This is a must-listen episode that could save your family's financial future… Seriously. Estate planning is important, we know that, but what happens when things go wrong, very wrong?

In this episode, we delve into true stories of oversight and missed opportunities, each one a powerful lesson in what not to do.

Learn how simple mistakes today can cause chaos tomorrow and discover the steps you can take to avoid these pitfalls. Don't let your hard-earned legacy become a cautionary tale.

More specifically, I discuss:

• When multiple executors/trustees disagree
• Who has the power to make decisions when you’re gone?
• Corporate trustee failures tie up significant family wealth
• Digital recordkeeping in the 21st century put beneficiaries at a stand still
• Outdated estate plans can create tax time bombs

Resources:

• Retired-ish Newsletter Sign-Up
• Get a 2nd Opinion on Your Estate Planning Strategy
• Get Show Notes Here

Key moments:

(02:00) Sibling Disagreements and Executor Conflicts (08:22) Who Holds the Power After You’re Gone? Decision-Making in Trusts (13:04) Corporate Trustee Mishaps (20:25) Digital Recordkeeping Issues (24:32) Retirement Accounts and Trusts (29:57) The Expensive Dangers of Outdated Estate Planning Strategies

Long-term care insurance typically becomes a consideration for people in their 50s and 60s after they experience helping out with their aging parent’s care and realizing the substantial hit it can make on their life savings.

But one of the most overlooked aspects of long-term care insurance is the potential tax benefits that can be had. When considering long-term care insurance, understanding the potential tax benefits and how they pertain to your own financial situation can help you make a more informed decision.

More specifically, I discuss:

• How does the potential deduction for long-term care insurance work?
• What are the limitations when trying to deduct qualified long-term care insurance premiums?
• How might changes in tax law allow for or increase your long-term care premium deduction?
• What types of long-term care insurance are considered “qualified”?
• Can you deduct premiums paid for hybrid or asset based long-term care insurance?
• Can business owners get a deduction for long-term care insurance premiums paid?
• When can’t you deduct premiums paid for long-term care insurance?

Resources From The Episode:

• Retired-ish Newsletter Sign-Up
• Get Show Notes Here

Key moments:

(03:02) Are Long-Term Care Insurance Premiums Deductible? (05:33) Deducting Medical Expenses Above 7.5% Adjusted Gross Income (06:14) Long-Term Care Premium Deduction Limits By Age (10:53) Issues With Itemizing Deductions & The SALT Cap (13:24) What Constitutes a “Qualified” Long-Term Care Policy (15:31) Deducting Hybrid or Asset Based LTC vs. Traditional Long-Term Care Insurance (19:19) Deducting Long-Term Care Premiums for Business Owners (22:19) When Can’t You Deduct Your Long-Term Care Premiums?

Since President Trump took office for the second time in 2025, tariff talks are all the rage and markets have entered a new phase of extreme volatility.

Since tariffs can be a good and a bad thing, we think it’s necessary to have some additional context beyond what the mainstream media seems to be focused on specifically - which is higher prices and inflation.

To understand the potential economic impacts moving forward and how these tariffs might affect markets and your investment portfolio, we need to zoom out and take a look at more than just the current headlines.

More specifically, I discuss:

• What are tariffs in layman’s terms, and why do they exist?
• What are the potential impacts of tariffs?
• What has happened historically with tariffs in the U.S. and how did the stock market react?
• What happened to inflation and the stock market during President Trump’s first term and his “America First” trade policies?
• What can happen with inflation and volatility in the stock market when tariffs are increased?
• LISTENER QUESTION: Collecting Social Security Benefits while working and when benefit payments adjust for additional years of earnings.

Resources From The Episode:

• Retired-ish Newsletter Sign-up
• Get Show Notes Here

Key moments:

(02:01) What are tariffs and why do they exist?

(03:14) Potential impact of tariffs

(04:19) Historical facts about U.S. tariffs

(06:53) Potential impacts of tariffs on your investment portfolio

(07:36) What happened the last time President Trump’s Administration increased tariffs?

(14:42) Listener question: Collecting Social Security while working and benefit adjustments

Due to the increasing political and market uncertainty, and recent stock market correction, we felt it was more important than ever to reintroduce this episode of the Retired·ish Podcast throwing it back to episode #8!

In this episode we defined the downside of what is called Sequence of Returns Risk - which is in my opinion can be the greatest threat to your retirement savings and income.

