Kelly Financial: Saturday, March 7, 2026

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Episode Transcript

Speaker 1 (00:12):
It's coming to us, So.

Speaker 2 (00:20):
Ladies and gentlemen, welcome to Safe Money Strategies on WRKO.
I'm William Kelly and it's an honor to carry on
a family legacy rooted in real world values and practical advice.
Kelly Financial was founded in two thousand and three by
my parents, my late father Bill Kelly and my mother
Kelly Kelly and Braintree and Burlington, Massachusetts. Just two years later,

(00:41):
Dad launched Safe Money Strategies on WRKO as a no
nonsense callin radio show focused on common sense planning and
protecting wealth. Over the past two decades, Dad became a
pillar in New England finance, an engineer, turn entrepreneur, author
and philanthropist who believed in giving back and walking the talk.
Since five, our show has remained a Saturday morning staple,

(01:03):
offering insight and empowerment. Here at Kelly Financial, we help
steward over eight hundred million dollars across our affiliated business,
including more than six hundred million dollars managed by our
sec registered investment advisory, where fiduciary care and our family
first philosophy guides us on safe money strategies. You'll hear
candid conversations with the team, my mother Kelly, myself, advisors

(01:26):
Charlie Gable, Mike Ducett, Greg Workman, Greg Murray, my sister
Mary Madeline, and Tom Schlager. We live by two rules,
never quit and carry on, and we're here to help
you do the same when it comes to your money.
Stick around, take notes and join the conversation. To learn
more or get our free guides or schedule consultation, visit

(01:46):
Kellyfinancial dot org or call us at eighty eight eight
eight hundred one eight eight one. This is Safe Money Strategies.
Next up Forever Young with Kelly Kelly and myself, William
Kelly Junior.

Speaker 3 (02:02):
Safe Money Strategies with William Kelly and Kelly Kelly eight
hundred eighteen eighty one.

Speaker 4 (02:13):
Each week on Safe Money Strategies, we take a moment
to step back from the headlines and have a real conversation,
the kind you might have around the kitchen table. This
is a part of the show we call Forever Young
is where I sit down with my son, my handsome son, Wow,
William Kelly Junior, and we talk about life, what's going

(02:33):
on in the world, in our family, and what really
matters most when you're planning for the future.

Speaker 5 (02:39):
Sometimes is light, sometimes is thoughtful, but it's always real.
Good morning William.

Speaker 1 (02:45):
Good morning Mom. Those almost week two in a row,
but you save yourself there.

Speaker 2 (02:49):
Last week she forgot to call me handsome, and I
was so offended that I mentioned in the conversation.

Speaker 1 (02:54):
But it seems like you've redeemed yourself.

Speaker 6 (02:56):
Mom.

Speaker 5 (02:56):
I pretty good. Yes, yes, my handsome son. So how
are you?

Speaker 1 (03:01):
I'm great. The weather, we had one really good day.

Speaker 2 (03:04):
It was like basically fifty something degrees out over at
school at Bryant.

Speaker 1 (03:09):
It was awesome and I.

Speaker 2 (03:11):
Caught as much sun as possible until the weather went
back to gloom and then.

Speaker 1 (03:15):
You know, it's been going up and down. I'm very
excited for the springtime.

Speaker 5 (03:19):
I'll tell you that I think we all are yes.
All of New England is yes.

Speaker 1 (03:24):
We had bad news about my grade.

Speaker 5 (03:27):
I know this. I don't mean didn't erupt.

Speaker 4 (03:30):
But it feels like every Saturday when we when we
do our segment together that you confess about something.

Speaker 5 (03:39):
I know there's always some confession.

Speaker 1 (03:41):
There always is a confession.

Speaker 7 (03:42):
Parties is not that bad, it's horrible.

Speaker 4 (03:46):
But I just happened to ask about your test and.

Speaker 1 (03:50):
It just wasn't good.

Speaker 2 (03:51):
But you know, luckily he expected people to do poorly
on the first one, so you made that exam only
ten percent worth of our grade. And the good news
is that I still have an A in the class good,
so it wasn't catastrophic.

Speaker 1 (04:03):
But and Creative Writing class, I was in class.

Speaker 2 (04:08):
It was online because of the blizzard, and my professor
she goes and she holds me back. She said, Welliam,
do you stay after class? Just you alone? And I'm like,
do I do something wrong? I don't think I did
anything wrong, you know, and so I'm staying there. She said, William,
sorry to keep you after class. I just want to
hold you. I didn't want to say this in front
of anybody else to make them, you know, jealous, or.

Speaker 1 (04:27):
To cause an issue.

Speaker 2 (04:28):
But she said, William, that was one of the best
papers I've ever read. And I just sat there. I
was like, what you know she gave me? We had
an assignment which was a rough draft on her essay.
And the rough draft was basically, you submit it intentionally
as a rough draft, and then she grades it and
then she puts her comments, and then you submit the fund.

Speaker 5 (04:47):
And did she give you the topic or did you
choose the topic.

Speaker 2 (04:50):
The topic was we had to write a rhetorical analysis
on a civil rights or a politically civil like a
civil rights struggle, essentially of any kind, any kind of injustice,
social injustice, not like social Justice Warrior, but like Martin
Luther King for examples, who I picked. I picked a
letter from the Birmingham Jel that he wrote, and I

(05:12):
did do a rhetorical analysis. And you had to pick
out like the logos, the ethos, the cairos, and the pathos,
and you had to define those how doctor Martin Luther
King for me in particular, how he used those tools
in his essay to write a really compelling letter. I
threw in some background information, but she said, William, you
didn't write a summary.

Speaker 1 (05:32):
You wrote an analysis. Is exactly what I wanted.

Speaker 2 (05:34):
Do I have your permission to use this as an
example for future classes?

Speaker 7 (05:38):
And I was just like, wow, I'm calling my mom.

Speaker 1 (05:40):
Right after this.

Speaker 5 (05:41):
She said, so excited.

Speaker 1 (05:42):
Summit the essay. She said, don't worry about it. You know,
I'm not saying you have to come to class.

Speaker 2 (05:46):
But like if you don't come, I won't mark anything,
So don't worry about attendance.

