation and is nervous.
(06:27):
But to your point, james,valuing time, the only
non-renewable currency, is hethinking of hey, I have to work
10 more years because I couldn'timagine having that
conversation in like five years,because that would just I mean,
my manager loves me so much andthere's just no way that's
possible.
So the reason I'm going to gothrough this in just a moment
I'll probably do this near theend of today's episode but the
(06:48):
thing that I want all of you tobe aware of when we're talking
about planning.
I will joke in my videos and Iwill say I'm the meanest
financial advisor.
I promise I'm not mean, I'mvery transparent.
But my dad used to say I'm themeanest dad there is.
And I used to say, dad, it'snot fair, why isn't I wasn't
picked on this team, and he'dsay life's not fair.
That coach didn't pick you, andI'd say it's not fair, why
(07:10):
aren't you as fast as them?
He goes, it's not fair.
And he used to say it's notfair and it's, to be honest, out
of your control.
So the earlier you learn that,the better.
Now, did I like hearing thatearly on?
No, but he used to say onething that I still think about
today Choose your heart.
It's hard to go, break up Mightbe harder to live in that.
(07:32):
So is there a story orsomething that comes to mind,
james, from either somethingyou've spoken to a client about
who really couldn't leave, thenfinally did and went oh my gosh,
my life's so different.
Or in your personal life whereyou went look, this really was
hard, but I realized this wouldbe harder personal life where
you went.
Speaker 2 (07:51):
Look, this really was hard, but I realized this would
be harder Tons of things.
I don't know why this storycomes to mind and this might not
connect, so apologies and we'lledit this out of.
This story Sounds completelyridiculous.
I was at this was right afterhigh school ended and a friend
invited me out to their, theirriver place I think it was Lake
Havasu, and they had the jetskis and the fun stuff.
And we went out there and I hadnever ridden one before and I
(08:12):
was like, oh, this is so fun,this is so cool.
And we were a bunch of, I mean,we were 18.
We were dumb and we were justriding those.
And I remember I had a friendriding the back and I was trying
to do you know the back of it.
And I did that as other friends.
I did not realize we're goingreally quickly behind us.
(08:33):
So I was going full speed, Iwhipped it around, threw him off
, thought it was so funny.
And then the water subsides,the spray kind of clears, and I
see my other friend coming rightat me and thankfully I had
about a split second to jump offand I jumped off but those
water skis collided and it was apretty direct hit, like they
(08:55):
kind of hit the side and thencreamed off and I messed up this
jet ski and no one was hurt,everyone was good.
But I just remember feeling thislike pit in my stomach of I've
got to go tell my friend's dadthat I just crashed her jet ski.
This isn't mine.
They're so gracious, theyinvited me on this trip.
I've never been here Like thisis a group of friends.
They come every summer.
I'm like the new kid into thisthing and I just got on as fast
(09:18):
as I could and gunned it back tothe house and I just went right
up and told him and I think I,I just I don't remember.
I think my mind was just, youknow, you're 18.
You're so nervous, this is yourfriend's dad.
I just blacked out.
I don't know what happened, butI remember after that my friend
who I threw off was like wow,that was really amazing.
You just like went and said it.
(09:40):
You just went and did the hardthing.
And in that moment I kind ofrealized, yeah, what else would
you do?
What else would you do?
Why prolong the inevitable?
And what you start to realizeis there's a difference between
hard and suffering.
Like to me, the conversationwas hard, but the anticipation
of it, that's where thesuffering is.
(10:01):
The suffering is the sense ofI've got to do it.
It's weighing on me.
Is there anything else I can do?
And you relate that to everyother aspect of life, of I've
got to have this difficultconversation.
Can I respond to emails instead?
Can I reschedule it?
And that's where the sufferingis is in the prolonging of the
inevitable.
Do the hard, not the suffering.
I think that there's a sayingthat says hard choices easy life
(10:27):
, easy choices hard life.
And it's that same sense.
If you want life to go well, ifyou want to live life, easy
choices, hard life.
And it's that same sense.
If you want life to go well, ifyou want to live life on your
terms, make those hard decisions.
Short-term pain for thatlong-term gain.
If you want a hard life,continually make the easy
decision, continually put offthe things that you know you
should do.
There's a famous book, bronnieWare.
I don't know if it's a book,but she wrote like the five
(10:48):
regrets of the dying.
She's this Australian hospicenurse and she got the chance to
interview I don't know how manypeople, but tons and tons and
tons of people who were on theirdeathbed about.
What are your five biggestregrets?
And one of the top five regretswas too much time spent at work
.
People who felt like they hadto give their all to their
employer.
And what they realized inretrospect is I never actually
(11:10):
lived my own life.
I always felt like I was tryingto please someone else or give
to someone else or do something.
That was time Again.
A yes to that means a no tosomething else.
That was no that I had to sayto my family because of that.
That was no that I had to sayto myself, to my health, to
whatever.
And sometimes we get on this,this jag, I feel like, where it
seems like work is bad andretirement is good.
(11:30):
That's not the case.
Like, I think work in itspurest form is amazing.
We, we both love what we get todo with work.
We have a lot of clients lovewhat they get to do with work.
So this is not a get out ofwork as fast as you can, but
it's a have that honestconversation with yourself of is
this contributing to yourversion of the life that you
want to live, yes or no?
