Retire Today

Jeremy Keil examines how tax law changes might affect Roth conversion strategies for retirees in 2026.

A few years ago, Roth conversions felt like one of those rare financial strategies that was almost too obvious to ignore. Taxes were historically low. The Tax Cuts and Jobs Act had put a clear expiration date on those lower brackets. And for many retirees, the logic seemed airtight: pay taxes now at a lower rate so you don’t pay more later.

Fast forward to today, and that certainty just isn’t the same.

With new tax legislation making today’s lower tax brackets permanent—at least for now—many retirees are asking a very different question: Are Roth conversions still worth it in 2026 and beyond?

The short answer is yes. But not for the reasons many people think.

The real problem isn’t Roth conversions themselves. The problem is the assumptions people make about them.

Roth conversions exploded in popularity when it appeared obvious that taxes were about to rise. The assumption was straightforward: convert while rates are low, avoid higher taxes later, and you’ll come out ahead.

But that assumption rested on two ideas that don’t always hold up:

That tax rates would definitely rise.

That income in retirement would naturally fall.

For some people, both are true. For many others, neither is.

Markets have been strong. Retirement accounts are larger than expected. Capital gains, pensions, and Social Security stack on top of one another. And suddenly, retirement income isn’t as “low tax” as it once looked on paper.

The Difference Between Tax Bracket and Tax Cost

One of the most common mistakes retirees make is focusing on their tax bracket instead of their tax cost.

On a tax return, you might see yourself in the 12% or 22% bracket and assume Roth conversions are inexpensive. But once Social Security enters the picture, the math becomes more complicated.

As additional income comes in, Social Security benefits that were once tax-free begin to become taxable—up to 85% of the benefit. In that phase-in range, every dollar withdrawn from a traditional IRA can cause more Social Security to be taxed. The result is an effective tax cost that can be significantly higher than the bracket suggests.

This is where many well-intentioned Roth strategies quietly go off track.

Medicare Premiums Change the Equation

Taxes aren’t the only cost that matters.

Medicare income-related premium adjustments—often called IRMAA—are triggered when income crosses certain thresholds. These surcharges commonly appear in two situations: when required minimum distributions begin, and when one spouse passes away and income thresholds are suddenly cut in half.

A Roth conversion that pushes income just over one of these lines can increase Medicare premiums for years. That added cost has to be weighed alongside any future tax savings the conversion might create.

A Cautionary Roth Story

This is where a real-world example brings the point home.

I once worked with a woman to determine the right amount of Roth conversions to do. We carefully mapped out a plan to spread conversions over three tax years so she could stay within reasonable tax and Medicare thresholds.

She was comfortable with the plan. The numbers made sense. We executed the first conversion near the end of the year and agreed to revisit the second one in January.

But after our meeting, she decided to take matters into her own hands.

Rather than following the plan, she converted everything at once. That single decision pushed her income from a moderate tax bracket into much higher ones, triggered additional Medicare premium costs, and permanently locked in taxes that were far higher than necessary.

The intent was good. The outcome was not.

The mistake wasn’t believing in Roth conversions—it was assuming that “more” was always better.

The Real Takeaway for 2026 and Beyond

Roth conversions are not dead. But Roth assumptions are.

Lower tax rates today don’t automatically mean Roth conversions are cheap. A future tax increase isn’t guaranteed. And a zero-tax retirement is not always worth the price paid to get there.

Roth conversions should always be considered—but never assumed.

When done thoughtfully, in the right amounts, and at the right times, they can improve retirement income and flexibility. When done without planning, they can quietly undermine both.

And in retirement, the goal isn’t to win a tax strategy.
The goal is to create a better retirement.

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

Are Roth Conversions for Retirees Dead in 2026 Because of the New Tax Law? By Jeremy Keil, Kiplinger.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

A candid conversation with Eric Brotman on why retirement planning needs structure, flexibility, and fewer assumptions.

One of the things I’ve learned after years of retirement planning conversations is that most people aren’t short on opinions — they’re short on clarity.

They’ve heard plenty of rules.
They’ve absorbed countless headlines.
They’ve picked up advice from coworkers, friends, and financial media.

But when you slow things down and ask a simple question — “Why are you doing it this way?” — the answer is often some version of, “That’s just what I’ve always heard.”

I recently sat down on the “Don’t Retire… Graduate!” podcast with host Eric Brotman (author of “Don’t Retire, Graduate” and previous guest of my podcast back in the “Retirement Revealed” days) to discuss why building a better retirement plan starts with asking better questions.

Eric is the author of Don’t Retire, Graduate, and his core message is relatable to everyone entering retirement: retirement isn’t a finish line. It’s a transition — and transitions deserve thoughtful planning, not assumptions.

As Eric put it during our conversation, “Most people think retirement is a decision. It’s not. It’s a process.”

