
What does it actually mean to win at retirement? A bigger house, more expensive vacations, and a larger income during your working years may look like success, but they don't necessarily determine how satisfying retirement will be.
Jeremy Keil compares two composite retiree stories drawn from situations he's encountered over the years. One represents someone who never earned more than $80,000 in a year but consistently saved, paid off a mortgage, accumulated rental real estate, and built investments worth roughly 10 times their income. The other represents a retiree who earned around $300,000, enjoyed spending bonuses along the way, retired with a mortgage, and accumulated investments worth roughly five times their final salary.
Which one is winning at retirement? Learn Jeremy’s answer in this episode!
For disclosures and conflicts visit keilfp.com/disclosures.
Aug 18
7 min

Retirement tax planning isn't simply about following IRS rules or minimizing what you owe this year. Jeremy Keil answers three listener questions that demonstrate why focusing on one tax return at a time can lead retirees to miss opportunities to manage their taxes over the course of retirement.
Jeremy breaks down two different five-year rules that can apply to Roth IRAs, including what happens when you complete a Roth conversion after having an existing Roth IRA for years. He then explains why taking only the required minimum distribution from an inherited IRA isn't automatically the best strategy under the 10-year rule, and how qualified charitable distributions may be available from inherited IRAs for eligible account owners.
For disclosures and conflicts visit keilfp.com/disclosures.
Aug 11
15 min

How much money do you actually need to retire? Many people approach retirement with a specific number in mind—$1 million, $2 million, or another target they believe will finally make them feel financially ready. But Jeremy Keil has seen how easily that finish line can move, even when the retirement plan already shows someone has enough.
Rather than choosing an arbitrary retirement number, Jeremy challenges prospective retirees to determine what their lifestyle actually requires and test that against a retirement calculation. Knowing what "enough" means for your retirement may help you recognize when you've already reached it.
For disclosures and conflicts visit keilfp.com/disclosures.
Aug 4
7 min

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.
Jul 28
19 min

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.
Jul 21
32 min

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.
Jul 14
43 min

Jeremy Keil explains how putting your cash in the wrong spot could prevent you from earning thousands in interest during your retirement.
Many retirees spend a lot of time thinking about how to get better returns on their investments.
But very few spend time thinking about the return on their cash.
That’s a problem.
Because for many retirees, cash isn’t a small side account. It can be a meaningful portion of their overall financial picture—and if it’s sitting in the wrong place, it may be quietly costing thousands of dollars each year.
The average new retiree may have around $100,000 sitting in bank accounts, often earning around 0.4%, while higher-yield options closer to 3%+ are available.
That difference can mean roughly $3,000 per year in missed interest.
And it happens more often than you might think.
Why Cash Gets Ignored
There are a few common reasons retirees leave cash sitting in low-interest accounts.
First, it’s easy.
Many people have used the same bank for years. There’s a sense of familiarity and convenience. Moving money feels like work.
Second, there’s a perception of safety.
Cash in a local bank feels secure. And while safety is important, many retirees don’t realize that other options—like high-yield savings accounts—can offer similar protections when properly insured.
Third, there’s inertia.
Cash tends to become an afterthought. Investors focus on stocks, bonds, and market performance, while cash quietly sits in the background.
But ignoring cash doesn’t make it harmless.
In some cases, doing nothing is actually the riskier move.
What Retirees Actually Want from Cash
When I ask retirees what they want from their cash, the answers are surprisingly consistent.
They want it to be:
Available
Safe
Easy
Those are reasonable goals.
But what if you can achieve all three and earn more interest at the same time?
The idea that higher interest automatically means higher risk isn’t always true—especially when comparing FDIC-insured accounts or certain money market options.
Rethinking “Just in Case”
One of the most common reasons people hold large amounts of cash is “just in case.”
That makes sense.
But it’s worth examining how often that “just in case” actually happens.
According to the Center for Retirement Research at Boston College, about 10% of annual expenses tend to be unexpected—things like medical costs, home repairs, or other surprises.
That’s exactly why cash matters.
But it also raises a question:
If you’re holding significantly more than what you typically need for unexpected expenses, could some of that money be working harder for you in the meantime?
Cash doesn’t have to sit idle to be available.
The Real Risk of Doing Nothing
There’s a common belief that staying put is the conservative choice.
But that’s not always true.
I once met with an investor who described herself as conservative, but in reality, she was heavily exposed to stock market risk without realizing it. 
She didn’t want to make a change to her investment strategy because she’d been doing it the same way for so long, the change felt risky.
When her investments tanked by 90% later on, the desire to “conservatively” keep things the same ended up being the very reason why her losses were so dramatic.
The lesson applies to cash as well.
Sometimes, not making a change feels safe—but it can lead to outcomes that are far from conservative.
If your cash is earning near-zero returns while inflation is around 3%, you’re effectively losing purchasing power each year.
That’s a quiet risk, but a real one.
Simple Ways to Improve Your Cash Strategy
Improving your cash return doesn’t require a complex overhaul.
There are a few straightforward places to start:
High-yield savings accountsOften available online, these can offer significantly higher interest rates than traditional banks. Sources to find these accounts include Bankrate.com and DepositAccounts.com.
MaxMyInterest.com I recently was joined by Gary Zimmerman, president of MaxMyInterest, on the “Retire Today” podcast–make sure you listen to that episode to learn more about how this system works as a cash growth strategy.
Money market funds in brokerage accountsMany brokerage accounts offer options that pay higher interest—but the default cash setting may not.
Cash Is a Tool, Not an Afterthought
Cash plays an important role in retirement.
It provides stability. It covers short-term needs. It gives you confidence that money will be there when you need it.
But cash should be treated as a tool, not an afterthought.
Used well, it supports your income plan and helps you stay flexible.
Ignored, it can quietly drag down your overall financial picture.
If you haven’t reviewed where your cash is sitting lately, now might be a good time.
Because sometimes the easiest improvement in your retirement plan isn’t found in the stock market.
It’s sitting in your savings account.
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 Are Emergency Expenses for Retirees and Are They Prepared?” – Center for Retirement Research at Boston College
“Here’s How to Earn a Fistful of Interest on Your Cash in 2026” – Jeremy Keil, Kiplinger.com
“Growing Your Cash as a Retirement Asset with Gary Zimmerman” – Retire Today Podcast on the Mr. Retirement YouTube channel
“The average amount in U.S. savings accounts–how does your cash stack up?” – Bankrate.com
Compare high yield savings account options: Bankrate.com, DepositAccounts.com
MaxMyInterest.com
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
Mar 24
16 min
Video