And if the answer is no.
Have that difficultconversation.
(11:52):
Obviously, have the financialplan in place, have a financial
advisor review that do workthrough it with you, but then
have the ability to have thatconversation.
And one more thing I'll say onthis is understand why you're
having that conversation,because sometimes it's not as
binary, it's not as black andwhite of either continue working
and I'm miserable or I'mretired and I love it.
Why do you want to retire?
(12:13):
I, lots of people, just I, justI can't stand the commute, I
can't stand all the travel thatI have to do.
I get okay.
Well, maybe you go like that'sone of the cards you have, is
you go to this and if they wantto negotiate, your negotiation
card is okay, I I'll stay, butI'm not doing any more travel,
I'm not commuting to the office.
I'm not.
(12:34):
For so many people now theyactually get the parts of work
that they love and they carveout what they don't love.
So when you're preparing tohave this conversation, to leave
work, go and do it with theunderstanding of what are you
actually trying to get away from?
Is it actually the work itself?
Is it the team you're on?
(12:54):
Is it the department you're in?
Is it the commute.
Is it the?
You fill in the blank.
Is there a way of holding on towhat you do love?
Hopefully there's somethingthat you do love.
Maybe there's not Meaning.
Do you want a full exit, a fullbreakup?
If so, be firm.
Say no to work so you can sayyes to everything else.
If not understand what thosethings are, so that it's either
(13:14):
ranking your priorities.
Best case scenario is I keepworking with no commute.
Second, best is I retire fully.
Third, best is I keep stayingin the same thing that I've been
doing and nothing changes.
So just having a deepunderstanding of why are you
making the decision that you'remaking.
Speaker 1 (13:27):
The jet ski story is incredible, perfectly relates,
by the way.
I was thinking what are yougoing to do Now?
When you were saying it, I wasthinking I know you, you're
going to go up and tell him.
But look, I didn't know if apart of you was going to go up
and strategize and go.
Oh my God, how should I tellhim?
Should I?
Should I describe that it wasmy fault and I don't want to be
at blame?
I really want to still comehere.
(13:49):
Were you thinking about, oh mygosh, how is he going to react?
Because I want to make sure Iget invited back?
Did you and there's a legitquestion before a few other
things I want to make sure weget through in today's quick
episode.
Did you worry about oh my gosh,will I be invited back?
Were you thinking that?
Or did you think I'm gunning itto get to the doc, to go up
there and tell him right away?
Speaker 2 (14:10):
I, I.
It was just that maybe now thiswas what, how, 18 to 30, 17
years ago, 18 so heart, I.
I don't remember.
And I do remember, almost likethat flood of adrenaline of you
don't even remember what yousaid.
It was just a I I crashed, I'llpay for it, I'll, but I didn't
know some paper.
I think I was working a minimumwage smoothie king job at the
(14:31):
time, so I would have figured itout, but it was just the sense
of I don't want this naggingfeeling, this dread hanging over
me.
So, instead of avoiding it andhaving that existential dread go
with you everywhere, it's yeah,I, I.
It was a good lesson.
I'm learning everywhere.
It's yeah, I, I.
It was a good lesson inlearning that dealing with
things head on, even if youdon't have a perfect strategy.
(14:54):
I think that's the right thing.
Like I've had conversations withteam like how to let a team
member go in the past where it'slike can I'm rehearsing this?
What am I going to say?
How do you do it?
But at the end of the day, it'sjust like, hey, you just send
them the message and say can wechat?
You have a hard conversationwith a spouse or friend or
whatever you rehearse it, how isthis going to go At the end of
the day?
Yes, prepare to an extent, butyou just need to do it, and it's
(15:16):
just the message that needs tobe said.
And we spend so much timeobsessing over the little
what-ifs and how do we do it?
That's that avoidance behaviorcoming out.
It doesn't actually matter,it's just us going through that,
because that's easier to try torole play a different way or
try to you know, see what otherwhat if?
(15:38):
Scenario might happen.
It's easier to try to distractyourself with that than just to
address the issue head on, whichthe issue is.
You got to let someone down.
You're saying I'm going toretire, I'm going to.
You got to let your boss down,or at least you feel that way.
For all you know, they mighthave your replacement ready.
For all you know, there mightbe someone else who's doing a
great job that they can't waitto fill your position.
For all you know, they don'tappreciate you as much as you
(16:01):
appreciate them.
So keep that in mind and justmake sure that you're having the
conversation and don't worryabout hitting it perfectly as
much as just making sure thatmessage is heard and that you're
staying firm with what thenon-negotiables for you are.
Speaker 1 (16:13):
I think you're dead on and I think it's powerful for
everyone to hear hey, it'snormal, we are not perfect.
No one expects you to be.
I have a quick story that I'lltell because it helped a client.
If it helps anyone else, that'swhy we do this, but I'm going
to go through responses at theend.
(16:34):
I've not forgotten, because alot of you are wondering yes,
how did other people deal withit?
It's one thing to hear what youand James have to say on here,
but I want to hear with otherpeople, because I'm about to
tell you about people who said30 years with same company, I
gave my employer X amount ofmonths.
Here's how it went down.
So there was a time where I wasspeaking to a couple and they
wanted to quit, but they didn'twant to do nothing.
