How to Ensure Financial Misery 😳


Good morning! Today's email includes...

A guide to living a terrible financial life (so we can choose the opposite)...

A conversation tackling a few hotly debated ideas in retirement planning.

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How to Ensure Financial Misery

One of Charlie Munger’s famous speeches is “How to Live a Life of Misery.” Rather than tell graduates how to live happily, he delivered the opposite message. Because if you avoid life’s surefire miseries, what’s left but happiness? Right!?

Munger was famous for quoting famous mathematician Carl Gustav Jacobi who said,

“Invert. Always invert.”
Jacobi

Some math problems, quite simply, are easier to solve if you turn them inside-out.

Today we’ll do the same, but for personal finance and investing.

What follows are my best recommendations for living a poor (in every way) financial life.


Debate! We Discuss 10 Big Retirement Ideas

For appetizers in this episode, I explain some "selection bias" from the Bogleheads and FIRE communities, and then I explain a really cool research idea about "needles in the haystack" in the stock market.

For the main course, Andrew Giancola joined me for a fast-paced, opinionated conversation tackling some of the most debated ideas in investing and retirement planning.


Jesse on the "FI Minded" Podcast

Big thanks to Justin Peters for inviting me onto his "FI Minded" podcast.

Early retirement isn’t just “normal retirement…earlier.”

Most financial advice is built around retiring at 65 with a 25–30 year time horizon, Medicare coverage, and limited tax planning flexibility.

But if you’re aiming to retire in your 40s or 50s, the rules change.


Top 3 of the Week

From Motley Fool: a simple, clear "if I die" roadmap for your spouse

From Marketplace: OG Burton Malkiel on the AI bubble and beating the market

From Retirement Researcher: the costs of getting tax planning slightly wrong


What Are *Your* Questions?

My most popular episodes are the "ask me anything" episodes. Check them out here:

I'm collecting questions for AMAs 19 and 20.

Reply to this email or send questions to
jesse@bestinterest.blog


Looking for a Financial Planner?

Retirement planning can be complex.

But I help!

If you'd like to learn more or explore working together, visit PlanWithJesse.com and fill out the form.


Until Next Week

Thank you for reading, listening, and writing back.

People like you send me questions every day.

Go ahead! I'd love to hear from you. ​​

Until next week,

Jesse

Jesse Cramer

Retirement is a different game. You’ve spent decades building wealth. Now comes the harder part - turning it into a paycheck that lasts. I’m Jesse Cramer. I help DIY investors turn their savings into a clear, cohesive retirement plan. Join 4000+ weekly readers and 20,000+ podcast listeners.

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