Welcome to One for the Money! In Episode 88, we explore retirement as a journey—and each important stop along the way. From your 20s through your 60s (and beyond), you’ll learn what to focus on at each stage, how to avoid costly pitfalls, and how to test-drive retirement with a mini-retirement that just might change your life.

🔑 In This Episode, You’ll Learn:

• The 5 key retirement milestones: Before 50, 50, 55, 60, and 65—and what you should be doing at each one.
• How to use catch-up contributions at age 50+ to turbocharge your savings.
• Why age 55 offers hidden opportunities for penalty-free withdrawals and boosted HSA contributions.
• The “Danger Zone” around age 60 and how to protect yourself from market volatility.
• Why claiming Social Security early (at 62) may cost you big time—and how to decide when to claim.
• What to know about Medicare deadlines at age 65 to avoid lifelong penalties.
• The latest updates to 401(k) contribution limits and Required Minimum Distribution (RMD) ages for 2025.

🧠 Tips, Tricks & Strategies Segment: The Power of a Mini-Retirement

Taking a break between jobs? Consider a mini-retirement—a planned sabbatical where you rest, recharge, and test-drive your future lifestyle. Learn:

• What a mini-retirement is (and why it’s more than just a vacation).
• How mini-retirements can offer massive tax advantages (yes, really!).
• Why experiencing other cultures in your 40s or 50s might beat waiting until your 70s.
• How to time it right when switching jobs for minimal disruption and maximum impact.

📺 Referenced Episodes:

• Episode 6: Making Retirement Meaningful
• Episode 26: Mini-Retirement & Tax Benefits

📌 Key Quote:

“We don’t rise to the level of our dreams—we fall to the level of our planning.”

✅ Action Steps:

1. Review your financial plan at each milestone age: 50, 55, 60, 62, 65, 67, 70, and beyond.
2. Assess your plan using the 5 Domains: income, investments, insurance, taxes, and estate planning.
3. Explore the option of a mini-retirement—especially during a career transition.
4. Talk to a Certified Financial Planner (CFP®) to optimize your strategy.

📬 Want More?

👉 Subscribe to One for the Money on your favorite podcast platform.

👉 Ready to plan your ideal retirement? Schedule a free consultation with our team.

Welcome to episode 87 of the One for the Money podcast. Retirement is the ultimate dream for many, but there are realities of retirement that everyone needs to be aware of. Better retirement planning will incorporate these realities so it leads to a better life in retirement.

In the tips, tricks, and strategies portion, I will share ten tips when you are 10 years from retirement.

In this episode...

• Your Biggest Expense Isn’t What You Think [2:08]
• Your Biggest Fear is Misplaced [3:20]
• Regret is More Common Than You Think [4:40]
• The Real Risk Isn’t a Market Crash [5:08]
• Your Most Expensive Years Are… Surprising [5:59]
• Your Health = Your Wealth [6:26]
• Identity Crisis Incoming [6:48]
• Estate Planning is About More Than Money [7:30]

We often forget that retirement is only a recent invention. It hasn’t been around for that long. For most of human history, people worked until death or until their family could care for them when they were unable to work any longer. Retirement allows one to enjoy a life of leisure even though one is still capable of work. It really is a more amazing concept than we give it credit, and it truly is an absolute luxury of both the modern and first world. It’s amazing to think that a person can work and invest for 30-40 years and then live off that work for another 30-40 more years.

Your great-grandparents would’ve thought that was science fiction. And honestly, for billions around the world, it still is.

If you are literally and figuratively fortunate enough to enjoy such a dream as retirement, here are the most important retirement realities as I see them.

💸 Retirement Reality #1: Your Biggest Expense Isn’t What You Think

When I ask people to guess their largest retirement expense, I hear the usual suspects: housing, healthcare, maybe travel, or groceries. But nope. The winner — and it's not even close — is taxes.

Yes, Uncle Sam (and sometimes Cousin State) will still want a piece of your pie. Social Security? Taxable at the federal level and in some states. IRAs and 401(k)s? You bet. Medicare surcharges? Yep, that’s a thing.

