Retire Today

By Jeremy KeilBusiness Investing

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Typical duration
19 min
per episode

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Retire Today episodes

July 28 Social Security Questions Married Couples Ask Before Retirement
Choosing when to claim Social Security can have a lasting impact on your retirement income, but many retirees make this decision without fully understanding how the rules work. In this Q&A episode, Jeremy Keil answers three listener questions that uncover some of the most common Social Security misconceptions facing married couples.
Jeremy explains why your retirement date and your Social Security claiming date are two separate decisions, how poor health should factor into your planning, and why survivor benefits often deserve more attention than the higher earner's own benefit. He also clarifies common confusion around spousal benefits, outdated claiming strategies, and the way delayed retirement credits are actually applied after full retirement age.
Whether you're approaching retirement or helping a spouse make these important decisions, this conversation offers practical guidance to help you coordinate your retirement plan and make more informed Social Security choices.
For disclosures and conflicts visit keilfp.com/disclosures.
20 min
July 21 300th Episode Special: The Biggest Retirement Lessons I’ve Learned Featuring Nicole Gebhardt
Three hundred episodes into the Retire Today podcast, the microphone is turned around as author and business strategist Nicole Gebhardt interviews Jeremy Keil about the journey that shaped his retirement philosophy and the framework behind his book, Retire Today: Create Your Retirement Master Plan in 5 Simple Steps.
Rather than focusing on a single retirement topic, Jeremy shares the evolution of his business, the development of the "Mr. Retirement" brand, and the mindset shifts that matter most for people approaching retirement. He explains why so many successful savers struggle to become confident spenders, why retirement planning is as much about psychology as it is about numbers, and how learning the math behind retirement decisions creates confidence to retire on your own terms.
As the Retire Today podcast celebrates its 300th episode, Jeremy reflects on lessons learned from working with thousands of retirees and explains why thoughtful planning isn't about predicting the future—it's about creating the flexibility to enjoy it.
For disclosures and conflicts visit keilfp.com/disclosures.
33 min
July 14 Is the Healthcare System Working Against You? With Dr. Jordan Grumet
Healthcare is one of the biggest expenses retirees face, yet few people understand how the system behind their care actually works. Jeremy Keil welcomes physician, hospice doctor, and author Dr. Jordan Grumet to discuss the ideas behind his new book, The Healthcare Heist. Discover how financial incentives have reshaped modern healthcare, the growing influence of private equity, and why patients and providers often feel caught in a system that prioritizes business interests over care.
Dr. Grumet explains the differences between physician-owned practices and corporate healthcare systems, discusses direct primary care and concierge medicine, shares his perspective on Medicare Advantage versus traditional Medicare with supplemental coverage, and offers guidance for becoming a more informed healthcare consumer. Healthcare aside, hear why Dr. Grumet rejects the traditional definition of retirement and what he's learned since beginning the decumulation phase of his own financial life.
For disclosures and conflicts visit keilfp.com/disclosures.
44 min
July 07 Why Spending in Retirement is Often Harder than Saving
Saving for retirement is a skill that most people spend decades developing. But once retirement begins, the challenge changes completely. Instead of accumulating wealth, retirees must learn how to confidently spend it—and for many, that's much harder than expected.
In this episode, Jeremy explores why so many retirees struggle to spend the money they've worked so hard to save. Learn about the psychology behind "fear of running out," why many retirees underspend despite having more than enough assets, and how changing your mindset from "saver" to "planner" can transform the retirement experience. Jeremy also shares practical strategies for creating retirement income that feels like a paycheck and discusses how to spend with purpose while minimizing future regret.
If you've ever hesitated to enjoy your retirement because you're worried about spending too much, this episode offers a practical framework for turning your savings into the meaningful retirement you've spent a lifetime building.
For disclosures and conflicts visit keilfp.com/disclosures.
18 min
June 30 What Changes When a Retirement Expert Finally Retires? With David Conti
David Conti has spent decades writing about retirement, Social Security, Medicare, and personal finance. After helping others prepare for retirement throughout his career—including his time at Fidelity Investments—he reached an important milestone himself: turning 65. That experience gave him a new perspective on what retirement looks and feels like when the advice you've shared for years becomes your own reality.
