November 13, 2025 • 8 mins
"Hey Mike, I want to keep working but it’s getting in the way of my IRA to Roth Conversions. What can I do?"
Discover why your purpose and work may be more important than paying slightly less in taxes.
Text your questions to 913-363-1234.
Request Your Wealth Analysis by going to www.retireontime.com
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Mike (00:05):
Welcome to How to Retire On Time, a show that answers
your retirement questions. We'rehere to move past that
oversimplified advice you'veheard hundreds of times.
Instead, we're gonna dive intothat nitty gritty. So as always,
text your questions to (913)363-1234 anytime during the
week, and we'll feature them onthe show. Just remember, not
financial advice.
This is an educational show.David, what do we got today?
David (00:28):
Hey, Mike. I want to keep working, but it's getting in the
way of my IRA to Rothconversions. What can I do? Keep
working. Okay.
Because if you're taking income,and you tell me if I'm wrong,
this is just my shot in the darkhere, but if you're taking
income from your job and you'reconverting an IRA to Roth, that
counts as income as well, andsuddenly a lot of income?
Mike (00:48):
Yeah. You're in the 30 to 30 whatever percent tax bracket
potentially. Yeah. And that'smaybe not the best use of your
money. People are scared aboutRMDs because they're stuck on
perfectionism.
Hear me out on this.
David (01:00):
Okay. Okay.
Mike (01:01):
What's the point of your money? To support the lifestyle
you want?
David (01:04):
Yeah. To do the things that I wanna do. First of all,
to sustain life. Right? And thenon top of that though, like, do
the things I wanna do.
Mike (01:11):
K. Let's say you love your job, and you would do it for
free. You don't do it for free.No. You are compensated.
You need to be compensated forthe professional job that you're
doing. You don't work for free.That creates all sorts of
issues. And this is kind ofweird to say, but who cares
about a perfect IRA to Rothconversion if you were to retire
(01:34):
to try and save some money ontaxes and you end up actually
hurting your health, your mentalhealth, and your physical
health. Because if you don'thave purpose, if you don't fill
that void, you speed up yourcognitive decline.
You speed up your physicaldecline. You end up sad, lonely,
depressed. Even if you'remarried, your life is often
(01:54):
worse off because you have nopurpose in retirement. Why would
you wanna do that? To save a fewbucks on taxes?
That does not make any sense inthe world. Now that doesn't mean
you just do IRA Roth conversionsbecause you're still working and
that date might come up.Whatever. If you are enjoying
your life and you're gettingcloser to the RMD age, who
(02:15):
cares? Mhmm.
Because at the worst of it all,maybe you do take RMDs, and you
can't take an RMD and put it ina Roth, by the way.
David (02:22):
Okay.
Mike (02:23):
But what if you just took the RMD that you didn't need,
and you put it into yourbrokerage account, and you put
into a bunch of investments thatdon't pay a dividend? They're
just growth, and all that's nowset for legacy. Is that really
the end of the world?
David (02:35):
No. Sounds okay to me.
Mike (02:37):
So this is why we emphasize over and over again,
what's the life you wanna live?If working is your purpose, if
that's what helps you engagefrom a critical standpoint.
Critical not being like, youknow, a critical individual that
sucks, but like criticalthought, problem solving. You're
(02:58):
engaged. It's a healthy kind ofstress.
You know, you're part of a team,and you're accomplishing things.
And there's this positivefeedback loop of it's giving you
an exciting life. Why in theworld would you give that up?
David (03:11):
Yeah. Especially if you had nothing to replace it with.
Mike (03:13):
Yeah. And then you might say, well, but I'm working, so
I'm paying taxes. Yeah. Andyou're also getting paid. So for
all of those high income earnersthat love their job, I'm gonna
tell you what the financialservices space won't.
Don't retire. Keep working. Stayengaged. Retirement is a new
modern concept. Because back inthe day, for thousands of years
(03:37):
Yeah.
You worked until you youcouldn't work anymore, and then
you probably died a month later.
David (03:41):
Yeah.
Mike (03:42):
And that's how we're hardwired to live. Retirement
for many people is kind of likePleasure Island on Pinocchio. It
looks really cool at first, butafter you've traveled enough,
after you've seen all the sites,you've gone to the golf course
because you thought you weresupposed to and all these other
(04:02):
things that you're supposed todo, you end up miserable and
regretting the fact that youretired. People think, oh,
retire on time. Well, I wannaretire as soon as possible.