But here’s the kicker: the folks who pay the least in taxes during retirement aren’t lucky. They’re prepared. They’ve been implementing smart tax strategies years — even decades — before they stop working. We’re talking Roth contributions, conversions, HSAs, pre-tax vehicles, cash balance plans — all the good stuff.

And to do it right, you need a plan customized to your current and future tax situations. That’s exactly what we do for our clients — because the less you pay in taxes, the more you can spend on what actually matters: time, travel, and tacos with the grandkids.

😱 Retirement Reality #2: Your Biggest Fear is Misplaced

Everyone fears running out of money. But statistically, what they should be afraid of… is dying with too much.

No joke — a study by the Investments and Wealth Institute found that 84% of retirees only spend the earnings from their portfolios. They never touch the principal. It's called the "decumulation paradox." They’ve got the money — they’re just afraid to use it.

Why? Two big reasons:

1. Lifelong savers have trouble flipping the switch to spending mode.
2. The “just in case” fund: just in case the kids need help, or a health crisis hits, or Aunt Sally’s dementia story plays on repeat in your mind.

But here's the thing — the real tragedy isn't running out of money. It's running out of time to enjoy it.

Using the well-known 4% rule, retirees in over two-thirds of cases ended up with twice their original wealth, even after withdrawing every year.

So yeah, have a plan. But make it one that helps you live now, not just preserve your balance...

Welcome to episode 86 of the One for the Money podcast. In the late 1960s and early 70s, a famous psychological study was conducted that has since been called the Stanford Marshmallow test. The study was designed to explore the concept of delayed gratification. In this episode, I’ll share how life might be considered one giant marshmallow test.

In the tips, tricks, and strategies portion, I will share a tip regarding how to not eat the entire marshmallow.

In this episode...

• The Marshmallow Test [0:36]
• Delayed Gratification in Personal Finance [2:23]
• Investing Rewards Patience [10:01]
• Teaching Financial Discipline [10:46]

In the late 1960s and early 70s, a psychologist named Walter Mischel at Stanford University conducted what has become a famous psychological study. The study was designed to explore the concept of delayed gratification — the ability to resist the temptation for an immediate reward in order to receive a larger reward a short time later.

Here is how the Experiment was set up:

600 preschool-aged children, roughly 4-6 years old, participated in the study. Each child was placed in a room with a marshmallow placed on a table. The researcher told the child that they could either eat the marshmallow immediately or wait 15 minutes without eating it. If they waited without eating the marshmallow, they would be rewarded with a second marshmallow.

The researcher then left the room, leaving the child alone with the first marshmallow.

The Key Findings as a result of this research were that Individuals had varied Self-Control: Some children immediately ate the marshmallow, while others were able to wait the full 15 minutes for the larger reward.

Now you might be wondering what a 4-6-year-old eating a marshmallow has to do with personal finance? Well, that’s what was most remarkable about this study was what the follow-up studies revealed. The outcomes were very successful at Predicting Future Outcomes: Over the subsequent decades, Mischel and his colleagues followed up with many of the children who participated in the experiment, and the results were astounding:

It found that the children who were able to wait for the second marshmallow, decades later, tended to have significantly better life outcomes in terms of higher SAT scores, lower rates of obesity, more likely to be financially stable as well as to have greater job satisfaction. The ability to delay gratification was a more accurate predictor of future success than their scores on an IQ test.

Now it should be noted that while the Stanford Marshmallow Experiment became a widely discussed study about the power of self-control, later research showed that the environment in which a child grows up, including factors like trust in caregivers, socioeconomic status, and stability, can influence how well they are able to delay gratification. For instance, children in more unstable environments may have less reason to trust that the promised later reward will actually come.

But suffice it to say, the Stanford Marshmallow Experiment remains one of the most influential studies in psychology, because it exposed the impact that self-control has on later life outcomes.

I’ve read about this study numerous times over the years, but recently it has led me to this thought: is life really just one giant marshmallow test? Is delaying gratification part of the better planning one needs to implement to have a WAY better life?