Jeremy and David explore the lessons that surprised him most, including why retirement is about more than financial independence, the importance of keeping your investment strategy simple, navigating Medicare after enrolling for the first time, preparing emotionally for retirement, creating multiple streams of income, and finding greater purpose through charitable giving. David also shares why he believes everyone should "practice retirement" before leaving work and why taking time to reset may be one of the smartest retirement decisions you can make.
Whether you're five years from retirement or already making the transition, this conversation offers practical lessons from someone who has spent a career studying retirement—and is now living it himself.
For disclosures and conflicts visit keilfp.com/disclosures.
47 min
June 23 IRMAA: Why Your Medicare Costs are Higher Than You Expected (and What You Can Do About It)
Many retirees are surprised to learn that Medicare isn't always a fixed cost. If your income exceeds certain thresholds, Medicare can charge significantly higher premiums through a little-known rule called IRMAA (Income-Related Monthly Adjustment Amount). Even more surprising, those higher costs are often based on income from two years ago rather than what you're earning today.
In this episode, Jeremy Keil (Mr. Retirement) explains how IRMAA works, why Medicare uses prior-year tax returns to calculate premiums, and what retirees need to know when planning Roth conversions, managing retirement income, and preparing for required minimum distributions. He also shares real-world examples of retirees who successfully appealed their Medicare surcharges after retirement reduced their income.
If you've received an IRMAA notice—or want to avoid being surprised by one in the future—this episode will help you understand your options and how Medicare costs fit into a broader retirement tax strategy.
For disclosures and conflicts visit keilfp.com/disclosures.
26 min
June 16 Retirement Planning Needs More Than a Financial Plan with Toni Petrillo
Most people spend decades preparing financially for retirement.
They contribute to retirement accounts, pay down debt, evaluate Social Security strategies, and work with advisors to make sure their savings can support the next chapter of life. By the time retirement arrives, many have a well-developed financial plan that answers the most important question:
"Can I afford to retire?"
This week I spoke with retirement lifestyle coach Toni Petrillo about a different question—one that often surfaces only after retirement begins:
"Now what?"
Learn about what Toni calls the “in-between chapter” and how to navigate from a meaningful career to a purposeful retirement in this week’s episode of “Retire Today.”
For disclosures and conflicts visit keilfp.com/disclosures.
34 min
June 09 Flood Coverage: The Insurance Gap That Could Wash Away Your Retirement Plan
When evaluating flood insurance, many people focus on a single question:
Do I need it?
I think there's a better question.
If your home suffered significant flood damage tomorrow, where would the money come from?
This week I spent some time looking at flood insurance, flood risk, and what retirees should consider when deciding whether they need coverage.
Watch the full episode on the Mr. Retirement YouTube channel: Do I Need Flood Insurance in Retirement? https://youtu.be/XRZKfiY1jGg
For disclosures and conflicts visit keilfp.com/disclosures.
19 min
June 02Retire Against the Norm with Norman Calvo – A True Retirement Story
Norman Calvo explains how he found a third act in retirement by going against the norm and choosing adventure instead of a typical retirement.
https://youtu.be/81atmTUjBWE
One of the questions I ask people as they approach retirement is deceptively simple:
What are you retiring to?
Most retirement planning conversations focus on finances. That’s understandable. People want to know if they’ve saved enough, whether their investments are positioned correctly, how Social Security fits into the picture, and what taxes might look like in retirement.
Those are important questions, and they’re exactly the kinds of issues my team helps clients navigate.
But once the financial pieces are in place, another challenge emerges—one that often receives far less attention.
What will make retirement meaningful?
Norman Calvo and I dug deeper into how he was able to find meaning in retirement after decades as a successful business owner in this week’s episode of the Retire Today podcast. Norman discovered an entirely new chapter of life after work. His true retirement story illustrates a lesson I’ve seen repeatedly among retirees: financial independence creates freedom, but it doesn’t automatically create purpose.
The Risk Nobody Plans For
Most people spend years preparing for the financial risks of retirement.
They plan for market volatility.
They prepare for inflation.
They consider healthcare costs.
They evaluate longevity risk.
Yet many people never prepare for a different risk altogether: drift.
Drift rarely happens intentionally. In fact, most retirees who experience it worked incredibly hard to earn the freedom they now possess.
The challenge is that work provides structure. It creates goals, deadlines, responsibilities, relationships, and a sense of progress. For decades, many professionals wake up knowing exactly what needs to be accomplished that day.
