Jeremy Keil compares long-term care insurance to self-funding long-term care through the lens of 3 clarifying questions.

When most people start planning for retirement, they’re focused on investment returns, income, and taxes. But one of the biggest financial and emotional challenges retirees face isn’t about markets or money — it’s about health. Specifically, it’s about how to plan for long-term care.

I get this question all the time:

“Should I buy long-term care insurance or should I self-insure?”

Here’s the truth — I don’t like the term “self-insure.”

You can’t actually insure yourself. Insurance means pooling risk with other people, each paying a small amount to protect against a large potential loss. When you’re on your own, there’s no pool, no spreading of risk — you’re not “self-insuring,” you’re self-funding.

If you’re going to self-fund, it needs to be part of a plan — not just an afterthought. Everyone needs a long-term care plan, even if not everyone needs long-term care insurance.

When you’re creating your long-term care plan, there are three essential questions to answer:

Let’s walk through each.

This is both a question of geography and lifestyle. Do you want to receive care at home, in a facility, or somewhere near family?

Many retirees live far from their adult children, which can make in-home or family-supported care difficult. If your goal is to stay close to family support, you might want to plan for a move before care is needed.

And if your goal is to age in place, make sure your home will work for that. Adding features like a zero-entry shower, ramps instead of stairs, or widened doorways can make life easier down the road. The best time to make those upgrades is before a health crisis, not after.

This question is deeply personal. Some people assume their spouse or adult children will step in. Others would rather hire professional help to avoid burdening family members.

Neither approach is wrong, but you need to talk about it. If you’re relying on family, have that conversation today. Make sure they’re willing — and able — to provide that help.

A quote I once heard sums this up well:
“Your family can still care for you, even if they’re not the ones taking care of you.”

That distinction matters. Paid caregivers can provide hands-on support, while your family focuses on emotional and relational care. Whatever route you choose, don’t leave it unspoken.

This is where most people get stuck — and where the insurance vs. self-funding debate really comes in.

If you choose to self-fund, make it intentional. Set aside a specific “long-term care fund” within your retirement plan. Maybe that’s $200,000 of your portfolio earmarked for care costs, invested conservatively and available if needed.

If you choose to buy insurance, remember that it’s not about getting a perfect return. Long-term care insurance can help protect your savings and provide flexibility when you need help most.

Here’s how I like to think of it:

There’s no math formula that can tell you which one will be better for you. It’s about peace of mind. Ask yourself:

“Which would I regret more — buying insurance I never use, or needing care I can’t afford?”

That’s often the best guide.

I’ve seen both sides. Some of my clients feel more confident knowing they have a policy that will step in if they need care. Others prefer to rely on their own savings.

Personally, I lean toward having some level of insurance coverage. Not necessarily because it’s cheaper — but because of the mindset it creates.

When you’ve paid premiums for years, and later in life you need care, it might be easier to say, “It’s time for this policy to do its job.” You might find it easier to get the help you need when you need it.

Long-term care planning isn’t about predicting the future. It’s about preparing for it. Whether you self-fund or buy insurance, the goal is the same: to protect your independence and your loved ones from unnecessary stress.

So ask yourself those three key questions — Where? Who? How? — and start shaping your plan today.

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:

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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Rona Guymon and Jeremy Keil discuss how the recent economic changes have affected retirement plans and strategies.

Is inflation forcing you to rethink your retirement plans? You’re not alone.

In a recent episode of the Retire Today podcast, I sat down with Rona Guymon from the Nationwide Retirement Institute to discuss how recent economic changes are reshaping retirement expectations. Rona and her team commissioned a study through The Harris Poll that revealed some surprising — and concerning — trends among pre-retirees.

According to the data, 42% of people nearing retirement say that the past five years of economic conditions have changed their vision of retirement, and 59% report that their retirement expectations have shifted significantly. That’s nearly six in ten Americans reconsidering what “retirement” even means.

So, what’s going on?

It’s easy to feel confident about your portfolio when the market is performing well — until you go to buy groceries or fill your gas tank. Everyday costs have increased dramatically, and even with inflation starting to cool, people are still feeling the pinch.

