Norman Calvo explains how he found a third act in retirement by going against the norm and choosing adventure instead of a typical retirement.

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.

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.

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.

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.

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:

These questions may seem less urgent than investment allocation or tax planning, but they often determine whether retirement feels fulfilling.

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.

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:

Connect With Jeremy Keil:

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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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.

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:

That combination creates opportunities.

But it also creates a different set of retirement decisions.

For decades, these retirees did what they were told:

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:

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.

Joe offered a simple framework.

Your money ultimately goes somewhere.

You can:

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:

Because choosing not to decide is still a decision.

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:

The right answer isn’t universal.

It’s personal.

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.

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.

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:

Connect With Jeremy Keil:

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

Jesse Cramer and Jeremy Keil detail 7 real world lessons learned from working with hundreds of retirees.

There’s a big difference between studying retirement…

…and actually sitting across the table from retirees for years.

This week I sat down with Jesse Cramer and instead of doing a typical “Retire Today” interview, we decided to compare notes from working with hundreds of retirement clients and shared the lessons that rarely show up in textbooks or headlines.

Experiences often speak louder than theory, so let’s dive into the 7 main lessons.

If you spend time searching YouTube or Amazon for retirement advice, you’ll likely come across the “retirement purpose crisis.” In our real-world experience working with retiree, this doesn’t seem to show up the way financial media suggests.

Yes, some retirees need time to adjust.

But most aren’t spiraling into an identity crisis after leaving work.

Why?

Because many workers weren’t necessarily emotionally attached to the structure of their jobs—they were looking forward to having control of their time again.

A lot of retirees quickly find purpose in:

The bigger adjustment often isn’t purpose.

It’s learning how to structure time differently.

One of the clearest themes in the conversation was timing.

Many people first show up to retirement planning webinars only months before retirement—or even after they’ve already retired.

That creates problems.

Important decisions around:

…all work better when there’s time to think through options.

Jesse’s recommendation was simple:

Start seriously planning at least 12 months before retirement—and ideally earlier.

Not because every detail must be finalized years in advance, but because retirement works best when decisions are intentional instead of rushed.

Retirement isn’t an individual decision when you’re married.

But many couples approach it that way.

We find it is common for spouses to have completely different views on:

Sometimes one spouse wants maximum security.

The other wants maximum freedom.

And if those conversations don’t happen early, conflict can show up later.

I’ve seen couples who struggle with spending expectations and pension decisions because both people weren’t fully involved in the planning process.

The takeaway was clear:

Retirement planning works better when both spouses understand the plan—even if only one person enjoys the financial details.

One of Jesse’s most interesting ideas was describing Social Security as a “pressure release valve.”

Instead of viewing Social Security as a rigid decision with one perfect claiming age, retirees can think about it more dynamically.

For example:

That flexibility can help reduce sequence of returns risk—the danger of withdrawing heavily from investments during a market downturn early in retirement.

The key insight?

Retirement planning isn’t static.

Good plans adapt.

Many retirees focus heavily on avoiding losses.

That’s understandable.

But Jesse shared a cautionary example of a retiree with roughly 90% of investable assets in annuity products because she wanted maximum stability.

The problem?

Over-emphasizing one risk can create others.

Oftentimes retirees “over-index” against market risk while unintentionally increasing:

Safety itself can become risky if growth disappears entirely.

I once had a client who wanted 10% retirement income and concentrated his entire portfolio into one high-dividend bank stock.

Within days:

It was a reminder that retirement success often comes less from finding perfect strategies…

…and more from avoiding catastrophic mistakes.

As Jesse referenced through Charlie Munger’s thinking:
Sometimes the smartest retirement planning question is:

“What should I absolutely avoid doing?”

This may have been the most emotional lesson in the episode.

Many retirees struggle to switch from saver to spender—even when the math clearly says they can afford it.

I once worked with a widow with more than $1 million saved who refused to withdraw money to visit her grandchildren because emotionally she couldn’t bring herself to spend her savings.

That’s where framing matters.

As Jesse summarized:
You’re not changing identities from “saver” to “spender.”

You’ve always been a retirement planner.

Earlier in life, prudent planning meant saving.

Now, prudent planning may mean spending intentionally on things that matter.

Retirement planning isn’t just math.

It’s behavior.
It’s psychology.
It’s communication.
It’s flexibility.

And many of the most important lessons aren’t learned from spreadsheets.

They’re learned from real retirees living real lives.

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:

Connect With Jeremy Keil:

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

Jeremy Keil walks through three critical questions future retirees can answer before their paycheck stops

Most people spend decades preparing for retirement by focusing on one number:

How much have I saved?

But retirement isn’t really about the size of your portfolio.

It’s about whether you can turn that portfolio into reliable income that supports the life you want.

That transition—from saving money to living on it—is where retirement planning becomes real.

And if you’re retiring within the next 12 months, there are three questions you can answer before your paycheck stops.

Unfortunately, this is where many people start with the wrong approach.

Most retirees try building a budget from scratch. They estimate utilities, groceries, gas, dining out, subscriptions, and dozens of other categories.

The problem?

Those budgets are almost always wrong.

They tend to assume:

Instead of trying to build a perfect budget from zero, Jeremy recommends a simpler and often more accurate approach:

Look at what already happened.

Specifically:
What actually went into your checking account over the last 12–24 months?

Because in most households, what goes into checking eventually gets spent.

That “take-home pay” becomes a much better starting point for estimating retirement income needs.

But there are a few important adjustments.

Your paycheck today already has several things removed before it hits your checking account:

Once you retire:

That means your gross salary is not the same as your retirement income need.

Many find it valuable to separate out:

Retirement spending isn’t just monthly bills.

It’s the full picture.

Most people already have an answer to this question before they ever run the numbers.

And often, that decision is emotional.

Maybe a parent died young. Maybe a friend claimed at 62. Maybe someone simply wants to “get their money.”

But what if you about Social Security differently?

Not as an investment.

As insurance.

The official name of the program is Old-age, Survivors, and Disability Insurance. That framing matters.

Social Security exists to help:

In other words, Social Security is there to protect against things not going according to plan.

That’s why filing decisions shouldn’t be based only on “break-even” calculators.

The better question is:
What role does Social Security play in protecting your retirement?

One of the biggest mistakes retirees make is treating retirement like a light switch.

They assume:
Growth before retirement.
Income after retirement.

But markets don’t work on your timeline.

Jeremy shared a powerful example from 2020:
People planning to retire within a year stayed fully invested in stocks because markets had been performing well.

Then COVID hit.

Markets dropped sharply, and many panicked—selling near the bottom because they suddenly realized they needed that money soon.

The issue wasn’t just the market drop.

It was that their investments weren’t aligned with their time horizon.

Get your investments ready to retire three years before retirement.

Why?

Because roughly half of retirees stop working earlier than expected.

If your investments are prepared ahead of time:

But there’s balance here too.

Retirement doesn’t mean abandoning long-term growth entirely.

If retirement could last 25–30 years, some money still needs long-term growth potential.

The key is having:

Not all one or all the other.

Retirement isn’t just about stopping work.

It’s about replacing a paycheck with a plan.

And before your paycheck disappears, you should know:

Because when those three pieces work together, retirement becomes much more than a date on the calendar.

It becomes sustainable.

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:

Connect With Jeremy Keil:

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