Are you sure? Are you sure?Gotta be sure. On time means
that it's financially prudentfor you and emotionally prudent
for you. On time might be laterthan you thought because you
(04:25):
don't want to speed up your dateof death just to go on a couple
more cruises a year.
And you might think, well, Iwanna spend more time with my
family. I wanna travel. Do itwhile you work. Maybe take a few
more vacations. Maybe negotiate.
Say, hey. I wanna keep working,but can I just get more PTO?
I'll take a salary reduction.Yeah. I just want a little bit
more flexibility, but I love myjob.
(04:47):
Who's gonna be upset with that?Right. I mean, really. Yeah.
They're keeping you there for areason.
And if you just got laid off byyour job, a lot of government
employees have been laid off,get another job. Maybe you
retired for six months, evenenjoyed a little bit, but you're
still looking for another jobbecause it gives you purpose.
Just don't assume and here's theconflict of interest. The entire
(05:10):
financial services space wantsyou to retire so you can roll
your four zero one k over intotheir account, charge you 1%,
and make money off of it whilethey hope that you're happy.
David (05:18):
Yeah.
Mike (05:19):
That's not in your best interest from a psychological
standpoint, but that's nottalked about. It's more
profitable for the financialservices space to roll your
funds over and charge you 1% or1.5% or whatever it is, and we
do that. We don't do thepercentages. We do a flat fee up
to $600 a month, but still,everyone has this conflict of
interest. We get paid when youmove your funny money over from
(05:41):
a four zero one k.
And I'm telling you, don't do itif it doesn't give you purpose.
And, yeah, I mean, if you're 65,70 years old, yeah, you can roll
your funds over and still work.So I guess I'm not fully
representing the argument there,but it's not about retiring
quickly. What is the lifestylethat you should be living?
(06:02):
That's the most important thing.
And if you're really good atyour job and you wanna keep
doing it, whether it's in yourcurrent position or as a
consultant or something else, gofor it. We call it your encore
career. And it's actually a lotof fun too if you end up being a
consultant to do your own LLC.You take your salary. You've got
your already long term contractswith a couple of clients, and
(06:23):
you could do some tax planningaround this because you're
earning income, so you can stilldo Roth contributions.
You can still set up like asimple IRA, do your own
contributions as well, or a SEPIRA if you're individual.
There's a couple of optionsthere. Then you could I'm just
kinda spitballing here a coupleof these options. You could file
your taxes as an s corp, LLC asan s corp, then you're taking
(06:44):
income off of a reasonable wage,whatever that is determined by
your job, and then the rest isprofits. Now you've just done
some more tax efficiency on yourincome, so you're getting more
out of your work as it is.
So many things that could bedone. Mhmm. And that's the easy
tax form to file every year.You've got more purpose. You're
still earning money, so you'vegot more assets for legacy or
for other reasons.
You got more flexibility forvacations. I mean, who wouldn't
(07:07):
want something like that? Theidea that we're all supposed to
stop working is a farce. We allneed to work. It's just which
path do you want?
Is it with a church? Is it witha charity? Is it with a
professional career as an encoreor something else?
David (07:23):
Maybe you're helping your kids by watching your grandkids
or something.
Mike (07:27):
Yeah. But don't become codependent on them. There's
boundaries.
David (07:30):
I set a trap for you there, and you you didn't get
caught.
Mike (07:32):
Nope. Can't get me. But that's that's the point. Set up
your lifestyle to give youpurpose, to help breed
happiness, joy, well-being, notquickly go to a vacation because
that's what everyone else seemsto wanna do. That's all the time
we've got for the show today.
If you enjoyed the show,consider subscribing to it
wherever you get your podcasts.Just search for how to retire on
(07:53):
time. Discover if your portfoliois built to weather flat market
cycles or if you're missing taxminimization opportunities that
you may not even know exist.Explore strategies that may be
able to help you lower youroverall risk while potentially
increasing your overall growthand lifestyle flexibility. This
is not your ordinary financialanalysis.