They wanted to quit and then dosomething else more meaningful,
and we did pros and cons and Ihelped them with it and part of
my job as an advisor, as I seeit, is, could I tell them go do
(16:56):
pros and cons when I'm offline?
Of course I could, but it's mebeing there, it's the
accountability.
I was with them and we're goingthrough it and I was seeing
they would say pro yep, this isawesome.
More time, con.
Not enough money.
Is it worth it?
I'm worth more than 80,000 ayear.
I could tell it really wasn'thelping.
They were writing it down, butI could really tell that wasn't
(17:18):
the issue.
So I said pause and they saidreally, I'm starting to.
I think we're gaining tractionhere I go look, you could be
right.
I don't think we and you founda job that paid way less, but
you enjoyed it more.
Once again, you don't have totell them you quit, you're gone.
(17:40):
You start your new job Tuesday.
What do you do?
And all I cared about was thespeed of the response.
And they said I do it.
And they looked at me and Iwent that's all I needed to know
.
We can keep pros and conningall you want.
You do not want to work hereany longer.
And you were saying before am Iworth 80,000 a year?
I feel like I give more valuethan that.
You just said you would dosomething else if it paid less,
(18:03):
if you enjoyed it more.
So now this conversation isabout what do we want to do?
And it made them start writingreally fast.
I'd actually love to volunteerwith pets.
You know what, even Ari, if itturns out, they don't pay me
anything.
If my plan, let me do it, Iwould just do that.
I go, okay.
Well, that's very differentfrom you.
Are not valuing yourself at80,000.
And that's because of aquestion.
(18:23):
So the value of what Jamestalks about in the Root Ready
show, which we talked about afew weeks ago, is how do you, as
an advisor, know when to askthe right questions, know when
to shut the heck up and letsomeone keep exploring because
they're thinking, and that'sreally our role.
So, with that being said, I'mgoing to just tell you guys a
few responses here so you cansee all of this.
(18:45):
We're going to actually put thethread to this in the
description.
So if you want to read all 40plus responses, you can.
I'm not going to obviously gothrough all of them, but just a
few to finish out.
Someone here, john Hawkins, saysI gave my employer six months.
I worked for the company foralmost 30 years.
(19:06):
The CEO and I are close, workedout really well for
transitioning all of myresponsibilities, but I got a
few calls after I left toclarify things.
But because we did such a goodjob transitioning in two phases.
It was seamless.
Phase one was we're helpingpeople taking over my accounts,
attended calls and I led thediscussions.
In phase two, I had themleading discussions and I found
(19:26):
this decreased my anxiety.
But it wasn't perfect.
I was available to help but Iactually found I gave more time
than I wanted to.
The reason I find that aninteresting response is here's
someone who quit.
His responsibility is to retireand enjoy his life now, but
he's still kind of working Now.
Maybe he enjoys that and heactually wants to do that.
(19:46):
We don't know.
But don't be the person that'sjust going to offer, just to be
nice.
Yep, I'm going to help trainthe next six months or a year
and now all of a sudden you feellike you're being taken
advantage of.
So that's the first one.
The other story I want to sayhere.
This comes from Tommy C, who wequote a lot.
He says I was prepared to sayno when I turned in my paperwork
(20:08):
.
I had a great relationship.
If they offer me more money tostay one more year, my prepared
response was I just love this,so why didn't you offer me more
before today?
And I don't I?
I there's a little bit ofattitude I can kind of feel, but
there was some resentment I cankind of.
But it's kind of cool, rightit's, it's cool.
Speaker 2 (20:28):
Yeah, and it's I like it.
I don't know the context, butthere is that sense of like you
talk when someone's about toleave or someone's about.
Then you offer more.
It's like, well, why did?
Why didn't you come with yourbest and final first?
If they're committing all theyare to you, why don't you commit
all you are to them, or atleast on equal ground?
Speaker 1 (20:46):
And yeah, I like it, it's, it's, I like it too.
Last thing here is he says beprepared.
And I think this is a reallyhelpful piece.
Some colleagues willcongratulate you, some will be
indifferent, some will avoid youlike the plague.
It's a real eye opener to seewhich category some of your
colleagues fall into.
And don't get it twisted.
You will need people inretirement.
(21:07):
It's not as fun alone.
So I like the way he was sayingdon't get it twisted, you're
going to still want people,you're going to want to
communicate.
So it's not like, hey, I'm justout of here, I'm under
retirement.
It's hey, what do I?
And if you find someone'sreally nice to you all the time
at work, but the minute you sayyou're retiring, they're like
well, you're not of value to meanymore.
(21:28):
Well, that's telling.
Speaker 2 (21:29):
Yeah, the final thing there's so often you hear this
of the company doesn't value youas much as you value them.
And it's, oh well, not mysituation.
Like you don't understand therelationship I have with my boss
, with my company, my role.
That was me.
Like I remember, like I I neverwanted to start a company
before route, I'd never thoughtI would, I thought I was going
(21:50):
to be at my last company forever.
And I remember even thinkinglike I don't even know how I
could say to my boss like I'mleaving, like I feel like
they've been so good to me, I'velearned so much here, yada,
yada.
And then, within a matter of 24hours, one day I was asked to
resign and it was like this bigwake-up call of oh, maybe the
company never really does feellike that the same way to me as
(22:14):
I do to them, that the same wayto me as I do to them.