Why One-Time Decisions Matter So Much to a Retirement Plan

When you’re working, mistakes are usually correctable. Save too little one year? You can increase contributions later. Invest poorly early on? Time often smooths things out.

Retirement doesn’t work that way.

Retirement is full of one-way doors — decisions you can’t easily undo. Social Security claiming. Pension elections. Medicare choices. Tax strategies. 

Once those decisions are made, you often live with them for decades.

This is where many retirement plans quietly fail. Not because the investments are bad, but because the planning skipped the hard questions upfront.

The Quiet Problem of Underspending

One of the most interesting threads in our conversation was something I see often with clients but rarely see addressed directly: underspending.

People spend decades being disciplined savers. They’re rewarded for delaying gratification. Then retirement arrives — and suddenly they’re supposed to flip a switch and start spending confidently?

That transition is harder than most people expect.

Eric described it bluntly: “A lot of retirement plans are designed to avoid failure, not to support a great life.”

When plans are built entirely around extremely high “success rates,” the tradeoff is often living smaller than necessary. Retirees follow conservative rules, spend cautiously, and end up with more money at the end of life than they started with — not because they needed it, but because no one ever gave them permission to use it.

That’s how an effort to preserve your money in retirement can turn into a missed opportunity.

Why Rules of Thumb Aren’t Enough

Rules like the 4% withdrawal guideline exist for a reason — they’re simple and memorable. But that simplicity comes at a cost.

Rules of thumb can be useful starting points, they become problematic when people treat them as guarantees rather than guidelines that require context.

Markets change. Taxes change. Spending changes. Life changes.

A retirement plan that assumes constant spending and ignores flexibility is solving a math problem that doesn’t exist in the real world.

What works better is a framework that expects adjustment — not perfection.

Retirement as a Graduation, Not an Ending

The phrase “Don’t retire, graduate” isn’t about working forever. It’s about intention.

Some people want to fully step away from work. Others want to consult, volunteer, or stay mentally engaged. Neither approach is right or wrong — but drifting into retirement without deciding is where dissatisfaction often starts.

What makes a difference for most retirees? Having a purpose to your life in retirement as a new chapter, not a conclusion to the entire book.

When you treat retirement as a graduation into something new, the planning naturally becomes more thoughtful. Spending decisions align with values. Time gets treated as intentionally as money. And confidence replaces guesswork.

The Real Goal of Retirement Planning

At its core, this conversation wasn’t about beating markets or optimizing spreadsheets. It was about aligning math with real life.

A good retirement plan doesn’t just aim to avoid running out of money. It aims to help you live well — without constant second-guessing.

For many, effective retirement planning isn’t about dying with the most money. It’s about using the money you’ve earned to live well, without fear or constant second-guessing.

That’s a goal worth planning for.

If you’re approaching retirement — or already there — this episode will challenge some comfortable assumptions and help you think differently about what your plan is actually designed to do.

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

Eric Brotman on LinkedIn

“Don’t Retire…Graduate!” podcast

“Don’t Retire…Graduate!” on Amazon

BFG Financial Advisors

BFG University on YouTube

Build Your Retirement Master Plan in 5 Simple Steps

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

Retirement researcher Stefan Sharkansky explains why the 4% rule often leaves retirees underspending — and how a more flexible, math-driven approach can lead to a better retirement experience.

For decades, the 4% rule has been treated as a gold standard for retirement spending. In fact, I made video about it on my YouTube channel. If you ask most retirees how much they can safely spend, the conversation quickly turns to probabilities, simulations, and avoiding failure.

But what if the real risk isn’t running out of money — it’s not using it well?

In this episode of Retire Today, I’m joined by Stefan Sharkansky, whose background in math and computer science led him to question how retirement spending strategies are actually designed — and what they optimize for.

As Stefan put it plainly, “Under the average market scenario, following the safe withdrawal rate of 4% would leave you with more when you passed away than when you started.” In other words, many retirees are leaving too much money on the table in their retirement spending plan.

The Problem With “Safe” Withdrawal Rates

Most retirement spending research focuses on one outcome: not running out of money.

Advisors often present plans as probabilities — a 90% or 95% chance of success — where “success” means the portfolio never hits zero. But this framing runs the risk of missing what retirees actually care about.

After all, if you have a 90% probability of success, what that really means is that 89% of the time, you could have spent more.

That insight flips traditional planning on its head. Instead of asking, “What’s the safest amount I can withdraw?” the better question becomes, “What level of spending lets me live well — while staying adaptable if conditions change?”

Why Retirement Spending Isn’t Constant

One major flaw in the 4% rule is the assumption that spending stays flat year after year. Real life doesn’t work that way.