Rona shared a powerful example: her brother took his family of six to a fast-food restaurant, and the bill came to over $100. If that’s what “quick and affordable” looks like in 2025, it’s no wonder people are anxious about maintaining their lifestyle in retirement.

In fact, 51% of survey respondents said the cost of living is their single biggest long-term concern for their retirement portfolio. People might be growing their assets on paper, but they’re questioning whether that will truly keep up with the real-world cost of living.

One of the most surprising findings from Nationwide’s study was that 64% of pre-retirees no longer believe that retiring at age 65 applies to them. Instead, 35% plan to work during retirement, and 27% plan to delay it altogether.

This shift isn’t necessarily bad — in fact, for many, it reflects a new kind of retirement that blends purpose, social engagement, and part-time work. As Rona put it, many retirees aren’t giving up work entirely; they’re just finding something more enjoyable, flexible, or meaningful to do.

In other words, “retirement” doesn’t mean quitting — it means redefining what work looks like.

Another big takeaway from Rona’s research is that confidence in retirement planning is directly tied to working with a professional. Despite this, only 4% of survey respondents said they currently work with a financial advisor.

That’s a huge missed opportunity.

Partnering with a financial professional can help you uncover strategies to manage inflation, taxes, and income needs — and, most importantly, give you peace of mind about your financial future.

If you’re reading this now and you aren’t working with an advisor, follow the link at the bottom of this article to explore your options.

The survey also asked pre-retirees about traditional financial rules, like the 4% withdrawal rule and the “100 minus your age” investing rule.

That’s a major shift. For decades, these have been go-to benchmarks for financial planning. But as Rona explained, many people feel they haven’t saved enough or that inflation will erode their nest egg — so those old rules just don’t feel realistic anymore.

Interestingly, most financial advisors still believe those rules have value. That difference highlights a major disconnect: advisors often serve people who already feel confident in their finances, while the average pre-retiree may feel far less certain.

The key lesson? Retirement isn’t one-size-fits-all. The “rules” might provide a starting point, but your plan should reflect your unique goals, resources, and lifestyle.

As Rona and I discussed, the goal of a retirement plan isn’t just to maximize returns — it’s to create confidence. For some people, that means exploring income options like annuities, which can help supplement Social Security and create a personal pension-style income stream.

Others may find peace of mind by working longer or by creating flexible income plans that balance security with growth potential.

The bottom line is this: retirement looks different today than it did 20 or even 10 years ago. It’s about designing a plan that gives you freedom, purpose, and control — even when the economy feels uncertain.

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

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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Kanwal Sarai of “Simply Investing” explains his 12 rules for dividend investing and how this strategy could be used in retirement planning.

When most people think of investing, they picture charts, constant news updates, and the stress of trying to time the market. But as my guest Kanwal Sarai shared on the Retire Today podcast, successful investing doesn’t have to be complicated—or stressful. In fact, Kanwal says it’s so simple that even his nine-year-old kids could do it.

Kanwal is a software professional turned dividend value investor who founded SimplyInvesting.com. He’s also the host of The Simply Investing Dividend Podcast and designer of the “12 Rules of Simply Investing.” His story is a powerful reminder that investing isn’t just about growing wealth—it’s about building long-term financial independence through education and discipline.

Kanwal didn’t start out as an investor. He spent 30 years in the software industry, working for startups and Fortune 500 companies alike. But his interest in investing began in a surprising way—during late nights walking his newborn son to sleep.

“I saw a book I’d bought years ago, and I decided to read it while pacing back and forth,” Kanwal said. That book introduced him to Warren Buffett and Benjamin Graham, two icons of value investing, and started him down a lifelong path toward financial literacy and independence.

At first, he made the same mistake many beginners make—chasing hot tech stocks in the late 1990s. “I bought Nortel just because everyone was talking about it,” he recalled. “When it went bankrupt, I lost my entire investment.” That experience convinced him that investing based on hype or emotion isn’t a plan—it’s gambling.

Kanwal’s philosophy combines two approaches: dividend investing and value investing.

By focusing on companies that are profitable, stable, and consistently pay (and raise) dividends, Kanwal has built an investment strategy that rewards patience and discipline over speculation.