And and this isn't to say thatit should be this purely
transactional relationshipbetween work and between the
people that work there Likehopefully there is something
special there.
I would like to think at root,we have a lot of loyalty and
want to make sure that this is aplace that people could stay
for a long time and it would notbe that transactional
relationship.
But there, there, it does needto be that gut check of.
(22:34):
We always think we're differentin a lot of ways, our
circumstance is different.
I can't tell them I'm retiringbecause of how much that would
hurt.
Maybe, true, but going back toyou, continuing to say yes if
you're in a position where youshould retire and need to retire
and want to move on todifferent things, continuing to
say yes to work is saying no tothe things that you actually
want to do, which is the firstpoint.
(22:55):
But then, number two, thatfeeling might not actually be
mutual, and I say that becausesometimes that's the thing
that's keeping people going,because they feel like there's
this thing that they would neverdo that to me.
So how could I retire from them?
How quickly would you bereplaced if you left, is a
question I would ask, and theanswer is probably as soon as
(23:15):
they possibly could, which wouldnot be that long.
So it's a difficult thing to do.
It is a breakup.
You are breaking up with them,but at some point along the way
you need to do that to make sureyou can do what you're actually
trying to do with the rest ofyour life.
Speaker 1 (23:28):
It's true.
So just a super happy episodetoday, guys.
Hope you enjoyed this and wewill be back in a few weeks.
More fun topics Once again.
Go to the Root Collective.
That is where you can go if youwant to really comment about
anything, and that's how we'rechoosing what we discuss.
Additionally, if you arethinking, hey, honestly, I know
I need to break up, it's mainlythe financial side.
(23:49):
How do I even know where tobegin?
We help clients with everything, so that's from.
Hey, here's how we would havethat conversation to financially
, are you in a spot to make ithappen?
This is what we love to do.
So go to rootfinancialcom.
In the upper right.
You'll see a button that sayssee if you're a fit, and you can
click that to get started.
Speaker 2 (24:05):
Awesome.
Thank you everyone for watchingand we will see you next time.
See ya, thank you.
The Root Collective is our free community where you
can go and learn from otherpeople in a similar stage of
life to you.
It's one thing to hear fromJames or myself hey, you should
go retire early.
Hey, you should consider thisstrategy.
It's different when someoneelse is saying, hey, I'm 54.
I want to retire early.
It's healthcare that'sbothering me.
It's oh my gosh, how am I goingto fulfill my time?
But today's episode is aspecial one.
(00:22):
I alluded to it two weeks ago,but it's about actually how do
you quit.
We're talking aboutlogistically how do I tell my
boss or myself if you're runningyour own business, hey, I'm
going to walk away.
And this was prompted by a postin the Root Collective.
And that is how we select whatwe're going to talk about.
And this comes from Eric, whosays what was your experience
(00:44):
when you told your employer youwere retiring?
He writes a lot of awesomestuff.
Here I'm going to summarize it.
And he says here I'm going togive my employer two months
notice so they can find areplacement.
I know they're going to try totalk me out of it.
They're going to make promises,they're going to throw more
money.
I will certainly beprofessional and thank them for
the opportunity, but more moneyis not what I'm looking for.
(01:05):
I need to start valuing my timeover money.
So start valuing time overmoney.
I don't know how old Eric is,but the first thing I'm seeing
is was that not happening before?
Why now?
These are thoughts that go intoour heads.
He further goes on to say I wascurious if others here, who may
have retired, experienced thesethings, and how did you deal
(01:25):
with it?
So that's what we're going tobe talking about today.
Speaker 2 (01:29):
Let's do it and I there's.
There's kind of three maincategories that I think through.
The first is obviously thefinancial side.
Like, don't go say you're goingto retire if you don't have
that dialed in.
The big things I look at is doyou have income to replace your
paycheck Obviously thepaycheck's going away Do you
have insurance coverage thatwill see you through and that
you'll maintain the right healthinsurance coverage?
Have you made the appropriatechanges to your investments?
(01:49):
And do you have a tax strategyto minimize whatever your tax
liability might be when youstart lifting off your
investment?
So that's obviously step one.
But I think Eric I've got toassume has gone through those
steps.
It's more of the call it, theemotional side or the fear side,
or what do you do when you feellike you're letting people down
side of this I got so manythoughts.
If people I was fired from mylast job, I was asked to resign
(02:12):
and I think that one thing thatpeople don't realize or maybe we
fail to think of we are soreplaceable as employees we feel
like I mean I had a goodrelationship with my last firm.
I had a great relationship withmy boss and with the owner.
I employees, we feel like Imean, I had a good relationship
with my last firm.
I had a great relationship withmy boss and with the owner.
I thought I was going to bethere forever and then,
literally in a span of 24 hours,that was gone, and so it kind
(02:34):
of got me to think of I feellike I've given so much to this
organization and I'm justeffectively forced out on a dime
like that.
And I think that a lot ofpeople have that experience of
this extreme loyalty to acompany, which is great.
I think you should have loyaltyto your company.
I think that you should dogreat work, but you should never
.
You know, people talk about workbeing like family.
Hopefully, it feels like thatin some ways, but work is never
(02:56):
going to be family.
Family is going to be thisgroup that, for better or worse,
they're with you through it.