(08:14):
Learn more about Your WealthAnalysis and what it could do
for you regardless of your age,asset, or target retirement
date. Go toww.yourwealthanalysis.com today
to learn more and get started.
Welcome to How to Retire On Time, a show that answers
your retirement questions. We'rehere to move past that
oversimplified advice you'veheard hundreds of times.
Instead, we're gonna dive intothat nitty gritty. So as always,
text your questions to (913)363-1234 anytime during the
week, and we'll feature them onthe show. Just remember, not
financial advice.
This is an educational show.David, what do we got today?
David (00:28):
Hey, Mike. I want to keep working, but it's getting in the
way of my IRA to Rothconversions. What can I do? Keep
working. Okay.
Because if you're taking income,and you tell me if I'm wrong,
this is just my shot in the darkhere, but if you're taking
income from your job and you'reconverting an IRA to Roth, that
counts as income as well, andsuddenly a lot of income?
Mike (00:48):
Yeah. You're in the 30 to 30 whatever percent tax bracket
potentially. Yeah. And that'smaybe not the best use of your
money. People are scared aboutRMDs because they're stuck on
perfectionism.
Hear me out on this.
David (01:00):
Okay. Okay.
Mike (01:01):
What's the point of your money? To support the lifestyle
you want?
David (01:04):
Yeah. To do the things that I wanna do. First of all,
to sustain life. Right? And thenon top of that though, like, do
the things I wanna do.
Mike (01:11):
K. Let's say you love your job, and you would do it for
free. You don't do it for free.No. You are compensated.
You need to be compensated forthe professional job that you're
doing. You don't work for free.That creates all sorts of
issues. And this is kind ofweird to say, but who cares
about a perfect IRA to Rothconversion if you were to retire
(01:34):
to try and save some money ontaxes and you end up actually
hurting your health, your mentalhealth, and your physical
health. Because if you don'thave purpose, if you don't fill
that void, you speed up yourcognitive decline.
You speed up your physicaldecline. You end up sad, lonely,
depressed. Even if you'remarried, your life is often
(01:54):
worse off because you have nopurpose in retirement. Why would
you wanna do that? To save a fewbucks on taxes?
That does not make any sense inthe world. Now that doesn't mean
you just do IRA Roth conversionsbecause you're still working and
that date might come up.Whatever. If you are enjoying
your life and you're gettingcloser to the RMD age, who
(02:15):
cares? Mhmm.
Because at the worst of it all,maybe you do take RMDs, and you
can't take an RMD and put it ina Roth, by the way.
David (02:22):
Okay.
Mike (02:23):
But what if you just took the RMD that you didn't need,
and you put it into yourbrokerage account, and you put
into a bunch of investments thatdon't pay a dividend? They're
just growth, and all that's nowset for legacy. Is that really
the end of the world?
David (02:35):
No. Sounds okay to me.
Mike (02:37):
So this is why we emphasize over and over again,
what's the life you wanna live?If working is your purpose, if
that's what helps you engagefrom a critical standpoint.
Critical not being like, youknow, a critical individual that
sucks, but like criticalthought, problem solving. You're
(02:58):
engaged. It's a healthy kind ofstress.
You know, you're part of a team,and you're accomplishing things.
And there's this positivefeedback loop of it's giving you
an exciting life. Why in theworld would you give that up?
David (03:11):
Yeah. Especially if you had nothing to replace it with.
Mike (03:13):
Yeah. And then you might say, well, but I'm working, so
I'm paying taxes. Yeah. Andyou're also getting paid. So for
all of those high income earnersthat love their job, I'm gonna
tell you what the financialservices space won't.
Don't retire. Keep working. Stayengaged. Retirement is a new
modern concept. Because back inthe day, for thousands of years
(03:37):
Yeah.
You worked until you youcouldn't work anymore, and then
you probably died a month later.
David (03:41):
Yeah.
Mike (03:42):
And that's how we're hardwired to live. Retirement
for many people is kind of likePleasure Island on Pinocchio. It
looks really cool at first, butafter you've traveled enough,
after you've seen all the sites,you've gone to the golf course
because you thought you weresupposed to and all these other
(04:02):
things that you're supposed todo, you end up miserable and
regretting the fact that youretired. People think, oh,
retire on time. Well, I wannaretire as soon as possible.