Speaker 1 (05:49):
I started laughing.

Speaker 2 (05:51):
But she was gone all week because she was in
Atlanta and she had a trip. It was like a
civil rights trip, a history and doctor Martin Luther King's
personal driver, he was nineteen years old when he was
his personal family driver, was leading the tour of his
house of all sorts of history and like lectures and stuff. Wow,

(06:12):
this guy's running in Atlanta and she highly recommended it
to me.

Speaker 1 (06:16):
I looked him up.

Speaker 2 (06:17):
Really interesting guy, and I just thought it was magnificent.
So we had a great conversation. It was really it
was a fun paper. I really liked writing it. She's
also a fantastic teacher and that helps as well. So
it was very good news.

Speaker 1 (06:30):
Hearing that now, that is so exciting. That completely threw.

Speaker 2 (06:33):
Away any bad nerves I had about the ECON exam,
and I felt great. I also my political science professor
said that my essays are perfect.

Speaker 1 (06:42):
He says, keep writing them the way you're writing them.

Speaker 7 (06:44):
Good.

Speaker 1 (06:45):
There you go. It's been a great week.

Speaker 5 (06:47):
Good was good to see you. Good to see You're
a little stuffed.

Speaker 1 (06:50):
Up a little bit. Something's going around campus, but it's
not terrible.

Speaker 5 (06:54):
Yeah, you seem to sort of dodge it.

Speaker 2 (06:56):
Yeah, more or less. But yeah, first, I've been second forever. Yeah,
didn't miss it?

Speaker 4 (07:02):
Yeah, well I had some chicken noodle soup homemade ready
for you. Do keep us on your dial. We've got
a lot of great content coming your way. Mike dust
and Greg Workman will break down the hidden tax traps
that can quietly impact retirees and the smart planning strategies

(07:22):
designed to help families stay ahead of them. Mary, Madeline
Kelly and Greg Murray will explore a powerful question many
savers overlook. Are you preparing responsibly for the future while
still allowing yourself to fully enjoy the life you've worked
so hard to build. When William and I return, we

(07:44):
will introduce a new retirement trend called the Great Digital
Nomad and what it could mean for your future. And
of course we'll close the hour with some wit and
wisdom from the late Bill Kelly. His words continue you
to inspire and guide us. That's a wrap for forever
young Thank you for listening, and William, thank you for

(08:07):
joining me.

Speaker 5 (08:08):
We'll be back with more great content.

Speaker 8 (08:11):
I love you, honey, I love you too.

Speaker 6 (08:21):
Okay, my friends, let's be honest.

Speaker 9 (08:24):
Most young people don't get real financial advice they get
high social media, quote unquote experts and a lot of
bad advice. Only The Good invest Young, written by William
Kelly Junior from Kelly Financial Services, takes a different approach.
It focuses on fundamentals, avoiding unnecessary debt, understanding risk taking

(08:47):
long term, No get rich quick schemes, no fantasy economics.
The emphasis is on practical ideas around money, responsibility and discipline,
and of course, worse, like anything involving investing, there's always
risk and that includes the possibility of losing principle. And
that's exactly why learning how to think about money early matters.

(09:10):
If the book is designed as an educational resource for
those starting out, or for parents and grandparents looking to
begin the conversation. To request a free copy called eight
eight eight eight hundred eighteen eighty one or email Kelly
at Kelly Financial dot org.

Speaker 7 (09:29):
Welcome back to Save Money Strategies.

Speaker 10 (09:31):
I'm Mike Dussat, Chief Operating Officer at Kelly Financial and
alongside me, as always is Greg Workman, investment Advisor. Each
week we talk about the decisions that can make or
break your retirement, not just investment returns, but income taxes,
social security, pensions, estate planning, and most importantly, how all
of those pieces fit together. Last week, we covered what

(09:54):
we called the retirement tax trap. We talked about how
many retirees unknowingly build large tax deferred accounts such as
four oh one k's iras four or three b's, and
how those accounts can turn into ticking tax time bombs
once required minimum distributions begin. We discussed how today's historically
low tax brackets may not be here forever, and we

(10:18):
talked about the danger of waiting too long to address
tax exposure. Today, we're taking the conversation one step further. Greg,
there's another tax trap that most retirees never see coming,
and it doesn't show up until one spouse passes away.

Speaker 6 (10:34):
That's where Mike, and this one is emotional and financial
at the same time. We call it the widow's penalty,
or what I often describe as tax bracket shock. It
happens when a married couple files jointly. They benefit from
wider tax brackets and a higher standard deduction. But when
one spouse passes away, the surviving spouse eventually files as

(10:58):
a single taxpayer. And here's the problem. The tax brackets
shrink dramatically at that time.

Speaker 7 (11:04):
That's the part that surprises people.

Speaker 10 (11:07):
Income may not drop much, but the tax bracket gets compressed.
Let's walk through a hypothetical client example. For illustration purposes only,
we'll call them John and Linda. They're both sixty eight
years old, recently retired. Between social Security, a pension, and
withdrawers from their IRA, their total income is about one

(11:28):
hundred and forty thousand per year. Married filing jointly, That
keeps them comfortably within a moderate tax bracket. Nothing extreme,
very manageable. Now let's fast forward ten years. John passes
away at seventy eight. Linda is now widowed Greg.

Speaker 6 (11:44):
What happens well, First, emotionally, it's devastating, but financially the
structure changes immediately. Linda now files as a single taxpayer.
Her social Security benefit may stay relatively similar because she
can step into the hire of the two benefits, so
between hers and her late husbands. The pension may drop

(12:07):
depending upon the survivor option that was elected. But here's
the key. Their IRA balance hasn't disappeared, and required minimum
distributions don't stop. So even if her income drops from
one hundred and forty thousand to say one hundred and
ten thousand, she could easily move into a higher tax

(12:29):
bracket because now she's filing single.

Speaker 10 (12:31):
So she's earning less but potentially paying more in taxes.
That's the widow's penalty. And here's where it gets even
more dangerous. When we combine that bracket compression with ongoing rmds,
capital gains distributions, medicare, premium searcharges, possible long term care expenses,

(12:52):
the surviving spouse often experiences more financial pressure at the
exact moment life fills.