Then retirement arrives.
The calendar empties.
The obligations disappear.
The structure that guided daily life for years suddenly vanishes.
For some retirees, that freedom feels exhilarating. For others, it becomes surprisingly disorienting.
Why Purpose Doesn’t Automatically Appear
Norman explained how many people gradually lose touch with the activities that once excited them. Careers expand, family responsibilities increase, and life’s demands naturally push hobbies and interests to the side.
By the time retirement arrives, some people have forgotten what they enjoyed doing before work consumed most of their attention.
As a result, retirement can unintentionally become a period of maintenance rather than growth.
Days become predictable.
Weeks begin to blend together.
And while there’s nothing wrong with relaxation, most people don’t spend decades saving and investing simply to become passive observers in their own lives.
The Power of One New Decision
Norman’s transformation didn’t begin with a grand retirement vision.
It started with a single decision.
A coworker encouraged him to train for a half marathon. At the time, he weighed 247 pounds, worked long hours, and had never been a runner. He wasn’t looking for a new identity. He simply agreed to try something different.
That one decision led to another.
Running led to additional races, including the New York City Marathon. Along the way, he discovered interests and opportunities he never would have anticipated. He joined a choir, performed in cabaret productions, taught English overseas, and even began learning handstands in his seventies.
What stands out isn’t the specific activities.
It’s the willingness to remain curious.
Too often we assume retirement is a time to narrow our world. Norman’s experience suggests the opposite may be true.
Retirement can be a time to expand it.
Create a Plan for Your Life
Throughout our working years, we create plans for almost everything.
Businesses have strategic plans.
Families have financial plans.
Organizations establish goals and objectives.
Yet many retirees never develop a plan for how they want to spend the freedom they’ve worked so hard to create.
That doesn’t mean every hour needs to be scheduled.
It does mean thinking intentionally about questions such as:
What experiences would I regret never having?
What skills would I like to develop?
What interests have I neglected?
What challenges would energize me?
What relationships deserve more of my attention?
These questions may seem less urgent than investment allocation or tax planning, but they often determine whether retirement feels fulfilling.
Retirement Is More Than Financial Independence
Many successful retirees continue to grow long after they stop working.
They volunteer.
They mentor.
They travel.
They learn.
They teach.
They pursue interests that were postponed for decades.
Not because they have to.
Because they can.
Financial independence gives people options. The real challenge is deciding how to use those options in a way that creates a life that remains engaging and meaningful.
The Bottom Line
When people think about retirement, they often focus on what they’re leaving behind.
Work.
Commutes.
Deadlines.
Stress.
But retirement is ultimately less about what you’re leaving and more about what you’re building next.
The financial plan creates the opportunity.
The life you create afterward is what gives that opportunity meaning.
As Norman’s story demonstrates, some of the most rewarding experiences in life may not happen before retirement.
They may happen because of it.
Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!
Subscribe to Retire Today to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337
Spotify Podcasts: https://bit.ly/RetireTodaySpotify
About the Author:
Jeremy Keil, CFP®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.
Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.
Additional Links:
Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Norman Calvo’s Substack
“Against the Norm” podcast
AgainstTheNorm.net
Email Norman Calvo
Connect With Jeremy Keil:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Mr. Retirement
Book an Intro Call with Jeremy’s Team
Media Disclosures:
Disclosures
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
Additional Important Disclosures
31 min
May 27Are You In the 2% Club in Retirement? With Joe Schmitz Jr.
Joe Schmitz Jr. and Jeremy Keil explore the 2% Club of retirees and the unique challenges that come with significant retirement savings and a pension.
https://youtu.be/G04JKpKyLJ0
Most retirement conversations focus on one question:
Will I have enough?
But there’s another retirement challenge that doesn’t get talked about nearly enough:
What happens when you’ve done everything right?
Joe Schmitz Jr. has been working with a very specific group of retirees he calls the 2% Club.
His definition:
People who have both:
A pension
And $1 million or more saved for retirement
That combination creates opportunities.
But it also creates a different set of retirement decisions.
Success Creates Different Problems
For decades, these retirees did what they were told:
Saved consistently
Avoided lifestyle inflation
Built meaningful retirement assets
Earned pensions
Stayed disciplined
Now retirement arrives…
…and suddenly the challenge isn’t accumulating wealth.