Are you sure? Are you sure?Gotta be sure. On time means
that it's financially prudentfor you and emotionally prudent
for you. On time might be laterthan you thought because you
(04:25):
don't want to speed up your dateof death just to go on a couple
more cruises a year.
And you might think, well, Iwanna spend more time with my
family. I wanna travel. Do itwhile you work. Maybe take a few
more vacations. Maybe negotiate.
Say, hey. I wanna keep working,but can I just get more PTO?
I'll take a salary reduction.Yeah. I just want a little bit
more flexibility, but I love myjob.
(04:47):
Who's gonna be upset with that?Right. I mean, really. Yeah.
They're keeping you there for areason.
And if you just got laid off byyour job, a lot of government
employees have been laid off,get another job. Maybe you
retired for six months, evenenjoyed a little bit, but you're
still looking for another jobbecause it gives you purpose.
Just don't assume and here's theconflict of interest. The entire
(05:10):
financial services space wantsyou to retire so you can roll
your four zero one k over intotheir account, charge you 1%,
and make money off of it whilethey hope that you're happy.
David (05:18):
Yeah.
Mike (05:19):
That's not in your best interest from a psychological
standpoint, but that's nottalked about. It's more
profitable for the financialservices space to roll your
funds over and charge you 1% or1.5% or whatever it is, and we
do that. We don't do thepercentages. We do a flat fee up
to $600 a month, but still,everyone has this conflict of
interest. We get paid when youmove your funny money over from
(05:41):
a four zero one k.
And I'm telling you, don't do itif it doesn't give you purpose.
And, yeah, I mean, if you're 65,70 years old, yeah, you can roll
your funds over and still work.So I guess I'm not fully
representing the argument there,but it's not about retiring
quickly. What is the lifestylethat you should be living?
(06:02):
That's the most important thing.
And if you're really good atyour job and you wanna keep
doing it, whether it's in yourcurrent position or as a
consultant or something else, gofor it. We call it your encore
career. And it's actually a lotof fun too if you end up being a
consultant to do your own LLC.You take your salary. You've got
your already long term contractswith a couple of clients, and
(06:23):
you could do some tax planningaround this because you're
earning income, so you can stilldo Roth contributions.
You can still set up like asimple IRA, do your own
contributions as well, or a SEPIRA if you're individual.
There's a couple of optionsthere. Then you could I'm just
kinda spitballing here a coupleof these options. You could file
your taxes as an s corp, LLC asan s corp, then you're taking
(06:44):
income off of a reasonable wage,whatever that is determined by
your job, and then the rest isprofits. Now you've just done
some more tax efficiency on yourincome, so you're getting more
out of your work as it is.
So many things that could bedone. Mhmm. And that's the easy
tax form to file every year.You've got more purpose. You're
still earning money, so you'vegot more assets for legacy or
for other reasons.
You got more flexibility forvacations. I mean, who wouldn't
(07:07):
want something like that? Theidea that we're all supposed to
stop working is a farce. We allneed to work. It's just which
path do you want?
Is it with a church? Is it witha charity? Is it with a
professional career as an encoreor something else?
David (07:23):
Maybe you're helping your kids by watching your grandkids
or something.
Mike (07:27):
Yeah. But don't become codependent on them. There's
boundaries.
David (07:30):
I set a trap for you there, and you you didn't get
caught.
Mike (07:32):
Nope. Can't get me. But that's that's the point. Set up
your lifestyle to give youpurpose, to help breed
happiness, joy, well-being, notquickly go to a vacation because
that's what everyone else seemsto wanna do. That's all the time
we've got for the show today.
If you enjoyed the show,consider subscribing to it
wherever you get your podcasts.Just search for how to retire on
(07:53):
time. Discover if your portfoliois built to weather flat market
cycles or if you're missing taxminimization opportunities that
you may not even know exist.Explore strategies that may be
able to help you lower youroverall risk while potentially
increasing your overall growthand lifestyle flexibility. This
is not your ordinary financialanalysis.
(08:14):
Learn more about Your WealthAnalysis and what it could do
for you regardless of your age,asset, or target retirement
date. Go toww.yourwealthanalysis.com today
to learn more and get started.
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Are You A Charlotte?
In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.