Speaker 6 (12:57):
Most fragile and most couples never see a because when
both are alive, everything looks fine. Their CPA is filing jointly,
their tax rate feels manageable, and they assume if income
drops later, taxes will follow suit. But that assumption is
often wrong.

Speaker 7 (13:17):
When you look at the tax tables.

Speaker 10 (13:18):
Married filing jointly, brackets are roughly double the size of
single brackets, not exactly double, and the higher you go,
the more compressed it becomes.

Speaker 6 (13:28):
So if a couple was sitting comfortably and say the
twenty two percent bracket while married, the surviving spouse might
find herself pushed into the twenty four or thirty two
percent bracket at a lower income threshold. And remember this
often happens at later ages late seventies or eighties, when

(13:50):
required minimum distributions are mandatory, Investment flexibility is reduced and
planning options while they become narrower.

Speaker 7 (14:00):
And that's the key point. Options shrink with time.

Speaker 10 (14:03):
The earlier you plan, the more control you have greg
This is where we see the power of proactive tax planning,
especially in the early retirement years before URMDA.

Speaker 6 (14:14):
Exactly, the window between retirement and age seventy three before
required minimum distributions begin is often the most powerful tax
planning window a couple will ever have. If we know
bracket compression is likely later, if we know one spouse
will eventually file single, if we know tax deferred balances

(14:38):
are large, why not start managing that exposure intentionally while
both spouses are alive and filing jointly.

Speaker 10 (14:48):
I want to pause here for a moment, because this
topic isn't just math. Most couples don't like talking about
one spouse passing away. It's uncomfortable, it feels morbid, but
ignoring it doesn't make it go away. In fact, thoughtful
planning is one of the most loving things spouses can
do for each other, because the goal isn't just maximizing returns.

(15:08):
It's reducing stress for the surviving spouse. It's making sure
they're not learning about tax bracket compression from the irs.

Speaker 7 (15:15):
That's right.

Speaker 6 (15:16):
We've seen situations again, hypothetically speaking, where a surviving spouse
comes in after a loss and says, I had no
idea our tax picture would look like this, and unfortunately,
at that point many of the best strategies are no
longer available. Roth conversion opportunities were missed, income smoothing windows

(15:39):
were closed, and bracket management was never done. Now we're
reacting instead of doing some proactive planning.

Speaker 10 (15:48):
Now here's the encouraging part. This is preventable. Bracket shock
is not inevitable. It's predictable. And when something is predictable,
it can be planned for. That's what we do inside
the Money Strategies planning process. We don't just look at
this year's tax return. We project forward. We ask what
happens at first death, what happens at RM d AH,

(16:10):
what happens if tax rates rise, what happens if one
pension stops? And when we stress test those scenarios in advance,
families gain clarity, and clarity reduces anxiety. Greg As we
head into the break, what's the one takeaway you want
listeners to remember from the first half.

Speaker 6 (16:26):
If you're married and retired or within ten years of retirement,
and most of your assets are in tax deferred accounts,
you likely have exposure to bracket compression at first death.
The question isn't whether one spouse will pass first. The
question should be whether this surviving spouse will be financially

(16:48):
prepared when it happens.

Speaker 7 (16:50):
That's powerful.

Speaker 10 (16:51):
When we come back, we're going to talk about specific
strategies that can reduce or even eliminate the widow's penalty,
including roth conversions, pension elections, social security timing, and coordinated
to safe planning.

Speaker 7 (17:03):
You're listening to safe money strategies, stay with us.

Speaker 3 (17:10):
Kelly Financial Services eight eight eight eight hundred, eighteen eighty one.

Speaker 4 (17:16):
I'm Kelly Kelly from Kelly Financial. Is your financial advisor
a fiduciary? In other words, are they legally required to
act in your best interest? My complimentary book, Retire Your Fear,
Plan Your Future explains what a fiduciary is and will
help you understand if an advisor is really putting you first.

Speaker 6 (17:35):
For the book.

Speaker 4 (17:36):
Call eight eight eight eight hundred eighteen eighty one or
email Kelly at Kellyfinancial dot org.

Speaker 5 (17:42):
We're Kelly Financial. Come retire with us.

Speaker 3 (17:46):
The Money Wrap with Kelly Financial Advisors Greg Murray and
Mary Madeline Kelly.

Speaker 7 (17:53):
Hello.

Speaker 11 (17:53):
This is Greg Murray, Senior vice president and Chief Compliance
Officer at Kelly Financial Services. Joining me today is Mary
Mavielle and Kelly, one of our wealth advisors. How are
you doing today?

Speaker 1 (18:02):
Hi?

Speaker 6 (18:03):
Greg.

Speaker 8 (18:03):
I'm doing great, and I'm especially excited because by the
time this airs, I will be in vacation in Japan,
which has been on my bucket list for a long time.
I just love traveling because it reminds me of how
important it is to enjoy the experiences you work so
hard for.

Speaker 11 (18:19):
That's fantastic, and I'll be a way too. I'm heading
to Finland, hopefully seeing some snow, maybe even the Northern
lights if I'm lucky. It's funny because trips like these
really highlight why we plan financially in the first place.

Speaker 8 (18:30):
That's awesome. I'm excited to hear how it goes, and
that actually leads perfectly into today's topic because we're talking
about something we see pretty often with clients. Are you
oversaving and underliving?

Speaker 11 (18:42):
That's such an interesting question because most financial advice focuses
on saving more, spending less, and preparing for the future.
These are all important things, but sometimes people get so
focused on the future that they forget to enjoy the present.

Speaker 8 (18:54):
Yes, and we especially see this with people who've been
disciplined savers for years. They've done everything right, maxed out
retirement accounts, paid down debt, built strong portfolios, but they
still feel hesitant to spend even when they absolutely can, and.

Speaker 11 (19:10):
That hesitation usually comes from uncertainty. People worry what if
I need this later, what if the market drops, what
if I live longer than expected?

Speaker 8 (19:17):
And those are valid concerns, longevity, health care costs, market volatility.
They're real factors, But sometimes fear of the unknown leads
to missing out on meaningful experiences today.