As I thought about this more, I came to the belief that generally speaking, life is one giant marshmallow test and that individuals can both learn and develop the skills so they too can have much better life outcomes. It also seems to me that businesses and politicians can hijack our desires for immediate gratification to their advantage.

Individuals...

Welcome to Episode 85 of the One for the Money podcast! Some of you may remember that best-selling book The Automatic Millionaire. It told readers how to easily become a millionaire with a few simple steps. But in this episode, I’ll reveal the sad truth: too many people aren’t becoming automatic millionaires because they’re spending too much money on automobiles. Yes, cars and trucks are putting the brakes on a better future for many Americans. I'll also share the massive benefit of driving one’s car until the wheels come off.

In the tips, tricks, and strategies section, I’ll share some car-buying tips.

In this episode...

• Automating Savings [1:23]
• The Financial Impact of Car Ownership [2:04]
• When Is It Ok to Buy a Nice Car? [6:35]

The Automatic Millionaire, written by David Bach, became an international bestseller because it gave us that magical formula for becoming a millionaire.

Bach’s magic trick? Automating your savings and spending. He basically tells you to set it and forget it. You set up automatic contributions to your 401k or IRA, and it’s that easy to be on the road to riches. He even argues that you don’t need to be making a six-figure income to become a millionaire—you just need to make sure your savings and spendings are adjusted on autopilot and viola, decades later you reap the rewards.

And yet, despite this brilliant advice, millions of people are still missing the automatic millionaire bus, and they’re doing it by throwing too much of their money at automobiles. While an automobile is designed to take you places, far too often, it takes owners to a future that is much poorer and less fulfilling than it otherwise could be.

Now, you might ask, is car ownership really that impactful? Let’s look at the numbers from 2024:

• Americans owe around $1.655 trillion in auto loan debt. That’s right, trillion with a T.
• Over 80% of new car purchases in 2024 are financed, and the average car payment is $742 for new cars and $525 for used ones. (That’s a lot of money that could be used to build wealth instead.)

Now, why is this a problem? I mean, cars are cool, right? But here's the thing—unless you’re driving a classic car like a 23-window VW van (I can dream), cars lose value. In fact, a new car drops thousands of dollars in value as soon as you drive it off the lot. So, people are paying $525-$747 a month for years... for something that’s losing value fast. In fact, over 30% of people with car loans have negative equity, meaning their car is worth less than what they owe. Here is something even scarier: When a car is damaged, such as in a natural disaster, insurance will either pay to repair a car’s damage or give the driver a lump sum equal to the value of the car. When the damage is severe, insurers usually choose the lump sum. That means if your car with negative equity is totaled. You will be out of a car and still have money you owe on it. Even when the damage isn’t severe, it can still pose a huge financial challenge. An Oct 2024 article from the WSJ featured a 34-year-old gentleman who had noticed the main display screen on his new vehicle would often disappear. The car’s backup camera didn’t always work, and the car would make a screeching noise when in reverse. He decided to bring the car into a local dealership, hoping to trade it in. Only to have the dealership tell him it was worth roughly $24,000, which was just under half of the roughly $50,000 he still owed on his loan.

Now, I should confess that I drive a 15-year-old Toyota Prius that I had purchased used. It’s been a great car, and I hope it will continue to be for years to come. My wife’s car is 7 years old, and it replaced her 16-year-old car at the time.

However, I must also...

Welcome to episode 84 of the One for the Money podcast. This episode airs on April 15 which means it’s the tax filing deadline. Now no one likes paying more taxes than they have to, and a great way to accomplish this is by using a Roth Retirement account. In this episode, I’ll share how everyone can have a Roth.

In the tips, tricks, and strategies portion, I will share a tip on how for the same amount of money it may make more sense to complete a Roth conversion than a Roth contribution.

In this episode...