Spending often starts higher in early retirement with travel and experiences, dips in later years, then rises again due to healthcare needs. Taxes also change as retirees shift between taxable accounts, IRAs, and Roth accounts.

As Stefan noted, “This idea of constant spending never exists in the real world.”

Any retirement spending plan that assumes otherwise is solving the wrong problem.

A Salary-and-Bonus Approach to Retirement

Stefan’s research introduces a different framework — one that mirrors how people actually lived during their working years.

He described a model where retirees create:

A stable, inflation-protected income base using Social Security and a ladder of TIPS (Treasury Inflation-Protected Securities)

A variable ‘bonus’ income driven by long-term stock performance

“You have your salary from Social Security and your TIPS,” Stefan explained, “and then you get a bonus based on how the stock market does.”

In strong markets, spending can increase. In weaker years, spending adjusts — while working to help maintain long-term security. The key is that adjustment is assumed, not treated as failure.

Rethinking Risk Tolerance

Traditional risk tolerance focuses on portfolio volatility — how much account values swing up and down. Stefan argues retirees should think differently.

“Risk tolerance should be about how much variability in income you’re comfortable with,” he said, “not just what percentage of stocks and bonds you hold.”

Some retirees prefer a higher guaranteed income floor with less variability. Others are comfortable with more income fluctuation in exchange for higher long-term spending. The right plan aligns income stability with personal preferences — not arbitrary rules.

Why This Matters

Many retirees say the 4% rule “doesn’t work for them” — not because it’s unsafe, but because it doesn’t generate enough income to support the life they want.

Stefan’s research shows that when you plan for flexibility, rather than perfection, you can often spend more, not less — while still maintaining control.

The goal isn’t to maximize your ending balance. It’s to maximize your retirement experience.

Ultimately, you need to make your retirement spending plan in a way that not only is within your means, but meets your retirement goals. 

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

Is the 4% Rule Outdated? New Research Reveals the TRUTH – Mr. Retirement YouTube Channel

Stefan Sharkansky on LinkedIn

TheBestThird.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

Author Jesse Hurst explains how retirement planning helps reduce the guesswork of retiring through his book “PopEnomics”.

A lot of people approach financial planning with one big fear: that it’s going to feel restrictive. Budgets. Rules. Spreadsheets. Being told what you can’t do with your money.

But in this episode of Retire Today, I sat down with Impel Wealth Management president and author of “PopEnomics”Jesse Hurst to talk about why that assumption gets things exactly backward — and how the right kind of planning actually creates freedom.

As Jesse put it early in our conversation, “A lot of people think financial planning is very constrictive… and I think it’s exactly the opposite. I think it’s very freeing.”

Why Guessing Is the Default (and the Problem)

Most people don’t lack motivation. They lack clarity.

Jesse explained that many retirees have vague hopes rather than defined goals. “Someday I want to retire and live a comfortable life,” sounds nice — but it’s not a plan. Without specifics, people end up guessing on some of the most important decisions of their financial lives.

How much should I save?
Should I prioritize paying off the mortgage?
Is Roth or pre-tax better for me?
Am I saving enough — or too much?

Without a defined target, people default to hearsay. “My coworker did this.” “I read an article that said 8% is enough.” That’s not planning — it’s outsourcing your decisions to someone else’s guess.

Why Stories Stick When Numbers Don’t

Jesse has a way with analogies. By tying retirement planning ideas to pop culture — music, movies, and familiar stories — he finds people actually remember them.

During the COVID period, Jesse began using pop-culture analogies more intentionally. One comparison between Federal Reserve policy and the movie Animal House took off online — and made him realize he’d found a powerful teaching tool.

That insight ultimately led to his book PopEnomics, where retirement planning meets rock anthems, movie classics, and everyday analogies.

Access to Information Isn’t the Same as Wisdom

One of the most important observations Jesse shared came from reflecting on his decades in the profession.

Early in his career, the challenge was simply educating people about what options existed. Today, the challenge is the opposite. “There’s a big difference between access to information and the wisdom to apply it,” Jesse said.

Retirees today are overwhelmed with data — articles, headlines, opinions — but often still unsure what applies to them. That’s where planning shifts from information to interpretation.

The Retirement Puzzle

Jesse described retirement planning as a puzzle — one where each piece matters.

You can’t decide how to invest if you don’t know when you’ll retire.
You can’t know how much risk to take if you don’t know when you’ll need the money.
You can’t spend confidently if you don’t know whether your income supports it.

One story he shared involved a couple who lost track of where they stood financially after COVID, inflation, and market volatility. Using an airport analogy, Jesse explained, “If you don’t know where you are, you can’t figure out how to get to your gate.”

Clarity begins with knowing your starting point.

The Saver’s Mindset — and the Permission Problem

Many people who retire successfully built wealth through discipline — spending less than they earned, avoiding debt, and saving consistently. But those same habits can make it emotionally difficult to switch from accumulation to spending.