He looks for what he calls “hidden gems” that are undervalued today but have a long track record of profitability—companies like Coca-Cola, Johnson & Johnson, and Procter & Gamble, which have raised their dividends for 60+ years.

“These are mature businesses,” Kanwal explained. “They’ve been around for decades, they’re profitable, and they pay you regularly. That’s the kind of predictability investors near retirement should want.”

Kanwal shared an important lesson from his early investing years: don’t fall into what he calls the “dividend trap.”

The trap happens when investors chase high dividend yields without looking at the company’s fundamentals. If a stock’s price drops sharply, its dividend yield may look attractive—but often it’s a warning sign.

“One of my big mistakes was buying Washington Mutual,” he said. “The yield looked amazing—9%! But I ignored my own rules. The company went bankrupt.”

Kanwal’s Rule #7 from his 12 Rules of Simply Investing addresses this exact issue: only invest in companies with a payout ratio of 75% or less. That means the company should be paying out no more than 75% of its earnings in dividends. Anything higher is unsustainable and could signal financial trouble.

For Kanwal, the beauty of dividend investing lies in its simplicity and long-term payoff. When a company increases its dividend year after year, your income grows without any extra effort.

“It’s like giving yourself a raise every year—without working more hours,” he said. Companies like Coca-Cola and Johnson & Johnson have been increasing dividends for over 60 years. That kind of consistency, especially through multiple market downturns, gives investors confidence and stability.

And it’s not just theory—Kanwal practices what he preaches. His own children began investing as teenagers, using money from birthday gifts to buy dividend-paying stocks. “Their first dividend was only $10,” he laughed, “but that $10 showed them what financial independence feels like.”

Kanwal’s 12 Rules form the foundation of his investing philosophy. Here are a few highlights:

These simple rules, combined with patience and discipline, may help investors avoid emotional mistakes and focus on long-term wealth building.

As Kanwal explains, dividend investing isn’t about getting rich overnight—it’s about creating steady, predictable income for life. Whether you’re still working or already retired, dividend investing is one of the many options on the table to explore with your investment portfolio. Investing in dividends includes risk of loss (as we talked about in this podcast) and possible loss of principle, so be sure to consult your advisor and understand how this strategy might impact your 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 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

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

Andrew Motiwalla explains how to prepare for long-term travel and how to incorporate travel into your retirement plan.

When I sit down with people to talk about retirement, one of the first things I hear is, “I want to spend more time with my grandkids and I want to travel.” And while grandkids may not need much planning, travel does—especially if you want to do it in a way that truly enriches your retirement years.

That’s why I was excited to sit down with Andrew Motiwalla, founder of The Good Life Abroad, on the Retire Today podcast. Andrew has spent 30 years in the travel industry and has built something unique for retirees who want more than just a quick trip. His company helps retirees live abroad for one or two months at a time, creating deeper, more immersive travel experiences.

Andrew described three “phases” of travel that many retirees experience. The first is what he calls checklist travel. This is when you finally make it to those bucket-list destinations—the Eiffel Tower, Machu Picchu, the Taj Mahal—and snap the pictures you’ve dreamed of for years. It’s exciting, it’s rewarding, and for many, it’s where retirement travel begins.

But then comes phase two—intentional travel. This is when you begin asking bigger questions: Who am I? What do I really want out of retirement? Maybe you’ve always loved art and decide to spend a month in Florence studying Renaissance masterpieces. Or perhaps your family roots are in Poland, and you want to show your children and grandchildren where your story began. It’s travel with a deeper purpose.

Finally, there’s immersive travel. This is when travel becomes more than just a trip—it’s part of your lifestyle. Retirees may take language or cooking classes at home, then use extended travel to practice and grow their skills. Instead of being tourists, they start to live like locals, even if just for a short time.

One of the biggest differences Andrew sees between standard vacations and what The Good Life Abroad offers is time. When you live abroad for a month or two, you’re not rushing from one destination to another. You can settle into an upscale apartment, shop at local markets, and develop routines—like a favorite café or a walking route through your neighborhood. You start to feel part of the community.