Speaker 11 (19:29):
And of course, we always remind listeners that investing involves risk,
including the potential loss of principle, so planning needs to
balance both growth and protection.

Speaker 8 (19:37):
Exactly, this conversation isn't about spending recklessly, it's about balance,
making sure your financial plan supports both future security and
present enjoyment.

Speaker 11 (19:47):
Because money ultimately exists to support your life, not the
other way around.

Speaker 8 (19:51):
Yes, and interestingly, retirees sometimes struggle most with this. They've
spent decades saving and when retirement comes, switching from savings
mode mode to spending mode can feel uncomfortable.

Speaker 7 (20:02):
We hear that a lot.

Speaker 11 (20:03):
People will say, I know I have enough, but I
still feel nervous about spending.

Speaker 8 (20:07):
That's where having a clear income plan helps. When you
understand how your assets translate into sustainable monthly income, confidence
usually increases.

Speaker 11 (20:15):
And that confidence can make it easier to enjoy travel, hobbies,
of family time, whatever matters most to you.

Speaker 8 (20:21):
Another factor is perspective. Experiences like travel, time with family,
health and wellness often provide lasting value that isn't reflected
on a balance sheet.

Speaker 11 (20:31):
Absolutely, and interestingly, people rarely regret the thoughtful experiences they had.
More often they regret the things they postponed too long.

Speaker 8 (20:38):
But on the flip side, there are certainly cases where
people undersave, So this isn't a one direction conversation. It's
about making sure saving levels match your goals right.

Speaker 11 (20:49):
The key question is and should I save less? It
is my saving aligned with my life priorities?

Speaker 8 (20:54):
And long term needs, and that's where planning comes in.
A good financial plan looks at cash flow, retirement per injections, taxes,
healthcare considerations, risk tolerance, all the moving parts.

Speaker 11 (21:05):
Once those pieces are clear, becomes much easier to find
the balance between preparing for tomorrow and.

Speaker 8 (21:09):
Enjoying today exactly. And sometimes just having permission backed by
numbers helps people feel comfortable spending intentionally.

Speaker 11 (21:17):
So for our listeners, here are a few signs you
might be oversaving or underliving, Consistently delaying experiences you value,
feeling guilty about reasonable spending, or accumulating savings without a
clear future purpose.

Speaker 8 (21:29):
And conversely, if you're not sure whether you're saving enough,
that's another great reason to review your plan.

Speaker 11 (21:34):
As always, every financial situation is unique, and investing involves risk.
Decisions should be tailored to your financial timeline and comfort level.

Speaker 8 (21:42):
But the takeaway is simple. Financial planning isn't just about accumulation.
It's about creating a life that feels both secure and fulfilling.

Speaker 11 (21:50):
Well said, and hopefully both of us will be practicing
what we preach over the next week.

Speaker 8 (21:54):
Absolutely, I'll report back on Japan and you report on Finland.

Speaker 7 (21:58):
Deal.

Speaker 8 (21:59):
All right, Greg, I'll see you soon.

Speaker 3 (22:00):
To get in touch with Greg Murray or Mary, Madeline
Kelly or any member of the Kelly Financial team called
eight eight eight eight hundred, eighteen eighty one. Safe Money
Strategies with William Kelly and Kelly Kelly. Call the team
on eight eight eight hundred, eighteen eighty one.

Speaker 4 (22:29):
Welcome back to Safe Money Strategies. I'm Kelly Kelly here
with my son, William Kelly Junior, and we're so glad
you're spending part of your weekend with us. Today we're
talking about something that reflects a much bigger shift happening
across the country and really around the world. Retirement is

(22:50):
being redefined. For decades, retirement followed a traditional pattern. You
worked for thirty or forty years and then you slow down.
That was the expectation. But today that model simply doesn't
fit everyone anymore. Research from the National Institute on Aging

(23:12):
shows that retirement satisfaction increases when older adults remain meaningfully engaged,
not necessarily working full time, but engaged, connected, purposeful, and
technology has completely changed what that engagement can look like.

(23:33):
High speed internet, video conferencing, cloud based software, secure digital tools.
Today you can work from almost anywhere in the world,
and we're seeing more adults over fifty and sixty choosing
not to fully disengage, but to redesign. There's even a

(23:54):
term for it now, the gray digital nomad. Retirement today
is less about withdrawal and more about intentional engagement.

Speaker 2 (24:05):
And what's interesting, mom, is this isn't about a hustle
culture or working endlessly into your seventies.

Speaker 7 (24:11):
It's really about autonomy.

Speaker 2 (24:12):
A great digital nomad is typically someone over fifty or
sixty who works remotely, well traveling, or living somewhere new.
Sometimes that means consulting part time, sometimes freelance work. Sometimes
it's combining remote income with social security or portfolio withdrawals.
There's no single blueprint, only the one that fits your life.
Some retirees choose what's called slow travel, staying in one

(24:34):
country for several months instead of constantly moving. Others relocate
to places where the US dollar may stretch further. Countries
like Portugal, Spain, or Mexico are often mentioned because living
expenses can be lower than in many parts of the
United States, and when expenses are lower, pressure on long
term savings can decrease, and.

Speaker 4 (24:52):
That's where this becomes interesting from a planning standpoint. Reports
are showing a sharp rise in digital nomads over fifty
and the reasons are consistent adventure, technology, financial considerations, and
redefining retirement itself.

Speaker 5 (25:12):
Some people want to see.

Speaker 4 (25:13):
The world while they're healthy enough to truly enjoy it.

Speaker 5 (25:17):
Others want purpose.

Speaker 4 (25:19):
Many retirees tell us they don't want twenty five or
thirty years of complete idleness. They want meaningful activity without
the stress of a traditional career. Purpose doesn't retire, it evolves. But,
and this is important, becoming a digital nomad requires thoughtful preparation.

(25:43):
Freedom works best when it's researched exactly.

Speaker 2 (25:47):
There are practical considerations. Visa requirements vary by country, healthcare
systems differ. Reliable internet becomes no negotiable if you're working remotely.
Cybersecurity matters, especially if you're accessing financial accounts over public
Wi Fi. Even something as simple as time zones can
affect how you.