Work's not that Like you hope.
That work is a place where youcan have an amazing life, you
can have amazing friendships,you can do incredible work for
people.
It's not a family.
There are some standards thatyou have to hit to continue to
be part of that, and I thinkthat that goes both ways.
(03:20):
We feel this extreme loyalty towork.
But sometimes, especially inthe corporate world, you see
this all the time.
How many times do you go onLinkedIn and you see all these
people from a certain company.
I gave my all to this company.
I worked weekends for thiscompany, I sacrificed everything
for this company.
Then layoffs and I was asked tojoin a Zoom meeting with 300
other people and we were toldour positions are gone.
(03:42):
And it's that sense of of coursewe don't properly, I think,
view our relationship with workin the right context.
Have that loyalty, have thatduty of care, have those things
that you do, but let's neverforget that we're replaceable
and so we have to have that samemindset of is work still giving
us what we need?
But I think the biggest thingfor Eric here is anything you
(04:03):
say yes to by default, you aresaying no to something else.
So by you not retiring, by yousaying yes to the money, by you
saying yes to it doesn't soundlike it's about that.
Maybe it's yes because youdon't want to let them down.
Just keep in mind that everysingle time you do that, you are
saying no to your freedom.
You are saying what did you sayTime?
You are saying no to your fillin the blank that you want to do
(04:27):
.
Are you okay with that?
And then be honest withyourself, because I think we
would say, no, I'm not okay withthat.
But then we would justify sixmore months, then we would
justify one more year, then wewould justify I'll stay on until
they find my replacement.
And this isn't to say you shouldjust drop out cold turkey.
Yes, if your company has beengood to you, if you've got a
great relationship, don't justleave them high and dry, but set
(04:51):
a very real end point for this.
I am going to do this.
Here's a time I can commit,here's what I'm going to do.
And then do it and recognizethat these conversations are not
always.
It's a breakup.
We're growing fast here at Rootand we are onboarding great
advisors.
They're very excited to joinRoot.
(05:11):
They're also nervous to telltheir current firm, hey, we're
leaving.
They've got great relationships.
They're not trying to leavesomewhere, they're trying to
come to Root.
And that's hard.
And so I think that it's what'son the other side of that hard
conversation is what you have tokeep in mind and what's on the
other side of that conversationwhether it's joining a great
firm that you're really excitedto join, whether it's retirement
and being able to do what youwant to do.
(05:32):
That hard conversation doesn'tget easier because you push it
off, and so just recognizing thefact that you continuing to say
yes to more work is you say noto whatever you could have been
doing with that time instead.
Speaker 1 (05:46):
I'm going to read some of these responses in just
a moment, because the questionwas what was your experience
when you told your employer youwere retiring?
And the amazing thing aboutthis community is you guys went
and told them and there's over.
It looks like 30 to 40responses in here and there are
people just like you going andI'm reading a few of them.
Now I plan to retire in 10years.
(06:06):
I've already begun to imaginethe conversation might be like
10 years out.
He says, like you, I expectpushback, more money thrown,
even a possibly moreadvantageous work schedule.
Very curious for an update inyour story as it will help me.
So this is someone who's 10years out thinking about that
conversation and is nervous.
(06:27):
But to your point, james,valuing time, the only
non-renewable currency, is hethinking of hey, I have to work
10 more years because I couldn'timagine having that
conversation in like five years,because that would just I mean,
my manager loves me so much andthere's just no way that's
possible.
So the reason I'm going to gothrough this in just a moment
I'll probably do this near theend of today's episode but the
(06:48):
thing that I want all of you tobe aware of when we're talking
about planning.
I will joke in my videos and Iwill say I'm the meanest
financial advisor.
I promise I'm not mean, I'mvery transparent.
But my dad used to say I'm themeanest dad there is.
And I used to say, dad, it'snot fair, why isn't I wasn't
picked on this team, and he'dsay life's not fair.
That coach didn't pick you, andI'd say it's not fair, why
(07:10):
aren't you as fast as them?
He goes, it's not fair.
And he used to say it's notfair and it's, to be honest, out
of your control.
So the earlier you learn that,the better.
Now, did I like hearing thatearly on?
No, but he used to say onething that I still think about
today Choose your heart.
It's hard to go, break up Mightbe harder to live in that.
(07:32):
So is there a story orsomething that comes to mind,
james, from either somethingyou've spoken to a client about
who really couldn't leave, thenfinally did and went oh my gosh,
my life's so different.
Or in your personal life whereyou went look, this really was
hard, but I realized this wouldbe harder personal life where
you went.
Speaker 2 (07:51):
Look, this really was hard, but I realized this would
be harder Tons of things.
I don't know why this storycomes to mind and this might not
connect, so apologies and we'lledit this out of.
This story Sounds completelyridiculous.
I was at this was right afterhigh school ended and a friend
invited me out to their, theirriver place I think it was Lake
Havasu, and they had the jetskis and the fun stuff.
And we went out there and I hadnever ridden one before and I
(08:12):
was like, oh, this is so fun,this is so cool.
And we were a bunch of, I mean,we were 18.
We were dumb and we were justriding those.
And I remember I had a friendriding the back and I was trying
to do you know the back of it.
And I did that as other friends.
I did not realize we're goingreally quickly behind us.
