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