Just as important, Andrew’s company helps retirees avoid some of the biggest pitfalls of going it alone, such as loneliness or confusion about local customs. They provide a “community manager”—someone who knows both the local culture and the American mindset—to guide you to hidden gems like university concerts or local cooking classes. They also bring together a community of like-minded retirees, so you’re never traveling alone unless you want to be.

What struck me most in this conversation is how immersive travel can actually help retirees find new meaning and identity. For decades, your sense of self may have come from your job or raising your family. In retirement, those roles shift. Travel—done with purpose—can fill that space. You might start to identify as a “traveler,” a “culture lover,” or an “art enthusiast.” And along the way, you’ll meet others who share that passion.

This isn’t just about checking boxes; it’s about transformation. As Andrew put it, travel can be a vehicle for reinvention.

Of course, planning extended travel comes with questions. What about health care? What about visas? Andrew explained that for trips under 90 days, Americans can generally travel freely in most of Europe, and The Good Life Abroad includes travel medical insurance and access to English-speaking doctors in every city they serve. For longer stays, you may need to look into visas and local insurance, but for most retirees, a one- or two-month trip fits perfectly within the rules.

And if you’re traveling solo, Andrew reassured us that this model works just as well. Many of their travelers are single—widowed, divorced, or just pursuing retirement independently—and the built-in community makes it easy to form new friendships and connections.

Whether you’re a lifelong learner eager to expand your horizons or simply someone who’s always wanted to “live like a local,” immersive travel may be one of the best gifts you can give yourself in retirement. As Andrew said, it’s never too late to keep learning, growing, and exploring.

Retirement isn’t just about financial freedom—it’s about personal freedom. And travel, when done thoughtfully, can be one of the best ways to embrace that freedom.

If you’ve ever dreamed of living abroad—even just for a month—this episode is for you. I invite you to listen to the full conversation with Andrew Motiwalla on the Retire Today podcast and start envisioning what your own “good life abroad” might look like.

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

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

Discover how step 5 of building your retirement master plan can help you leave a lasting legacy while avoiding the big 3 retirement risks.

When most people think about retirement planning, they picture saving money, managing investments, and planning income. But retirement is about more than how you live—it’s also about what you leave behind. And as I often remind my clients, it’s not what you leave them, it’s how you leave them that counts.

This is Step 5 in creating your retirement master plan: Leave. This final step ensures that the legacy you leave for your loved ones is intentional, meaningful, and well-prepared.

Before we talk about estate documents, let’s step back and consider the risks that could derail your retirement if you don’t prepare for them. I call these the big three retirement risks:

Once you’ve planned for the risks, you can move to estate planning, which I like to think of as your legacy protection plan. This has two main goals:

Leaving a legacy isn’t just about dollars—it’s about leaving clarity, direction, and peace of mind. Too many families are left to navigate confusion, disputes, and court battles because the planning wasn’t done ahead of time. By planning for risks, creating the right documents, and making thoughtful decisions, you can leave behind more than just assets—you can leave behind confidence, stability, and a sense of care for those you love.

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

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

Learn the number 1 investing mistake people make in retirement and how to build a retirement investment plan.

The market goes up, the market goes down, and too often retirees get caught chasing returns or trying to predict the next big winner. In Step 4 of the Retirement Master Plan, I want to help you avoid the number one investing mistake I see retirees make: trying to control what you can’t control.

Instead of focusing on the unpredictable, like short-term stock market moves or economic headlines, you can create a retirement investment plan built on the things you can control. 

After years of working with retirees, I’ve noticed a consistent pattern. The people who struggle the most with investing are the ones who try to outsmart the market. They want to pick the hottest stock, time their withdrawals perfectly, or find a “magic bullet” investment that bails them out of overspending.

But all too often I find the reality is this: the stock market isn’t the problem—spending is. Trying to control what you can’t control almost always leads to disappointment. The better approach is to focus on two things you can control:

One of the most effective ways to simplify your retirement investing is by using a bucket strategy. Instead of viewing your portfolio as one big pool of money, divide it into two separate buckets:

This framework takes the guesswork out of retirement investing. Short-term needs are protected, and long-term needs are invested for growth.

That’s the big question: how much should you set aside in your income bucket? The answer depends on your comfort level and your retirement spending needs.