Speaker 5 (26:03):
Structure your work.

Speaker 7 (26:04):
And if someone plans to.

Speaker 2 (26:05):
Supplement retirement income with remote work, that decision needs to
be integrated thoughtfully into their overall financial picture.

Speaker 5 (26:12):
And that's really the heart of this.

Speaker 4 (26:14):
We're not talking about chasing a trend we're talking about
designing retirement with intention. Supplemental income can reduce pressure on savings,
but only if you understand how it fits into your
broader plan. Living abroad may stretch dollars, but only if
you've evaluated healthcare access, tax implications, and long term sustainability.

(26:42):
Adventure should energize you, not exhaust you. Health becomes even
more important when you're on the move. Sleep routines matter,
physical activity matters, social connection matters. Loneliness can quietly become
a risk if someone isolates instead of integrating into community.

(27:04):
Flexibility is appealing, but sustainability is essential, and this is
where financial clarity becomes foundational. At Kelly Financial Services, our
approach has always centered around education first. In my book
Retire Your Fear, Plan Your Future, I talk about defining

(27:27):
what retirement means to you before making major lifestyle shifts,
because freedom feels different when it's supported by clarity. If
someone wants to consult part time from Spain, or teach
online while splitting time between two states, or simply reduce
full time hours and work remotely from a different location,

(27:49):
those decisions should align with their income structure, tax considerations,
healthcare access, and long term goals. Retirement freedom does it
come from impulse. It comes from understanding your foundation.

Speaker 2 (28:07):
And I think that's the biggest takeaway here. The great
Digital know my lifestyle isn't about escaping retirement, It's about
reshaping it. It's asking what can make these next twenty
to thirty years meaningful and then building the financial clarity
to support that answer.

Speaker 4 (28:21):
Exactly Quinn, retirement is supported by understanding flexibility can feel
empowering instead of stressful. If you'd like a complimentary copy
of my book, Retire your Fear, Plan Your Future, you
can request it by calling eight eight eight eight hundred
and eighteen eighty one or visiting Kellyfinancial dot org. When

(28:44):
we return, we'll explore how to design this lifestyle intentionally
and sustainably, including how to structure remote income, create boundaries,
and protect your financial foundation. While you're on the move,
stay with us.

Speaker 5 (29:02):
We'll be right back.

Speaker 3 (29:06):
Safe money strategies brought to you by Kelly Financial Services.
Call eight at eight eight hundred eighteen eighty one or
visit Kellyfinancial dot org.

Speaker 12 (29:16):
Ready to enjoy your golden years without worry. At Kelly Financial,
we know retirement planning can be overwhelming. With more than
twenty two years of experience. Our friendly team of advisors
makes it easy and stress free. Trust us to help
you create a secure and enjoyable future. For a free
initial retirement consultation called eight eight eight eight hundred eighteen

(29:39):
eighty one or email Kelly at Kelly Financial dot org.
We're Kelly Financial. Come retire with.

Speaker 3 (29:45):
Us Safe Money Strategies with William Kelly and Kelly Kelly.
Call the team on at at eight eight hundred eighteen
eighty one.

Speaker 4 (30:01):
Welcome back to Safe Money Strategies. I'm Kelly Kelly here
with my son, William Kelly Junior. In our last segment,
we talked about how retirement is being redefined and how
more adults over fifty and sixty are choosing flexibility instead
of full disengagement.

Speaker 5 (30:23):
We introduce the idea of the gray.

Speaker 4 (30:25):
Digital nomad, retirees who combine travel with remote work in
a way that feels purposeful and intentional. Now we want
to talk about how to design that lifestyle thoughtfully and sustainably,
because becoming a gray digital nomad isn't about impulse travel.

(30:46):
It's about building a system that supports freedom and that
begins with clarity before anyone changes their address, especially internationally,
there needs to be a financial and lifestyle assessment. What
are your assets, what are your income sources, what are

(31:07):
your fixed expenses? And what does sustainable travel actually cost?
There are cost of living comparison tools available today that
allow retires to evaluate expenses country by country, But beyond
those numbers, there's a deeper question. Is remote income supplemental

(31:29):
or is it foundational?

Speaker 5 (31:31):
That distinction matters.

Speaker 4 (31:33):
If remote work is simply enhancing flexibility, that's one structure.
If it's covering essential expenses, that's a different level of reliance,
and it requires careful evaluation.

Speaker 5 (31:47):
Intention prevents regret.

Speaker 2 (31:50):
And once that financial foundation is clear, the next step
becomes practical, identifying realistic remote income options. What advantage retirees
have is experience consulting, teaching, writing, bookkeeping, coaching, project.

Speaker 7 (32:04):
Based advisory work.

Speaker 2 (32:06):
Many of these roles translate well into digital platforms, and
today there are online Marketplace is specifically designed for remote opportunities.
But building a remote work portfolio doesn't happen automatically. It
may involve refreshing skills, updating a LinkedIn profile, creating a
simple online presence that reflects credibility, even exploring continuing education
to remain competitive in a changing marketplace. Experience becomes portable

(32:30):
when skills go digital, and for many retirees, the goal
isn't maximizing income, it's preserving flexibility while staying engaged. And
that's where structure becomes essential. Because working without boundaries.

Speaker 4 (32:43):
Remote work can quietly expand beyond what was intended. If
someone enters retirement seeking freedom but ends up rebuilding a
full time workload from a different location, the lifestyle can
lose its balance. Guardrails create freedom, define working hours even

(33:04):
if you're in a different time zone. Limit client loads
so work remains manageable. Build rest days into travel schedules.
Separate travel mode from work mode. Retirement identity should not
disappear into work. The purpose of this lifestyle is autonomy,

(33:25):
not recreating career pressure in a new environment.

Speaker 7 (33:29):
And technology becomes part of your lifeline.

Speaker 2 (33:31):
In this model, reliable high speed internet is an optional,
it's foundational. Before committing to a destination, retirees need to
evaluate connectivity.

Speaker 7 (33:39):
Secure networks matter.