• What is a Roth Retirement Account? [1:56]
• Direct Roth IRA Contributions [2:46]
• Roth 401ks, SIMPLE IRAs, and SEP IRAs [3:44]
• Roth Conversions [7:36]
• Backdoor Roth IRAs & Pro-Rata Rule [8:36]

I remember years ago a coworker of mine shared with me that she and her husband hoped that their income would one day be high enough that they would no longer be eligible to contribute to a Roth IRA. It’s true, that certain individuals, can make too much income to contribute to a Roth IRA. But in this episode, I will share how everyone, regardless of their income level can contribute to a Roth IRA or put differently, how everyone can Roth this way. Okay, that was pretty bad but I had to try.

But first, it would be helpful to provide a brief explanation of what exactly a Roth retirement account is and how they came about. A Roth retirement account is merely a retirement account on which you invest monies on which you already paid taxes. Because you are contributing money after it’s been taxed all of the growth and all of the distributions are 100% tax-free (provided you follow the required distribution rules; age 59.5, etc). These are a fantastic way for individuals to build a tax-free bucket of money that they can utilize in retirement that won't have any taxable implications.

Roth IRA Contributions

The first way to contribute to a Roth IRA is to make direct Roth IRA contributions. For the 2025 tax year, individuals who earn less than $150,000 or married couples who earn less than $236,000 can contribute directly to a Roth IRA. For those under 50, they can contribute $7000 and for those 50 and older they can contribute $8000. Roth IRAs are a fantastic way to build a tax-free bucket of money for retirement. I set these up for my wife and me early in our marriage and I’m so glad I did. These can be especially great for kids as well. I call them Kid Roths and I’ve set these up for our three boys. That way they can benefit from decades of compound growth. If you are early in your career it can be a great time to invest in a Roth IRA.

Roth 401ks/Simple IRAs and SEP IRAs

Roth 401ks/Simple IRAs and SEP IRAs are another great way for anyone regardless of income level to contribute to a Roth investment account. For whatever reason, Roth 401ks, Simple IRAs, and SEP IRAs have no income limits like Roth IRAs do. So regardless of one's income, they can contribute to a Roth 401k. Roth 401ks are great for lower earners as they can allow you to put away even more money on a tax-free forever basis. Individuals can put up to $23,500 in 2025 and for those 50 and older they can put away an extra $30,500. Oddly enough, for those specifically between the ages of 60-63 they can put away $34,750. Why especially those ages, not sure, you’ll have to ask Congress.

Roth Simple IRAs have lower contribution limits namely $16,000 for those under 50 and $19,500 for those 50 and older. Roth SEP IRA limits are based on a percentage of one's income.

These all are great vehicles where individuals can put a lot more money away on a tax-free forever basis. These can make a lot of sense for individuals in their lower-income years such as those early in their career or for those that are late in their career when they are working part-time prior to retirement.

However, these can also...

Welcome to episode 83 of the One for the Money podcast. This episode airs in April, which means we are in the final days of tax season. I’ve never met anyone who likes paying more taxes than they have to, and in this episode, I’ll share how you can utilize the standard or itemized deductions so you don’t have to pay them. Hence the title of this episode, not your standard tax savings strategy.

In the tips, tricks, and strategies portion, I will share a tip regarding how paying it forward can save you on taxes.

In this episode...

• Standard vs. Itemized Deductions [2:15]
• Tax Planning Strategies for Deductions [7:04]
• Benefits of Donating Stock vs. Cash [9:17]
• Importance of Tax Planning in Financial Strategy [11:32]

MAIN

One of the best financial planning quotes I’ve read is this “In America, there are two tax systems; one for the informed and one for the uninformed. Both are legal.”

How true that is. But the challenge with being “informed” about taxes is that Taxes are incredibly complex. Just the federal tax code alone is over 6700 written pages, and the US treasury’s interpretations of the tax code, because it isn’t sufficiently clear, are tens of thousands of pages more. For these reasons and others, many individuals ignore the tax laws altogether and consequently pay more taxes than required. However, with a little bit of better tax planning, you can have a better life because you will pay less in taxes and have more money to spend on great experiences.