(08:33):
So I was going full speed, Iwhipped it around, threw him off
, thought it was so funny.
And then the water subsides,the spray kind of clears, and I
see my other friend coming rightat me and thankfully I had
about a split second to jump offand I jumped off but those
water skis collided and it was apretty direct hit, like they
(08:55):
kind of hit the side and thencreamed off and I messed up this
jet ski and no one was hurt,everyone was good.
But I just remember feeling thislike pit in my stomach of I've
got to go tell my friend's dadthat I just crashed her jet ski.
This isn't mine.
They're so gracious, theyinvited me on this trip.
I've never been here Like thisis a group of friends.
They come every summer.
I'm like the new kid into thisthing and I just got on as fast
(09:18):
as I could and gunned it back tothe house and I just went right
up and told him and I think I,I just I don't remember.
I think my mind was just, youknow, you're 18.
You're so nervous, this is yourfriend's dad.
I just blacked out.
I don't know what happened, butI remember after that my friend
who I threw off was like wow,that was really amazing.
You just like went and said it.
(09:40):
You just went and did the hardthing.
And in that moment I kind ofrealized, yeah, what else would
you do?
What else would you do?
Why prolong the inevitable?
And what you start to realizeis there's a difference between
hard and suffering.
Like to me, the conversationwas hard, but the anticipation
of it, that's where thesuffering is.
(10:01):
The suffering is the sense ofI've got to do it.
It's weighing on me.
Is there anything else I can do?
And you relate that to everyother aspect of life, of I've
got to have this difficultconversation.
Can I respond to emails instead?
Can I reschedule it?
And that's where the sufferingis is in the prolonging of the
inevitable.
Do the hard, not the suffering.
I think that there's a sayingthat says hard choices easy life
(10:27):
, easy choices hard life.
And it's that same sense.
If you want life to go well, ifyou want to live life, easy
choices, hard life.
And it's that same sense.
If you want life to go well, ifyou want to live life on your
terms, make those hard decisions.
Short-term pain for thatlong-term gain.
If you want a hard life,continually make the easy
decision, continually put offthe things that you know you
should do.
There's a famous book, bronnieWare.
I don't know if it's a book,but she wrote like the five
(10:48):
regrets of the dying.
She's this Australian hospicenurse and she got the chance to
interview I don't know how manypeople, but tons and tons and
tons of people who were on theirdeathbed about.
What are your five biggestregrets?
And one of the top five regretswas too much time spent at work
.
People who felt like they hadto give their all to their
employer.
And what they realized inretrospect is I never actually
(11:10):
lived my own life.
I always felt like I was tryingto please someone else or give
to someone else or do something.
That was time Again.
A yes to that means a no tosomething else.
That was no that I had to sayto my family because of that.
That was no that I had to sayto myself, to my health, to
whatever.
And sometimes we get on this,this jag, I feel like, where it
seems like work is bad andretirement is good.
(11:30):
That's not the case.
Like, I think work in itspurest form is amazing.
We, we both love what we get todo with work.
We have a lot of clients lovewhat they get to do with work.
So this is not a get out ofwork as fast as you can, but
it's a have that honestconversation with yourself of is
this contributing to yourversion of the life that you
want to live, yes or no?
And if the answer is no.
Have that difficultconversation.
(11:52):
Obviously, have the financialplan in place, have a financial
advisor review that do workthrough it with you, but then
have the ability to have thatconversation.
And one more thing I'll say onthis is understand why you're
having that conversation,because sometimes it's not as
binary, it's not as black andwhite of either continue working
and I'm miserable or I'mretired and I love it.
Why do you want to retire?
(12:13):
I, lots of people, just I, justI can't stand the commute, I
can't stand all the travel thatI have to do.
I get okay.
Well, maybe you go like that'sone of the cards you have, is
you go to this and if they wantto negotiate, your negotiation
card is okay, I I'll stay, butI'm not doing any more travel,
I'm not commuting to the office.
I'm not.
(12:34):
For so many people now theyactually get the parts of work
that they love and they carveout what they don't love.
So when you're preparing tohave this conversation, to leave
work, go and do it with theunderstanding of what are you
actually trying to get away from?
Is it actually the work itself?
Is it the team you're on?
(12:54):
Is it the department you're in?
Is it the commute.
Is it the?
You fill in the blank.
Is there a way of holding on towhat you do love?
Hopefully there's somethingthat you do love.
Maybe there's not Meaning.
Do you want a full exit, a fullbreakup?
If so, be firm.
Say no to work so you can sayyes to everything else.
If not understand what thosethings are, so that it's either
(13:14):
ranking your priorities.
Best case scenario is I keepworking with no commute.
Second, best is I retire fully.
Third, best is I keep stayingin the same thing that I've been
doing and nothing changes.
So just having a deepunderstanding of why are you
making the decision that you'remaking.
Speaker 1 (13:27):
The jet ski story is incredible, perfectly relates,
by the way.
I was thinking what are yougoing to do Now?
When you were saying it, I wasthinking I know you, you're
going to go up and tell him.
But look, I didn't know if apart of you was going to go up
and strategize and go.
Oh my God, how should I tellhim?
Should I?
Should I describe that it wasmy fault and I don't want to be
at blame?
I really want to still comehere.