Speaker 2 (33:41):
Virtual private networks for VPNs can help protect sensity data
when accessing financial accounts or communicating with clients. Cloud based
backups protect important documents updated software protect devices. Your office
may fit into a backpack, but it still needs protection,
and banking systems need to support international access. That includes
understanding how currency exchange, foreign transaction fees, and international withdrawals function.

Speaker 7 (34:04):
Digital preparedness supports confidence.

Speaker 4 (34:07):
And then there's healthcare, which is often the most underestimated factor.
Before relocating, retirees should research local health care systems, insurance options,
in medication availability, International health insurance policies vary widely. Some
countries have excellent care systems, others require more navigation. Emergency

(34:33):
access should be clearly understood, and tax implications must also
be evaluated carefully. Living abroad may create reporting obligations or
residency considerations. Slow travel often reduces administrative complexity. Staying in
one location longer allows for better understanding of healthcare providers, services,

(35:01):
and community integration. Adventure is better when your safety net
travels with you, because no matter how flexible retirement becomes,
stability still matters, and this brings us back to education.
In my book, Retire Your Fear, Plan Your Future, I

(35:21):
emphasize defining retirement goals before making structural changes. Lifestyle shifts
should align with financial understanding, not replace it. Working remotely
in retirement should feel empowering, not reactive. If someone is
choosing this path because they are inspired by the possibility,

(35:43):
that's very different than feeling financially pressured into it. At
Kelly Financial Services, we help clients evaluate how part time income,
travel or international living may interact with their overall plan
that includes understanding cash flow, investment structure, healthcare considerations, and

(36:08):
long term sustainability. Retirement freedom begins with informed decisions.

Speaker 2 (36:15):
And what stands out to me is that this lifestyle
isn't about movement for the sake of movement. It's about
flexibility supported by foundation. Design your retirement before you redesign
your address. That phrase really captures it, because when someone
understands their financial base, travel becomes a choice, not an escape.
In some cases, remote income becomes optional, not essential, and
flexibility becomes sustainable.

Speaker 4 (36:37):
Exactly when clarity comes first, confidence follows.

Speaker 5 (36:42):
And for those.

Speaker 4 (36:43):
Listening who are intrigued by this concept, whether it's international travel,
part time consulting, or simply redefining what retirement looks like,
start with education. If you'd like a complementary copy of
my book, Retire Your Fear, Plan Your Future, you can
request it by calling eight eight eight eight hundred eighteen

(37:06):
eighty one or visiting Kellyfinancial dot Org. Is designed to
help you think through your vision before making major changes.
Retirement today offers more flexibility than ever before, but flexibility
works best when is grounded in understanding. We'll continue bringing

(37:28):
you informative content designed to help you navigate today's evolving
retirement landscape with confidence and clarity.

Speaker 5 (37:38):
Thank you for spending part of your weekend with us.

Speaker 4 (37:41):
We'll see you next week right here on Safe money Strategies.

Speaker 3 (37:48):
Safe money Strategies brought to you by Kelly Financial Services.
Call eight eight eight eight hundred eighteen eighty one or
visit Kellyfinancial dot Org.

Speaker 7 (38:00):
Back to Safe Money Strategies.

Speaker 10 (38:01):
I'm Mike dust, chief operating Officer here with Greg Workman,
investment Advisor. Before the break, we introduced what we call
the widow's penalty or tax bracket compression, and how a
surviving spouse can end up paying higher taxes even though
their household income has gone down. We use a hypothetical couple,
John and Linda to show how this plays out. Now,

(38:22):
the important part this is manageable. Greg, Let's talk about
the solutions.

Speaker 6 (38:27):
The first and often most powerful tool is wroth conversions.
If John and Linda retire at sixty five and delay
r and ds until age seventy three, that eight year
window may be the lowest tax bracket window of their
entire retirement. Instead of waiting for the irs to dictate

(38:47):
with Charles later, they can intentionally move portions of the
traditional IRA into a WROTH IRA while filing jointly filling
up lower tax brackets with intent. That does three things.
It reduces future r and ds or required minimum distributions,
It lowers future taxable income for the surviving spouse, and

(39:11):
it creates tax free income flexibility to use later on
in the planning cycle.

Speaker 10 (39:16):
And flexibility is everything, because once one spouse passes, the
surviving spouse cannot unconvert money. You either did the bracket
management early or you didn't. Let's talk pensions, because this
is another major lever. Many retirees must choose between a
single life payout higher income while both alive or joint
and survivor payout lower income but continues for spouse.

Speaker 7 (39:40):
Great. What's the mistake people make here?

Speaker 6 (39:43):
They focus only on maximizing income today. But if a
single life option is chosen and the pension disappears at
first death, the surviving spouse may lose a major income
stream while r and ds and fixed expenses were made
that force. This is larger i RA withdrawals, which increases

(40:03):
taxable income, which accelerates bracket compression. The right pension election
isn't just about income, It's about tax sustainability for the
surviving spouse.

Speaker 10 (40:14):
Now let's bring in social security because this decision also
plays into survivor protection.

Speaker 6 (40:19):
Exactly when mound spouse passes away, the surviving spouse keeps
the higher of the two benefits. So if the higher
earning spouse delays claiming social Security until age seventy, that
permanently increases the Social Security survivor benefit. That decision alone
can add hundreds of thousands of dollars in lifetime income protection.

(40:44):
But again it has to be coordinated with good tax planning.
If we delay social Security while intentionally doing roth conversions
and lower tax brackets, we are reshaping the tax profile
of the household before tax compression ever hits.

Speaker 10 (41:00):
We often talk about smoothing income, what does that mean
in practical terms?

Speaker 6 (41:05):
Instead of allowing income to spike at age seventy three
when required minimum distributions kick in, we level it out earlier.

Speaker 7 (41:13):
Think of it like this.

Speaker 6 (41:14):
If we know R and DS are going to force,
say sixty thousand per year out of an IRA later,
why not start pulling thirty or forty thousand intentionally in
years when tax brackets are lower. Pay some tax on
purpose now to avoid paying much more later, especially when
filing single. This is long term bracket engineering.

Speaker 10 (41:38):
Most retirees think diversification only applies to investments, stocks, bonds, cash,
but we believe in tax diversification exactly.