A particular area that many taxpayers don’t understand is the deductions everyone receives on their income. Deductions are the amount of your income that is not taxed at all. Taxpayers will take one of two forms of these deductions, which are known as either the standard deduction or itemized deduction. The standard deduction is a default amount of income that you would pay no taxes on. The itemized deductions are for those individuals who have certain key items (such as medical expenses, mortgage interest, gifts to charity, and state and local taxes) that would provide a higher amount of their income that is not subject to tax.

Just what are the amounts not subject to tax, well in 2025 the standard deduction for an individual is $15,000, and for a married couple it is just double that or $30,000. A reminder, what that means is on the first $15,000 of income an individual pays 0% in taxes. So if a person has $65,000 of income in 2025, they would only have to pay Federal taxes on $50,000 because the first $15,000 of their $65000 salary is not taxed.

I should note that the standard deduction wasn’t always this high, but back in 2019 when the Tax Cuts and Jobs Act was passed, it doubled the standard deduction from what it was previously. Before this doubling of the standard deduction, just over two-thirds of taxpayers took the standard deduction and just under one-third itemized deductions, but now with the increase of the standard deductions, over 90% of taxpayers claim the standard deduction with just around 9% taking itemized deductions. That’s a good thing for most tax payers as lower earners had more of their income not subject to tax.

Just what are these itemized deductions? Itemized deductions are when individuals have items on which they spent their income, that in total, were higher than the standard deduction. Itemized deductions are captured on Schedule A of the tax forms. There are primarily four items. The first is Medical expenses, the second is mortgage interest on your primary and secondary residence, the third is state and local taxes, and the fourth is charitable contributions.

For medical expenses, it is only for those that are above 7.5% of your AGI. So if your adjusted gross income was $100,000, you would include with your itemized deductions any medical expenses that were more than $7500 for that tax...

Welcome to episode 82 of the One for the Money podcast. This episode airs in March which means we are in the midst of tax season and there are numerous ways to reduce taxes. One of those ways is to make pre-tax contributions to your 401k or IRA. You don’t pay taxes now but will pay taxes later in retirement when you withdraw these funds. But in this episode, I’ll share a perspective that argues that certain high earners should halt pre-tax 401k and IRA contributions.

In the tips, tricks, and strategies portion, I will share tax savings tips utilizing a trust.

In this episode...

• 401(k) Contribution & Tax Efficiency [1:20]
• Higher Earners & Pre-Tax Contributions [2:47]
• Beneficiary Impact [6:59]
• Tax Mitigation Strategies [9:09]

In the episode before this one, I shared that saving in a 401k is a great way to ensure you have sufficient income in retirement and a 401k can allow you to do it in an incredibly tax-efficient manner. With a traditional 401k or IRA, you can contribute funds on a pre-tax basis, this is also known as a traditional 401k or IRA. This will lower your taxable income for the year of the contributions. You will pay taxes later when you take distributions from the account in retirement.

And recently Congress passed legislation to help certain individuals save even more. Those are individuals that are between the ages of 60-63 who can now contribute an additional $3750 to their 401k accounts. For those under 50 they can put away in a 401k up to $23,500, and those between 50-59 and 64 and older put away up to $31,000 but retirees between ages 60-63 will be able to contribute up to $34,750 in 2025. Why those specific ages, 60-63, and not 65 or 67, well you’d have to ask Congress.

While this may seem like something one should take advantage of, Ed Slott, a well-recognized tax and retirement expert has argued that certain higher earners should stop funding pre-tax 401ks and IRAS altogether.

Now Ed Slott is a certified public accountant and is a nationally recognized IRA and retirement planning distribution expert, best-selling author, professional speaker, and television personality. So he’s no crackpot. He has even hosted several public television programs, including his latest, Retire Safe & Secure! with Ed Slott which was featured on PBS.

But the key is understanding the specific people that Ed Slott argues should stop contributing to their pre-tax IRAs and 401ks. Specifically, it is for people who have very large pre-tax 401k and/or IRA balances that should stop because the income forced out of these plans in retirement, via required minimum distributions, will result in them possibly being in even higher tax brackets than they are now.