It’s using it wisely.
Joe shared one statistic that stood out:
“80% of people out there will pay no federal income taxes in retirement… while this 2% club is part of that 20% that will have to pay taxes and typically much more.”
That means retirement planning shifts.
Less focus on accumulation.
More focus on:
Taxes
Spending
Distribution strategy
Legacy
Purpose
Why High-Income Retirees Can Accidentally Become Under-Spenders
One of the most interesting parts of this conversation was Joe’s concept of the Midwestern Millionaire.
His description:
Hard-working.
Frugal.
Disciplined.
Excellent savers.
Often reluctant spenders.
And that creates an unexpected retirement problem.
People who spent 40 years training themselves to save don’t automatically become comfortable spending.
Even when they can afford it.
Joe described clients who had millions saved but still struggled emotionally to use their money because restraint had become part of their identity.
That’s where retirement planning becomes less about spreadsheets and more about permission.
The Four Places Your Money Can Go
Joe offered a simple framework.
Your money ultimately goes somewhere.
You can:
Spend it
Gift it
Give it
Pay taxes on it
That framework creates an important question:
If you’re not spending your money intentionally…
where is it going?
That doesn’t mean everyone should spend aggressively.
But it does mean retirees should think intentionally about:
Lifestyle
Family impact
Charitable goals
Taxes
Because choosing not to decide is still a decision.
Pension Decisions Deserve More Attention Than Most People Give Them
Joe also emphasized something I see frequently:
People often make pension elections based on coworkers.
Someone retires.
Takes a lump sum.
Everyone follows.
But pension elections are often irreversible.
Joe’s advice was simple:
Run the numbers.
Questions like these matter:
Lump sum or monthly pension?
Survivor benefits?
Age differences between spouses?
Existing assets?
Insurance needs?
The right answer isn’t universal.
It’s personal.
Don’t Let Tax Fear Control Retirement
For some retirees, fear of crossing an income threshold and triggering Medicare IRMAA surcharges becomes bigger than the actual cost itself.
Joe’s point wasn’t to ignore taxes.
It was to understand them.
Tax planning matters.
But taxes shouldn’t become the only goal.
Because avoiding taxes at all costs can sometimes prevent people from living the retirement they actually built.
The Real Goal
One story Joe shared captured this perfectly.
A retired couple promised each other they’d spend intentionally during their early retirement years.
Two years later…
They had spent nothing.
Not because they couldn’t.
Because they hadn’t learned how.
Eventually they created a spending plan and began enjoying experiences they had delayed for decades.
That’s the shift retirement requires.
You don’t stop being disciplined.
You simply redirect that discipline.
The Bottom Line
Retirement success isn’t measured by how much money you leave untouched.
It’s measured by whether your money helps support the life you actually wanted.
Because after decades of saving…
Retirement planning becomes deciding what your wealth is for.
Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!
Subscribe to Retire Today to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337
Spotify Podcasts: https://bit.ly/RetireTodaySpotify
About the Author:
Jeremy Keil, CFP®, CFA is a retirement financial advisor with Keil Financial Partners, author of Retire Today: Create Your Retirement Income Plan in 5 Simple Steps, and host of the Retirement Today blog and podcast, as well as the Mr. Retirement YouTube channel.
Jeremy is a contributor to Kiplinger and is frequently cited in publications like the Wall Street Journal and New York Times.
Additional Links:
Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
“How Much Taxes Will Retirees Owe on Their Retirement Income?” – Center for Retirement Research at Boston College
Peak Retirement Planning
Joe Schmitz Jr. on YouTube: https://www.youtube.com/@peakretirementplanninginc.
Articles by Joe Schmitz Jr. on Kiplinger
“Joe Knows Retirement” podcast with Joe Schmitz Jr.
Books by Joe Schmitz Jr.
Connect With Jeremy Keil:
Keil Financial Partners
LinkedIn: Jeremy Keil
Facebook: Jeremy Keil
LinkedIn: Keil Financial Partners
YouTube: Mr. Retirement
Book an Intro Call with Jeremy’s Team
Media Disclosures:
Disclosures
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
Additional Important Disclosures
23 min

About Retire Today

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In the Retire Today podcast, Jeremy Keil, CFP®, CFA® shows you how to turn your retirement savings into retirement income. Listen in as Jeremy and his guests guide you towards making smarter…