This risk can present itself when markets happen to be volatile to the downside at nearly the same time that you enter retirement when you go from saving to spending your retirement nest-egg – which can be a very nerve-wracking experience to go through.

We explained why it is crucial to understand that saving for retirement is actually the easy part, and how spending what you’ve saved up in your investment portfolio can quickly become a risky endeavor, especially if you have no strategy to mitigate the downside of Sequence of Returns Risk.

More specifically, I discuss:

• What is the greatest threat to your retirement savings?
• Examples of sequence of returns risk in the savings phase of your life
• Examples of sequence of returns risk in the spending phase of your life
• The difference between monitoring account balances vs. average investment returns
• What types of strategies can you implement to try and reduce sequence of returns risk

Resources From The Episode:

• Retired-ish Newsletter Sign-Up
• Get Show Notes Here

Key moments:

(05:23) "Sequence of Returns Risk": Retirement's Hidden Threat (08:06) When The Sequence of Returns is Irrelevant (10:34) Impact of Return Sequence When Spending in Retirement (20:51) Emotion-Free Investment Strategy (23:09) Short-Term Retirement Fund Strategy (26:11) Investment Growth and Legacy Strategy

When the stock market produces double digit returns over multiple years in a row, investors and retirement savers naturally begin to get nervous and anticipate some sort of inevitable financial bubble. 

This fear often stems from two things, from living and investing through recent historic market crashes such as the dot-com bubble and the great financial crisis, as well as the mere thought about how the recent and exuberant growth of your financial nest egg can sharply and suddenly be given back – and ultimately the thought of how that hit to your investments might impact your livelihood in retirement.

In this episode, we take a historical look at financial bubbles and what a “bubble” entails.

More specifically, we discuss:

• Insights from Howard Marks’ memo: “On Bubble Watch” and defining a financial “bubble”
• What causes financial or asset bubbles?
• How bubbles and market crashes can negatively affect investor behavior
• Media headlines and stock market bubbles
• Understanding the cycle of investment fads: My “Asset Bubble Circular Calculation”
• How an investment plan can guide you through market turmoil

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!
• “On Bubble Watch” – Howard Marks https://www.oaktreecapital.com/insights/memo/on-bubble-watch

Key moments:

(03:36) Exploring Stock Market Bubbles and What They Really Are

(04:15) What Actually Causes Stock Market & Other Asset "Bubbles"

(09:55) Bubbles Can Cause Negative Changes To Your Investing Behaviors

(12:49) The Impact of Media Headlines

(15:17) "The Asset Bubble Circular Calculation"

If you’re a diligent retirement saver, you’ve likely heard of - and maybe even explored - executing a Roth conversion of some of your pre-tax retirement savings.

Executing the Roth conversion itself is the easy part, but trying to figure out whether or not it makes sense and will benefit your particular financial situation is the hard part - since you will voluntarily pay taxes when you convert and the conversion can’t be undone.

Rather than start converting to Roth on a whim, a thorough analysis should be done before making any decisions since a Roth conversion has risk and could end up being a very expensive mistake, but when done opportunistically, can save tens of thousands or more in taxes.

More specifically, we discuss:

• What has to happen for a Roth conversion to make sense?
• What is a Roth conversion and why do people and their professional advisors typically do them?
• What are the potential benefits that can come from a Roth conversion?
• Understanding Net Present Value (NPV) when determining whether or not a conversion makes sense
• When might a Roth conversion hurt you?

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!
• Blog Article: Roth 5 Year Rule
• Previous Podcast Episode: What is a Roth Conversion and Should I Consider It?
• Decision Chart: Should I Consider Doing a Roth Conversion?

Key moments:

(05:01) What is a Roth Conversion?

(07:50) When Does It Make Sense to Consider a Roth Conversion?

(12:30) “Net Present Value” and Why It’s Important to Understand

(15:55) Recouping The Costs of a Roth Conversion Depends on Multiple Factors

(19:25) Roth Conversions with The Fastest Pay-Off

(20:25) When a Roth Conversion Might Hurt You

(25:40) Roth Conversions Carry Risks

Investing in the stock market by selecting a handful of individual stocks is tempting for many investors who dream of making substantial gains by picking the "next big thing." But despite the allure, there are many compelling reasons why investors should think twice before diving into individual stock picking and market speculation…

More specifically, we discuss:

• The most important question for DIY investors picking stocks and funds
• What does the research say about stock picking and market speculation?
• A surprisingly small percentage of stocks generate an overwhelming majority of shareholder wealth
• Investor emotions serve as a significant roadblock in making investment decisions
• Your Family Risk Profile

• Resources:

  • Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
  • Ask Cameron A Question!
   