The rest belongs in the growth bucket, invested according to your personal risk tolerance. A simple way to figure this out is to ask yourself: on a scale of 1 to 10, how much risk am I comfortable with in the stock market? Your answer provides a starting point for how much of your growth bucket belongs in stocks versus bonds.

Retirement investing isn’t a one-time decision. Markets move, portfolios drift, and your needs evolve. That’s why rebalancing and refilling are so important.

This ongoing process ensures that your retirement plan adjusts with you, rather than leaving you vulnerable to market swings.

Remember, you can’t control the stock market, the economy, or political changes. But you can control:

When you focus on these controllable factors, you’ll build a retirement plan that is far more resilient and less stressful.

Step 4 of the Retirement Master Plan is all about creating a clear, practical investment strategy. By focusing on the income and growth buckets, regularly rebalancing, and refilling when needed, you’ll avoid the trap of trying to control what you can’t.

Next week, I’ll share the final step—planning for what you’ll leave behind. But for now, take some time to assess your own retirement buckets. Are you balancing safety with growth in a way that supports your dream retirement?

Because when you know more about your money, you’ll feel better about your money—and you’ll make better decisions for your future.

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

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

Learn how to keep more of your retirement income through tax planning in step 3 of the 5 step retirement plan.

When people think about retirement planning, they usually focus on two big questions: How much do I need to spend? and How much will I make in retirement? Those are important, but there’s a third question that often gets overlooked—and it could make or break your plan: How much of your money do you actually get to keep?

That’s what Step 3 of creating your retirement master plan is all about: keeping more of your hard-earned money through smart tax planning.

During your working years, your income is pretty straightforward. You earn a salary, and taxes get withheld from your paycheck. In retirement, things look very different. You now have more control than ever before over what your tax bill will look like. That’s because you can decide when and how to pull money from your accounts.

Two factors play the biggest role here:

Making smart decisions with timing and type could mean saving thousands of dollars in unnecessary taxes over the course of your retirement.

Here’s a simple example: if you withdraw money on December 31st versus January 1st, that income falls in two completely different tax years. Just a week’s difference could completely change your tax outcome.

But timing isn’t just about the calendar—it’s about your retirement phases:

Every one of these milestones creates “before and after” windows where your tax planning can make a huge impact. If you’re not planning around these, you might end up paying more than you need to.

Not all withdrawals are created equal:

The key is mixing and matching withdrawals across these account types in a way that minimizes taxes now and later.

If there’s one strategy that makes the biggest difference in retirement, it’s Roth conversions. Converting part of your traditional IRA into a Roth lets you pay taxes now (often at a lower rate) in exchange for withdrawals later.

But there are three big myths I hear all the time:

This is what I call the Golden Rule of Roth Conversions: choose the right year and the right amount. Get that right, and you could save tens of thousands of dollars. Get it wrong, and you might pay unnecessary taxes you can’t undo.

I worked with a couple who had room to do Roth conversions while staying in the 24% tax bracket. We created a plan to spread their conversions out over three years. But they decided to convert everything at once, thinking it wouldn’t matter.

Unfortunately, it did matter. Instead of keeping their conversions at the 24% tax bracket, much of their income spilled into the 32% and even 35% bracket. The result? I estimate they paid $23,000 more in taxes than they needed to.

That’s why timing and amount are so important. Tax planning in retirement isn’t a yes-or-no decision. It’s about making the right move at the right time.

At the end of the day, Step 3 of your Retirement Master Plan is all about keeping more of what you’ve worked so hard to save. Taxes are one of your biggest expenses in retirement, but with careful planning, you can reduce their impact and free up more money to spend, share, and enjoy.

If you’d like to dive deeper into this, check out my book Retire Today: Create Your Retirement Master Plan in 5 Simple Steps, or head over to JeremyKeil.com to learn more.

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

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

Learn how to maximize your Social Security and pension benefits in your retirement income plan.

Just because you’ve stopped working doesn’t mean you’ve stopped making money. In fact, some of the most important financial decisions you’ll ever make happen right at the start of retirement—and many of them are one-time, often irreversible choices. Get them right, and you could add hundreds of thousands of dollars in lifetime income. Get them wrong, and you may leave that money on the table.