Speaker 6 (41:48):
Ideally, retirees have money in three buckets, tax deferred accounts
like pre tax or traditional iras, four to one case,
tax free accounts such as roth iras, and taxable brokewards accounts.
When one spouse passes away, their surviving spouse can choose
which bucket to pull from to control taxable income. Without

(42:11):
that flexibility, every withdrawal becomes a taxable event. Tax diversification
creates control, control, reduces bracket shock.

Speaker 10 (42:22):
Let's walk through another hypothetical scenario. We'll call this couple
Mark and Susan, both age sixty six. They have one
point two million in traditional arrays, modest taxable savings, no
WROTH accounts combined income of one hundred and twenty five thousand.
They assume taxes will go down later because one income
will disappear.

Speaker 6 (42:41):
But here's what their projection shows. At age seventy three,
their rm ds alone could exceed seventy thousand dollars annually,
not including social Security. When Mark passes at age eighty two,
Susan is filing single, still taking her rm ds, still
receiving Social Security, but now she's firmly in a higher
tax bracket than what they were when they were married.

(43:04):
If nothing is done, she also faces higher Medicare premiums
because of income thresholds. But if they begin partial roth
conversions at age sixty seven and continue for six years,
they reduce their IRA balance significantly before URMDH. The result

(43:24):
multiple benefits lower forced distributions, lower taxable income later, more
tax free income flexibility for Susan, and reduced Medicare surcharge exposure.
That is what proactive planning looks like.

Speaker 10 (43:40):
This is where tax planning and estate planning intersect. If
most assets remain in tax deferred accounts at second death,
children may inherit large iras subject to accelerated distribution rules.
Under current law, many non spouse beneficiaries must distribute inherited
iras within ten years. That can push adult children into

(44:02):
higher tax brackets during their peak earning years. So bracket
compression doesn't just affect the surviving spouse. It can cascade
into the next generation. When we coordinate tax strategy with
the state planning, we are safeguarding your family's future, not
just an individual's. Greg If you had to summarize this
entire conversation into one planning principle, what would it be plan.

Speaker 6 (44:23):
For the second life while both spouses are still here.
Because when one spouse passes, flexibility decreases dramatically. The time
to manage taxes is when you have the widest tax
brackets available, married filing jointly pre R and D, and
lower lifetime income years.

Speaker 10 (44:42):
Retirement planning isn't just about building wealth. It's about strategies
for preserving it. It's about reducing uncertainty.

Speaker 6 (44:49):
It's about making sure that if one spouse has to
navigate life alone, the financial structure is steady and predictable.
The widow's penalty is real. Bracket compression is re but
so are the solutions.

Speaker 10 (45:02):
If you'd like to see whether your current retirement plan
exposes your spouse to unnecessary tax shock. We encourage you
to request a copy of our Safe Money Strategies workbook.
Inside we walk through tax bracket mapping, income sequencing, pension
election analysis, social security coordination, as state alignment.

Speaker 6 (45:21):
There's no cost, no obligation, just education, because the more
clarity that you have today, the less stressed you will
face tomorrow. With that, I'm Greg Workman and.

Speaker 10 (45:33):
I'm Mike du said, thank you for joining us on
Safe Money Strategies.

Speaker 7 (45:37):
We'll see you next week.

Speaker 2 (45:43):
I'm William Kelly Junior, and many families are thinking about
fresh starts, not just financially, but how young people prepare
for what comes next. I've had the unique experience of
growing up around real conversations with our clients, families, parents
and grandparents about money, responsibility and low long term thinking.
Not theory, real life, and it's important to remember that

(46:04):
all investing involves risk, including the potential loss of principle,
which is why habits, education, and perspective matter so much
from the start. That's why I wrote Only the Good
Investor on It's a straightforward guide to the basics of money,
habits and decisions. That matter over time, whether you're a client,
a parent or grandparent, or someone just starting out. This
is meant to be practical, clear, and encouraging. For offering

(46:27):
complimentary signed copies to our WRKL listeners and clients. It's
also available on Amazon in softcover or kindle. Call eight
at eight eight hundred and one or email Kelly at
Kelly financial dot org. Good habits start early and they
last a lifetime.

Speaker 9 (46:42):
Joining us now as she always does at this time,
she is the co founder, CEO, and president of Kelly
Financial Services, and yes, that is her wonderful name.

Speaker 6 (46:57):
Kelly, Kelly, Kelly, how are you?

Speaker 5 (47:03):
Good morning, Jeff, I am good.

Speaker 4 (47:06):
You know we've been talking about something really interesting right now.
Most retirees are choosing to stay active in different ways.
Some are consulting part time, some are working remotely, and
some are even spending part of the year somewhere new
while generating income digitally. And that can be exciting, but

(47:28):
it works best when you truly understand your overall financial picture,
where your income is coming from, how your plan is structured,
and how much flexibility you actually have. When those pieces
are clear, lifestyle choices tend to feel empowering. Instead of stressful.

(47:49):
And that's exactly why I wrote my book, Retire Your Fear,
Plan Your Future. It's designed to help you better understand
your income sources, find your goals, and make thoughtful decisions
before making big lifestyle changes.

Speaker 5 (48:06):
If you'd like a.

Speaker 4 (48:06):
Complimentary copy, you can call us or email Kelly at
Kellyfinancial dot org. Jeff, have a wonderful weekend. My best
of Grace and the kiddos.

Speaker 9 (48:18):
Thank you, Kelly, all the best to you and everyone
at Kelly Financial to get a free copy of that guide,
and I urge all of you if you can do
get it call now eight eight eight eight hundred eighteen
eighty one eight eighty eight eight hundred eighteen eighty one,
or you can actually email Kelly herself personally Kelly at

(48:40):
Kellyfinancial dot org. That's Kelly Kelly Financial dot org.

Speaker 3 (48:51):
Safe Money Strategies at eight eight hundred one, eight eight one.

Speaker 4 (48:58):
This next reflection from Bill takes us back to the
basics what a stock really is, how the market truly works,
and why understanding value.

Speaker 5 (49:08):
Matters more than emotion.