Key Moments:

(02:15) DIY Investing: Picking Individual Stocks

(04:15) Stock Pickers Typically Underperform Market. What Does The Research Say?

(10:12) Very Few Stocks Drive All of The Market’s Growth Over Time

(17:04) Emotions Make Investing Extremely Difficult

(19:33) The #1 Question You Should Ask Yourself When Picking Stocks or Timing The Markets

Retirement is often imagined as a permanent vacation that’s been earned over many years of sacrifice. You envision yourself traveling the world on cruises, playing endless rounds of golf or pickleball, or telling yourself that you will finally spend more of your time with family and start exercising more.

While these dreams can certainly be part of your retirement, it’s essential to understand that this is just one side of the coin.

More specifically, we discuss:

• How retirement has changed over the past few decades
• What it means to be Retired·ish
• Your dream retirement vs. the realities of day-to-day life in retirement
• Emotional aspects of retirement and sense of self-worth
• Changes to your social network in retirement
• The importance of financial and retirement planning before retiring.

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!

Key moments:

(00:00) Redefining Retirement: A Lifestyle Choice (06:17) Plan Retirement Activities Early (10:00) Reconnecting with Social Circles in Retirement (11:14) Dynamic Retirement and Financial Planning Essentials

Two of the most prominent provisions – the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) - that can substantially reduce Social Security benefits for some federal, many public sector and civil service employees were just eliminated after being in effect for the last 40 years!

Teacher, police officers, firemen, and some federal workers are some of the most common groups affected by these provisions, and as of December 31st, 2023, they may see a bump in benefits or expected benefits they’re eligible to receive.

More specifically, we discuss:

• President Biden passes the Social Security Fairness Act on January 5th, 2025
• What are the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) and how do they work?
• How were some public sector and federal employees and retirees affected by these Social Security provisions?
• What are the potential benefits now that these provisions have gone away?
• Retroactive 2024 lump-sum payments
• Tax implications now that the WEP and GPO have been eliminated
• What you need to do to receive potential additional Social Security benefits

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!

Key moments:

(00:00) WEP & GPO provisions reduce Social Security benefits for public servants.

(07:00) How do the WEP and GPO provisions work?

(08:51) GPO reduces public pension spouse's Social Security w/ examples.

(13:25) How might your benefits change moving forward in 2025 and beyond?

(14:19) Lump sum back-pay of Social Security benefits for 2024.

(14:55) Tax implications of lump sum payments and increased benefits.

There’s no question about it, that when it comes to saving for retirement, the financial mass media pounds the table with all things retirement accounts like IRAs and 401(k)s, but there’s a vastly underutilized investment vehicle that can help retirees enjoy a potential 6-figure retirement income, entirely tax-free.

We are referring to the good olé brokerage account.

A brokerage account is simply an investment account you open where you deposit money from your own bank account and then you can use that cash to invest in various investments held inside that brokerage account. Most commonly, people will invest in things like stocks, bonds, mutual funds, ETFs, things of that nature. In this episode, I teach you how you might utilize a brokerage account for a 6-figure retirement income, tax-free.

More specifically, we discuss:

• The difference between a brokerage account and a retirement account such as an IRA or 401(k)
• How a pre-retiree might accumulate funds inside of a brokerage account
• How taxes work when it comes to brokerage accounts and the investments held inside them
• How exactly you can end up paying no federal taxes on over 6-figures of income
• Hypothetical scenarios (basic concept and real-world)
• The importance of a retirement income plan and investment strategy

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!

Key moments:

(03:44) Build brokerage account for retirement income flexibility (07:35) Pre-Tax IRA/401(k) assets taxed as ordinary income, brokerage assets can be subject to lower long-term capital gains rates (10:08) 0% capital gains tax up to $96,700 for married filing joint in 2025 (12:07) Conceptual Scenario: high 6-figure income in retirement, zero taxes (15:24) Real-World Scenario: high 6-figure income in retirement, zero taxes (23:02) Key points when using brokerage accounts as part of your retirement income strategy