(13:49):
Were you thinking about, oh mygosh, how is he going to react?
Because I want to make sure Iget invited back?
Did you and there's a legitquestion before a few other
things I want to make sure weget through in today's quick
episode.
Did you worry about oh my gosh,will I be invited back?
Were you thinking that?
Or did you think I'm gunning itto get to the doc, to go up
there and tell him right away?
Speaker 2 (14:10):
I, I.
It was just that maybe now thiswas what, how, 18 to 30, 17
years ago, 18 so heart, I.
I don't remember.
And I do remember, almost likethat flood of adrenaline of you
don't even remember what yousaid.
It was just a I I crashed, I'llpay for it, I'll, but I didn't
know some paper.
I think I was working a minimumwage smoothie king job at the
(14:31):
time, so I would have figured itout, but it was just the sense
of I don't want this naggingfeeling, this dread hanging over
me.
So, instead of avoiding it andhaving that existential dread go
with you everywhere, it's yeah,I, I.
It was a good lesson.
I'm learning everywhere.
It's yeah, I, I.
It was a good lesson inlearning that dealing with
things head on, even if youdon't have a perfect strategy.
(14:54):
I think that's the right thing.
Like I've had conversations withteam like how to let a team
member go in the past where it'slike can I'm rehearsing this?
What am I going to say?
How do you do it?
But at the end of the day, it'sjust like, hey, you just send
them the message and say can wechat?
You have a hard conversationwith a spouse or friend or
whatever you rehearse it, how isthis going to go At the end of
the day?
Yes, prepare to an extent, butyou just need to do it, and it's
(15:16):
just the message that needs tobe said.
And we spend so much timeobsessing over the little
what-ifs and how do we do it?
That's that avoidance behaviorcoming out.
It doesn't actually matter,it's just us going through that,
because that's easier to try torole play a different way or
try to you know, see what otherwhat if?
(15:38):
Scenario might happen.
It's easier to try to distractyourself with that than just to
address the issue head on, whichthe issue is.
You got to let someone down.
You're saying I'm going toretire, I'm going to.
You got to let your boss down,or at least you feel that way.
For all you know, they mighthave your replacement ready.
For all you know, there mightbe someone else who's doing a
great job that they can't waitto fill your position.
For all you know, they don'tappreciate you as much as you
(16:01):
appreciate them.
So keep that in mind and justmake sure that you're having the
conversation and don't worryabout hitting it perfectly as
much as just making sure thatmessage is heard and that you're
staying firm with what thenon-negotiables for you are.
Speaker 1 (16:13):
I think you're dead on and I think it's powerful for
everyone to hear hey, it'snormal, we are not perfect.
No one expects you to be.
I have a quick story that I'lltell because it helped a client.
If it helps anyone else, that'swhy we do this, but I'm going
to go through responses at theend.
(16:34):
I've not forgotten, because alot of you are wondering yes,
how did other people deal withit?
It's one thing to hear what youand James have to say on here,
but I want to hear with otherpeople, because I'm about to
tell you about people who said30 years with same company, I
gave my employer X amount ofmonths.
Here's how it went down.
So there was a time where I wasspeaking to a couple and they
wanted to quit, but they didn'twant to do nothing.
They wanted to quit and then dosomething else more meaningful,
and we did pros and cons and Ihelped them with it and part of
my job as an advisor, as I seeit, is, could I tell them go do
(16:56):
pros and cons when I'm offline?
Of course I could, but it's mebeing there, it's the
accountability.
I was with them and we're goingthrough it and I was seeing
they would say pro yep, this isawesome.
More time, con.
Not enough money.
Is it worth it?
I'm worth more than 80,000 ayear.
I could tell it really wasn'thelping.
They were writing it down, butI could really tell that wasn't
(17:18):
the issue.
So I said pause and they saidreally, I'm starting to.
I think we're gaining tractionhere I go look, you could be
right.
I don't think we and you founda job that paid way less, but
you enjoyed it more.
Once again, you don't have totell them you quit, you're gone.
(17:40):
You start your new job Tuesday.
What do you do?
And all I cared about was thespeed of the response.
And they said I do it.
And they looked at me and Iwent that's all I needed to know
.
We can keep pros and conningall you want.
You do not want to work hereany longer.
And you were saying before am Iworth 80,000 a year?
I feel like I give more valuethan that.
You just said you would dosomething else if it paid less,
(18:03):
if you enjoyed it more.
So now this conversation isabout what do we want to do?
And it made them start writingreally fast.
I'd actually love to volunteerwith pets.
You know what, even Ari, if itturns out, they don't pay me
anything.
If my plan, let me do it, Iwould just do that.
I go, okay.
Well, that's very differentfrom you.
Are not valuing yourself at80,000.
And that's because of aquestion.
(18:23):
So the value of what Jamestalks about in the Root Ready
show, which we talked about afew weeks ago, is how do you, as
an advisor, know when to askthe right questions, know when
to shut the heck up and letsomeone keep exploring because
they're thinking, and that'sreally our role.
So, with that being said, I'mgoing to just tell you guys a
few responses here so you cansee all of this.
(18:45):
We're going to actually put thethread to this in the
description.
So if you want to read all 40plus responses, you can.
I'm not going to obviously gothrough all of them, but just a
few to finish out.
Someone here, john Hawkins, saysI gave my employer six months.