As Jesse explained, “They have a hard time giving themselves permission to spend.”

He shared a powerful story of longtime clients who had ample income and assets — but struggled to enjoy them. The breakthrough came when they realized that if they didn’t use their money intentionally, someone else eventually would.

That shift — from fear to permission — is often one of the most important transitions in retirement.

The Bottom Line

Financial planning isn’t about restriction. It’s about clarity.

When you know what you’re saving for, what you’ve already done, and what your money can support, decisions become easier. Spending becomes intentional. And retirement becomes something you can enjoy — not just hope works out.

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

Create Your Retirement Master Plan in 5 Simple Steps

Jesse Hurst on LinkedIn

Impel Wealth Management

PopEnomics.com 

PopEnomics: 12 Relatable (and Not Boring) Pop Culture Insights for Retirement Success

Jesse Hurst on YouTube

Jesse Hurst on Instagram

Jesse Hurst on X

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

Happiness expert Monique Rhodes explains why retirement often feels disorienting at first — and how creating a personal retirement roadmap can turn this transition into one of the most fulfilling stages of life.

Retirement is often marketed as the ultimate reward. After decades of work, deadlines, and responsibility, you finally arrive at a chapter filled with freedom, rest, and happiness.

But for many people, that moment doesn’t feel the way they expected.

In this episode of Retire Today, I sat down with Monique Rhodes, a happiness expert who works with people around the world — especially those approaching or entering retirement — to talk about why this transition can feel unsettling and how to approach it with intention.

Why Retirement Can Feel So Uncomfortable

For years, work provides structure, identity, and a built-in sense of purpose. 

Then one day, it’s gone.

Monique explained that retirement often removes all of that at once. “The structure, the identity, the daily sense of purpose — they all fall away at the same time,” she said. What’s left can feel like freedom… or confusion.

In fact, research shows that many people experience lower happiness in the first year of retirement than when they were working. Feelings of restlessness, anxiety, loneliness, and even grief are common — but rarely talked about.

This doesn’t mean retirement was a mistake. It means the transition requires more than financial preparation alone.

Comfort vs. Happiness

One of the most thought-provoking ideas Monique shared is that too much comfort can actually work against happiness.

She described how modern life is designed to remove friction — from climate-controlled homes to effortless entertainment. But living without any “edge” can dull creativity, resilience, and engagement.

“If we’re consistently living in comfort, we lose our ability to adapt,” she explained. Happiness, she argues, comes from a balance — not too tense, not too relaxed.

Monique used powerful metaphors throughout the conversation, from surfing ocean waves to tuning a guitar string. Too loose or too tight, and it doesn’t work. The same is true for life in retirement.

Retirement Is Not a Holiday — It’s a Redesign

Many people enter retirement expecting it to feel like a permanent vacation. Monique sees this expectation create unnecessary disappointment.

“Retirement is sold to us as a never-ending holiday,” she said. “But when that structure disappears overnight, people are suddenly faced with the question of who they are.”

This is where her Retirement Roadmap comes in — a framework designed to help people intentionally rebuild purpose, routines, relationships, and meaning.

Rather than drifting through unstructured time, retirees are encouraged to create days that feel energizing and aligned with who they are now — not who their job required them to be.

Rebuilding Purpose From the Inside Out

One of the most powerful moments in the conversation was when Monique talked about building a new relationship with yourself.

After years of serving careers, businesses, and families, many retirees struggle to answer a simple question: What do I enjoy?

Monique often starts by asking clients to think back to childhood interests — art, music, movement, creativity — and explore those again without pressure. “Your purpose isn’t gone,” she said. “It’s just no longer handed to you by a job description.”

She emphasized that this phase of life offers something rare: the freedom to choose intentionally — where you live, how you spend your time, who you invest energy in, and what brings joy.

Three Questions Worth Asking

Toward the end of our conversation, Monique shared three questions she believes are foundational for a fulfilling retirement:

Where do I want to be that makes me happiest?

What do I want to do that makes me happiest?

Who do I want to be with that makes me happiest?

These questions don’t have one-time answers. They evolve — and that’s part of the beauty of this stage of life.

The Bottom Line

Retirement isn’t just a financial transition. It’s a psychological and emotional one as well.

When approached consciously, it can become one of the most liberating and meaningful chapters of life — not because everything is perfect, but because you’re living with intention.

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 financial advisor in Milwaukee, WI, author of the bestseller Retire Today: Create Your Retirement Master Plan in 5 Simple Steps and host of both the Retire Today Podcast and Mr. Retirement YouTube channel

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps

Create Your Retirement Master Plan in 5 Simple Steps

Monique Rhodes website

In Your Right Mind Podcast with Monique Rhodes

Monique Rhodes 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.

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