That’s why Step 2 of creating your retirement master plan is all about building a lifetime income plan. At its core, this step focuses on Social Security and pensions, two of the most significant income sources for retirees. Unfortunately, I see too many people making decisions based on myths rather than math. Let’s walk through some of the most common misunderstandings and what you can do instead.

This is one of the biggest misconceptions I hear. People think that if you file early at 62, you’ll get a smaller benefit for longer, and if you file late at 70, you’ll get a larger benefit for fewer years—so it must all balance out.

That logic might have been true back in 1983, the last time major Social Security changes were made. But two big things have changed since then:

The bottom line: today, the math overwhelmingly favors waiting, especially for the higher earner in a couple.

I see spreadsheets all the time where people try to “prove” that filing early and investing the money comes out ahead. But those spreadsheets rarely account for important realities:

Research has shown that, on average, you’d need an 8% annual investment return to come out ahead by filing early. That’s possible in the market, but it’s far from guaranteed—whereas the higher Social Security benefit from waiting is.

Some people dismiss delaying Social Security because they think the odds of living long enough to benefit just aren’t there. But the statistics tell a different story.

So if you think delaying isn’t worth it because you might not live long enough, the math shows that you’re actually betting against the odds.

It helps to think of Social Security for what it really is: old-age and survivor’s insurance. It’s designed to protect you if you live longer than expected, if inflation rises faster than you planned, or if your investments don’t perform as well as you hoped. Filing decisions should be based on maximizing that protection for you and your spouse.

Many retirees also have pensions, and similar myths apply. But there are two key differences:

Here’s where caution is critical. Financial advisors sometimes push clients toward lump sums because they get paid for managing that money. Monthly pensions don’t generate fees, which means there’s less incentive for advisors to recommend them—even if they’re the better choice for you.

That’s why you need to do the math carefully. Compare the actuarial value of the monthly payment versus the lump sum, and factor in survivorship benefits for your spouse. This isn’t a decision to make lightly.

The truth is, most people make costly mistakes with Social Security and pensions. Studies show that couples, on average, lose about $180,000 in lifetime benefits because of poor Social Security decisions. That’s why I urge you to base your retirement plan on math, not myths.

Your Social Security and pension are designed to provide steady, reliable income for life. By making smart, math-driven decisions today, you can ensure that income is maximized—not just for you, but also for your spouse and family.

Step 2 of your retirement master plan is all about creating your lifetime income plan. That means thinking carefully about Social Security, pensions, and how they’ll support you over the decades of retirement. Don’t rely on guesses, gut feelings, or myths. Instead, take the time to do the math—or better yet, work with someone who can walk you through the analysis.

If you want to dig deeper into these strategies, you can check out my book Retire Today: Create Your Retirement Master Plan in Five Simple Steps at JeremyKeil.com. And for more resources, head over to FiveStepRetirementPlan.com.

Because knowing more about your money will help you feel better about your money—and that leads to making better money decisions in 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

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

Order your copy of Jeremy Keil’s new book “Retire Today” available now.

I am so excited to share some big news with you: my new book, Retire Today, is officially available!

This book is the result of years of helping people transition into retirement and seeing firsthand what works—and what doesn’t. My goal in writing Retire Today was to give you a simple, step-by-step guide to creating your own retirement master plan. Because the truth is, retirement doesn’t have to be overwhelming. With the right process, you can feel confident, prepared, and ready to enjoy life on your terms.

Over the years, I’ve met countless people who’ve asked me the same questions:

What I realized is that most people don’t need complicated formulas or jargon—they need a clear framework that helps them make smart choices and avoid costly mistakes. That’s exactly what Retire Today delivers.

It’s not about chasing the “perfect” retirement plan. It’s about creating a personalized plan that works for you.

Inside Retire Today, I walk you through the five steps to creating your retirement master plan. Each step is designed to answer the most important questions you’ll face:

Each chapter includes real-life examples from people I’ve worked with. These aren’t just theories—they’re practical lessons that show you how small changes can make a big difference in your financial future.

We live in uncertain times. Markets go up and down, tax laws change, and healthcare costs continue to rise. But no matter what happens, you can take control of your retirement today by following a clear, proven process.