Author Ethan Lohr shares how the four buckets retirement income strategy helps retirees behavior-proof their retirement.
Many retirees face one similar problem that they struggle to name: the emotional shift from saving money to spending it. Retirement typically means going from “decades of saving to decades of retirement where you’re spending,” and that transition creates real anxiety for people who want their money to last.
Ethan Lohr’s answer is not just a better spreadsheet. It’s a “behavior-proof approach to reliable retirement income,” designed to help retirees make sound decisions even when fear, uncertainty, or market volatility show up. 
Retirement isn’t just a financial transition. It’s a psychological one. 
That mindset shift—from accumulation to distribution—creates anxiety for many retirees.
So while the biggest risk retirees often fear is a market drop, oftentimes the greater risk is a struggle to change your behavior.
The Real Risk in Retirement
Markets fall. Headlines scream. Fear creeps in.
Suddenly people make decisions they wouldn’t normally make—selling investments, abandoning a plan, or withdrawing too little money because they’re afraid to spend.
That’s why Ethan calls his framework a “behavior-proof approach to reliable retirement income.”
The goal isn’t just building a portfolio that works mathematically.
The goal is building a system that still works when emotions show up.
Because they always do.
The Four Buckets of Retirement Income
To help retirees think through their income strategy, Ethan uses a four-bucket framework.
Most people are familiar with the idea of dividing money by time horizon. But Ethan’s approach focuses more on the source of income rather than just the timing.
The four buckets include:
1. Cash ReservesShort-term funds designed to cover near-term spending and provide stability during market fluctuations.
2. Earned IncomeSome retirees continue to work part-time, consult, or pursue a business venture. This income can reduce pressure on investment withdrawals.
3. Secure IncomeReliable income streams such as Social Security, pensions, or annuity payments.
Ethan makes an interesting observation about this category. Many people say they dislike annuities, yet they happily accept Social Security each month.
“Virtually every American has an annuity right now called Social Security,” he noted.
4. Growth and Legacy InvestmentsLong-term investments designed for growth, flexibility, and potentially leaving assets to heirs.
The goal isn’t to split assets evenly among these buckets. Instead, the framework helps retirees understand where their income will come from and whether their plan aligns with their comfort level.
Why Frameworks Matter
One of the most helpful parts of Ethan’s approach is that it provides structure.
Without structure, retirement decisions can feel overwhelming. Every market move, every headline, every conversation with a friend can trigger doubt.
A framework helps retirees answer a simple question:
Where is my income coming from?
Once that question is clear, the rest of the planning process becomes easier.
The Spending Gap
Another interesting challenge Ethan discussed is what advisors often call the retirement spending gap.
When retirees are surveyed, most say they want their money to help them live the life they want.
But when you look at their actual withdrawals, many spend far less than they could comfortably afford.
They say they want to enjoy retirement.
But their behavior suggests they’re afraid to.
Ethan describes the solution as helping retirees “live fully.”
In other words, the goal of retirement planning isn’t just preserving wealth.
It’s helping people feel confident enough to actually use it.
Retirement Is About More Than Math
Retirement planning often focuses on investment returns, withdrawal rates, and tax strategies.
Those are important.
But they aren’t the whole story.
Retirement also involves psychology, identity, and the emotional shift from saving to spending.
A plan that only works on paper isn’t enough.
The best retirement plans are designed to work with human behavior—not against it.
That’s what makes them truly durable.
And that’s what makes them behavior-proof.
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
Lohr & Company
The Four Buckets
“The Four Buckets: A Behavior-Proof Approach to Reliable Retirement Income” by Ethan Lohr 
Ethan Lohr on LinkedIn
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
Mar 17
32 min
Video

