Blog Feed

Too Much Risk? The 6 Components of Behavioral Loss Tolerance

Too Much Risk? The 6 Components of Behavioral Loss Tolerance

What are the six components of "behavioral loss tolerance," and where do you stand as an investor?

Even Multi-Millionaires Can’t Get This Basic Idea Right

Even Multi-Millionaires Can’t Get This Basic Idea Right

I suppose a lot of this comes down to how much "wonderful" you want, and where you’re willing to sacrifice for your "wonderful."

0% Capital Gains vs. Roth Conversions: How to Optimize in Your Financial Plan?

0% Capital Gains vs. Roth Conversions: How to Optimize in Your Financial Plan?

If I have limited space in my financial plan, am I better off paying 0% capital gains or doing low-tax Roth conversions?

RMDs + Sequence Risk = Retirement Destruction?

RMDs + Sequence Risk = Retirement Destruction?

Do required minimum distributions (RMDs) have a destructive synergy with the sequence of returns risk? Can this combo "sink your boat?"

Stocks For Wealth, Bonds for Sanity

Stocks For Wealth, Bonds for Sanity

This is why we own both stocks and bonds. They serve simple, important, and drastically different purposes.

Why I Don’t Offer Hourly Financial Planning

Why I Don’t Offer Hourly Financial Planning

"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"

Why I Don’t Offer Hourly Services

Why I Don’t Offer Hourly Services

"I'd gladly pay you $150 or $200 per hour for a few hours of your time. I'm curious why you don't work hourly?"

The Retiree’s Financial Decathlon

The Retiree’s Financial Decathlon

What are the 10 most important aspects of a financially sound retirement, and how do we start preparing for that future today?

Your Retirement Withdrawal Order of Operations

Your Retirement Withdrawal Order of Operations

A deep (and I mean *DEEP*) dive into optimizing your retirement withdrawal order of operations to make your money last.

11 Ways Retirees Damage Their Retirement Success

11 Ways Retirees Damage Their Retirement Success

Want a successful retirement? Let's use the principal of inversion. We'll identify the common mistakes, and then NOT do those things!


Podcast Feed

How to Be Smart About Inheritance Planning  |  AMA #8 - E113

How to Be Smart About Inheritance Planning | AMA #8 - E113

Jesse tackles six thoughtful listener questions spanning a range of personal finance topics. He begins with a question about using Social Security an…

Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112

Reset Your Portfolio Expectations, Before It's Too Late | Peter Lazaroff - E112

Jesse welcomes back Peter Lazaroff to discuss the psychology and strategy of investing during uncertain times. They explore how media narratives and …

When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111

When Smart Financial Planning Backfires - ChooseFI Companion Episode - E111

Today’s episode is a special bonus episode, a companion to Jesse’s discussion on episode 555 of ChooseFI! Jesse examines the risks of over-optimizati…

Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110

Buffett’s Blueprint - 8 Examples of Warren’s Timeless Wisdom - E110

Jesse explores the timeless wisdom of Warren Buffett, highlighting both his disciplined investment philosophy and his unwavering emphasis on trust an…

Scrimping, Splurging, and Other Crazy Spending Stories - E109

Scrimping, Splurging, and Other Crazy Spending Stories - E109

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, J…

Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108

Go Roth Now Before It’s Too Late? And Other Listener Questions | AMA #7 - E108

Jesse answers a range of listener questions on topics including estate planning, life insurance, financial benefits of marriage, tax strategies for h…

19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107

19 Questions to Uncover Good, Bad, and Ugly Financial Advisors | Don McDonald - E107

Today, Jesse is joined by Don McDonald to offer a critical examination of the financial advising and annuity industries, warning retirees and near-re…

Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106

Retirees’ Mistakes and Wake-Up Calls: Expectations vs. Reality - E106

Jesse explores insights from the Retirements and Perspectives study, which captures the experiences and expectations of individuals transitioning int…

It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

It’s Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

Jesse explores the financial journey of late starters with guest Bill Yount, co-host of Catching Up to FI. In the opening monologue, Jesse shares his…

Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode

Tariffs, Turbulence, and the Harsh Truths We Must Now Face - Bonus Episode

Today, Jesse critiques emotional, reactive investing during volatile market conditions—especially in response to tariffs and recession fears—while pr…


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