Speaker 4 (49:10):
He reminds us that markets are driven by human behavior,
not heroics, and that clarity can help steady your thinking
when prices moved.

Speaker 5 (49:22):
Here's Bill Kelly.

Speaker 13 (49:24):
Maybe we should start out with the basics this week,
ladies and gentlemen. What is the basis of most retirements?
The basis of the investments within most retirements nowadays when
they are self directed iras four one k's are securities stocks.
So why don't we begin with the definition of a stock.

(49:45):
It's a share in the company. It's an equity share,
and for that risk, you are given a reward. In
other words, if you buy a share in the company,
you are going to share in the success unfortunately also
of the failure of that company. And you do so
without having to work. You simply invest, So it's sort

(50:06):
of a unilateral contract. You buy the stock, they do
the work. You don't have to perform. All you have
to do is pay the money, own the stock, and
share in the proceeds. And you want to do that wisely. Now,
what is a share of common stock worth? Generally it's
worth one vote, and it's worth a percentage or a
pro rata average of what the company is worth. So,

(50:29):
as companies want to expand, sometimes they offer more stock.
So when you hear about a new offering, somebody might say, well,
we really think the company's worth two hundred thousand dollars more,
we're going to sell one hundred thousand more shares, and
it's going to dilute the people that already own stock,
But eventually it's going to bring everyone up because we're

(50:50):
going to take the new money and we're going to
make things a lot nicer in the company, going to
do some more product development, we're going to do some
more advertising, more market we're going to do some research.
So that's what stock is. It's a share in the company,
and generally we look at earnings of the company to
give us a gauge and what the stock might be worth.

(51:13):
So if our stock is one hundred dollars a share
and the earnings of the company, when divided up by
the number of shares, are twenty dollars a share, then
the pe ratio is five, and that's fairly low for
a technology company or a manufacturing company, or let's say
somebody like Procter and Gamble places like that. That's a

(51:34):
low pe. So some people think when pes are low,
it's good time to buy. Sometimes stocks have low pes, however,
simply because they're out of favor. So you have to
be aware of that also. Now, what really creates the
value of a share of common stock, ladies and gentlemen,
it's the price someone is willing to pay for that

(51:55):
stock that, more than anything else on earth, determines the
value of us stock. And how are the stock sold?
On the New York Stock Exchange. Every morning, when that
gong rings, there's an auction. And as my friend who's
an auctioneer, once told me, the reason I sell things
that auction is because I get the most money the fastest,
and I don't have to wait around. So that's why

(52:17):
they have auctions, and that's why stocks are auctioned off
every day. There are people on the floor of the
New York Stock Exchange and they're in charge of making
sure that a stock trades within certain parameters. They have
to hold up the position if there's a sudden downturn. Well,

(52:38):
basically that's what they're there for, to regulate the way
that stock is traded somewhat on the floor. So if
they're in charge of a position, let's say they're a
specialists there for certain stocks, they're in charge of that
position and making sure, if at all possible, there's an
orderly market and that the bottom doesn't fall out of it.
If something is a SkELL, that's unavoidable and the specialists

(53:02):
can't help it. When certain things happen on the floor,
or certain things happen in the economy with certain companies
like General Motors, doesn't matter what they're doing down there
with the specialists or whoever's in charge of that stock
on the floor, it just means sometimes it's a dead issue.
There's nothing that anyone can do. So you own the stock,

(53:24):
and certain people think, well, I'm a stockholder and you're
going to share in the company's success. They might have
a dividend which will create a yield, and they'll have
a price earnings ratio, which, if it's low, means that
the price of the stock is very low compared to
the earnings of the company. When that happens, then some
people think that's a buying opportunity if the company is

(53:48):
out of favor, but they need people to purchase the stock.
Sometimes they'll have a higher dividend, or if a dividend
remains the same and a stock price decreases dramatically, the
yield of that stock might look terrific. Unfortunately, many times,
when the yield is way out of whack. It simply

(54:09):
means the stock is out of favor, the company might
be having troubles, and the yield is way too high.
And many, many times I have seen the various companies
just simply reduce the dividend because they can no longer
pay it when the yields get up in the seventeen
eighteens and twenties. So that's what happens with your shares

(54:30):
of stock. Every day on the New York Stock Exchange.
They are auctioned, and at the end of the day,
your dollar in Exxon could be worth a dollar ten,
it could be worth ninety cents, depending on what happens
on the floor of the exchange, with the economy or
with the general view on the street, which is Wall Street,

(54:53):
as to whether or not the stock that you hold
has value. Now those stocks have been combined into other
investments now so that you don't have to buy a
particular stock. You can buy investments that bundle stocks, and
in investing in those positions, you're able to buy multiple
stocks at once bundled up. It has some wisdom, it

(55:15):
also has some pitfalls. I found that a collection of
stocks generally if there's twenty five stocks, you're going to
have eight that of super five or six out of dogs,
and you're going to have ten or twelve that are
middle of the road, so you end up reflecting the market.
For the most part. It's important not to panic ladies

(55:35):
and gentlemen. So we're thinking safety is best. However, you
can define that word so that it makes you comfortable,
is what the meaning of safety is going to be
for you. But you don't have to be heroic, and
being heroic in the market, ladies and gentlemen, has no meaning.
The only thing you're doing by being heroic and hanging
in is you're allowing people to make money off of

(55:58):
the low prices of your stock, especially when you finally
capitulate and throw in the towel. It allows somebody somewhere
to buy your stock at a much lower price, and
it creates regrets for you later on that you haven't
been able to just hang in there.

Speaker 3 (56:20):
We'll call Kelly Financial Services eight eight eight eight hundred
eighteen eighty one.

Speaker 5 (56:25):
I'm Kelly Kelly from Kelly Financial.

Speaker 4 (56:27):
Whether you're in your sixties, seventies, or eighties, financial advice
is important when it comes to preserving your nest egg.
We have a free investor guide called designing your Fiscal
House to Weather the Elements, which highlights the steps needed
to build a balance portfolio. For the guide, call eight
eight eight eight hundred eighteen eighty one or email Kelly

(56:49):
at Kellyfinancial dot org.

Speaker 5 (56:52):
We're Kelly Financial. Come retire with us