This highlights an issue that I see countless times in my own financial planning practice which is that far too often tax saving strategies can be very short-sighted. The focus often is on how to get a larger refund in the current year and not considering the ticking tax time bombs that we may be setting ourselves up for in the future. The absolute best tax mitigation strategies consider both short-term and long-term implications when it comes to lowering your lifetime tax bill.

The reason why high earners with large 401ks and IRAs should consider stopping funding is that when they reach the required minimum distribution age, they may have to take some significantly high distributions. People would be amazed by how many of the retirees I work with don’t want these distributions. And my financial practice isn’t alone. There are a number of advisors who work with individuals who don’t want the funds from their IRAs.

I’ll share a hypothetical example to give you an idea. Let’s say you have a large pre-tax retirement account at age 60 with a balance of ~$2 million and it grows at a relatively modest 7% until...

Welcome to episode 81 of the One for the Money podcast. I am always glad and grateful you have taken the time to listen. There are a host of options when it comes to investing and there is an order of priority in which these should occur. In this episode, I’ll share my thoughts on that order.

In the tips, tricks, and strategies portion, I will share a tip regarding 401k contributions for those nearing retirement.

In this episode...

• Cash Flow Management [1:58]
• Emergency Fund [4:17]
• Contributing up to Company Match [5:51]
• Paying Down High-Interest Debt [6:20]
• Funding an HSA [7:50]
• Saving Further into a 401(k)/IRA [9:03]
• Extra Savings [10:12]

I recently re-read the classic book, The Richest Man in Babylon. It’s a great story on how simple steps can help one build wealth, even those who are mired in debt. The truths contained therein are conveyed so well through the story that I’m having my oldest two boys read the book.

In the book The Richest Man in Babylon, its emphasis was more on savings than investing. Presently there are almost countless ways one can invest. For that reason and others the investment world can be overwhelming and as a result, many choose not to participate. And that is literally and figuratively unfortunate as far too many fail to make small changes that over time have massive results. This episode is meant to help demystify which investments one should select and in what order.

But of course, before we can even think of investing we need to ensure we are monitoring our cash flow. That is the money coming in and the money going out. Some call that a spending plan others call it a budget. I’ll go with the former as it seems more palatable and less restrictive than a budget.

The general rule of thumb when it comes to spending plans is pretty straightforward. One should allocate ~20% of your spending plan to your savings. Those savings can include an emergency fund as well as your retirement and non-retirement savings vehicles. I mention savings first as you should always get in the habit of paying yourself first. It’s an absolute game-changer. As Warren Buffett said so well, Do not save what is left after spending but spend what is left after saving.

Approximately ~50% of one’s budget should be spent on their needs. This would include housing (be it a mortgage or rent), groceries, electricity, transportation, etc. Finally, ~30% of your budget should be allocated to your wants such as a gym membership, eating out at restaurants, travel, etc. However, this should only be the case if all one’s higher interest-rate debt is paid off. I would define higher-interest debt as over 6% which is not your mortgage. Now some might argue that one’s health is paramount and that you should devote money to gym memberships, etc. I agree that one’s health is critical as I recently shared in episode 78 how the first wealth is health, but one can work out without the need of a gym. Additionally, one can eat without the need to go to a restaurant. For those reasons, these are considered “wants instead of their needs” expenditures.

Now that I’ve set a framework regarding cash flow planning the next step is to consider what should be the order of where one puts their money. This may seem similar to the baby steps that Dave Ramsey has made famous. I will share a few key differences between those steps. Dave’s Ramsey’s Baby Steps are great as a general rule and the impact he has had on thousands upon thousands of Americans is nothing short of remarkable so I’m in no way trying to belittle his steps.

The first step, which I will call 1a, which is similar to Dave Ramseys, is building up an emergency fund. As JP Morgan notes in its Guide to Retirement - Life is uncertain –spending shocks and/or job losses can happen at any time. Emergency savings can...