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

Building up a substantial amount of savings in your 401(k) or IRA may serve as an indicator for a job well done in saving for retirement.
But what soon-to-be retirees need to realize is that if the majority of your retirement savings is in pre-tax dollars, taxes will eventually be owed while in retirement and taking distributions.

Depending on your tax situation in retirement and the tax laws in place at that time, these large account balances may cause a tornado of taxation that you weren’t expecting - which can cause you to have to rethink your retirement strategy altogether.

In this episode, Cameron discusses why pre-retirees should reconsider building up their pre-tax retirement account balances, and what to do instead.

More specifically, we discuss:

• The potential tax problem Cameron has seen recently when talking with those age 50+
• The “shadow taxes” that await you in retirement
• The potential tax ramifications of building up large pre-tax IRA and 401(k) balances
• Alternatives to saving money on a pre-tax basis
• Why tax rates are likely to be higher in the future
• Roth conversions
• How to mitigate or avoid estimated tax penalties when implementing Roth conversions

Resources:

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

A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply.

(01:58) Those age 50 and over should slow down building up pre-tax 401(k) and IRA.

(06:01) Roth 401(k) employer match/profit sharing is taxable; 401(k) plan document dependent.

(07:48) Tax deduction today, or in retirement? Time Value of Money concept isn’t always what it seems.

(10:13) Consider choosing Roth IRA/401K over traditional savings moving forward.

(15:09) Optimize tax strategies with underutilized brackets.

(16:22) Potential tax changes could affect inheritance complexities.

(18:27) How to pay for taxes due from a Roth conversion and avoid underpayment penalties.

The landscape of taxes, retirement savings and Medicare are ever changing.
Every year we see changes to the laws and limitations such as tax rates, brackets, and deductions, limitations on retirement plan contributions, and premium changes to Medicare to name a few.

2025 brings us some run of the mill changes sprinkled with substantial changes that can largely benefit retirees and soon to be retirees.

In this episode, we discuss some of the most important changes and how they may affect you.

More specifically, I discuss:

• Important adjustments to common tax deductions and tax rates
• Changes in the gift and estate tax landscape
• New retirement savings laws and updates for those still working in 2025
• Important changes for Medicare and prescription drug plans
• Social Security related updates for 2025

Resources:

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

Key moments are:

(00:00) 2025 standard deduction amounts increased for inflation.
(05:32) Estate tax exemption may significantly decrease post-2025.
(09:40) Those ages 60-63 can now put more into their employer sponsored retirement plan in 2025
(12:29) Employers can now contribute Roth, impacting taxes.
(17:41) High out-of-pocket costs for Medicare prescriptions.
(20:07) Out-of-pocket drug costs capped at $2,000.
(22:59) 2.5% COLA for Social Security in 2025. Wage limit increases 4.5%.

If you’ve built or inherited an investment portfolio alongside the savings in your retirement accounts, you are likely to face some taxation every year on things like interest, dividends, and capital gains generated from the investments.

These might be investments such as stocks, bonds, mutual funds, or ETFs held in a brokerage account to name a few.
While these investments can serve as a fantastic compliment to your other retirement savings, you’ll want to be sure to manage this money in the most tax-efficient manner each year to allow your money to last as long as possible.

In this episode we discuss 6 year-end strategies to help you reduce the annual tax bill from your portfolio.

More specifically, I discuss:

• 7 basic tax rules you need to know when it comes to non-retirement investment portfolios
• Properly offsetting gains and losses
• Properly use long-term losses
• Avoiding the wash-sale rule
• Make use of lower tax brackets
• Donating appreciated stock to charity
• Do not donate depreciated stock to charity

Resources:

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

Key moments:

00:00 Non-retirement accounts have annual tax implications

05:29 Capital gains can be taxed between 0% to 40.8% based on income and nature of gain

09:02 Properly offset short and long-term gains with losses to defer taxes and optimize savings

10:22 Consider strategic tax planning for mutual funds held in non-retirement accounts

15:04 Transfer appreciated stock to family in lower tax brackets

17:22 Donate appreciated stocks if itemizing deductions and charitably inclined