I worked for the company foralmost 30 years.
(19:06):
The CEO and I are close, workedout really well for
transitioning all of myresponsibilities, but I got a
few calls after I left toclarify things.
But because we did such a goodjob transitioning in two phases.
It was seamless.
Phase one was we're helpingpeople taking over my accounts,
attended calls and I led thediscussions.
In phase two, I had themleading discussions and I found
(19:26):
this decreased my anxiety.
But it wasn't perfect.
I was available to help but Iactually found I gave more time
than I wanted to.
The reason I find that aninteresting response is here's
someone who quit.
His responsibility is to retireand enjoy his life now, but
he's still kind of working Now.
Maybe he enjoys that and heactually wants to do that.
(19:46):
We don't know.
But don't be the person that'sjust going to offer, just to be
nice.
Yep, I'm going to help trainthe next six months or a year
and now all of a sudden you feellike you're being taken
advantage of.
So that's the first one.
The other story I want to sayhere.
This comes from Tommy C, who wequote a lot.
He says I was prepared to sayno when I turned in my paperwork
(20:08):
.
I had a great relationship.
If they offer me more money tostay one more year, my prepared
response was I just love this,so why didn't you offer me more
before today?
And I don't I?
I there's a little bit ofattitude I can kind of feel, but
there was some resentment I cankind of.
But it's kind of cool, rightit's, it's cool.
Speaker 2 (20:28):
Yeah, and it's I like it.
I don't know the context, butthere is that sense of like you
talk when someone's about toleave or someone's about.
Then you offer more.
It's like, well, why did?
Why didn't you come with yourbest and final first?
If they're committing all theyare to you, why don't you commit
all you are to them, or atleast on equal ground?
Speaker 1 (20:46):
And yeah, I like it, it's, it's, I like it too.
Last thing here is he says beprepared.
And I think this is a reallyhelpful piece.
Some colleagues willcongratulate you, some will be
indifferent, some will avoid youlike the plague.
It's a real eye opener to seewhich category some of your
colleagues fall into.
And don't get it twisted.
You will need people inretirement.
(21:07):
It's not as fun alone.
So I like the way he was sayingdon't get it twisted, you're
going to still want people,you're going to want to
communicate.
So it's not like, hey, I'm justout of here, I'm under
retirement.
It's hey, what do I?
And if you find someone'sreally nice to you all the time
at work, but the minute you sayyou're retiring, they're like
well, you're not of value to meanymore.
(21:28):
Well, that's telling.
Speaker 2 (21:29):
Yeah, the final thing there's so often you hear this
of the company doesn't value youas much as you value them.
And it's, oh well, not mysituation.
Like you don't understand therelationship I have with my boss
, with my company, my role.
That was me.
Like I remember, like I I neverwanted to start a company
before route, I'd never thoughtI would, I thought I was going
(21:50):
to be at my last company forever.
And I remember even thinkinglike I don't even know how I
could say to my boss like I'mleaving, like I feel like
they've been so good to me, I'velearned so much here, yada,
yada.
And then, within a matter of 24hours, one day I was asked to
resign and it was like this bigwake-up call of oh, maybe the
company never really does feellike that the same way to me as
(22:14):
I do to them, that the same wayto me as I do to them.
And and this isn't to say thatit should be this purely
transactional relationshipbetween work and between the
people that work there Likehopefully there is something
special there.
I would like to think at root,we have a lot of loyalty and
want to make sure that this is aplace that people could stay
for a long time and it would notbe that transactional
relationship.
But there, there, it does needto be that gut check of.
(22:34):
We always think we're differentin a lot of ways, our
circumstance is different.
I can't tell them I'm retiringbecause of how much that would
hurt.
Maybe, true, but going back toyou, continuing to say yes if
you're in a position where youshould retire and need to retire
and want to move on todifferent things, continuing to
say yes to work is saying no tothe things that you actually
want to do, which is the firstpoint.
(22:55):
But then, number two, thatfeeling might not actually be
mutual, and I say that becausesometimes that's the thing
that's keeping people going,because they feel like there's
this thing that they would neverdo that to me.
So how could I retire from them?
How quickly would you bereplaced if you left, is a
question I would ask, and theanswer is probably as soon as
(23:15):
they possibly could, which wouldnot be that long.
So it's a difficult thing to do.
It is a breakup.
You are breaking up with them,but at some point along the way
you need to do that to make sureyou can do what you're actually
trying to do with the rest ofyour life.
Speaker 1 (23:28):
It's true.
So just a super happy episodetoday, guys.
Hope you enjoyed this and wewill be back in a few weeks.
More fun topics Once again.
Go to the Root Collective.
That is where you can go if youwant to really comment about
anything, and that's how we'rechoosing what we discuss.
Additionally, if you arethinking, hey, honestly, I know
I need to break up, it's mainlythe financial side.
(23:49):
How do I even know where tobegin?
We help clients with everything, so that's from.
Hey, here's how we would havethat conversation to financially
, are you in a spot to make ithappen?
This is what we love to do.
So go to rootfinancialcom.
In the upper right.
You'll see a button that sayssee if you're a fit, and you can
click that to get started.
Speaker 2 (24:05):
Awesome.
Thank you everyone for watchingand we will see you next time.
See ya, thank you.
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