The sooner you start, the more flexibility and confidence you’ll have. That’s why I encourage you not just to read the book—but to act on it.

You can get your copy of Retire Today right now by visiting JeremyKeil.com.

And here’s my challenge to you: don’t just buy the book and put it on the shelf. Work through the steps. Build your plan. And take that first action toward the retirement you’ve always dreamed of.

This isn’t just the title of the book—it’s a mindset. Retire Today means having the confidence to know you’re prepared, whether you retire tomorrow, five years from now, or later down the road.

So if you’ve been waiting for the right time to take your retirement seriously, that time is now.

Grab your copy of Retire Today, start building your retirement master plan, and take control of your future.

Because your best years are ahead—and they start today.

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: Retire Today – Podcast

Spotify Podcasts: https://bit.ly/RetireTodaySpotify

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 explains step 1 of the 5 step retirement plan: retirement spending.

When it comes to retirement planning, one of the biggest questions people ask is: Where do I start? The truth is, before you think about investments, taxes, or even when to claim Social Security, you need to figure out one thing—how much you’re going to spend in retirement.

This is what I call Step One in creating your retirement master plan, which I’ve outlined in my book Retire Today. While many people assume retirement planning begins with assets and income, I believe it begins with spending. After all, if you don’t know what you’ll spend, how can you know how much income you’ll need?

When I sit down with people, their first instinct is often to start building a retirement budget. They think they need to track every coffee, grocery run, and gas fill-up to get an accurate picture. But here’s the problem—budgets are almost always wrong.

People underestimate their spending, forget about irregular costs, and end up thousands of dollars off the mark. I’ve seen it happen time and again. Instead of building from the ground up, there’s a simpler formula that works nearly every time:

Income – Savings = Spending.

Whatever comes from your paycheck into your checking account typically gets spent—unless you’re intentionally saving it. By starting here, you can find your true monthly lifestyle amount without overcomplicating things.

Take Thomas, for example. He had what I thought was the best budget I’d ever seen—two years of detailed expense tracking. Every expense logged, every penny accounted for. He proudly told me he spent $7,000 per month.

When we broke it down, though, we realized he didn’t need years of tracking to figure this out. His income was $104,000 per year. He saved $20,000 into investments. That left $84,000 for spending—or $7,000 per month. Exactly what his “perfect” budget said, but it took him two years to arrive at something the formula showed in minutes.

One caution I often give people is not to confuse saving with growing. If you’re putting $500 into savings every paycheck, but pulling it out later for property taxes or vacations, that’s not saving—it’s managing cash flow. True saving means money you set aside for the long-term, not just for short-term annual expenses.

This distinction matters because when you’re projecting retirement spending, you need to know what’s truly ongoing versus what’s temporary or irregular.

Even when people nail down their monthly lifestyle amount, I often see them forget two of the biggest retirement costs:

Your monthly lifestyle spending is the foundation, but retirement also comes with non-lifetime expenses—costs that won’t last forever, but you should still plan for.

These often include:

If you don’t plan for these, they’ll sneak up and throw your retirement plan off track.

Retirement is not about hitting a magic savings number—it’s about matching your income to your lifestyle. Step one is figuring out your lifestyle amount: how much you need each month to live comfortably. Once you know that, the rest of the retirement plan—your investments, your tax strategy, your Social Security timing—can all be built around it.

Too many people start at the wrong end of the problem. They focus on how much they’ve saved, and then try to make their lifestyle fit. But if you start with your lifestyle first, you’ll have a plan that feels realistic, sustainable, and personalized.

If you’re planning for retirement, start today. Look at your income, subtract your true savings, and you’ll know your lifestyle amount. Then, don’t forget to factor in health insurance, taxes, and those one-time expenses.

This is step one of creating your retirement master plan. Once you’ve got it, you’ll have a clear starting point to build the retirement you deserve.

And if you want to go deeper, my book Retire Today walks you through all five steps in detail.

Because the truth is simple: if you know more about your money, you’ll feel better about your money—and you’ll make better decisions in 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: Retire Today – Podcast 

Spotify Podcasts: https://bit.ly/RetireTodaySpotify

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