Jeremy Keil explains 3 smart ways to help your kids with money while avoiding IRS paperwork
Early in the year, I received an email from a couple asking a question I hear all the time:
“What’s the maximum we can give our kids?”
That question usually shows up in December. Parents are trying to get a last-minute gift in before the year ends, and the conversation quickly becomes about tax limits.
But that’s the wrong starting point.
If you’re thinking about giving money to your kids, the first question shouldn’t be “How much can I give?”
The better question is “What problem am I trying to solve?”
Many financial mistakes don’t come from bad intentions. They come from rushed decisions. And when it comes to family money, rushed decisions can create tax surprises—or even family tension.
If 2026 is the year you’re considering helping your kids financially, the smartest move is to think it through early.
Why Giving Money Isn’t Always the Solution
Financial gifts don’t always produce the results we hope for.
In fact, research highlighted in The Millionaire Next Door suggests that frequent financial gifts can sometimes create the opposite of what parents want. Instead of building independence, they can unintentionally create dependency.
That doesn’t mean giving money is wrong.
It simply means the purpose behind the gift matters.
Once you understand the purpose, the decision becomes much clearer.
Over the years, I’ve noticed that most thoughtful financial gifts fall into three categories.
1. Timing
Sometimes parents simply want their children to enjoy the money earlier.
Many retirees know they’ll likely leave assets to their children someday. Instead of waiting until inheritance years down the road, they prefer to give some of that money earlier in life.
When kids are in their 30s or 40s, the financial impact of extra money can be significant. It may help them buy a home, invest earlier, or reduce financial stress during busy family years.
There’s also something meaningful about watching your kids benefit from the gift while you’re still around to see it.
Some people call this “giving with a warm hand instead of a cold hand.”
2. Relief
Sometimes money can relieve a specific burden.
Maybe a child is changing careers and needs additional training. Maybe there’s a medical situation that insurance doesn’t fully cover. Maybe they’re dealing with a difficult life transition and just need a little financial breathing room.
In those situations, the goal isn’t simply giving money.
The goal is removing a barrier so your child can move forward.
That’s a very different type of gift than simply writing a check because it’s December and the tax calendar says you can.
3. Experience
The third category is the one I see most often.
Parents want to create experiences with their kids and grandkids.
That might mean taking the entire family on a trip. Renting a large vacation home for a week together. Booking a cruise where everyone can spend time together.
These moments often become some of the most meaningful uses of money in retirement.
You’re not just transferring wealth.
You’re creating memories.
The Tax Rules (Yes, They Matter)
Of course, taxes still play a role.
For 2026, the annual gift tax exclusion allows you to give $19,000 per person per year without triggering any IRS reporting requirements.
But remember: the tax impact often comes before the gift happens.
If the money comes from a traditional IRA withdrawal, that withdrawal is taxable income. If it comes from selling appreciated investments, capital gains taxes may apply.
In other words, giving $57,000 to three kids might require withdrawing significantly more money depending on where those funds come from.
That’s why focusing only on the IRS limit can miss the bigger financial picture.
Share the “Why”
Here’s one final idea I encourage families to consider.
When you give money, share the reason behind it.
Explain why you’re making the gift.
Is it about helping them move forward in life?Is it about reducing stress during a tough moment?Is it about creating family memories?
When children understand the meaning behind the money, they’re far more likely to appreciate the intention behind the gift.
And often, that meaning is far more valuable than the dollars themselves.
Start the Conversation Early
If you’re considering helping your kids financially this year, don’t wait until December.
Start the conversation now.
Ask yourself what you’re really trying to accomplish.
Because when giving money aligns with your intentions—not just tax rules—it can strengthen families, create meaningful experiences, and turn financial gifts into something much more valuable.
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
Read Jeremy’s article in Kiplinger magazine: “How to Give Your Kids Cash Gifts Without Triggering IRS Paperwork”
What is the IRS Gift Tax Limit for 2026? – Mr. Retirement YouTube Channel – https://youtu.be/nGeT9SUd3qI
Should You Give Away Your Money in Retirement? – Retire Today Episode 270
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
Mar 10
12 min
Video

The retirement mindset mentor George Jerjian explains how a second chance at life inspires him to help coach people into retirement.
When George Jerjian was 52 years old, he was diagnosed with a bone tumor and given six months to live.
For three weeks, he believed that was it.
Then he was told he belonged to what he calls “the 2% club.” The cancer hadn’t spread. He would live.
That experience didn’t just save his life. It reframed it.
“Too often we just drift,” George said. “Even in retirement, we drift.”
That word — drift — captures something many retirees feel but rarely articulate.
For decades, retirement is the goal. You save. You invest. You plan. You finally reach the day when work stops.
But then what?
The Retirement Mirage
George calls it the “retirement mirage.”
Culturally, we’ve been sold an image: golf, travel, grandchildren, freedom from responsibility. And for a season, those things can be wonderful.
But George challenges that assumption directly:
“If you retire at 65, you could last till 90 and beyond these days… but what people don’t realize is that no matter how much money they’ve saved, longevity has kind of wrecked the retirement equation.”
Retirement used to be short. Now it can last 20, 25, even 30 years.
That’s not a vacation. That’s a life stage.
In the Retire Today framework, we talk about SPEND, MAKE, KEEP, INVEST, and LEAVE. But underneath all five steps is identity. Who are you when the title on your business card disappears?
George put his experience plainly:
“When you retire, who am I now? I’m a nobody. I’m useless.”
That identity vacuum is where drifting begins.
From Bucket List to Purpose
George doesn’t dismiss the bucket list. He just reframes it.
“Don’t delay that. Get on to that. Do the stuff you want to do. Because once you’re satiated, you’ll start looking for something more meaningful to do.”
Travel. Play golf. Visit family. Do the things you’ve postponed.
But don’t confuse activity with purpose.
Retirement, he argues, is a rite of passage. A hero’s journey.
He references Joseph Campbell’s idea that “the cave you fear to enter holds the treasure you seek.” In other words, the discomfort you avoid may contain the growth you need.
That’s why one of the first exercises George gives clients is confronting mortality:
“On your deathbed, what is it you haven’t yet done that you always wanted to do?”
It’s uncomfortable. But clarity often lives on the other side of discomfort.
The D.A.R.E. Method
To guide retirees through this transition, George created the D.A.R.E. method:
Discover – Understand what retirement truly is (and what it isn’t).Assimilate – Learn how your mind works. Shift from a fixed mindset (“I can’t do this”) to a growth mindset (“I can’t do this yet”).Rewire – Build new habits through repetition. The subconscious mind thrives on stability and patterns.Expand – Step into growth rather than contraction.
That last one is particularly interesting.
Traditionally, retirement advice has focused on shrinking. Reduce risk. Cut expenses. Preserve capital. Prepare for decline.
George pushes back:
“With 20 years to go, this is not the time to settle in safe investments… your life has to match your investments.”
He isn’t dismissing prudent planning. But he is challenging the mindset of slow fade.
Retirement, in his view, is not about “drifting into oblivion.” It’s about repurposing.
Joy vs. Happiness
Another distinction George made is between happiness and joy.
“Happiness is ephemeral… it comes and goes. But joy is something you can still have even if you’re going through challenging times.”
Retirement won’t remove hardship. Health issues, family stress, and loss still occur.
But joy — rooted in gratitude and meaning — can persist.
“If you’re not thankful, you’re not thinking,” he said, connecting gratitude to awareness.
Gratitude expands possibility. Resentment contracts it.
From Retirement to Repurpose
Perhaps the most powerful shift in the conversation came near the end:
Move from the retirement mirage → to retirement meaning → to retirement repurpose.
Financial planning gives you options. But mindset determines whether you use them well.
You can save diligently and still drift. Or you can treat retirement as what it truly is: not an ending, but a new beginning.
And that beginning requires courage.
Because if you don’t choose who you’ll become in retirement, drift may choose for you.
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
GeorgeJerjian.com
George Jerjian on LinkedIn
George Jerjian on FacebookGeorge Jerjian on Instagram
George Jerjian on Twitter/X
George Jerjian on YouTube
Books by George Jerjian
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
Mar 3
33 min
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